The Redhead Piano Bar
16 W. Ontario St.
This River North nightspot is a throwback to a bygone era, with crowds gathering around one of the bar’s first-rate entertainers. In their own words, they strive to be “reminiscent of a simpler time – when a good drink and great music were sure things in downtown Chicago.” A different entertainer is at the piano every night, playing everything for Gershwin to Jerry Lee Lewis. Photos courtesy: Chicago Bar Project
Jilly’s Piano Bar
1007 N. Rush St.
Here you’ll find a throwback to the days when Rush Street was the place to see top live musical acts and be seen by Chicago’s who’s who, Jilly’s Piano Bar includes a sidewalk café, a dance floor, and the stylings of piano man Nick Russo. Swing and Frank Sinatra classics are his specialties. Crooners Tony Ocean and Colby Bessera also perform.
1383 N. Milwaukee Ave.
At this Wicker Park favorite, you can join the waitstaff in sing-alongs at the piano bar. In the next room, look for old-fashioned cabaret performances in tribute to legends from Stevie Wonder to Petula Clark, and regular shows by the Chicago Red Line ensemble. Photo courtesy: Chicago Bar Project
1220 N. State Pkwy.
Just steps from the frat party atmosphere on Division Street, this piano bar is tucked away on the ground floor of the unassuming Canterbury Court apartment building. But once the piano man arrives, this small with its retro zebra motif will pack up fast. Photo courtesy: Chicago Bar Project
3160 N. Clark St.
The nearby alternative and punk scene at Clark and Belmont will seem like a world away in this Lakeview venue formerly known as Annex 3. Locally and nationally-known entertainers will sit down at the piano, and cabaret master Dan Stetzel hosts an open mic every Tuesday night.