The Zebra Lounge holds the third oldest liquor license in Chicago. It opened either in 1929 or on December 5, 1933 depending on who you ask and whether you count the speakeasy years. Either way, it's been there for a very long time, and it looks like it.

The room fits about 40 people, the walls are painted maroon, zebra-striped lamps line the bar, and there's a piano in the corner that gets played every single night of the year. Every night. Pianists take requests. The music is good. Drinks are affordable in a way that genuinely surprises people who've been paying Gold Coast prices all evening.

It gets crowded after 10pm, sometimes uncomfortably so given the size. Weeknight visits before 9pm are the move if you want to actually have a conversation and get a seat. The address is off the main strip on State Parkway inside a Canterbury Court apartment building, which means first-timers walk past it at least once before they find it.