5. Checkerboard Lounge
The authentic blues experience offered at the Checkerboard Lounge draws students, tourists, locals, and die-hard blues fans to this Southside venue every night of the week. The neighborhood may not be as inviting as inside this classic blues joint, but anyone desiring a true blues experience should definitely make the trek.
6. Andy’s Jazz Club
Jazz and blues have had an intertwined relationship over the years, and there is no better place in all of Chicago to witness the delight of jazz than Andy’s. In addition to traditional swing and bebop, sometimes blues fills the air here as well. With music played all day long, you can stop by this Hubbard Street venue any time of the day for a rompin’ good time.
7. Pops for Champagne
This champagne and music bar has been going strong for over 25 years. Upstairs, patrons can usually be found sipping spirits and mingling around the stylish bar, while downstairs, the sweet sounds of blues and jazz envelope the intimate space. In addition to 125 varieties of champagne, Pops also has a full raw bar and comprehensive up-scale menu.
8. Close Up 2
The Close Up 2 may not specialize in blues, but the sultry sounds of smooth jazz performed by local and national artists at this intimate venue make it a favorite spot for many of Chicago’s music aficionados. The music, lights, and overall ambiance provide a perfect date night destination.