Chicago: Where to Play
By Parker Marie Molloy
While many of Chicago’s most well-known LGBT hot spots are located in Boystown, there are a number of off-Halsted gems worth exploring.
5024 N Sheridan Road
By day, Big Chicks is Tweet, home to some of Chicago’s best brunch. By night, Big Chicks transforms into one of the top gay bars on the north side. With a fun, relaxed atmosphere, Big Chicks is a great place to knock back a few drinks, listen to some music, and dine on some of the best bar food the city has to offer.
3349 N. Halsted St.
Not for the faint of heart, an evening a Sidetrack is more of an endurance challenge than anything else. The Boystown bar features nightly events, like its famous Musical Mondays.
3356 N. Halsted St.
A Chicago staple since the mid-80s, Roscoe’s has something for just about everyone. If you’re feeling adventurous, try your hand at their weekly live band karaoke night (Mondays). On Tuesdays, the bar plays host to their amateur drag competition.
Little Jim's Tavern
3501 N. Halsted St.
A Boystown dive, Little Jim’s is the place to go when you’ve tired of the more standard Halsted street locations. With the charm of everyone’s favorite neighborhood bar, Little Jim’s provides a rowdy-yet-relaxed environment to catch up with friends.
Zanies Comedy Night Club
1548 N. Wells St.
With admission ranging anywhere from $10 to $25, Zanies is one of the more affordable ways to enjoy some stand-up comedy while visiting the town. Located in Old Town, Zanies plays host to established and unknown acts.
954 W. Belmont Ave.
If you’re looking for a night of music and dancing, Berlin is the place to be. Open until 4am (5am on Saturdays), Berlin is truly a place you can pull an all-nighter. Located right off the Belmont CTA Red Line stop, Berlin is easy to reach by public transportation.
3325 N. Broadway St.
The Closet is a perfect warm-up to a more raucous evening out on the town. With a relaxed environment offering video games, darts, and WiFi, this cash-only bar is a great place to regroup with friends for a drink before taking on the town.
3702 N. Halsted St.
Another Boystown bar, CellBlock offers a number of drink specials throughout the week. On Fridays, the bar offers “easy listening music and easier prices” to mark the end of the work week, making this another escape from those weary from the club and dance scene.
The Baton Show Lounge
436 N. Clark St.
Featuring nightly drag performances, The Baton Show Lounge is one of Chicago’s most well-known performance bars. Be warned, however, that the location has been nearly overrun by the exuberant “woos” of bachelorette parties.
3441 N. Halsted St.
Open until 11 p.m. on weeknights and midnight on the weekends, Halsted’s Bar and Grill is ideal for those with an interest in dinner versus those looking to have a rowdy night. The bar offers daily drink specials, and the food menu features gems like the low-calorie farmer’s market wrap.
800 W. Belmont Ave.
Located at Belmont and Halsted, in the location of the legendary and closed Spin, Chloe's is gay Chicago's new mega-club.
4804 N. Broadway
Calling themselves “Chicago’s premier gay sports bar and grill,” Crew lives up to the hype. Whether you’re a Bears, Bulls, Blackhawks, Sox or Cubs fan, Crew is a great place to grab a drink with friends and watch the game.
1328 W. Morse Ave.
Comedy, concerts, musicals, plays, and other events - Mayne Stage has it all. Attached to Act One Pub, Mayne Stage is home to a friendly waitstaff, exceptional bar food, and an extensive beer selection, making it one of Roger’s Park’s best bets for a night out.