* = Includes Audience Choice


Best of the Best: Andersonville (2002)
Best of the Best: Blommer Chocolate (2002)
Best of the Best: Boystown (2002)
Best of the Best: Chicago Federal Center (2002)
Best of the Best: Cicero (2002)
Best of the Best: The Daley machine (2002)
Best of the Best: Devon Avenue (2002)
Best of the Best: Grant Park (2002)
Best of the Best: Greektown (2002)
Best of the Best: Hilliard Homes and Marina City (2002)
Best of the Best: Holy Trinity Russian Orthodox Cathedral (2002)
Best of the Best: The intersection of Damen, North and Milwaukee (2002)
Best of the Best: John Hancock Center (2002)
Best of the Best: The Lakefront (2002)
Best of the Best: Lincoln Park (2002)
Best of the Best: Little Italy (2002)
Best of the Best: The Market District (2002)
Best of the Best: Navy Pier(2002)
Best of the Best: Parakeets in Hyde Park (2002)
Best of the Best: Pullman (2002)
Best of the Best: Sears Tower (2002)
Best of the Best: The Sun-Times’ writers (2002)
Best abiding sorrow mistaken for performance art (2007)
*Best accomplishment not yet carved on Burris’ tombstone (2009)
Best activist in the interest of the public defense (2015)
Best addition to the local green economy (2015)
*Best airport security story, post-9/11 (2002)
Best (and tastiest) way to support merchants who are struggling while the city builds a forward-thinking streetscape (2015)
Best architectural restoration (2007)
Best argument for automated speed-enforcement cameras (2013)
Best attempt by a media organization to ignite social change (2014)
*Best baby name for the Pete Wentz-Ashlee Simpson offspring (2008)
*Best Barack Obama moment (2008)
*Best bet about where Groupon’s stock price will be in 2017 (2012)
*Best bet to be the “next Oprah” from Chicago (2010)
*Best big Chicago company to work for (2008)
Best bike path for misanthropic cyclists (2015)
Best bilingual community radio station (2012)
Best “Blues Brothers” location still in Chicago (2015)
Best budding media mogul (2009)

*Best candidate for governor (2002)
*Best candidate for governor
*Best candidate for governor of Illinois (2009)
*Best candidate for mayor, whether declared or not (2014)
*Best candidate for mayor who is likely to run (2010)
*Best candidate for mayor who is unlikely to run (2010)
*Best candidate for president, regardless of whether he or she is from Chicago (2012)
*Best candidate for senator (2014)
Best celebrity sighting in the past year (2007)
Best cemetery (2015)
Best chance of making Time’s 100 Most Influential List in 2012 (2011)
Best Chicago-accent diatribe by someone in public office in the last year (2013)
*Best Chicago holiday tradition (2010)
Best Chicago landmark, Leader of Culture (2015) 
Best Chicago landmark coming in 2016 (2015)
*Best Chicago Twitterer for news (2013)
*Best Chicago news columnist (other than Tony Fitzpatrick, of course)
Best choreographic homecoming, Leader of Culture (2015)
*Best city of Chicago department head (2013)
Best city of Chicago sustainability initiative that is suffering the most push back (2013)
Best city-sponsored energy-efficiency Initiative
Best classical theater, Leader of Culture (2015)
Best commercial Pinterest account (2012)
Best crosswalk update (2012)
Best CTA Blue Line mishap (2014)
Best CTA success story (2013)
*Best dating nightmare (2002)
Best day trip to Bedford Falls (2010)
Best David beats Goliath moment (2015)
*Best Democratic candidate for US president (2007)
Best desperate attempt to land the 2016 Olympics (2008)
Best diabolically Trump-hating cat to follow on Twitter, Leader of Culture (2015) 
Best-dressed artist (2013)
Best developer-held land portfolio (2015) 
Best El line for napping (2015) 
Best El ride for graffiti (2013)
*Best El station (2011)
*Best El station for an earache (2002)
Best El station to witness a free musical performance (2012)
Best election that never happened (2015) 
Best European import
*Best example of a memo that Tribune executives Lee Abrams or Randy Michaels might write, but haven’t (2008)
Best example of how Chicago continues to neglect its great blues heritage (2015)
Best example of Chicago’s global footprint (2012)
Best example of fighting the man and winning (2011)
Best example of former mayor Richard M. Daley channeling Gertrude Stein (2013)
Best example of the failing of local television, Leader of Culture (2015)
Best example of why some folks are oblivious to the real estate crash and financial meltdown (2008)
Best execution of media activism
Best free outdoor activity, Leader of Culture (2015)
Best funeral procession (2014)
Best fusion of passion and commerce (2009)
Best future candidate for president, regardless of whether he or she is from Chicago (2012)
*Best future owner of the Chicago Tribune (2011)

Best global foresight (2012)
Best guess about why the CTA decided to implement the new Ventra card system (2013)
*Best guess as to which project gets done first: Redevelopment of US Steel Southworks site on south lakefront; construction of the Chicago Spire; redevelopment of Old Chicago Main Post Office or CTA Red Line extension to 130th Street (2014)
*Best haunted site (2013)
Best hidden park (2010)
*Best hotel lobby (2010)
*Best iconic Chicago personality now that Studs is gone (2009)
Best iconic landmark you could buy, Leader of Culture (2015) 
Best iconic transformation (2008)
*Best idea for the next civic spectacle, after this year’s Great Chicago Fire Festival triumph (2014)
*Best idea to fix the CTA (2007)
*Best idea to forget about from Chicago 2016 (2009)
*Best idea to salvage from Chicago 2016 (2009)
Best idea we’d like to really see catch fire (2008)
*Best imaginary Oprah moment that won’t likely actually happen but, well, might have (2010)
*Best imaginary Oprah moment that won’t likely actually happen but, well, no, it never would (2010)
*Best imaginary Sun-Times headline (2002)
*Best imaginary Twitter post by Patti Blagojevich (2009)
*Best imagined dialogue between Sun-Times editor Jim Kirk and Michael Ferro, parent company Wrapports chairman, in deciding to eliminate the entire photography staff (2013)
Best immobile street performer (2013)
Best impersonation of a true Chicago politician (2011)
Best implement for calling dibs (2015) 
Best indicator that America needs a new healthcare policy (2009)
Best indicator(s) that America still needs a new healthcare policy (2012)
Best indoor make-out spot (2010)
Best international trip within Chicago, Leader of Culture (2015) 
Best internet station to soon hit the radio dial
Best investigative reporting on Chicago crime (2015)
Best Kickstarter campaign (2012)
Best live Twitter feed of roadwork, Leader of Culture (2015) 
*Best local daily newspaper
Best local digital controversy (2007)

Best local drug scare(2013)
*Best local general-interest blog (2009)
*Best local general-interest blog
Best local Instagram (2015)
Best local internet muckraker (2012)
Best local nonprofit (2007)
*Best local podcast (2010)
*Best local radio station (2011)
Best local transit app (2013)
*Best local TV weatherman (2011)
Best local window on the world (2012)
Best location for the Obama Presidential Library (2014)
Best-looking female local TV personality (2011)
*Best-looking male local TV personality (2011)
Best macrocosmic El stop (2010)
Best makeout spot (2015)
Best mascot (2015)
*Best mayoral campaign slogan for Rahm (2010)
*Best Mayor Daley accomplishment of the past year (2009)
*Best Mayor Emanuel accomplishment of the past year
*Best Mayor Emanuel debacle of the past year (2014)
Best Mayor Daley debacle of the past year (2009)
Best memorial to heroic animals and circus performers (2013)
*Best memory from the trial of Rod Blagojevich (2010)
Best missed but little-known local figure (2008)
Best mid-century modern thoroughfare you never stop on (2015)
Best moment that made us proud of our country (2008)
Best museum award that probably won’t make the corporate stationery (2011)
*Best name for the building formerly known as Sears Tower (2009)
*Best name for The 606, other than The 606 or the Bloomingdale Trail (2013)
*Best neighborhood in which to weather the possible decline in real estate values precipitated, among other things, by the mortgage crisis (2007)
*Best neighborhood in which to exploit the possible decline in real estate values precipitated, among other things, by the mortgage crisis (2007)
Best neighborhood in which to shoot a movie, Leader of Culture (2015)
Best neon sign to evoke the good life (2002)
Best new bikeway (2013)
Best new building built in the last year or so (2009)
*Best new career for deposed Channel 5 news reporter Amy Jacobson (2007)
Best new CTA station (2012)
Best new feature of the newly redesigned Tribune (2008)
*Best new gig for the Reverend Jeremiah Wright (2008)
Best new idea for public transportation (2013)
Best new innovative civic art event
*Best new name for Humboldt Park (2007)
*Best new nickname for Sam Zell (2008)
Best new perfume (2013)
*Best new piece of architecture (2008)
Best new online radio station
Best new open-air co-working space (2015)
Best new tourist attraction (2009)
*Best new work of architecture finished in the last year or so (2013)
Best newish downtown attraction (2012)
Best newly minted Chicago celebrity (2008)
*Best newsroom street level fish bowl (2009)
*Best next career for failed gubernatorial candidate Scott Lee Cohen (2010)
*Best next career for Jesse Jackson, Jr. (2010)
Best next dubious mascot for Chicago after “Chalkie” (2009)
Best next media moguls (2011)
*Best next neighborhood to gentrify, now that Humboldt Park’s on its way (2007)
Best next next next Wicker Park (2013)
*Best next thing for the city to privatize after selling off Midway Airport and the parking meters (2008)
*Best next thing for the state to privatize after selling off the Illinois Lottery (2008)
*Best next Twitter subject for Dan Sinker of @MayorEmanuel fame (2011)
Best niche website (2010)
Best nickname for that really enormous snowstorm last February (2011)
*Best nickname for the cops on Segways that patrol the parks (2007)
Best nickname from the Joey Lombardo mob trial (2007)
Best non-corporate neighborhood (2013)
Best novelty Twitter account (2012)
Best odd monument and tribute to The Great Migration (2015)
Best oh-so-Chicago scandal of 2015 (2015)
*Best opening paragraph from the memoirs of Richard M. Daley (2010)

*Best opening paragraph of an imaginary staff memo from Mayor Rahm Emanuel (2012)
*Best outcome from the Chicago Public Schools teachers strike (2012)
*Best outcome of the CNN miniseries “Chicagoland”  (2014)
Best outdoor make-out spot (2010)

