Best Of Chicago

Top 5 Boystown Gay Bars

September 22, 2010 12:12 PM

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If you’ve only made it to the Halsted Street strip in Boystown for the Pride Parade and Market Days, you’re missing out. It’s one of the nation’s premier destinations for gay nightlife, and on any given night of the week, it’s one of the city’s most vibrant nightlife districts.

The bars that line the strip from Broadway and Grace to Clark and Barry offer something for every taste. Here are five suggestions:




3356 N. Halsted St.
(773) 281-3355

In the front, the main bar dominates, with décor that changes with the seasons and trendy music videos playing. In the back, the dance floor sizzles on weekends. You’ll also find pool tables and an outdoor terrace. And in the way of events, Roscoe’s is the only local bar with an amateur drag contest (Drag Race, every Tuesday.)


3349 N. Halsted St.
(773) 477-9819

This spacious club spans more than eight storefronts, with three bars on the main level, a multi-level rooftop deck, and a front patio looking onto the street. Sidetrack is known for its selection of slushy vodka drinks, and its wide array of video selections. And on Sundays, Mondays and Fridays, come for showtunes, and sing along to Broadway classics.


3359 N. Halsted St.
(773) 477-1420

A flashing red arrow draws you to this nightspot, with its black crystal chandeliers and Greek onyx bar. Eight resident DJs spin the latest grooves, and go-go boys strut their stuff onstage six nights a week. Come Wednesday nights for Twisted Trivia, and see a professional Cher impersonator on the first and last Friday of every month.

(Credit: / Chris Blaski)

(Credit: / Chris Blaski)


3548 N. Halsted St.
(773) 975-9244

Walk in the door to find two rooms with vibrant colors (one blue, one red) and ever-changing décor. The weekly “Hydrag” show features some of the city’s finest female impersonators, and an array of resident DJs spin nightly. Hydrate is open until 4 a.m.

Little Jim’s

3501 N. Halsted St.
(773) 871-6116

This bar opened in 1975, and it’s held on ever since. And it’s quite the contrast to the other bars in the area with their sleek design concepts and event listings. At Little Jim’s, look for pinball machines, jukeboxes, a couple of TVs, and a crowd content just to sit back and enjoy a drink and strike up a conversation. Little Jim’s is also open until 4 a.m.

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