Best Things to Do
On one of your mornings in Chicago, make sure to wake up early and hurry over to Brendan Sodikoff's always-bustling Doughnut Vault; when the piping-hot wonders run out, that's it for the day. Or head to the Pilsen neighborhood for carnitas at Don Pedro. Served family-style with red and green salsas and heaping bowls of pico de gallo and pickled peppers, they're a fiery, design-it-yourself beginning to an active day.
When lunchtime arrives, keep things casual but cool with a stop at The Gage, Irish-born Billy Lawless' pub with upscale grub. You can also opt for dim sum at Phoenix, a second-floor Chinatown staple serving solid barbecue pork buns, spring rolls and congee.
Since it's impossible to visit the Windy City without tackling a deep dish pizza, we suggest chowing down at Lou Malnati's Pizzeria, which prides itself on crispy crusts, tangy-sweet tomato sauce and iconic fillings, like Italian pork sausage laid over a bed of mozzarella.
For a memorable dinner, grab a table at Girl & the Goat, where Stephanie Izard plates inventive flavors for scenesters. There's also Gibsons Bar & Steakhouse for some of the city's finest prime cuts, football-sized lobster tails and über-cold martinis. As if the walls decked with autographed publicity photos didn't clue you in upon your entry, you might want to keep your eyes peeled for the smattering of in-town celebrities, famous tycoons and local athletes who frequent this haunt.
If you want something away from the hustle and bustle, try Owen & Engine, where the curated beer list is long and strong. For dining with a view, reserve a spot at Sixteen, the 16th-floor stunner situated in the Trump International Hotel and Tower. Can't get a table there? Another hot spot, though much more low key, is The Bristol, a welcoming Bucktown joint focusing on local, seasonal eats. Either sets the stage for cocktails at The Violet Hour, a swanky, pre-Prohibition-era lounge with a French salon feel.
Now that you're on a roll, it's time to take in some of the city's legendary nightlife. Most Chicagoans would tell you blues and jazz are where it's at. Although there are more frequently treaded spots like Buddy Guy's Legends and Green Mill, for your money Kingston Mines is the place to go for a non-stop tune fest. Live music is kicked out on two stages every night, and the cover charge is surprisingly affordable.