Debonair Social Club
Hipsters and yuppies collide at this intimate video club where a color-changing lightbox and thematic videos set the mood.
Dazzling light shows and progressive DJs lure clubby crowds to this meatpacking district up-and-comer.
Pops for Champagne
Great jazz exists city-wide in Chicago, but Pops tops them all when it comes to atmosphere. The elegant champagne bar (over 100 varieties on offer) lures thirty- and forty-somethings with fizzy libations and primo people watching in a simultaneously modern and classic space with cool blue accents and state-of-the-art sound complementing the building’s original stone walls and low ceiling.
This perennial gay favorite is a sprawling video bar with one of the best rooftop decks in town. Don’t miss Monday’s raucous showtunes night.
The Green Mill
Al Capone is among the legendary patrons to have climbed into one of the giant curvy booths at this legendary jazz joint and speakeasy.
The ubiquitous zebra theme is the only distraction at this laid-back piano bar where unpretentious Gold Coasters cobble together for conversation and live music.
Our Experts save you money with travel deals and advice
Grab an extra banana or muffin from the complimentary breakfast at your hotel so that you have snacks when you're on the go.
Jaymie DeGaetano Travel Deal Expert
Sign up for the Top 25 Newsletter
to get exclusive weekly deals