5 Best Bars in Chicago (2026)

Three Dots and a Dash is a subterranean tiki bar in River North, tucked down an alley behind an unmarked door. It runs a full menu of tropical cocktails inspired by tiki bars around the world alongside food and punch bowls built for groups, and the kitchen and bar work daily to keep the fruit and spice mixes fresh. The speakeasy setup and dim, decorated interior have made it one of the most-talked-about rooms in the neighborhood.

Gus' Sip & Dip brings a classic River North tavern feel with a beverage program built around approachably priced, high-quality cocktails. The kitchen pairs the drink menu with tavern dishes like dips and shareable plates, and the whole operation runs on a first-come, first-served basis with no reservations. It holds the highest rating of any bar on this page.

Miller's Pub is a Loop institution that has served the area since 1935, pairing a 50-foot bar and deep beer selection with a full American menu of Greek-influenced dishes, ribs, and steaks. The dark wood, stained glass, and wall of celebrity photos give it a genuinely old Chicago feel, and it stays open into the early morning most nights. Its review count is the second-largest of any bar here.

Exchequer Restaurant & Pub has served the Loop since 1969 and is known for Chicago-style deep dish pizza alongside ribs and a full bar. It occupies a former Al Capone hangout, complete with his old booth and an escape tunnel staff will point out on request, and it also runs a hidden speakeasy, Club X, on site. The pizza and ribs draw as much attention in reviews as the drinks do.

Brando's Speakeasy is a karaoke and cocktail lounge that has run in Chicago since 2007, now with locations in the Loop and Lincoln Park. It stocks a library of more than 300,000 songs available on demand and pairs the sing-along format with small bites and house cocktails, and it also books private and corporate karaoke parties for groups over 100. It carries the lowest review count on this page but still clears more than two thousand reviews.