*Best outing on Metra, CTA or other public transit lines (2007)
Best part of the 2012 Chicago Cultural Plan (2012)
Best part of the 2012 Chicago Cultural Plan most likely to actually happen
Best path to take a romantic walk at night (2013)
*Best personal encounter with a Chicago cop, that may or may not have ended up with you getting beat down, and may or may not have been videotaped and shown on television (2007)
Best place for a kid’s outing (2015)
Best place for a romantic stroll (2002)
Best place for an intellectual shoving match about the role of design in the City with a capital C (2015)
Best place for dummies (2011)
Best place for children of the nineties to reminisce (2012)
*Best place to be in Chicago when the Ebola plague hits (2014)
Best place to chill out (2011)
Best place to drink in the forest preserves (2002)
Best place to enjoy a bag lunch by the river (2012)
Best place to find a panhandler (2007)
Best place to find people who are not necessarily rich but dress well (2012)
Best place to flaunt your genderfuck style (2013)
Best place to get a haircut, Leader of Culture (2015)
Best place to get lost in a crowd (2007)
Best place to get on Lake Shore Drive northbound from downtown (2007)
Best place to get on Lake Shore Drive southbound from downtown (2007)
Best place to meditate outdoors in safe seclusion (2015)
Best place to nonchalantly check out the opposite sex (2008)
Best place to not stand on the El (2012)
Best place to people watch (2013)
Best place to pretend you are outside during a Chicago winter, Leader of Culture (2015)
Best place to see grown Chicagoans acting like little kids (2014)
Best place to see random street performers who will blow your mind, Leader of Culture (2015) 
Best place to see tattoos, piercings, dreads and sweet rides (2012)
Best place to smell the chocolate cloud (2011)
Best place to spot an alligator (2008)

Best place to spot Walking Guy (2012)
Best place to walk off writer’s block (2015) 
Best potential buyer of Tribune Publishing, among those names bandied about (2013)
Best post-WWII motel sign still standing, though the motel is long gone (2011)
*Best prison name for Blago (2012)
Best proposal for Chicago’s next landmark (2010)
Best public edifice to name for Obama, now that Rahm’s yanked his name off the elite North Side school
Best public restroom (2013)
Best public space to read classic Chicago poetry and prose (North Side) (2015) 
Best public space to read classic Chicago poetry, prose and drama (South Side) (2015)
Best Rahm policy reversal (2012)
Best real life example of haters gonna hate (2015) 
Best reason for Chicagoans to boast to their lefty West Coast friends
Best reason for the real estate market to turn around soon (2009)

Best reason for vexillologists to live in Chicago (2013)
Best reason not to diss Richard Roeper (2007)
Best reason to appreciate the CTA’s long-lingering “slow zones” on the Blue Line (2007)
Best reason to endure months of downtown roadwork (2014)
Best reasons to stop seeing red over grungy El stations (2014)
Best reason to wonder if Mayor Daley is really in charge (2007)
Best refuge from drunken frat boys and other urban miseries (2011)
*Best relic of the “Devil in the White City” era still extant (2007)
Best reminder that no one is safe and the machine will swallow us all (2015)
Best reminder of Chicago’s grimy industrial past close to downtown (2015)
Best reproduction of a Monopoly game square (2010)
*Best Republican candidate for US President (2007)
Best rock icon spotted on the CTA (2014)
*Best Rod Blagojevich accomplishment of the past year and we’re being serious here (2009)
Best ruins (2015)
Best Russian orthodox church designed by an American architect (2012)
Best secret flower patch in Chicago
Best shot fired in “Chiraq” firefight so far (2015)
Best shoutout to Chicago’s gun violence by a national late-night talk-show host (2013)
Best sign of the Armageddon in 2008 (2008)
*Best sign that Rahm is not Richie (2011)
Best sign that Rosie is not Oprah (2011)
Best single-purpose fake Twitter account (2013)
*Best slogan for Chicago to make the world forget about all those nasty murders they keep hearing about (2012)
Best smelling bike lane
Best-smelling El stop (2013)
Best social service fundraiser party
Best South Side intersection for old-school dining and jazz (2010)
Best spot for celeb sightings (2010)
Best stereotypical, incomplete, single-minded documentary depicting the black men of Chicago (2014)
Best story… period (2014)
Best street to drive down (2007)
*Best suggestion for a more appropriate location for the controversial TRUMP sign (2014)
Best ten reasons not to leave Chicago (2011)
Best thing about Chicago, Leader of Chicago (2015)
Best thing about Governor Rauner’s proposed Thompson Center teardown (2015) 
*Best thing about Millennium Park besides the Bean (2009)
Best thing about Snowmageddon (2011)
Best thing about the otherwise-disastrous Bruce Rauner administration  (2015)
*Best thing about that whole NATO Summit business (2012)
Best thing about the Bloomingdale Trail, aka The 606 (2015)
*Best thing about the new Divvy bike-sharing system (2013)
Best thing about the new parking meters (2009)
*Best thing about the return of Bill & Walter to Channel 2 (2010)
Best thing to happen to Chicago nonprofits (2009)
*Best thing to name after Richard M. Daley (2010)
Best thing to never do on the Blue Line (2013)
*Best thing we can expect from the Tribune sale (2007)
Best threesome (2011)
Best touch of Paris (2007)
Best-to-date-but-certainly-not-last first-person account of the slow and painful death of the Chicago Sun-Times  (2015)
Best transvestite watching (2010)
Best Tweetathon, Leader of Culture (2015)
*Best tweeting by a local news or politics personality (2009)
Best under-the-radar local nonprofit (2007)
Best underground cafe (2014)
Best unexpected manifestation of the smoking ban (2008)
Best unhinged Twitter account linked to local public transit (2013)
Best university from which to be denied tenure (2007)
Best unknown state park within the Chicago area (2015) 
Best unrecognized historic tragedy (2012)
Best unrecognized landmark to Chicago’s gay community (2008)
Best update to Chicago’s bike infrastructure (2015)
Best use of $100 million (2012)
Best view from a parking garage (2007)
Best view of the Chicago skyline from a car (2015) 
*Best view of the Lake (2009)

Best view of the skyline you never expect (2012)
Best view without the Lake (2009)

Best warrior against the hegemony of car culture (2009)
Best way to anger a long line of commuters (2013)
*Best way for Chicago’s Olympics to outdo the Beijing Olympics (2008)
Best way to cement your status as a Chicagoan (2013)
*Best way to describe Chicago weather (2012)
*Best way to end Chicago’s budget woes (2010)

*Best way to end the city’s budget crisis (2009)
*Best way to end the city’s budget crisis, which we thought we’d never have to ask again after we posed the question five years ago, but here we are
Best way to explore Chicago, Leader of Culture (2015)  
Best way to feel like you’re helping the homeless without much effort
Best way to fight parking scarcity (2015)
Best way to impress a transplant Chicagoan using only a bookshelf (2015) 
Best way to keep your balance on the El (2013)
Best way to relive the terrors of your daily commute (2012)
Best way to squander $2.75 billion and defund public transportation (2013)
Best “Wild Kingdom In the Big City” moment, Leader of Culture (2015)
Best winter sanctuary, Leader of Culture (2015)
Best words to be rendered in 20-foot serif fonts on building facades
Best zoological additions to Chicago (2012)


Best of the Best: “The Adventures of Augie March” (2002)
Best of the Best: Art Institute of Chicago (2002)
Best of the Best: Berlin (2002)
Best of the Best: Brew and View at the Vic Theatre (2002)
Best of the Best: Buddy Guy’s Legends (2002)
Best of the Best: Chicago Botanic Gardens (2002)
Best of the Best: Chicago Cultural Center (2002)
Best of the Best: Chicago Symphony Orchestra (2002)
Best of the Best: Delilah’s (2002)
Best of the Best: Doc Films, University of Chicago (2002)
Best of the Best: Empty Bottle (2002)
Best of the Best: Field Museum (2002)
Best of the Best: Fireside Bowl (2002)
Best of the Best: Frank Lloyd Wright Home and Studio (2002)
Best of the Best: Garfield Park Conservatory (2002)
Best of the Best: The Gene Siskel Film Center of the School of the Art Institute (2002)
Best of the Best: Goodman Theatre (2002)
Best of the Best: Green Mill (2002)
Best of the Best: The Hideout (2002)
Best of the Best: House Music (2002)
Best of the Best: International Museum of Surgical Science (2002)
Best of the Best: Jazz Showcase (2002)
Best of the Best: Jimmy’s Woodlawn Tap & Liquor Store (2002)
Best of the Best: Lyric Opera (2002)
Best of the Best: Matchbox (2002)
Best of the Best: The Metro (2002)
Best of the Best: Museum of Science and Industry (2002)
Best of the Best: Music Box (2002)
Best of the Best: Newberry Library (2002)
Best of the Best: Northalsted Market Days (2002)
Best of the Best: Old Town School of Folk Music (2002)
Best of the Best: Printers Row Book Fair (2002)
Best of the Best: The Second City (2002)
Best of the Best: Steppenwolf Theatre Company (2002)
Best of the Best: Studs Terkel (2002)
Best of the Best: Tuman’s Alcohol Abuse Center (2002)
Best 12×12 solo exhibition at the Museum of Contemporary Art (2010)
Best abiding sorrow mistaken for performance art (2007)
Best actor to make Chicago proud this year (2009)
Best acoustics in a music club bathroom (2015)
Best adult show-and-tell experience (2015) 
Best advocate for queer theory in art
Best African music night (2013)
Best album covers by a local label (2014)
Best alkie end-of-nighter nightspot that we’ll never forget, or remember for that matter (2013)
Best all-ages, seasonal monthly lakefront event (2015)
Best all-nude cast (2013)
Best alternative art-space fundraiser (2009)
Best alternative dance club (2007)
Best alternative gallery show in the past year
Best amateur-band regional touring nightspot (2013)
Best anniversary fest for a music empire now gone (2011)
Best anniversary fest for a music empire still living (2011)
Best annual music festival (2007)
Best annual public art event (2012)
Best apartment gallery (2014)
Best apology for interrupting an opening-night performance (2013)
Best approximation of South Beach Miami (2007)

