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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.
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.
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.
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.
