- Goods & Services
- Best Pop-Up Vintage Shop
- Best Neighborhood Garage Sale
- Best Thrift Store
- Best Rock ‘n’ Roll Garden Designer
- Best Place to Get a Vintage Hairstyle
- Best Place to Buy Size 16 Jeans
- Best Place to Swap Black T-shirts With Dudes
- Best Mall
- Best Place to Buy an Unusual Engagement Ring
- Best Jewelry Designer
- Best Place to Buy a Thoughtful, Inexpensive Gift
- Best Place to Buy 78 RPM Records
- Best Art Sale
- Best Selection of Italian Horror-Movie Soundtracks
- Best Cheap Tickets for Great Seats for Broadway in Chicago
- Best Last-Minute Theater Tickets
- Best Theater Community Service Organization
- Best Place for a Musical Prodigy to Get a Free Education (or Close to It)
- Best Film School
- Best Dance School Everyone Thinks of as a Music School
- Best Dance Class
- Best Place to Buy a Restored Schwinn Cruiser
- Best Place to Restore Your Own Bike
- Best Pharmacy
- Food & Drink
- Best Mexican Restaurant Hiding in a Grocery Store
- Best Korean Restaurant Hiding in a Grocery Store
- Best Middle Eastern Restaurant
- Best Soup Dumplings
- Best Manti
- Best Use of a Pernicious Weed
- Best Use of a Pig Tail by Someone Other Than a Pig
- Best New Neighborhood Restaurant
- Best Hand Food
- Best New Burger
- Best New Veggie Burger
- Best Fries
- Best Pollo a la Brasa
- Best Theoretical Food Truck
- Best Macaroni and Cheese
- Best Octopus Confit
- Best Squid Balls
- Best Place to Sup Like Henry VIII
- Best Location for a Clandestine Tryst, With Dinner
- Best All-You-Can-Eat Experience, Upscale Division
- Best Unorthodox Pizza Topping
- Best Way to Stuff Your Face With Thai Food for Under $5
- Best Coffee Roaster
- Best Place to Get Hopped Up on Caffeine and Play Mike Tyson’s Punch-Out!!
- Best Restaurant Name
- Best Breakfast Cocktail
- Best Cocktail That Might Be Good for You
- Best Beer Cocktail
- Best Canned Beer Made in Chicago
- Best Use of Wild Midwestern Persimmons
- Best Place to Try Palm Wine
- Best Beer Selection at a Liquor Store
- Best Customer Service at a Liquor Store
- Best Macarons
- Best Chocolates
- Best Use of Leftover Cake
- Best Window Seat
- Best Place to Buy Secret Ingredients
- Best Regional Cheese
- Best Local Food Product
- Best Food Co-op
- Best Chef’s Blog
- Arts & Entertainment
- Best Dive Bar Full of Dummies
- Best Place to Get Drunk With Your Dog
- Best Dance Party
- Best Sporadic Queer Dance Party
- Best Nongay Bar in Boys Town
- Best Fashion Watching
- Best New Musical Group
- Best Old Musical Group
- Best New “Chicago Sound”
- Best Metal Supergroup
- Best Michael Jackson Cover
- Best Led Zeppelin Cover Band
- Best Cover Band That Plays One Gig a Year
- Best Totally Underground Rap Discovery via MySpace
- Best Band T-Shirt
- Best Amateur Music Blog
- Best Musical Use of Dry Ice
- Best Blues Bagpiper
- Best Mustache in a Local Band
- Best Rocker Sighting in a Nonrock Setting
- Best Experimental Music Presenter
- Best Place to Sit at the Empty Bottle if You’ve Spent More Than Ten Years Hanging Out at the Empty Bottle
- Best Opera Singer
- Best Lawn Seat at Ravinia
- Best Microscene
- Best New Gallery
- Best Alternative Comics Artist Behind the Counter at an Alternative Comics Mecca
- Best Free Movie Series
- Best Underground Filmmaker
- Best Web Site for Film Buffs
- Best Rainmaker for Chicago in Hollywood
- Best Independent Film Distributor
- Best Alternative Film Venue
- Best Theater Success Story
- Best Play I Saw by Mistake
- Best Moonlighting Witch
- Best Theatrical Hat Trick
- Best New Play
- Best New Theatrical Form
- Best Theater History Collection
- Best Effort to Keep Opera a Living Art
- Best Puppeteer
- Best Place to See a Seven-Man Pyramid Cross the High Wire
- Best Variety Show
- Best Improv Group
- Best Improviser
- Best Stand-up Comedian
- Best Sketch Show
- Best Commentary on Modern Technology by a Choreographer
- Best New Novelist
- Best Under-appreciated Chicago Novel
- Sports & Recreation
- Best Mini-Golf Course
- Best Public Golf Course
- Best Way to Spend a Summer Afternoon on the South Side
- Best Man-Made Geographical Wonder
- Best Alternative to the Lakefront Path
- Best Bike Tours on Which to Consume More Calories Than You Burn
- Best Free Workout
- Best Place to Set Up a Moth Light
- Best Place to Watch Peregrine Falcons
- Best Two-Fisted Sports Columnist
- Best Sports Talk Team
- Best Play-by-Play Man
- Civics
- Best Place for a New El Stop
- Best Place to Get Hit by a Car While Riding a Bike
- Best Alternative to the Kennedy in a Mad Dash to O’Hare
- Best Example of What’s Wrong With the TIF Program
- Best Place to Find Information About Your Local TIF District
- Best Diner for Politician Watching
- Best Place to Corner an Alderman Who’s Ducking Your Calls
- Best Orator at City Hall
- Best T-shirt Spotted on an Adult Picking Up a Child From Kindergarten
- Best Honorary Street
- Best Trove of Historic Chicago Photos
- Best Local Nonfiction Writer
- Best Local Blog
- Best Twitterer
- Best Tagger