Best architectural restoration (2007)
Best art beer (2013)
Best arts club (2015)
Best art exhibit at a gallery (2013)
Best art comeback (2013)
Best art exhibit in Second Life (2007)
*Best art exhibit (in the last year or so) (2007)
*Best art exhibit (in the last year or so) (2008)
*Best art exhibit (in the last year or so) (2009)
*Best art exhibit (in the last year or so) (2010)
*Best art exhibit in the last year or so (2011)
*Best art exhibit in the last year or so (2012)
Best art exhibit in the last year or so (2013)
*Best art exhibit (in the last year or so)
Best art exhibit (in the last year or so) held in the suburbs (2010)
Best art exhibition about architecture in an architecturally significant building (2011)
Best art-exhibition catalogue design (2011)
Best art exhibition catalogue design in the last year or so (2012)
*Best art gallery (2011)
Best art interview LP (2012)
Best art in a coffee shop/bakery, Leader of Culture (2015) 
Best art museum that is not an art museum (2012)
Best art-opening parties (2008)
Best art project to effect change in the criminal justice system
Best art reading (2012)
Best art road trip (2013)
Best art school for hobbyists (2011)
*Best art show (in the last year or so) (2002)
Best art YouTube channel (2014)
Best artist bookstore (2009)
*Best artist who has yet to play Lollapalooza but should (2008)
Best artist TED Talk that wasn’t actually A TED Talk (2015)
Best artistic response to bad art (2015)
Best arts center that also offers shamanism courses
Best artwork worth saving from destruction (2007)
Best atmosphere for musical improv (2015)
Best authentic German pub interior (2013)
Best awkward silence (2013)
Best backyard gallery (2015)
Best bar above Lawrence Avenue (2008)
Best bar couch (2015)
Best bar for free popcorn and NES video gaming (2011)
Best bar standup comedy night (2013)
Best bar that emulates your father’s basement (2007)
Best bar to close before it became legendary (2014)
Best bar to drink at to avoid watching the Mets eliminate the Cubs in the ever-loving postseason (2015)
Best bar to get a martini and manicure (2012)
Best bar to have a conversation in (2008)
Best bar to pick up a molecular biologist (with patents) (2002)
Best bar to pretend you’re someone else (2007)
Best bar to see a reading (2009)

Best bar to smoke on New Year’s Eve, before the non-smoking ban goes into effect (2007)
Best bar to time travel in (2010)

Best bar turned rock venue (2013)
Best bar-turned-rock venue (in the last year or so) (2007)
Best basement gallery (2011)
Best bathroom boot camp (2009)
Best big-budget horror comedy (2015)
*Best blues club (2011)
Best book-critic inspiration (2013)
Best book to get laid with (2014)
Best book written by a local author (in the last year or so) (2008)
Best bookstore-and-bar one-two punch (2015)
Best booth at EXPO Chicago (2013)
*Best bowling alley (2008)
Best breakout booze and lit reading series (2013)
Best bricolage
Best bridge to live under (2012)
Best British Invasion since the Beatles (2014)
Best brother/sister garage rock band (2010)

Best burgeoning Chicago film career (2007)
Best cabaret (2002)

*Best candidate for “One Book Chicago” still untapped (2007)
Best cantankerously comedic crooner and pleasantly perverse pianist (2015)
*Best celebrity art show to bring to Chicago after Bowie at the MCA (2014)
Best Chicago art boosters (2008)
*Best Chicago-as-Gotham moment in “The Dark Knight” (2008)
Best Chicago comic book convention (2011)
Best Chicago drinking blast from the past (2013)
*Best Chicago record label (2011)
Best Chicago-related TV series (2013)
*Best Chicago theater company (2013)
Best Chicago theater company not in Chicago (2013)
Best Chicago version of the Eurythmics (2011)
Best Christmas festival (2008)
Best collab (doing something they should have done a looooooonnnnnngggg time ago)
Best collaborative accomplishment in the arts (2011)
Best collaborative multimedia dance performance (2015)
Best college campus art gallery (2008)
*Best college campus art gallery or museum (2013)
*Best college radio station (2008)
*Best college radio station (2013)
Best combination of elasmobranchology and potty humor (2012)
Best combo of Chicago cultural traditions (2013)
Best comic-relief sidekick (2009)
Best commercial gallery revolt (2015)
Best commercial gallery show in the past year
Best commercial gallery show in the last year (2015)
Best community-based video game, Leader of Culture (2015)
Best concentration of employees who are also recording artists (2013)
Best conceptually complicated exhibition to be mounted in what is essentially an office (2012)
Best contemporary dance company you’ll never see again (2013)
Best controversy over a theatrical review (2013)
Best controversy where there was none (2011)
Best convention to combine comic-book culture, anime, manga, cosplay, video games, Power Rangers, Dr. Who, Game of Thrones, cult movies, cult TV, cult pop cult paraphernalia, in one big three-day-long, multi-floored jambalaya of fanboys and gamer girls, wannabes and gurus, rising talents, panelist pontificators, free screenings, and featured guests, photo op stalkers, pop artifact hawkers, cosplay gawkers and merchandise floor walkers (2015)
Best corner for public evangelizing (2012)
Best country album by a Chicago artist (in the last year or so) (2002)
Best country bar to belt Zac Brown Band without shame (2012)
Best creative use of an arboretum (2011)
Best creepy/cool art exhibit (2014)
Best critical art project in Chicago this year (2012)
Best crowd-sourced event in a museum
Best crowd-sourced Chicago History Museum exhibit (2015) 
Best curatorial hire of the year (2015) 
Best current Chicago band that sounds like a post-punk group from 1982 (2013)
Best dance advocacy effort (2015)
*Best dance club (2011)
Best dance company to take a date who’s afraid of contemporary dance (2014)
Best dance incubator (2014)
Best dance show about a presidential administration (2015)
Best date move (2013)
Best design slogan (2013)
Best decade-long queer dance party (2015)
Best digital tour through a museum’s collection (2011)
Best dining experience during a Federal raid (2015)
Best dinner party with fascists, anarchists and feminists (2012)
Best dive bar (2013)
Best dive bar featuring all-German beer (2010)
Best divey 4am LGBT bar without wood paneling (2013)
Best DJ masquerading as a lawyer (2014)
Best downtown dive bar you’ve never heard of (2013)
Best drag/art fusion (2013)
Best drag performer (2007)
Best drag queen pickup spot (2013)
Best dressed burlesque performer (2015)
Best-dressed improvised jazz musician (2014)
Best drink with a view (2012)
Best eighties dance night (2010)

Best El station art installation (2013)
Best embarrassing journal reading (2015)
Best emerging art gallery (2011)
Best emerging artist team-up (2014)
Best emerging endurance art performance (2015)
Best enigma of an exhibition (2013)
Best Evanston-based arts advocate (2014)
Best event to see (and swoon over) Ira Glass in person (2012)
Best example of overcoming secondcityitis (2007)
Best example of using music for cultural awakening (2014)
Best excuse to revisit the eighties
Best exhibition design (2013)
Best exhibition design
Best exhibition in the last year (2015)
Best exhibition to see for aspiring sculptors (2014)
Best expatriate turned international music community ambassador (2013)
Best facelift on a North Side bar (2012)
Best fact about Chicago wildlife (2013)
Best 50-cent beer night (2011)
Best family theater experience that might actually entertain the whole family (2015) 
Best first date (2010)

Best five dollars you can spend on a Thursday night (2008)
Best “flow” object manipulation dance event (2015)
*Best foreign cultural center in Chicago (2012)
Best foreign film festival in Chicago
Best foreshadowing of the smokers purgatory to come (2007)
Best free twice-monthly stand-up show (2015)
Best 4am bar worth a cab ride (2007)
*Best film festival
Best Frank Sinatra avatar (2015)
Best free art-exhibition catalogues (2011)
Best free indie parties sponsored by a corporation (2011)
Best free intra-city touring dance series (2015) 
Best free show (2013)
Best free theater (2014)
Best Friday night dance party no one knows about (2008)
Best funky theater venue (2012)
Best fusion (2015) 
Best gallery exhibition catalogues
Best gallery show in the last year (2009)

Best gallery showing Chicago artists (2011)
Best gallery space located in a bathroom (2009)

Best gallery to people-watch (2014)
Best German heritage event (2012)
Best group booty call (2013)
*Best guess as to where Billy Dec is and what he’s doing right now (2009)
Best handmade book publisher we’re all really rooting for (2013)
Best high-school murals to get teenaged boys interested in art (2009)
Best high-school spoken-word competition (2015)
Best hipster-free bar in Wicker Park/Ukrainian Village (2009)
Best hipster specialty dance night (non-Soul Night division) (2011)
*Best holiday-themed theatrical production (2010)
Best homage to a beloved Chicago artist and teacher (2015)
Best honky tonk hillbilly bar left over from Chicago’s second great migration (2015)  
Best hope to make us forget Chief Keef ever existed
Best houseplant garden in an art gallery (2012)
*Best hypothetical story line for “Trapped in the Closet” chapter 23 (2007)
Best “I gotta go back there just to see her” bartender
Best “I gotta go back there just to see her” hostess
*Best idea for Desiree Rogers to use to revive Chicago icon Ebony/Jet (2010)

*Best idea for Hugh Hefner to use to revive Chicago icon Playboy (2010)
Best idea to improve the moviegoing experience (2013)
Best illumination of a heartbreaking problem that few know about 
*Best imaginary Twitter post by Studs Terkel (2009)
Best improv club (2011)
Best improv troupe (2015) 
Best improvisational dance public forum (2015) 
Best independent comics event (2012)
Best independent curator (2013)
Best independent feminist bookstore you could own (2013)
Best individual accomplishment in the arts (2011)
Best initiative to make dance free and accessible
Best insider’s view of Chicago’s underground art scene (2013)
Best institutional accomplishment in the arts (2011)
Best international showing of Chicago artists (2012)
Best Irish bar (2008)

Best irreplaceable loss for the culture (2011)
Best itinerary for creeps (2002)

Best Japanese-inspired garden (2007)
Best jazz album by a Chicago artist (in the last year or so) (2002)
*Best jazz club (2011)
Best jazz musician to make us proud in the near future (2002)
*Best John Hughes movie set in or around Chicago (2009)
*Best Kanye West lyric he’ll likely never write (2013)
Best kinky dance party (2013)
Best late-night holiday-themed theatrical production (2010)
Best lesbian karaoke (2013)
Best literary impulse (2012)
Best literary magazine for young adults (2015)
Best literary monument (2010)

*Best live lit event (2014)
*Best live music show (in the last year or so) (2009)
Best live rendition of “Total Eclipse of the Heart” onstage (2013)
*Best local actor (2010)
*Best local arts, culture or nightlife blog (2009)
Best local band to almost make the cover of Rolling Stone (2011)
Best local Barack Obama propaganda (2008)
*Best local dance company (2012)
*Best local DJ (2010)

Best local mainstream-comic-book creator (2007)
*Best local music festival (2010)

Best local publisher (2002)
Best local talk show, Leader of Culture (2015)
Best local TED alternative (2012)
Best longest-running show in Chicago (2014)
Best-looking band (2007)
*Best-looking bartenders or wait staff (2007)
Best Lost Boys treehouse gallery (2014)
Best lost-and-found (or how to bring your idol to tears) story, Leader of Culture (2015) 
*Best mainstream movie theater (2010)

