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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.
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.
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.
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.
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.
