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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.
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.
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.