Best marching-band documentary by the best Chicago artist who is not a Chicago artist (2012)
Best martini selection (2008)
*Best memory shaken loose by the re-release of Liz Phair’s “Exile in Guyville”(2008)
Best merger of sports and art (2013)
Best microbrewery in a historic district (2012)
Best midweek jazz boite (2011)
Best missing attraction in Chicago (2002)
Best mobile art project
Best monthly improvisational dance gathering (2015)
Best monthly queer dance party (2007)
Best mother/daughter directorial effort (2013)
Best museum exhibit with really really really ambiguous educational value (2009)
Best music on a Thursday, Leader of Culture (2015)
*Best name other than “Nothing Like the Holidays” for renaming the movie once known as “Humboldt Park” (2008)
Best neighborhood music fest (2010)
Best new album by a local artist (in the last year or so) (2007)
Best new art gallery (2012)
Best new art gallery on a car bumper (2013)
Best new art residency (2010)
Best new artist book artist (2012)
Best new author title from a local indie press (2014)
*Best new bar (opened in the last year or so) (2007)
*Best new bar or club (opened in the last year or so) (2009)
*Best new bar or club (opened in the last year or so) (2011)
*Best new bar or club opened in the last year or so (2012)
Best new bar or club opened in the last year or so (2013)
*Best new bar (opened in the last year or so) (2002)
*Best new bar (opened in the last year or so) (2008)
*Best new bar or club (opened in the last year or so) (2014)
*Best new bar or nightclub (opened in the last year or so) (2010)
Best new book about Chicago’s sordid past (2007)
*Best new book by a Chicago author in the last year or so (2014)
*Best new Boystown spot (2007)
Best new cabaret venue (2015)
*Best new Chicago band (2002)
*Best new club (opened in the last year or so) (2007)
Best new communitarian art festival (2014)
Best new community-service festival (2015) 
Best new dance club (opened in the last year or so) (2002)
Best new dance venue that was already a dance venue renamed after a still-physically-existing-but-no-longer-a-venue-for-dance venue (2013)
Best new DIY event space (2014)
Best new folk music act (2014)
Best new free event in Chicago (2007)
Best new gallery of the future
Best new gay or lesbian club (opened in the last year or so) (2002)
Best new high-touch design venue (2014)
Best new housing for artists
Best new improvisational dance performance (2015)
Best new jazz venue (2015)
Best new literary event (2011)
Best new literary festival (2013)
*Best new live music club (opened in the last year or so) (2002)
Best new live music venue (2009)
Best new Monday night dance party (2008)
Best new mural (2011)
Best new music venue (2008)

*Best new nightclub (opened in the last year or so) (2008)
*Best new “nom de guerre” for Chief Keef to make everyone forget about the tragic Lil JoJo business (2012)
Best new podcast (2008)

Best new record-label mogul, workwear pioneer and proud owner of three chickens (2013)
Best new restaurant/lounge hybrid (2002)
Best new scene to be seen (2009)
Best new show by a MacArthur “genius” (2013)
Best new singles event (2007)
Best new source of empowerment for black artists (2014)
Best new strides taken for gender inclusivity in art school (2014)
Best new theater company for intellectuals (2013)
Best new tool for Impressionism nerds (2014)
Best new trend (2009)
Best new trend in free (or damn close) Chicago theater (2011)
Best new venue for experimental arts (2013)
Best new world record held by Chicagoans (2009)
Best new University of Chicago art space (2015)
*Best next foe for the rival film critic who smacked Roger Ebert at a screening (2008)
Best next local Twitter tracker after the “Tamale Guy tracker” (2009)
*Best next role for Jeremy Piven (2007)
Best night at the Music Box Theatre (2007)
*Best night ever at Smart Bar (2007)
Best non-senior, non-student discount (2008)

Best nonsense for your buck (2007)
Best nontraditional portrait (2013)
Best North Side artist lecture series (2015)
Best one-man-band (2015)
Best one-man show by a convicted rapist with a face tattoo (2013)
*Best ongoing event/night at a dance club (2002)
Best ongoing improvisational dance project (2015)
Best ongoing local music showcase (2015)
Best onstage birth (2013)
Best onstage magic (2015)
Best onstage mess-making (2008)
Best onstage rock band that never plays a song (2013)
Best onstage use of live rats (2013)
Best open mic (2010)
Best open mic host (2015)
Best open-studio holiday art sale (2009)
Best opportunity for emerging artists (2013)
Best outdoor bar (2010)
Best painter under the age of 25 (2009)
Best painting show (in the last year or so) (2011)
Best party where you won’t be surrounded by bros (2014)
Best performance art star under-recognized in his own hometown (2015) 
Best petulant and profound art intervention (2014)
*Best piano bar (2009)
*Best piano bar
Best Pilsen backyard art/performance spot hidden gem (2015)
Best ping-pong bar (2012)
Best place for a birthday bash (2015)
Best place for a first date (2008)
Best place for an unconventional haircut/color, Leader of Culture (2015)
*Best place for celeb sightings (2012)
Best place for Madonna madness (2010)
Best place to buy 78s (2015)
Best place to dance samba (2012)
Best place to drink champagne (2007)
Best place to eye a boy toy (2009)
Best place to fly your freakiest flag (2012)
Best place to get a Guinness float (2007)
Best place to get a one-dollar mug of Old Style (2009)

Best place to get drunk before 10am (2010)
Best place to get in touch with your inner Lemmy (2011)
Best place to get your pyromaniacal hippie on (2012)
Best place to get your stinkin’ wino on in greater Liquor Park (2007)
Best place to go when Lollapalooza rains out (2012)
*Best place to have a bachelor party (2010)

*Best place to have a bachelorette party (2010)
Best place to have Spring Break all summer (2007)
Best place to hear difficult, obscure and often excruciatingly loud experimental electronic music, Leader of Culture (2015) 
*Best place to hear world music year round (2012)
Best place to hook up with your future sugar baby or daddy (2013)
Best place to inhale Italian-American culture (2012)
Best place to play Anthony Haden-Guest (2014)
Best place to play board games (2008)
Best place to play darts (2008)
Best place to pregame for a Stravinsky concert (2013)
Best place to pretend you’re on a tropical vacation (2007)
Best place to read Faulkner (2007)
Best place to see a film longer than most people get to sleep each night (2007)
*Best place to see an author reading (2010)

*Best place to see art films (2009)
*Best place to see art films (2014)
*Best place to see comedy (2013)
*Best place to see contemporary dance performances (2007)
Best place to see emerging artists at work (2008)
Best place to see Italian movies for free (2015)
Best place to see live world music now that HotHouse is gone (2007)
Best place to see movies outdoors (2002)
Best place to see work by emerging Chicago artists (2015)
Best place to tip the bartender (2007)
Best place to volunteer your time and have a good time while doing it (2008)

*Best place to watch soccer on TV (2008)
Best Polish pub with tiki ambiance (2010)
Best political art performance reenactment (2012)
Best polyamory meet-up (2013)
Best portrayal of hipsters (2013)
*Best post-Cubs-game bar (2008)
Best printmaking studio (2010)
Best private club for artists and artistes
Best production of a play you may have expected to be boring (2008)
Best proof that we’re not in Kansas anymore (2008)
Best public art failure (2011)
Best puppy art (2013)
Best qualitative data on Chicago’s art scene (2014)
Best queer cabaret (2015)
Best quiet museum space with a striking collection of contemporary art (2010)
Best Reading Series at 9pm on a Tuesday (2013)
Best “Real World” cast member from Chicago (2002)
*Best reality-show contestant from Chicago (2009)
Best reason not to go to Lollapalooza (2007)
Best reason to cheat (2009)

Best reason to concede “Say Anything” is so twentieth century (2007)
Best reason to go to Lollapalooza (2007)
Best reason to learn how to pronounce Marisa Wegrzyn’s last name (2007)
Best reason to look up (2007)
Best reason to sit still for three-and-a-half hours (2007)
Best reason why we don’t deserve anything nice (2002)

Best reborn heritage event (2012)
Best reboot of a historic Chicago arts institution (2015)
*Best regular club night (2007)
Best regular magic show (2013)
Best regular trumpet gig (2010)
Best reminder of Chicago’s old Serbian community (2012)
Best retrospective exhibition of a Chicago artist in the last year (2015) 
Best revitalized old guard art space (2013)
*Best Riccardo Muti moment at the CSO (2010)
Best rise of the undead (2008)
Best RIP event
*Best rock album by a Chicago artist in the last year or so (2002)
*Best rock club (2011)
Best rock or pop album by a Chicago artist (in the last year or so) (2008)
Best rock performance/charity fundraiser fusion idea (2015) 
*Best rooftop bar (2009)
Best Russian literature class (2012)
Best SAIC collection at The Walk (2014)
*Best scenario for a future Joe (“Drinking Buddies”) Swanberg film (2014)
Best sculpture by a painter (2013)
Best sculpture in a garden (2012)
*Best Second City personality of the last fifty years (2009)

Best second coming of HAL (2008)
Best shout-out to the Black Power poet Amiri Baraka at EXPO Chicago (2012)
*Best show ever at the Metro (2007)
Best show in a parking lot (2015) 
Best simulacrum (2013)
Best smallest bar (2013)
Best SNL Chicago comedian grab (2012)
Best social media manager with the fastest response time (2014)
Best solo art show (in the last year or so)
Best sound art (2013)
Best source for jazz concert listings (2013)
Best South Side artist lecture series (2015)
Best splash made by a local press in the last year (2013)
Best sports bar named after an Irish playwright who wrote in English as well as French (2011)
Best stage reboot (2012)
*Best standup comedy club (2014)
Best stand-up comedy, Leader of Culture (2015) 
Best standup night (2015) 
Best street art delivery service (2010)
Best street party (2015)
Best stretch of street art (2015)
Best summer neighborhood arts fest (2014)
Best summer outdoor film screenings (2015)
*Best theater production (in the last year or so) (2002)
*Best theater production (in the last year or so) (2007)
Best theater production (in the last year or so) (2008)
*Best theater production (in the last year or so) (2009)
*Best theater production (in the last year or so) (2010)
*Best theater production in the last year or so (2011)
*Best theater production in the last year or so (2012)
Best theater production in the last year or so (2013)
*Best theater production (in the last year or so)
Best theater for everyone, Leader of Culture (2015)
*Best new theater space (opened in the last year or so) (2002)
Best theatrical cameo (2012)
Best theatrical illness (2013)
*Best thing about the Art Institute’s new Modern Wing (2009)
*Best thing about Tony Tasset’s “Eye” sculpture (2010)
Best tied house (2008)
Best time to get into the Green Mill for free (2013)
Best time that Chicago’s art scene stormed New York
*Best title for a future Fall Out Boy record (2007)
*Best title for a future Kanye West record (2007)
Best title for the next album by R. Kelly (2002)
Best tribute show that’s actually a play (2013)
Best Tumblr dedicated to semi-sarcastic Chicago-specific GIFs (2012)
Best TV series currently or recently set in Chicago (2011)
*Best TV show or movie filmed at Chicago Cinespace (2014)
Best TV show set in Chicago that actually filmed here (2011)
Best tweeting by an art personality (2011)
*Best tweeting by local arts and culture personality (2009)
Best twenty-four-hour performing-arts event (2013)
Best under-the-radar-but-still-toiling-away playwright (2010)
Best underground gallery (2009)
Best underground press (2007)
Best underrated late-night dance party
Best underrated museum (2014)
Best underplayed world premiere (2015)
Best unexpected exhibition in an unexpected museum (2011)
Best unexpected, off-the-radar, out-of-nowhere music festival where an Outkast reunion would have been fully appreciated (2014)
Best unexpected piano soloist (2010)
Best unexpected place to see Chicago artists (2013)
Best unexpected place to see contemporary art (2010)
Best unexpectedly touching eulogy (2009)
Best unknown party space in a bar (2008)
Best use of a washboard (2008)
Best use of abandoned property (2009)
Best use of AstroTurf by a museum (2013)
Best use of Lil’ Wayne and Rick Ross in art (2012)
Best venue launch (in the last year or so) (2009)

