Sidetrack is one of Halsted Street's most popular gay bars.
When it comes to sheer density of bustling gay bars, Halsted in Boystown can’t be beat. The street is the epicenter for LGBT nightlife in the city, and you can find groups bouncing between bars here almost any night of the week.
1. Hop a cab to Belmont and Halsted, where you can start your night at Spin (800 W. Belmont Ave. 773-327-7711) for a round of something on special—themes vary every night.
2. Next, head north down the main drag to Minibar (3341 N. Halsted St. 773-871-6227), where your group can split a few small plates to stay fueled for the night.
3. Ready for some fresh air? Walk down the block to Sidetrack (3349 N. Halsted St. 773-477-9189) for a round of cocktails on the huge rooftop deck.
4. If your crew can’t decide on dancing or another round, make a move to late-night bar Hydrate (3458 N. Halsted St. 773-975-9244), which has space for both drinking and dancing.
5. Haven’t seen enough? Hit the strip the next night for a tour of more of the greats. Start by soaking in some Boystown history at Little Jim’s (3501 N. Halsted St. 773- 871-6116), which opened in 1975, before Halsted was so crowded with clubs.
6. Next, hit Roscoe’s (3356 N. Halsted St. 773-281-3355), one of the city’s most well-known gay hangouts, where you’re sure to find something to drink at one of the club’s six bars.
7. Then head to Scarlet (3320 N. Halsted St. 773-348-1053), known for its crowd of loyal regulars and pop culture-inspired theme nights.
8. Get back on the dance floor at Circuit (3641 N. Halsted St. 773-325-2233), which sits just behind Rehab, a legendary lounge that occupied the space in the ’90s and just reopened a few years ago.
9. Make up for all those burned calories by ending the night at Jack’s on Halsted (3201 N. Halsted St. 773-244-9191), where the grill stays hot until 1 a.m.