Bar

1. Green Mill Cocktail Lounge

Historic jazz club$$Uptown

The Green Mill in Uptown is a historic jazz club with Prohibition-era links to Al Capone's Outfit, live music every night and the long-running Uptown Poetry Slam.

View details — Green Mill Cocktail Lounge

Bar

2. Kingston Mines

Blues club$$Lincoln Park

Kingston Mines is a Lincoln Park blues club open since 1968, with bands on two stages and music until 4am on Friday and Saturday nights.

View details — Kingston Mines

Bar

3. Buddy Guy’s Legends

Blues club and restaurant$$South Loop

Buddy Guy's Legends, opened in 1989 by the blues guitarist himself, is a South Wabash blues club with Cajun and soul food and his own shows every January.

View details — Buddy Guy’s Legends

Bar

4. The Violet Hour

Craft cocktail bar$$$Wicker Park

The Violet Hour on North Damen Avenue is a cocktail bar with a James Beard Award-winning programme, serving pre-Prohibition style drinks from a seasonal menu every night.

View details — The Violet Hour

Bar

5. Cindy’s Rooftop

Rooftop bar and restaurant$$$The Loop

Cindy's is a 13th-floor rooftop bar and restaurant on top of the Chicago Athletic Association, with a year-round terrace overlooking Millennium Park and Lake Michigan.

View details — Cindy’s Rooftop

Bar

6. Three Dots and a Dash

Tiki bar$$$River North

Three Dots and a Dash is a River North tiki bar entered from an alley off North Clark Street, serving house-made tropical cocktails and food, with The Bamboo Room inside.

View details — Three Dots and a Dash