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Business, theater, and shopping converge in the Loop, the downtown district south of the Chicago River distinguished by the elevated train that circles it. Long the city's financial center, the Loop is commuter central for inbound office workers. It’s also Chicago's historic home of retail, where the flagship Marshall Field's (now Macy's) once made State Street a great shopping destination. As a theater district, the Loop hosts the Tony-awarded Goodman Theatre, which mounts its own productions, as well as the Oriental, Cadillac Palace, and Bank of America theaters, which generally run Broadway tours. In feeding these diverse audiences, Loop restaurants run the gamut from quick-service to high-volume and special-occasion. Beware noontime and precurtain surges (you'll need a reservation for the latter). It tends to clear out on weekends, and many restaurants close up shop.
A short trip to the West Loop—particularly Randolph Street—is where you'll find Chicago's restaurant row. Nearly every celebrity chef in town has set up post here, including Grant Achatz, Paul Kahan, and Stephanie Izard. Whether you’re craving pizza and pasta or tapas and tacos, the flavors here are sure to satisfy any discerning foodie.
A menu packed with burgers, fries, and chopped liver might sound like a classic dive, but Au Cheval is no greasy spoon—exposed brick, dim lighting, and antique-inspired fixtures give a sultry feel, and rich takes on classic American diner dishes satisfy cravings. There’s a perennial wait, but sneak in after 10:15 pm Monday–Saturday for a limited menu consisting of the crowd-favorite cheeseburger and fries.
Head to this Euro-style wine bar when you're feeling gregarious; the warm, intimate space has seating for only 55 people, and the results are loud and lively, with shareable fare—a mix of small and large Mediterranean plates—that's reasonably priced.
At this local chain of Cuban coffeehouses, you can get the eponymous espresso drink or a café con leche, as well as a variety of pressed sandwiches including what might be the city's best Cubano. The South Loop location, attached to a hostel popular with young international travelers, makes for a lively atmosphere.
The street-food-style offerings at this indoor market go well beyond French fare. Find pizza, sushi, banh mi, Korean corn dogs, and more among the French Market's 20-plus vendors.
After walking through exhibits at the Art Institute, follow the local college crowd to this order-at-the-counter eatery, where the ambience is kitschy but the food is “more mindful." Epic Burger serves hand-shaped, natural beef burgers, as well as a plant-based Beyond Burger, all served atop a soft bun with add-ons like Wisconsin cheese, nitrate-free bacon, or an organic fried egg.
Kibitzing counter cooks provide commentary as they sling soul-nurturing soups, sandwiches, and other deli favorites at this classic cafeteria that often attracts local and national politicians. Though those cooks occasionally bark at dawdlers, it's all in good fun—though finding a table in the two teeming, fluorescent-lit rooms is not, so your best bet is to visit during off hours.
Tucked underneath Cloud Gate in Millennium Park is this multi-concept dining experience. Napolita Pizzeria and Wine Bar is open year-round in the indoor space, but if you're visiting between May and October, grab a seat on the expansive patio to people-watch with beers from Double Clutch Brewing and Mexican fare from Casa Bonita.
The specialty at the Loop location of Morton's, one of Chicago's premiere steak houses, is a 14-ounce (or more) taste of heaven for meat lovers. Excellent service and a solid wine list add to the principal attraction: beautiful, hefty steaks cooked to perfection. Non–meat eaters aren’t left out of the fun, thanks to notable seafood offerings and plenty of salads.
Cuts of all-natural Black Angus beef, dry-aged in-house, are the star of the show at this expansive steak house. The 1920s-inspired decor is upscale but not oppressive, and the menu checks all the classic steak house boxes, from a well-curated wine list to classic sides and rich desserts.
Grant Achatz's and the Alinea Group’s most casual, affordable restaurant is a rollicking good time, where the flavors are as bold as the soundtrack. Snag a seat by the roaring fire, which assists the chef with capturing smoky flavors, or squeeze into the tables that overlook a busy West Loop corner; either way, you’ll want to order a big meaty dish to share with the table, and some of the excellent cocktails.
You can eavesdrop on advertising types who do the after-five mix-and-mingle at this spot on the ground floor of the Leo Burnett Building. When it comes to the menu, there's no shortage of choices: fish and shellfish entrées come in various preparations, from grilled to seared to baked. Classic surf-and-turf combinations like Atlantic cold-water lobster tail and filet mignon mingle alongside Asian-inspired dishes like lemongrass shrimp and yellowfin tuna sashimi. The restaurant, with its marble, granite, and beautifully set woodwork, is an inviting space to relax, and the multilevel dining room provides plenty of eye candy, plus glimpses of the Chicago River beyond. A local jazz trio performs on Tuesday through Saturday evenings.
The name means "game" in Italian, and the restaurant fulfills the promise not with venison, but in the spirit of having fun. The decor is distressed-urban, with brick walls and well-worn hardwood floors—the space is said to have been used by the Chicago gangsters of early 1900s as a gambling house. But the menu is comfort-Italian, with dishes ranging from pizzas and homemade linguine with Manila clams to rustic fare like grilled Colorado lamb chops, and roasted branzino with puttanesca sauce. It's a cozy, neighborhoody spot that keeps the regulars coming back.
We don't know if the sardine reference was meant to telegraph the seating arrangements, but, yes, it's snug here. Still, the solid menu of traditional French bistro favorites—including steak frites, bouillabaisse, and beef Bourguignon—seems to put everyone in a convivial mood. Save room for decadent desserts like crème brûlée and warm apple tart, which are bound to evoke envious looks from adjacent diners.