Best venue to watch a mosh pit without having to be in one (2013)
Best vintage TV show filmed in Chicago (2010)
Best visual storytelling experience (2015)
Best visiting artist (2015)
Best viral form of mad cow disease (2007)
Best water fountain (2012)
Best way to blow five bucks and laugh about it (2010)
Best way to dance your way into the week (2015)
Best way to disband a performance company (2008)
Best way to experience a band in person that you will most likely never, ever, ever, never get to see play live. Ever. (2011)
Best way to get trashed and see a show at the same time and have it be appropriate (2011)
Best way to keep the memory of Terry Adkins’ work alive (2014)
Best way to see new movies cheap, even on a Saturday night (2012)
Best way to seem way more sinister than simply refusing art handlers’ unionization (2014)
Best weekly jazz jam (2015)
Best weekly live magazine (2015) 
Best whiskey bar (2013)
Best windowless no-frills neighborhood bar with cheap Cosmopolitans (2010)
Best witty use of live video projection
Best “Work of Art: The Next Great Artist” contestant from Chicago (2011)
Best world takeover by a local comics artist (2015)
Best Write Club contender (2015)
Best WWE-influenced feminist spectacle (2014)
Best zine scene (2011)
Best 150th anniversary exhibition (2015)


Best of the Best: Al’s #1 Italian Beef (2002)
Best of the Best: Aruns (2002)
Best of the Best: The Berghoff (2002)
Best of the Best: Billy Goat (2002)
Best of the Best: Blackbird (2002)
Best of the Best: Charlie Trotter (2002)
Best of the Best: Foodlife (2002)
Best of the Best: Frontera Grill (2002)
Best of the Best: Harold’s Chicken Shack (2002)
Best of the Best: Irazu (2002)
Best of the Best: La Pasadita (2002)
Best of the Best: Lem’s Bar-B-Q House (2002)
Best of the Best: Leo’s Lunchroom (2002)
Best of the Best: Lula Cafe (2002)
Best of the Best: Manny’s (2002)
Best of the Best: Margie’s Candies (2002)
Best of the Best: Mario’s Italian Lemonade (2002)
Best of the Best: Maxwell Street Polish (2002)
Best of the Best: Pizzerias Uno and Due (2002)
Best of the Best: Pompeii Bakery (2002)
Best of the Best: Superdawg (2002)
Best of the Best: Tru (2002)
Best of the Best: Vienna Beef (2002)
Best of the Best: Wiener Circle (2002)
Best after-work buffet (2009)
Best airport food (2002)
Best alcohol to trick your friends into drinking (2011)
Best al fresco dining(2013)
Best all-you-can-eat sushi buffet (2012)
Best Amaro cocktails menu
Best American culinary discovery(2007)

Best Amerindian-African food (2009)
Best (and perhaps only) surviving place to eat featured in “The Blues Brothers” (2015)
Best-anticipated German restaurant opening (2012)
Best argument that Chicago is a great food town(2007)

Best Argentinean food (2012)
Best authentic martini (2002)
Best award of Michelin stars (2010)
Best bakery tortes (2008)
Best ballpark dog (2002)
*Best banh mi (2010)
Best bar snack (2013)
*Best bar to drink with tourists
*Best barbecue (2010)
Best beer festival (2011)
Best Beijing (formerly Peking) duck service (2008)
Best Berlin-style sour beer (2012)
Best birrieria (2008)
*Best Bloody Mary (2002)
*Best bloody mary (2007)
Best boozy dessert (2013)
Best borscht (2010)
Best bottled cocktail (2013)
*Best bourbon selection
Best brains in Chicago (2010)
Best breadsticks (2007)
Best breakfast alternative to the wait at Cozy Corner (2009)
Best breakfast/lunch spot in a flower shop (2009)
Best breakfast spot for late risers (2012)
Best broccoli rabe (2010)

*Best brunch (2002)
*Best brunch (2007)
*Best brunch (2012)
Best brunch (non-frou-frou division)
Best bubble tea (2008)
*Best Buffalo wings (2009)
*Best burgers (2009)
*Best burgers (2014)
Best café for coffee and respect (2008)
Best café for sprawling out (2008)
Best cafe to experience a scene out of “Portlandia” (They can pickle that!) (2013)
Best cafe with a deceptively Russian name (2012)
Best caffeinated pastry (2015) 
Best Cajun/New Orleans-style restaurant (2008)
Best Camarones a la Diabla (2012)
Best Caribbean-style fish (2012)
Best case for kale (2015) 
Best caviar and ice cream combo (2013)
Best chai (2012)
Best “changing of the guard” in the restaurant world
Best cheap classy pizza and beer special (2014)
Best cheap eats feast in Chinatown (2015) 
Best cheap Mexican food (2011)
Best cheese curds (2015) 
Best chebapi plate (2014)
Best cheese sandwich (2011)
Best chef blogger (2009)

Best “Chicago” tamales (2010)
Best Chicago-themed restaurant on the North Side (2011)
*Best chicken (2013)
Best chicken sandwich (2007)
*Best chicken Vesuvio (2008)
*Best chili (2009)
Best chili dog (2007)
Best classic nachos, Leader of Culture (2015)
Best cocktails for the indecisive (2013)
Best coffee alternative (2015)
Best coffee shop for a writer, Leader of Culture (2015)
Best collegiate cookbook (2011)
Best contribution to the smell of Chicago (2013)
Best Costa Rican restaurant (2012)
Best crackers (2013)
Best craft honey
Best Chicago craft cupcake maker (2014)
Best cranberry borscht (2011)
Best croissant (2013)
Best crowd-sourced local brewery (2011)
Best Cuban sandwich (2008)
Best Cubano (2012)
Best culinary tours (2011)
Best cup of tea (2013)
Best cupcake from a vending machine (2012)
Best cupcake tours (2011)
*Best cupcakes (2011)
Best cured meat (2013)
Best damn muffins ever (2015)
*Best deli (2010)
Best designer cake shop (2008)
Best dessert platter (2014)
Best diner to take an uncomfortable suburbanite (2013)
Best dish that most closely resembles your grandma’s secret stuffing (2008)
Best dive-bar burger time capsule (2013)
Best dive bar with gourmet grub (2008)
Best downtown cafeteria (2010)
Best-dressed Irish bar owner (2012)
Best Earth Day celebration (2011)
*Best egg rolls (2014)
Best el pastor taco, Leader of Culture (2015)
*Best empanada (2009)
*Best Ethiopian restaurant (2007)
*Best Ethiopian restaurant (2012)
Best fake reason Laurent Gras left Lettuce Entertain You’s L20 after it was awarded three stars (2010)

*Best falafel (2007)
*Best falafel (2012)
Best faux Asian dish (2015) 
Best festival pastry treat (2014)
Best Filipino breakfast (2010)
*Best fish & chips (2007)
*Best fish and chips
*Best fish tacos (2010)

Best Flinstonian roast meat presentation (2012)
Best focaccia bread (2012)
Best foie gras, now that it’s legal again (2008)
*Best food at Taste of Chicago (2002)
Best food business move of the year (2010)
*Best food truck (2010)
*Best food station at Eataly
Best 4am pizza delivery (2013)
*Best french fries (2011)
Best French fry substitute (2014)
Best French toast (2009)
Best fresh bread (2015)
*Best fried chicken (2008)
Best fried meat (2013)
*Best fried shrimp (2008)
Best fried vegetables (2013)
*Best frozen cocktail (2008)
*Best gastropub, whether or not it calls itself a gastropub (2007)
Best gin & tonic (2013)
Best gourmet Asian (2012)
*Best gourmet carryout (2009)
*Best gourmet carryout
*Best gourmet doughnut shop (2012)
Best granitas (2009)

*Best Greek restaurant (2011)
Best grilling rub recipe (2011)
Best grocery store (2007)
*Best guacamole(2002)
*Best guacamole (2007)
*Best guess on what next media stunt the artist formerly known as Graham Elliot Bowles will employ to promote his burgeoning TV and restaurant empire? (2010)

Best hamburger empire based in Chicago besides McDonalds (2009)
Best handcrafted non-alcoholic drinks (2011)
Best Hawaiian lunch spot (2011)
*Best high-end chef serving low-end food (2010)
Best high tea (2010)
Best holiday potluck dish (2011)
Best hole-in-the-wall smoke shack, Leader of Culture (2015) 
Best hotdog shack (2008)
*Best house-made charcuterie (2009)
Best house-made radler (2014)
Best hummus (2013)
Best hummus alternative (2013)
Best humungous margaritas (2011)
*Best imaginary Twitter post by Herman Joseph Berghoff (2009)
Best impulse cash-register buy (2014)
Best Indian buffet (2012)
*Best Indian restaurant (2009)

Best Indonesian food (2012)
Best Injera bread (2012)
Best in-house flour mill bakery (2015) 
Best Italian beef sandwich (2011)
Best Italian breakfast (2012)
Best Jewish deli inside an Italian pharmacy, Leader of Culture (2015) 
Best juice (2013)
Best kept bartender secret
Best late-night industry darling (2013)
Best latte art (2010)
Best Lithuanian bakery (2011)
Best lentil soup (2015)
Best local bbq sauce (2010)

