Tony cruises around the Windy City, has a damn-good hot dog, has a drink with painter and blogger Bruce Cameron Elliott, and dines with Top Chef champion Stephanie Izard.Go to Episode
Tony stays at the Four Seasons Chicago, but recommends Longmen and Eagle in Logan Square for a younger crowd.
120 East Delaware Pl
Chicago, IL 60611
Chef Stephanie Izard sits down with Tony at her restaurant, The Girl & the Goat.
809 W Randolph St
Chicago, IL 60607
This legendary jazz/blues club is the perfect place to take in a show and a strong drink.
4802 N Broadway
Chicago, IL 60640
A lively bar with a great outdoor space, full bar and a ping-pong room.
1059 N Wolcott Ave
Chicago, IL 60622
Harold's Chicken Shack #27
This location of Harold’s has the best fried chicken on Chicago’s South Side.
10259 S Halsted St
Chicago IL 60628
Chicago Tribune contributor Mark Caro takes Tony to one his favorite drinking holes in Chicago, The Hideout. It’s also a great place to see live music.
1354 W Wabansia Ave
Chicago, IL 60642
Paul Kahan and Donnie Madia take Tony to one of their favorite spots to get some Polish sausages: Jimmy’s Red Hots.
4000 W Grand Ave
Chicago, IL 60651
Kuma’s Corner is an amazing burger joint and full bar that is known for naming its burgers after metal bands.
2900 W Belmont Ave
Chicago, IL 60618
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