10 Best Bars in The Loop, including the West Loop and South Loop, Chicago

Relocated from its original location a few doors down, Buddy Guy's Legends has a superb sound system, excellent sightlines, and more space to showcase Grammy Award–winning blues performer/owner Buddy Guy's collection of blues memorabilia. Look for local blues acts during the week and larger-scale touring acts on weekends. Don't miss Buddy Guy in January, when he performs a monthlong home stand of shows (tickets go on sale one month in advance). There's also a substantial menu of Cajun and Creole favorites.

Chef Grant Achatz applies his cutting-edge culinary style to cocktails at this West Loop bar, adjacent to his high-concept restaurant Next. Your newfangled old-fashioned might arrive injected into an egg of ice, or your drink's flavor might change subtly as its flavored ice melts. Inventive bar bites are on offer as well.

For a walk into history, stop by the Blues Heaven Foundation, which occupies the former home of the legendary Chess Records. Breathe the same rarefied air as blues (and rock-and-roll) legends Muddy Waters, Howlin' Wolf, Chuck Berry, and the Rolling Stones, all of whom recorded here. Check out the Chess brothers' private offices, the recording studio, and the back stairway used only by signed musicians. Be sure to see the eerie "Life Cast Portraits" wall showcasing the plaster heads of the Chess recording artists. Tour hours are 12–4 Monday through Saturday.

Once a metal factory and later a taxi cab repair shop, this 18,000-square-foot industrial conversion has an invitingly funky restaurant and bar up front. But the main draw is the midsize music room that accommodates 700 concertgoers—good for an up-and-coming underground act, or a higher-profile touring band looking for an intimate feel.

The eye-catching Carbide and Carbon Building has its first rooftop bar. The Pendry Chicago Hotel, the skyscraper’s latest occupant, turned a former private-event space on the 24th floor into a chic indoor-outdoor lounge overlooking the Chicago River. The wine list emphasizes rosés (there are even several rosé cocktails), the kitchen offers sushi and small bites, and after dark, DJs spin French house.

This handsome spot in the Hilton Chicago is an authentic Emerald Isle pub with all things Irish, including live music Thursday through Sunday, beer, food, and bar staff.

This inviting bar is the perfect spot to wait out the long lines at nearby restaurants Au Cheval or Girl & the Goat. The tiny but mighty menu of bar snacks (homemade corn dogs, grilled cheese, spicy fries) will tide you over nicely; solid takes on classic cocktails and a healthy rotating draft list make it a welcome addition to the restaurant-heavy ’hood.

Devoted to the Chicago-bred tradition of improv comedy, the Revival features top local talents. The theater relocated from Hyde Park to the South Loop in 2024.

One of the city's hottest perches, ROOF occupies the 27th floor of theWit Hotel. The outdoor space entices with firepits and panoramic city views; floor-to-ceiling glass windows make the indoor area equally breathtaking. DJs spinning eclectic beats and a menu of pricey cocktails and small plates complete the scene.

Despite being hidden away underneath the El tracks in a spooky stretch west of downtown, Transit is wildly popular with young clubgoers. Inside, the multiroom space has a crisp design and sumptuous VIP area. Don't miss the glowing black-and-white bar between the oval and chandelier rooms, or the mezzanine with its minimalist furniture and oversize mahogany table.