*Best local food blog (2009)
Best local jam (2012)
*Best local spirit/liquor (2010)

Best locally brewed beer (2008)
Best lunchtime fish special (2009)
*Best macaron (2010)
Best marinade
Best masochistic move by a local chef (2010)
*Best meatball sandwich (2010)
Best meatless tzimmes (2011)
Best meatloaf sandwich (2008)
Best menus
*Best metaphor that describes your feelings the day Hot Doug’s closed (2014)
*Best Mexican restaurant (2011)
Best Mexican restaurant open at 3am (and later) (2014)
*Best Middle Eastern restaurant (2010)

Best mignardise (2013)
*Best milkshake (2011)
Best mimosa deal for getting drunk before noon (2013)
Best mochi (2013)
*Best mojitos (2002)
*Best mojitos (2007)
Best Montreal-style poutine in Chicago (2009)

Best Moroccan (2012)
Best Moroccan recipe on a Chicago food website (2012)
Best museum-worthy cupcakes (2010)

Best mussels (2011)
Best neighborhood for urban foraging (2015)
Best never-before-revealed reasons why the Publican restaurant (from the Blackbird and Avec team) took so long to open (2008)
Best new Al Capone shrine (2007)
Best new brewery
*Best new chef (2009)

Best new craft foodie idea (2014)
Best new falafel sandwich bar (2009)
Best new fatty food trend (2011)
Best new innovative beverage idea (2014)
Best new Japanese fusion restaurant that’s not L20 (2008)

Best new Middle Eastern restaurant (2008)
Best new neighborhood brewery and restaurant (2012)
Best new one-two punch (2015) 
Best new pancake house (2008)

*Best new restaurant (opened in the last year or so) (2002)
*Best new restaurant (opened in the last year or so) (2007)
Best new restaurant (opened in the last year or so) (2008)
*Best new restaurant (opened in the last year or so) (2009)
*Best new restaurant (opened in the last year or so) (2010)
*Best new restaurant (opened in the last year or so) (2011)
*Best new restaurant opened in the last year or so (2012)
Best new restaurant opened in the last year or so (2013)
Best new restaurant (opened in the last year or so) (2014)
Best new South Side restaurant to earn a Michelin Bib Gourmand award (2010)
*Best newish Hyde Park resto
Best of the new steakhouses (2010)
Best nightclub trend we’d like to see catch on (2007)
Best $9 curry braised duck, pickled cauliflower and mint chutney yogurt on baguette at a BYOB
Best non-bbq rib (2009)
Best non-Italian spaghetti (2015)
Best non-traditional horchata (2012)
*Best noodles (2009)
Best octopus (2014)
*Best option for fancy hotdogs now that Hot Doug’s has closed
Best outdoor lunch (2002)
Best outdoor patio serving Middle Eastern food (2015)
Best overall deal, Leader of Culture (2015) 
*Best oysters
Best paleta (2015)
*Best pancakes (2010)
Best panna cotta
Best panzanella salad twist (2008)
Best Paris Brest
Best pasta dish (2009)
Best pastillas (2012)
*Best pastries (2009)
*Best pastries
*Best pastry chef (2013)
Best peach cobbler (2010)
Best Persian restaurant (2010)
*Best Peruvian restaurant (2013)
Best Philly cheesesteak (2013)
Best pistachio gelato (2015)
*Best pizza (2011)
Best pizza place for ghastly late-night madness and existentialism (2012)
Best pizza served in a non-delivery/not strictly Italian restaurant
Best place for a bowl of vegan chili and a show (2014)
Best place for an inexpensive lunch of unadulterated food in the North Michigan Avenue area if you are tired and hungry after gazing in the windows at Chanel or pondering the latest conundrums at the MCA but don’t want to go to a food court or an expensive restaurant (2010)
Best place for a bowl of meaty chili and a show (2014)
Best place for a midnight grilled cheese (2015)
Best place for a special meal, Leader of Culture (2015)
*Best place for craft cocktails (2007)
*Best place for craft cocktails (2012)
Best place for dessert (2008)
*Best place for dessert (2013)
Best place for fast food with a side order of social guilt (2013)
Best place for high-rise dwellers to emulate the backyard barbecue, any time of year (2007)
Best place for inexpensive French toast (2010)

Best place for Mayor McCheese to commandeer on Foursquare if McDonald’s fired him (2010)
Best place for wholesale tofu (2011)
Best place to buy Lechon in a trailer (2009)
Best place to buy Russian buckwheat, ginger cookies and kvass (2012)
Best place to eat brick (2007)
Best place to eat, drink, and party in a traditional-but-relaxed place with excellent food close to Chicago, thus immune to Hizzoner’s threatened smoking ban (2002)

*Best place to drink bourbon (2009)
Best place to drink caipirinha
Best place to eat Brazilian appetizers (2012)
Best place to eat head cheese (2009
Best place to get a decent meal after midnight (2010)
Best place to get dripped on by an errant a/c unit (2013)
*Best place to get a salad (2008)
Best place to get red caviar (2012)
Best place to get your bag lunch
*Best place to get your picnic (2007)
Best place to give back to the community without even trying, Leader of Culture (2015) 
Best place to go after a gallery opening that’s not Perez (2013)
Best place to have dinner and a dance party (2015)
Best place to keep kosher for lunch (2007)
Best place to lose yourself (2013)
Best place to meet strangers over breakfast (2008)
Best place to sit outside and eat nachos (2007)
Best place to stock up on fruits and nuts (2008)
Best place to take a date with whom you hope to grow old 
Best place to tip the barista by gratuitously exercising your First Amendment rights (2012)
Best place to try the most popular Russian cake named after a French Emperor (Napoleon)
Best place to try the national food of the former Kirghiz Soviet Socialist Republic (now Kyrgyzstan) (2012)
Best place to try the national food of the former Uzbek Soviet Socialist Republic (now Uzbekistan)
Best pop-up artisanal food experience (2015)
Best pork belly (2008)
Best prix-fixe lunch deal, Leader of Culture (2015)
Best prix fixé menu-quality dish not served in a prix fixé (2012)
Best proof that it’s not the bar, it’s the barkeep (2015) 
Best prosciutto lollipop (2009)

Best putdown from one liquor to another (2013)
Best quote from a local chef (2010)
*Best ramen
Best raw vegan pastries (2010)
Best real fried chicken shack now that it’s hip (2015) 
Best reason Dominick’s won’t be missed too much (2013)
Best reason for breakfast (2011)
Best reason to avoid the long lines at Xoco (2009)
Best reason to choose tofu over pork (2009)
Best reason to employ a personal cardiologist (2012)
Best reason to indulge in a 1980s restaurant cliché (2009)

Best reason to stop teasing vegetarians and become one (2009)
Best reason to visit the Garfield Park Conservatory (2007)
Best recently shuttered restaurant, Leader of Culture (2015) 
Best regional dinner series (2009)
Best reimagined nachos, Leader of Culture (2015)
Best reopening of an old favorite (2015)
Best restaurant bathroom (2015)
Best restaurant disaster and recovery (2009)
Best restaurant ever, Leader of Culture (2015)
*Best restaurant for a holiday meal if mom’s on a cruise (2010)
Best restaurant for talking, Leader of Culture (2015)
Best restaurant in the back of a supermercado (2010)
Best restaurant named after an extinct animal (2007)
Best restaurant near the Art Institute (2002)
Best restaurant street for a diverse palate, Leader of Culture (2015)
*Best restaurant to pop the question (2007)
Best restaurant to wait for your table (2007)
Best restaurant with a chalkboard menu (2008)

Best rock ‘n’ roll-inspired restaurant (2014)
Best Roman-style pizza (2012)
Best rotisserie chicken (2007)
Best salad (2013)
Best salad bar in a Brazilian steakhouse (2012)
Best salumeria (2012)
*Best sandwich shop
Best sangria
*Best sangria (2007)
Best sangria deal (2007)
Best savory cookie (2014)
Best savory dessert
Best savory, um sweet… no, savory dessert (2015)
Best savory waffle (2011)
Best seafood restaurant (2008)
*Best service story in a restaurant (by “best” we mean the story, not the experience)
Best slice of the United Kingdom (2014)
Best smelling food truck (2011)
Best South Side Mexican Restaurant with vegetarian options (2012)
Best South Side spot for convenience food (2014)
Best spicy drink that’s not a Bloody Mary (2013)
Best spinach pie (2010)
Best Steve Dolinsky television moment proving he’s not just another pretty food journalist with a shiny 8” x 10” headshot (2008)
Best sticky toffee pudding (2012)
Best sub sandwiches (2002)
*Best sub sandwiches (2007)
Best Sunday comfort food (2010)

*Best sushi (2013)
Best sushi in an airport Champagne bar (2012)
Best sushi in the Loop (2007)
Best Swedish breakfast (2011)
*Best Swedish restaurant (2007)
Best sweet use of horseradish (2011)
*Best taco from a non-traditional taqueria (2010)
*Best tacos (2013)
Best tamale food truck (2012)
Best tamale in the world (2015) 
Best tamale not served from a red cooler
Best-tasting bread for the Russian palate (2012)
Best tasting menu (2013)
Best Tex-Mex food, i.e. not Rick Bayless or organ-meat-serving, regional-taqueria-skewing Mexican food (2008)
Best Thai dish (2012)
Best Thai food and toy museum combo (2012)
Best Thai restaurant (2011)
*Best thing you’ve eaten recently that filled you with the most shame (2014)
*Best thing you’ve eaten recently that made you stop and think, “This might be the best I’ve ever eaten” (2014)
Best time-tested pizza parlor (2010)
Best timeless restaurant, Leader of Culture (2015)
Best tiny birthday cakes sold at a Thai restaurant (2011)
Best traditional neighborhood bakery with a contemporary twist (2011)
Best trip to Algiers without leaving Andersonville (2011)
Best turkey club (2007)
Best Turkish restaurant (2010)

*Best tweeting by a local food personality (2009)
Best underground dinner (2013)
Best underground supper club (2011)
Best under-the-radar Italian restaurant (2010)
Best under-the-radar Mexican (2012)
Best unkept bartender secret (2014)
Best unlicensed street food (2015)
Best unusual food item
Best use of avocado (2014)
Best use of chicken skin (2012)
Best use of eighties kitsch (2010)

Best use of smoke (2013)
Best use of Speculoos (2012)
Best use of tofu (2010)

Best vegan cafe connected to a production space (2013)
Best vegan cookie (2013)
Best Vegan Korean restaurant (2012)
Best vegan restaurant (2011)
Best vegetarian restaurant (2011)
Best Wagyu steak salad (2009)

