29 E. Ohio St. 312-321-1000
Put your name on the wait list at this classic pizzeria to get a taste of the famous deep-dish pizza that launched a national chain.
640 N. Wells St. 312-664-1707
For a burger and a milkshake with a side of verbal abuse, don’t miss this retro-style diner known for its comically snarky servers.
439 N. Wells St. 312-828-9800
This pizzeria delivers with thoroughly addictive crust that’s crispier and lighter than other Chicago-style options.
Green Door Tavern
678 N. Orleans St. 312-664-5496
Built in 1872, this bar doled out moonshine to mobsters during Prohibition. And no, you’re not imagining it—its wooden frame does lean.
612 N. Wells St. 312-280-9200
This barbecue institution specializes in hickorysmoked meats, with its slabs of baby back ribs ranking as a top seller.
100 W. Ontario St. 312-587-8910
This favorite does the Chicago-style hot dog proud. Sit indoors to marvel at historic city photos aplenty, or opt for the impressively speedy drive-through.
Harry Caray’s Italian Steakhouse
33 W. Kinzie St. 312-828-0966
The late Cub announcer’s Italian restaurant-steakhouse-sports bar mashup its known for aged steaks and generous portions of pasta, with plenty of sports memorabilia and athlete sightings to go around.
536 N. Clark St. 312-661-0100
This legendary 21-and-up music club books a blues band every night of the week.
House of Blues
329 N. Dearborn St. 312-923-2000
Music fans will want to take note of the latest acts booked at this legendary venue, where some concerts are all-ages or 17-plus in addition to 21-and-up.
Billy Goat Tavern
430 N. Michigan Ave. 312-222-1525
Follow the scent of grilling burgers to this timeworn tavern, hidden away in the shadows of Lower Michigan Avenue. It opened in 1934 and inspired the famous “Cheezborger, cheezborger” skit on “Saturday Night Live.”
Shaw’s Crab House
21 E. Hubbard St. 312-527-2722
This classic crab house has been shucking oysters for years before their recent return to trendiness, and the lobster roll is one of the best in the entire city.