WHERE TO EAT, DRINK, SLEEP, AND PLAY IN CHICAGO

Must-eat deep dish, sterling Mexican food, a killer bar scene—the Windy City has it all
Doves Luncheonette Counter

Don’t let the nickname fool you; the Second City is second-to-none when it comes to eating and drinking. Beneath the deep dish surface you’ll find a wealth of affordable regional specialties and life-changing restaurants. Dig a little deeper and you’ll find bars that distill their own spirits right before your eyes; markets that live and die by the farm-to-table mantra (yes, even in the Midwest); and hotels both boutique and colossal. And it gets better and better every month; be it a new fine dining destination, subterranean cocktail haunt, or specialty coffeeshop, Chicago’s showing no sign of slowing down.

There’s so much out there in this sprawling city that deciding where to eat can be intimidating for visitors. So we’ve compiled a guide of can’t-miss Chicago restaurants, bars, hotels, and culinary destinations to ensure your time in the Second City is first-rate.

Where to Eat:

Xoco Caldo

Courtesy Frontera Grill

Xoco
There are tortas and then there are Tortas. Rick Bayless’s immensely popular sandwich shop makes Capital-T-Tortas that truly are worth waiting in a (fast-moving) line for. With higher quality, more deeply flavorful meat options than most of the city’s Mexican sandwich shops, and a more cheffy attention to detail than average, Xoco easily rises above the competition as a sandwich destination, even in a city of destination-worthy sandwiches. From piquant chorizo to tender braised goat to whole sandwiches drowned in tomato broth, there’s a sandwich for everyone here.

Xoco
449 N Clark St. (Enter on Illinois), Chicago, IL 60654

Xoco Bistro (Wicker Park)
1471 N Milwaukee Ave, Chicago, IL 60622

Bacino’s
Few foods are more divisive than Chicago deep dish, so if you’re going to take the plunge, go ahead and do it right. While names like Giordano’s and Lou Malnatti’s get bandied about all over, our go-to deep dish is the dark horse Bacino’s, specifically for their stuffed crust pizza, a taller, mightier version of deep dish that includes an extra layer of pizza dough above the cheese and beneath the tomato sauce (remember, you’re going for broke here). Why Bacino’s specifically? Because every element of their pizza tastes a little more fresh and flavorful: bright and tangy tomato sauce; spinach that isn’t cooked to depth; mozzarella with just a touch of twang; and a crust that has some burnished flavor to go along with its heft. You won’t be lacking for gobs of cheeseand sauce with this stuffed crust, but the lighter, more flavorful touches from the kitchen mean you won’t feel like you got hit by a bus after eating, either.

Bacino’s
Multiple locations across Chicagoland.

Birrieria Zaragoza
Chicago is home to some excellent Mexican food, a fact often overlooked by visitors. But there’s no avoiding it at this family-run Mexican restaurant on the Southwest Side, because the menu has one simple star: birria, braised goat stew, and it’s spectacular. Birreria Zaragoza is a hike from downtown, all the way over on Pulaski Road near Midway Airport, but once you get a taste of meltingly soft, gently spiced goat meat in lipsmacking tomato consomme, you’ll start planning your next visit while still at your table, and that’s before you get a bite of the thick, toasty tortillas made by hand to order. The dining room is no-frills—bright lights and spare tables—so your eyes naturally fall on the gentleman behind the counter, chopping up hunks of goat meat with a fat cleaver on a well-worn butcher block.

Birrieria Zaragoza
4852 S Pulaski Rd, Chicago, IL 60632
(773) 523-3700

Floriole Cafe and Bakery
For classic French pastry, simple but excellent sandwiches, and even pizza (not the Chicago kind if that’s not your thing), Floriole is the bakery to know. The star here is the pastry case, hard to miss as you’re hit by a wall of butter as soon as you walk inside. Flaky croissants and creamy scones are a given, but don’t miss the bakery’s superlative caneles, which sell out early thanks to a perfect balance of burnished, crisp exteriors and fragrant, custardy centers. The bright, sun-lit interior makes for the perfect cafe to while away an afternoon while drunk on pastry.

Floriole Cafe and Bakery
1220 W Webster Ave, Chicago, IL 60614
(773) 883-1313

Al’s Italian Beef
Yes, be sure to eat some hot dogs while you’re here, but also be sure to partake in the less-talked-about Chicago specialty: the Italian beef sandwich, Chicago’s chief contribution to America’s great sandwiches. Effectively a roast beef sandwich topped with pickled vegetables and drowned in jus (a Midwestern dip, if you will), the Italian beef balances meaty heft with sweet-and-sour twang, and all that gravy means you’ll need a sleeve of napkins to get through it–a sure sign of a good sandwich. At Al’s, the

 

 

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