Best waiter in a pizzeria (2012)
Best way to deal with annual problems of persistently long lines and lack of food at Chicago Gourmet (2010)

Best way to deliver a restaurant check so the customer forgets it’s actually a bill (2011)
Best way to drink squash (2015)
Best way to keep an even buzz on a night of drinking, Leader of Culture (2015) 
Best wine blog
Best wine list few people know about (2010)
Best 1940s drive-in other than Superdawg (2015) 


Best of the Best: Dusty Groove America (2002)
Best of the Best: El train (2002)
Best of the Best: Facets Multimedia (2002)
Best of the Best: Marshall Field’s State Street (2002)
Best of the Best: Paulina Meat Market (2002)
Best of the Best: Prairie Avenue Bookstore (2002)
Best of the Best: Quimby’s (2002)
Best of the Best: Salvage One (2002)
Best of the Best: Sam’s Wine Warehouse (2002)
Best of the Best: Seminary Cooperative Bookstore (2002)
Best accessories to dance with
Best addition to Michigan Avenue (2011)
Best adult toys and novelties you won’t be tempted to put up an orifice (2007)

Best alternative to the post office(2007)
Best Amish market complete with walk-in refrigerator and fresh poultry (2011)
Best (and cheapest) way to see Chicago during the warmer months (2011)
*Best animal shelter (2011)
*Best antique shop (2009)

*Best antique shop or market (2014)
Best architecture and design book store
*Best art supply store (2011)
Best artisan design shop in Andersonville (2011)
Best artisan market (2013)
Best attempt to connect communities (2013)
Best attribute of the massive new 24-hour Dominick’s in West Town (2007)
Best bags to attach to your bike (2015)
Best bakery to buy your own pretzel buns (2010)
Best barbershop not in the movie “Barbershop” (2002)
Best bar alternative
Best BDSM-supply delivery service (2013)
Best bicycling revolution not fully espoused by a mayor who claims to be spot-welded to his own two-wheeler (2007)
*Best bike shop (2002)
*Best bike shop (2007)
*Best bike shop (2012)
Best bikini wax (2002)

Best birthday party accessories (2010)
Best bookstore, Leader of Culture (2015) 
Best bookstore to find undoubtedly fascinating cultural texts that you will never read (2014)
Best boutique for the stylish male (2015)
Best boutique mascot (2010)
Best breadsticks (2007)
*Best butcher shop (2007)
*Best butcher shop (2012)
Best camera store (2008)
Best cave-to-table concept (2014)
Best chair (2012)
Best chainmaille maker (2014)
Best chance to buy cheap books en masse (2013)
*Best cheap-chic chain in Chicago (2011)
Best cheap downtown bar (2010)
Best cheap haircut (2007)
Best cheap haircut (2014)
Best child play space (2015)
Best Chinese herb shop (2009)
*Best chocolatier (2010)
Best Christian bookstore on the North Side (2010)
Best church for getting your pets blessed (2010)
*Best comic book shop (2012)
Best comics shop (2007)
Best counter-intuitive name for a dental practice (2010)
Best crossover craft event (2014)
Best cultural combination in a neighborhood grocery store (2013)
Best custom bikes (2011)
Best custom-made designer boxes (2011)
*Best daily-deals site (2011)
Best design by a craft coffee mug-maker (2014)
Best discount shoe store (2008)
Best doctor when you cannot breathe or hear (2015)
Best dollar store (2007)
Best dry cleaners with an antique museum inside (2011)
*Best eco-retailer (2008)
Best electronic-cigarette shopping (2013)
Best ethnic bakeries in neighborhoods you don’t go to (2015)
Best example of DIY creativity gone global (2008)
Best excuse to shop for shoes (2011)
Best facial moment you’ll be thinking about for a month (2011)
Best fall craft fair (2014)
*Best farmers’ market (2010)
Best fashion future boutique (2010)
Best female designers, Leader of Culture (2015) 
*Best flower shop (2008)
*Best flower shop (2013)
Best foreign coin exchange (2013)
*Best framing shop
Best gallery for hand-painted African movie posters (2015)
*Best garden store (2008)
*Best garden store (2013)
Best gear for chicks who love kicks (2011)
Best gift shop in West Town, Leader of Culture (2015) 
Best gnarling dog restaurant t-shirt (2010)
Best greeting cards for Chicago aficionados (2015) 
*Best grocery store (2007)
*Best grocery store (2012)
Best hairstylist chat
Best handmade candles (2014)
Best handmade jewelry (2014)
Best handmade soap (2014)
Best handmade undies
Best handwoven (2014)
Best hotel with cool decor and affordable rates (2012)
Best humanity-enriching use of a Yelp review (2013)
*Best IKEA feature (2002)
*Best imaginary Twitter post by Marshall Field (2009)
Best imported German dirndl dresses (2010)
*Best independent bookstore (2002)
*Best independent bookstore (2007)
*Best independent bookstore (2012)
Best independent bookstore often overlooked (2012)
Best independent escort (2013)
Best indie film rental store (2010)
*Best indie record store (2010)
Best interior design shop (2015)
*Best iPhone app with Chicago relevance (2009)
Best kids birthday party destination (2013)
Best kids shoe store (2013)
Best lampwork-centric glass training and education center (2015) 
*Best lingerie shop (2013)
*Best liquor store (2010)
Best Lithuanian intellectual auto mechanic (2012)
Best living legend in the magic world who is Armenian and runs his own magic shop
*Best local cemetery (2009)

Best local personal style blogger (2014)
Best local shopping or consumerist blog (2009)
*Best local shopping or consumerist twitterer (2009)
Best local soap company (2011)
Best local tattoo artist who probably will not ink you (2010)
*Best locally made bread (2010)
Best location for a new boutique (2015)
Best magic shop (2011)
Best marijuana strain (2013)
Best masseuse (2011)
Best menswear boutique (2008)
*Best menswear boutique (2013)
*Best mobile-phone-service provider (2010)
Best mode of transportation to other, less-interesting midwestern cities (2013)
*Best museum store for jewelry (2008)
Best music school, Leader of Culture (2015) 
Best neighborhood clothing store, Leader of Culture (2015)
Best neighborhood jeweler (2008)
Best new boutique or shop (opened in the last year or so) (2007)
Best new boutique (opened in the last year or so) (2008)
*Best new boutique (opened in the last year or so) (2009)
*Best new boutique or shop (opened in the last year or so) (2010)
*Best new boutique or shop opened in the last year or so (2011)
*Best new boutique or shop opened in the last year or so (2012)
Best new clothing store (opened in the last year or so) (2002)
*Best new boutique opened in the last year or so (2013)
*Best new boutique or shop (opened in the last year or so)
Best new coffee shop to write a paper in while listening to good music (2009)
Best new fashion line, Leader of Culture (2015)
Best new hotel (2014)
Best new loyalty rewards program (2013)
Best new Old World sauna (2010)
Best new Pilsen vintage store (2013)
Best new permanent home for a Chicago printmaking institution (2015) 
Best new printmaking shop (2014)
Best new retail concept we hope catches on (2007)
Best new sex toy and where to get it (2013)
Best new salon/barbershop (2015)
Best new tabletop RPG gaming shop (2013)
Best new youth-only maker space (2015)
Best North Side dog rescue (2013)
Best nonprofit youth center/bike-shop fusion (2015)
Best ongoing vintage market (2012)
Best Paris Web site by a Chicagoan (2009)

*Best pet boutique (2002)
Best pet boutique (2010)
Best pet-pampering salon in Logan Square (2013)
Best place for discount home goods (2008)
Best place for fresh meat for pets (2010)
Best place for kids to have fun with science, Leader of Culture (2015) 
Best place for kitchen gadgets (2013)
Best place for matched, and mismatched, juice and drinking glasses (2011)
Best place to become an urban cowboy (2012)
Best place to be when you’re having a sudden wardrobe crisis (2014)
Best place to buy beads (2007)
Best place to buy Brazilian music (2012)
Best place to buy cheese (2002)
*Best place to buy coffee beans (2010)
*Best place to buy denim (2009)
*Best place to buy denim
*Best place to buy DVDs (2010)
Best place to buy fashionable t-shirts (2010)
*Best place to buy fresh seafood (2008)
*Best place to buy fresh seafood (2013)
*Best place to buy furniture (2007)
Best place to buy geometric accessories made by local designers (2012)
Best place to buy jeans, Leader of Culture (2015)
*Best place to buy kitchen gadgets (2008)
*Best place to buy men’s shoes (2009)
Best place to buy men’s shoes
*Best place to buy men’s underwear (2008)
*Best place to buy music (CD or vinyl) (2011)
Best place to buy new magazines (2011)
*Best place to buy records on the South Side (2010)
Best place to buy replicas of classic Chicago posters (2007)
*Best place to buy a skateboard (2007)
*Best place to buy tea leaves (2010)
Best place to buy tea leaves in the suburbs (2010)
*Best place to buy a tie (2007)
Best place to buy toffee (2007)
Best place to buy a toy you can display as art (2012)
*Best place to buy a used bicycle (2009)

Best place to buy a wedding gift (2012)
*Best place to buy women’s jewelry (2009)
*Best place to buy women’s jewelry
*Best place to buy women’s shoes (2009)
*Best place to buy women’s shoes
*Best place to buy women’s underwear (2008)
*Best place to buy yoga clothes (2013)
Best place to design your fantasy pad (2007)
Best place to design your own jewelry (2008)

Best place to donate a piano (2009)
Best place to get books on street art and graffiti (2010)
*Best place to get eyewear (2011)
Best place to get gas before you enter the city (2002)
Best place to get a handmade belt buckle (2009)
*Best place to get men’s hats (2008)
Best place to get orthopedic shoes, Leader of Culture (2015)
Best place to get ready for a night out (2013)
*Best place to get women’s hats (2008)
Best place to get your golf fix in the city, Leader of Culture (2015)
Best place to have your leather items cleaned (2013)
Best place to keep up with crime and mayhem, Leader of Culture (2015)
Best place to live out “A River Runs Through It” (2009)
Best place to make going to the dentist dreamy instead of dreadful (2010)
*Best place to open a checking account, now that the financial meltdown has wiped out a chunk of the banking system (2008)
Best place to play polo on wheels, Leader of Culture (2015) 
Best place to put your original zines and books on consignment and really make money
Best place to rent films about things your parents warned you about (2010)
*Best place to rent a limo (2007)
Best place to rent a tux (2007)
*Best place to sell your used books (2009)

