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Trickery Chicago
Photograph: Peter Serocki Trickery Chicago

The best attractions and things to do in Boystown

You'll find cool theaters, LGBTQ institutions and so many more attractions in Boystown

By Kris Vire, Marty Johnson and Morgan Olsen

Boystown has more to offer than epic parties and the best gay bars in Chicago. And while catching the Cubs game in nearby Wrigleyville is loads of fun, just a few blocks over you'll find a slew of attractions and things to do in Boystown, a vibrant North Side neighborhood known for its proud LGBTQ population. Check out some of the city's top storefront theaters, have a laugh at one of the best comedy clubs in Chicago and explore the area's iconic landmarks. Above all else, be sure to check out the best things to do in Boystown outside of Pride Month (though that's an awfully fun time to visit the neighborhood, too).

RECOMMENDED: Our complete guide to Boystown

Things to do in Boystown

Photograph: Steve Hall

1. Center on Halsted

Things to do Literary events Lake View

This shiny home for the LGBTQ community opened in 2007 as a LEEDS-certified ecofriendly delight (and check out the gargantuan Whole Foods attached to it!). The Hoover-Leppen Theater hosts LGBTQ-themed events and doubles as a house of queer-friendly worship on Sundays while the Billie Jean King Recreation Hall beckons sports enthusiasts, but it's the wide array of social services that lures LGBTQ youth, seniors and minorities from the South and West Sides. Hint: Don't miss the sparkling rooftop with its stunning neighborhood views.
Photograph: Shmura Campbell

2. The Legacy Walk

LGBTQ+ Boystown

Beginning in 2012, North Halsted Street became the world’s first LGBTQ outdoor museum as the Legacy Project began installing a collection of placards on the street’s rainbow-colored pylons (erected in 1998 by then Mayor Richard M. Daley), honoring heroes like Oscar Wilde, Harvey Milk, Antonia Pantoja, Frida Kahlo and Alvin Ailey.

Trickery Chicago
Photograph: Peter Serocki

3. Trickery

Theater Circuses & magic Boystown

Owner-illusionist Aaron Rabkin performs seven hyperintimate shows each week at this Halsted Street storefront theater, where his tricks are visible by sidewalk passersby. Each show is about an hour long, and the space is BYOB-friendly, so bring a bottle and watch in awe.

The Annoyance Theatre and Bar
Photograph: Kris Vire

4. Annoyance Theatre

Comedy Comedy clubs Lake View

Annoyance put itself on the map with its famously distasteful gross-out musical Co-Ed Prison Sluts. Decades later, it still cranks out bizarre, unconventional comedy. Its home on Belmont includes two performance venues, a bar and classroom space all in the same building.

Photograph: Scott Regan

5. Laugh Factory

Comedy Comedy clubs Lake View

Jamie Masada's SoCal comedy club empire established a Chicago foothold in 2012, refurbishing the former Lakeshore Theater space. The club offers lineups of local comics several nights a week, with the occasional touring headliner.

6. Briar Street Theatre

Theater Interactive Lake View

This theater might look unimposing from the outside, but inside you’ll find it seats hundreds. It has to, as most nights it’s packed with crowds that thrill to the colorful techno antics of Blue Man Group, which has occupied the space for years (and shows no signs of vacating soon).

Reckless Records Wicker Park
Photograph: Jaclyn Rivas

7. Reckless Records

Shopping Music and entertainment Lake View

Go crate digging at this Chicago institution, which has three locations scattered around the city. Weekly shipments of vinyl keep Reckless’ stock fresh, and you can always find a list of new releases on the shop's website. Stop in for live, in-store performances or to make a buck by selling your old CDs, DVDs and records.

8. The ComedySportz Theatre

Comedy Comedy clubs Lake View

A ref keeps the score as dueling improv troupes battle it out at the Chicago version of this national brand, which relies heavily on audience participation. In contrast to the Annoyance up the street, most shows here are squeaky clean and family-friendly.


9. The Leigh Gallery

Art Galleries Lake View

This Lakeview art gallery features works from local and national artists in an inviting and intimate space. Thanks to an eclectic curation of works, art novices and friends will be able to find something that speaks to them—be it modern, classic or somewhere in between.

Photograph: Maddie Blecha

10. Unabridged Bookstore

Shopping Bookstores Lake View

Hand-written, personal recommendations from employees line the shelves at the Unabridged Bookstore, offering helpful, heartfelt tips for customers. The 35-year-old Lakeview shop usually hosts at least one literary event per month and leads #readingisresistance, a book series that features a selection every month that's relevant to current political happenings.

Photograph: Maddie Blecha

11. The Playground Theater

Comedy Comedy clubs Boystown

The nation's only nonprofit co-op theater devoted to the art of improvisation is an excellent place for young teams to practice their craft. The programming is often experimental and incredibly hit or miss, but there's no denying the youthful, infectious energy that pervades the place.

12. Steamworks Baths

LGBTQ+ Lake View

Outwardly it’s marked only by discreet banners with the building number 3246, but inside this “private men’s gym, sauna and bathhouse” you’ll find gents wearing towels (or less) enjoying three levels of private rooms, gang showers, whirlpool, play areas, workout facilities, a sauna, steam room and more. Play safely.


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