The North End

Roscoe's Tavern in the heart of Boystown has been a leader of Chicago's nightlife and entertainment scene for over 30 years. It's a friendly neighbourhood bar where people of all identities come together and catch up over pool or a drink in the lovely outdoor spaces. Super friendly staff create a safe space for everyone to let go and have a great night of dancing, good food, and cocktails.

The Kit Kat Lounge and Supper Club is a premier destination for every type of occasion and every demographic. An imaginative and extensive cocktail list coupled with upscale contemporary cuisine makes for a super stylish night in even more stylish surroundings. Entertainment is provided by world famous drag queens, and Kit Kat Lounge is known across the country as a destination for a memorable meal and night out.

Cell Block is Boystown's premier leather and fetish gay club. The main front bar has a dance floor where anyone can let go and have fun with a casual leather dress code. If you're more of a serious leather fan, the back bar opens on Friday and Saturday nights for some more mature fun. This space has a strict leather dress code and hosts events catering to multiple fetishes such as monthly puppy patrol parties.

Progress Bar is a relatively new entry on the Boystown scene, and at the heart of the space is a cloud-like overhead sculpture installation made up of thousands of twinkling lights. Not only is this bar perfect for artsy photos, but it also boasts an enviable selection of craft beers on tap, pouring local brews alongside imaginative cocktails. Mixed crowds gather in the low-lit, rustic-industrial setting complete with two bars and a dance floor.

The North End is a long-running gay sports bar in Boystown that provides a laidback and unpretentious atmosphere. There are plenty of drinks specials to keep you in the moon as you watch whatever sports are on the TV or have a friendly game of pool or darts with the new friends you'll inevitably make. This is a classic sports bar at heart with a modern and stylish twist that suits the local gay community.

As the name suggests, Second Story Bar is hidden away above a restaurant in the River North area of Chicago. This bar is dark and divey with an old school charm that has remained untouched by the upscale modernity of the street below. Inside a sketchy looking unmarked entrance, you'll find a perfectly friendly bar serving cheap drinks to a soundtrack of camp dance classics. This is a true hidden gem and a unique venue among its modern neighbours.