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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.
Top Chef Season 4 champion Stephanie Izard's always-packed restaurant lives up to the hype, serving her personal brand of sharable, eclectic plates with seasonal flair amid rustic decor with communal butcher tables and an open kitchen. Dishes are grouped into straightforward categories, like vegetable, fish, and meat—with an array of offerings made with goat, naturally.
Classic meets innovative at chef Sarah Grueneberg’s forward-thinking Italian restaurant, where a strategically placed mirror grants diners a view of pasta makers rolling and filling select pastas to order. The West Loop location means the restaurant gets busy before Blackhawks games, but Top Chef finalist Grueneberg’s dishes, designed for sharing, are always a game changer.
There aren’t many restaurant dinners that start by entering through an alley and into a freight elevator, but nothing about Oriole is typical, from the secretive entrance to the warm, impeccable service to the hit parade of bites on Noah Sandoval’s tasting menu. Wine pairings are a must, since the old world, white-wine focus makes the flavors on the forward-thinking tasting menu truly sing.
Don't call this beer-focused hot spot a gastropub—chef Paul Kahan prefers "beer hall" (though wine is available, too) and with the long communal tables, at which beer connoisseurs sample from a selection hovering above 50 brews, the bustling space has the air of an Oktoberfest celebration. The seafood- and pork-focused menu gives an elevated nod to pub fare, though there are plenty of veggie-friendly dishes as well.
The name may evoke nostalgia for the building's gritty past as a print shop, but Sepia is thoroughly forward-thinking in both its design, which features glassed-in chandeliers and leather-topped tables, and chef Andrew Zimmerman’s elegant, seasonal four-course prix-fixe menu. A well-chosen, international wine list and thoughtfully prepared cocktails satisfy oenophiles and cocktail lovers alike; grab a spot on the lounge side for a predinner drink with a side of people-watching.
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.
Mid-century style reigns at this wood-paneled clublike restaurant, where the menu draws inspiration from the landmark space's previous incarnation as a tony men's club. The sweeping bar is perfect for sipping historic and house cocktails over bar snacks or raw seafood, or you can settle into a comfortable leather booth for private conversations and all manner of meat perfectly prepared.
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.
The popcorn here is so popular that there are several other Chicago outlets plus branches in Dubai, Hong Kong, Singapore, Japan, South Korea, Thailand, and Malaysia. Lines form early and stay throughout the day.
This Baja-inspired spot first opened in 2016 as the latest venture in chef Rick Bayless's exploration of Mexican cuisine. Bayless has since divested, but Leña Brava's all-wood-fired menu abides. Sit downstairs by the hearth, or opt for a quieter table upstairs overlooking Randolph Street, but regardless of your seat, be sure to order a glass or bottle of hard-to-find Mexican wine, the perfect complement to the food.
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.
This small but stylish café operated by local roastery Dark Matter Coffee serves up all kinds of joe, from drip to draft to canned varieties, amid playfully psychedelic decor. On the food side, look for savory breakfast tacos and empanadas, Do-Rite Donuts, and pastries from West Town Bakery.
Catalan-inspired restaurant Mercat offers a stylish respite from Michigan Avenue with a view of Grant Park and a menu of small to midsize plates, all of which are great for sharing. To get more bang for your buck, try the chef's tasting menu, with prices starting at $65.
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.
Grant Achatz's buzzworthy sophomore effort is big on concept: the restaurant completely transforms its menu, tableware, decor, and beverage program every three months to focus on a unique theme, whether that’s an homage to famed chef Auguste Escoffier's tenure at the Ritz Paris or to Ancient Rome. Tickets for the one-of-a-kind meal from executive chef Alan Mileykovsky are paid for in advance, nonrefundable, and only available online.
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.
Named 2020's Restaurant of the Year by Chicago's annual Jean Banchet Awards, Smyth features a 15-course tasting menu that's tweaked daily by husband-and-wife chefs John B. and Karen Urie Shields. The dishes are ever-changing and depend on what the kitchen can get from The Farm, just outside the city, which provides ingredients grown to the chefs’ specifications; for a more casual meal—including the Chicago Tribune's pick for the city's best burger—head downstairs to the Loyalist bar.
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.