*Best place to sell your used cds (2009)
Best place to smell pretty (2002)
Best place to spend nothing on trendy duds (2008)
Best place to study Portuguese (2012)
Best place to sweat with a Russian (2012)
*Best place to take a music lesson (2007)
Best place to watch a baseball game, Leader of Culture (2015) 
Best Polish store (2009)

Best popcorn company with a logo reminiscent of Julie Andrews (2011)
Best poster shop(2008)

Best proof positive that the Far East can manufacture practically anything cheaper than the USA (2002)
Best public restrooms for visiting senators (2007)
Best reason to have second thoughts about Bank of America (2007)
Best record store to dig for 45s (2013)
Best retail supply and display store (2010)
Best retro-fab barista fashion (2012)
Best retro luggage featured on a TV show about to get cancelled (2011)
Best retro lunch boxes (2010)
*Best running store (2007)
*Best running store (2012)
Best sale section in an indie bookstore (2014)
Best salon for a discount ‘do (2008)

Best salon for getting your Ramona Flowers on (2010)
Best selection of hanging Danish mobiles (2011)
Best seventies museum in a barbershop (2002)
Best store for moms
*Best street wear store (2014)
*Best sex shop (2008)
*Best shoe repair (2002)
*Best shoe repair (2007)
*Best shoe repair (2012)
Best shop for affordable, poofy tulle debutante ball gowns like Scarlett O’Hara once wore (2011)
Best shop to get your bike fixed at 9am (2009)
Best shopping street or intersection
Best sister stores with coordinating names (2010)
*Best smartphone app with Chicago relevance
*Best sneaker boutique (2010)
Best social service agency (2015) 
Best specialty used bookstore (2010)
Best store for nerds, Leader of Culture (2015) 
Best store for pink girlie stuff (2008)
Best store for vintage costume jewelry sorted by color (2010)
Best store to buy rehabbed hi-fidelity speakers (2013)
Best store to loiter in on the Mag Mile besides the Apple store (2010)
Best strike-one-for-the-little-guy moment (2007)
*Best tailor (2007)
Best taxicab experience (2010)
*Best thing about the Groupon craze (2010)
*Best thing you’d like to see the CTA spend your $3 fare on (2009)
Best thrift destination for brand-name clothes (2013)
*Best toy shop (2008)
*Best toy store (2013)
Best underappreciated junk store (2010)
Best unheralded sound-recording engineer (2013)
*Best used bookstore (2010)
Best used bookstore for wanderers (2013)
Best venue to record a studio-quality live album with your band for cheap (2013)
Best vintage-shop window display (2013)
*Best vintage store (2010)
Best voodoo shop (2010)
Best way to cheer up in traffic (2015)
Best way to design a new home or office (2015) 
Best way to fight winter depression (2014)
Best way to get around the city by water without buying a boat (2015)
Best way to profit from your giveaways (2008)
Best way to save money and still have fun (2009)

Best way to visit Spain without a plane (2009)
Best “we bring the spa to you” experience (2011)
Best weekend shopping development (2007)
Best wind-up tin robots (2011)
Best women’s-only workout space (2008)
*Best women’s shoe store (2011)
Best yogi, Leader of Culture (2015) 


Best of the Best: Diversey River Bowl (2002)
Best of the Best: National anthem at Blackhawks games (2002)
Best of the Best: North Avenue Beach (2002)
Best of the Best: Sammy Sosa (2002)
Best of the Best: Sixteen-inch softball (2002)
Best of the Best: Soldier Field (2002)
Best of the Best: Southport Lanes (2002)
Best of the Best: Wrigley Field (2002)
*Best alternative name for the bean-bag game sometimes called corn hole (2007)
Best bar for fantasy-football dorks (2010)
*Best bar in Bridgeport to watch the White Sox (2011)
*Best bar in Wrigleyville to watch the Cubs (2011)
*Best bar outside of Bridgeport to watch the White Sox (2011)
*Best bar outside of Wrigleyville to watch the Cubs (2011)
Best basecamp for a running event (2013)
Best Bears bar (2012)
Best beer man at United Center (2010)

*Best bet as to which team gets to the World Series first (2013)
*Best Big Ten fans in Chicago (2012)
Best bike-friendly addition to the Lakefront Trail (2014)
Best bowling alley (2008)
*Best bowling alley (2013)
Best boxing gym for beginners (2010)
Best brick-and-mortar place to seriously nerd out, old-school style (2011)
Best canoe or kayak launch on the Chicago River (2012)
Best chance to win a championship THIS season (2013)
Best character on the Lakefront Trail (2012)
Best Chicago baseball player this season (2008)
Best Chicago bird watcher
Best Chicago Cubs blog by a “chic” (2008)
*Best Chicago sports team owner (2013)
*Best city street to ride a bicycle on (2009)
*Best city street to ride a bicycle on
Best classic neighborhood pool hall (2010)
*Best coach of a Chicago pro sports franchise (2010)
*Best coach or manager of a Chicago team (2009)
*Best coach or manager of a Chicago team (2014)
Best craft bike maker (2014)
Best Cubs moment of joy in an otherwise sad season (2008)
Best ’85 Bear still making his living as an ’85 Bear (2002)
Best fantasy football team name with a Chicago Bear in it (2012)
Best feature of the planned Wrigley Field renovations (2013)
*Best guess as to how long Tom Ricketts will be “patient” with Theo Epstein’s plan to build a winner (2014)
Best half marathon (2007)
Best half marathon (2009)
*Best half marathon
Best haven for Western New Yorkers (2012)
Best hope for the Bears to win the NFC North (2014)
*Best imaginary Twitter post by Mike Ditka (2009)

Best indulgence where the penance comes first (2009)
Best late-night shopping (2015)
*Best lesson to be learned from the Cubs season this year (2008)
Best local party game (2013)
*Best local sports blog (2009)
Best mobile bike repair service
Best monthly fun run turned 5K (2012)
*Best name for the ballpark if the Rickettses decide to rename Wrigley Field (2009)
Best neighborhood 5K (2012)
Best new Bear (2002)
*Best new Bear (2007)
*Best new Bear (2008)
*Best new Bear (2009)
*Best new Bear (2010)
Best new Bear (2011)
*Best new Bear (2012)
Best new Blackhawk (2002)
*Best new Blackhawk (2008)
*Best new Blackhawk (2009)
*Best new Blackhawk (2010)
*Best new Blackhawk (2011)
*Best new Blackhawk (2012)
Best new Bull (2002)
*Best new Bull (2007)
*Best new Bull (2008)
*Best new Bull (2009)
*Best new Bull (2010)
*Best new Bull (2011)
*Best new Bull (2012)
Best new career for Tank Johnson (2007)
*Best new Chicago baseball manager (2011)
*Best new Cub (2002)
*Best new Cub (2007)
*Best new Cub (2008)
*Best new Cub (2009)
*Best new Cub (2010)
*Best new Cub (2011)
*Best new Cub (2012)
Best new gig for Jay Mariotti (2008)
*Best new gig for Rex Grossman (2008)
Best new park (2009)
*Best new Sox (2002)
*Best new White Sox (2007)
*Best new White Sox (2008)
*Best new White Sox (2009)
*Best new White Sox (2010)
*Best new White Sox (2011)
*Best new White Sox (2012)
Best new workout (2013)
Best news for Chicago bicycling (2010)
*Best next career for Ozzie Guillen (2007)
*Best next gig for Brian Urlacher (2013)
Best next move for the Baseball Hall of Fame after inducting Ron Santo (2011)
*Best nickname for Gordon Beckham (2009)
*Best nickname for Jay Cutler (2009)
*Best nickname to replace “the friendly confines” once Wrigley Field gets decked out in billboards and Jumbotrons (2014)
Best noticeable absence (2009)
Best park to let your dog off-leash (2013)
*Best personal encounter with a sports celebrity (2009)
Best pinball game in Lincoln Park
Best pinball game in Logan Square (2014)
Best pinball game in Wicker Park
Best place for a quiet bike ride (2013)
*Best place for bird watching(2014)
*Best place the Stanley Cup might have visited during its Chicago tour, but likely did not, at least not publicly (2010)
*Best place the Stanley Cup visited during its Chicago “tour” (2010)
*Best place to buy Cubs tickets for sold-out games (2007)
Best place to go around in circles (2011)
Best place to picnic (2010)
*Best place to play board games (2008)
*Best place to play chess (2013)
Best place to play darts (2008)
*Best place to play kickball (2007)
Best place to run in Chicago (2012)
Best place to run where you aren’t supposed to run (2014)
Best place to see a live sporting event (2013)
Best place to use protection
*Best place to watch Nebraska football games, as fans prepare for its Big 10 era (2010)
*Best place to watch soccer on TV (2008)
*Best player that the Cubs could have spent $30 million on instead of Milton Bradley (2009)
*Best post-Cubs-game bar (2008)
*Best potential buyer for the Chicago Cubs (2007)
*Best professional Chicago sports team other than Bears, Bulls, Blackhawks, Cubs or Sox? (2014)
*Best public beach (2010)
*Best public park (2010)
Best public pool to go swimming (2009)
Best public pool to have held Olympic swimming trials (2010)
Best public tennis facilities (2013)
Best race fiasco (2012)
Best race other than the marathon (2007)
*Best race other than the Marathon (2012)
Best reason the Bears will go back to the Super Bowl (2007)
Best reason to believe Northwestern is for real (2013)
Best reason to hold out hope for the Cubs (2013)
*Best replacement for Illini mascot Chief Illiniwek (2007)
Best section in the United Center to watch a Bulls game (2013)
*Best soccer bar (2013)
*Best sports bar to avoid Cubs fans (2007)
*Best sports bar to watch the Cubs pennant chase since you can’t get tickets for wrigley (2007)
Best sports-radio jocks (2008)
Best spot to spend a day on deck (2013)
*Best still-playing former Chicago athlete we wish were still in town (2010)
Best themed run (2012)
*Best thing about Northerly Island (2010)

*Best thing about the Bears playing in Champaign-Urbana (2002)
*Best thing about the Cubs’ Ricketts era so far (2010)
*Best thing about the Cubs-Sox World Series fantasy (2008)
*Best thing about the new Blackhawks regime (2008)
Best thing to happen on the South Side since Harold’s Chicken #17 opened (2014)
Best tweeting by a local sports personality (2009)
Best underrated park (2010)
Best way to spend $75 and get unlimited rides (2014)
Best weekend bike trip (2012)
Best Windy City Roller that we already miss (2009)

Best women’s-only workout space (2008)
*Best Wrigley Field renovation not yet proposed (2013)
*Best Wrigley renovation, not yet proposed (2002)
*Best yacht club in Chicago (2010)
*Best yoga studio (2011)