Piano Bars in Chicago

Old-school piano bars are still popular in history-loving Chicago. Chicago piano bars tend to be downtown, and their usual crowd is largely out-of-town businessmen and bachelorette parties, but everyone is invited for the sing-along.

For those who rock out in the shower but are too embarrassed to try karaoke, the pianists at Howl at the Moon offer an introvert’s alternative, playing crowd-pleasers late into the night to a packed and raucous crowd always ready to sing along. This dueling piano bar somehow gets finance types to belt out Journey and frat boys to preen through Pat Benatar tunes – albeit, often fueled by a free buffet or a few too many eighty-six-ounce buckets of something bright and blue.

A winking retro redhead on the sign of The Redhead Piano Bar surely draws in businessmen after their steak dinners around North/Division. Even the dress code at Redhead is a throwback to more refined times, as athletic or sloppy clothes are not allowed. You can’t smoke inside in Chicago anymore, but the Redhead has a cigar selection for fat cats to enjoy on their way home.

For mid-century Don Draper antics, check out piano bars in Chicago – just don’t forget to tip the piano man. Or piano lady.