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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.
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.
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.
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.
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.
