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1 / 10
Too cozy for the West Loop; too cool to be anywhere else. 925 W. Randolph St., 312-690-7295, Website
Photo: Anna Knott -
2 / 10
The burger timeline: September 2014, Umami Burger; November 2014, Shake Shack. GSE, enjoy your moment. 22 S. Wabash Ave., 312-854-3027, Website
Photo: Hilary Higgins -
3 / 10
The food here is so hip that the rib eye sports a black truffle tattoo. Virgin Hotel, 203 N. Wabash Ave., 312-940-4400, Website
Related: Browse photos of our night at the Virgin Hotel bar.
Photo: Hilary Higgins -
4 / 10
And pizzeria and bar and bakery and gelateria and … 535 N. Michigan Ave., 312-955-3100, Website
Photo: Hilary Higgins -
5 / 10
Ebi Tango. Angry Dragon. Latin Heat. Names of retro cocktails? Salsa dances? Pinball games? Don’t be silly. 4514 N. Lincoln Ave., 773-654-1277, Website
Photo: Hilary Higgins -
6 / 10
After all that weeping over the loss of Hot Doug’s, Avondale has come together again—this time for a Double Fatso Burger. 3324 N. California Ave., 773-482-1000 Website
Photo: Hilary Higgins -
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8 / 10
Think Archie Bunker’s Place with sexy cocktails and a rotisserie. 2701 S. Eleanor St., 312-724-8811, Website
Related: Check out photos of our visit and read more about the Bridgeport restaurant.
Photo: Anna Knott -
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10 / 10
With 10 different mix-ins on the menu, you can have zillions of frozen custard concretes before you repeat a flavor combo. 66 E. Ohio St., 312-667-1701, Website
Photo: Hilary Higgins