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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.
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.
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.
