Scarlet Bar

Bobby Love's is a gay karaoke bar in Boystown. During the day it's a neighbourhood bar that's home to loyal regulars enjoying a variety of specials that are on offer throughout the week. People pack into this tiny bar, especially on the weekends, to sing karaoke fuelled by strong drinks but throughout the week the jukebox is always playing great music as well.

Atmosphere is an upscale gay dive bar in Andersonville filled with neon lights and male dancers. You can dance the night away on the dance floor, take advantage of regular drinks specials, and of course admire the dancers! Drag shows, DJs, and events like bingo make for some lively nights with a mixed crowd.

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.

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.

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.

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.