An eclectic feast at Charlie Trotter’s
Splurge for one of the tasting menus by Chicago’s first and foremost celebrity chef, one of Chicago’s top food and drink things to do. The aroma of the always-surprising, ever-changing fare – succulent grilled bluefin or duck-breast salad – wafts through the airy yet clubby dining rooms. Let your server pair a wine with each course.
816 W. Armitage Ave., Lincoln Park 60614 Charlie Trotter’s Website
Dress up for a visit to the Tasting Room
Try a flight from the more than 100 bottles at this chic loft and drink in the skyline view. If you love a vintage, take a whole bottle back to your Chicago hotel.
1415 W. Randolph St., Loop 60607 Tasting Room Website
Deep-dish pizza where it all began
No Chicago food and drink break is complete without rich and gooey mile-high pizza, crammed full of sauce and meat. Locals head to the lively parlor where deep-dish was born. It’s worth the wait.
29 E. Ohio St., North Side 60611 Uno Chicago Grill Website
Little Italy’s Rosebud On Taylor
With every twirl, fettuccini Alfredo drips with rich cream, and deep-dish lasagna oozes with a zesty, beefy sauce at this homey trattoria. Add a glass of chianti.
1500 W. Taylor St., Little Italy 60607 Rosebud Website
Microbrews at Goose Island
More than 100 tasty varieties of ales, stouts and lagers are brewed at this sports-bar-cum-microbrewery. At least 10 are on draft. Create a custom sampler, order a blackened catfish po’boy and catch the Cubs on one of the nine TVs.
3535 N. Clark St., Wrigleyville 60657 Goose Island Brewing Company Website
Brunch at Ann Sather
Chicago’s Swedish heritage is celebrated with gusto at this old-fashioned diner. Start with coffee and a plate of sticky cinnamon rolls, then dig into the Swedish pancakes and meatballs. A post-brunch walk will take off the calories.
909 W. Belmont Ave., Wrigleyville 60657 Ann Sather Website
Blues and BBQ
Pair a plate of zesty baby-back ribs with some authentic Chicago blues at this rustic club. Here you’ll hear music from some of the best local acts – and you might even see the legendary namesake guitarist himself.
754 S. Wabash Ave., South Loop 60605 Buddy Guy’s Legends Website
Steak at Gibson’s Bar & Steakhouse
Gibson’s Art Deco dining room buzzes with well-dressed people, who come for prime Black Angus Chicago-cut steaks and hearty sides. Start with a namesake martini served by a bow-tied bartender, and then split a plate with your date.
1028 Rush St., Gold Coast 60611 Gibson’s Bar & Steakhouse Website
A friendly libation at Old Town Ale House
The décor may look slightly worn, but this friendly neighborhood saloon is a perfect spot to rest your feet. Grab a table, plug a quarter in the jukebox and imbibe to the sounds of Tony Bennett.
219 W. North Ave., Old Town 60610 Old Town Ale House Website
Dining in Cub history at Harry Caray’s
Sports fans come to see the memorabilia collected by the legendary namesake Chicago Cubs’ announcer. Locals line up for overstuffed sandwiches and bone-in rib-eye steaks – and to catch the Cubs on TV.
33 W. Kinzie St., River North 60654 Harry Caray’s Italian Steakhouse Website