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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.
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.
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.
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 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.
