The Redhead Piano Bar is for all the old souls out there that are yearning for a night accompanied by Billy Joel. This piano bar is full of the classics, and musicians are will willing and prepared to play a wide range of requests. It’s noted that the dress code tends to be strict, especially with men’s shoes. If men are wearing sneakers, the bar even offers an alternative pair that have been donated back in the day. The customers should come prepared to dance in a party atmosphere and possibly even smoke a cigar on the deck outside.
The Redhead Piano Bar, 16 W Ontario St, Chicago, IL, USA, +1 312 640 1000
A top choice, Howl at the Moon will not disappoint. Tip from the pros: you will want to go early to avoid the long line and to have a higher chance of your song being selected by the pianists. It’s noted to have some of the best buckets of alcohol. The bar is prepared to accompany the copious amounts of alcohol by serving a variety of hearty appetizers like meatballs, spring rolls, Caprese skewers, and more. If you’re heading there for a nightcap, expect to run into multiple people you know, a few bachelorettes and be ready to dance.
Howl at the Moon, 26 W Hubbard St, Chicago, IL, USA, +1 312 644 2262
At Shakers on Clark, there is always live music and events going on. While it’s generally known as a low-key sports and gay bar, it captures a variety of people with its location in Lakeview. Shakers holds events like ‘Stripper Bingo’ and ‘Couples of Shakers,’ where the staff will give away shots and gift cards. Even better, the bar has phone chargers available to the public in case your phone is about to die. If Shakers does not have a live music performance, there will always be something else going on, and if worse comes to worse, you can grab yourself one of their infamous 23-ounce iced teas and play some darts.
Shakers on Clark, 3160 N Clark St, Chicago, IL, USA, +1 773 327 5969
Selected to join this list as a final contender, Brando’s Speakeasy is a guaranteed fun night out, but it’s known because of its epic karaoke lounge. While there may not be a live pianist every night, this is a great place to warm up the vocals with an audience. It’s noted that the crowd may not cheer every time, but it’s one of the best karaoke bars – and there is nothing like it in the South Loop area. Brando’s may not live up to the definition of a ‘speakeasy,’ but it is a spot for regulars that do karaoke!
Brando’s Speakeasy, 343 S Dearborn St, Chicago, IL, USA, +1 773 216 3213