Boystown: Gay Travel Mecca in Chicago

With eccentric boutique shopping, streets adorned with colorful pylons and one of the largest lesbian, gay, bisexual and transgender communities in the United States, the East Lakeview neighborhood of Boystown has an energy all its own. Stroll along North Halsted Street, which touts fabulous shopping, trendy restaurants, lively bars and energetic dance clubs.

From brunch, to dinner, to late-night bites, dining out in this district will satisfy all appetites. Hutch is known for brunch staples with large portions, and foodies should try shared small plates from Michelin-starred Wood. Gather over wine and cheese at Bar Pastoral, or wine and pasta at Ceres' Table. Neighborhood classics include vegan-friendly The Chicago Diner and Yoshi's Cafe, which has been around over 30 years.

Watch a spectacular production at one of the neighborhood cultural venues, such as the long-running Blue Man Group at Briar Street Theatre or comedy at The Playground Theater, or attend one of the many events at Center on Halsted.

The Midwest's largest support center for the LGBTQ community is located in the middle of Boystown. Center on Halsted (3656 N. Halsted St.) offers support networks, cultural events and recreational programs to help meet the needs of the more than 1,000 people that walk through its doors daily. 

Head to Halsted Street for Nonstop Nightlife

Located in the middle of the bar-heavy stretch of Boystown, Sidetrack (3349 N. Halsted St.) is a lively gay bar that gets even more boisterous in the summer when the rooftop patio is open. Check the schedule for the weekly lineup; local favorites include their Sunday Funday Show Tunes and TRL Tuesdays, a blast from the past with TVs pumping out 90s music videos.

Famous for its leather theme nights, Cell Block (3702 N. Halsted St.) is a unique kind of nightclub where you're more likely to see black walls and exposed brick than flashing lights and dancing. But don't worry if that's not your thing. Everyone is welcome at this Boystown staple.

As the name would imply, the drinks are always flowing at this Halsted Street hotspot.Hydrate (3548 N. Halsted St.) features a lively calendar of special events including resident DJs and comedy nights. More dance party hot spots include Scarlet (3320 N. Halsted St.) and Berlin Nightclub (954 W. Belmont), a mainstay with an incredible mix of crowds, music — New Wave 80s to Electronica to House — and drink specials... think $3 bombs and even $1 shots.

Established in 1975, Little Jim's (3501 N. Halsted St.) is heralded as the city's first gay bar. With its signature turquoise décor and 4AM last call, this place keeps the Boystown party going all night.

At Kit Kat Lounge & Supperclub (3700 N. Halsted St.), the tableside diva drag show draws big groups each night, particularly the bachelorette set, but the martini list is reason enough to stop here.

Roscoe's Tavern (3356 N. Halsted St.) is an eclectic Boystown hangout that boasts a lively dance floor, as well as karaoke and amateur drag contests. If you lose your shirt during the party, don't worry about being refused service. This is Boystown, not 7-Eleven.


Beyond Boystown

From Boystown, travel north along the lake through Uptown, Edgewater, Andersonville and Rogers Park — all LGBTQ-friendly neighborhoods with independent shops, charming restaurants and dynamic nightlife and theater.

In Uptown, get a taste of the local vibe at cocktail lounge and art gallery Big Chicks, or head to an edgy show at award-winning Profiles Theatre.

With its outdoor dining patio, expansive drink menu and collection of high definition TVs, Crew Bar & Grill (4804 N. Broadway St.) is Chicago's premier gay sports bar. If you're looking to catch the game in a gay-friendly atmosphere, check out this charming tavern in the Uptown neighborhood.   

Head to Rogers Park to watch a literary adaptation at Lifeline Theatre or dazzling song and dance at Theo Ubique Cabaret Theatre. This neighborhood is home to the Gerber/Hart Library & Archives ‒ the Midwest's largest LGBTQ circulating library.

Devoted to fetishism, sadomasochism, and alternative sexual practices, the Leather Archives & Museum (6418 N. Greenview Ave.) is an unusual (but worthwhile) cultural institution in Rogers Park. The museum collection contains original erotic art and artifacts from alternative sex organizations and individuals. The archival collection contains unpublished papers and records from notable activists, artists, businesses, and organizations related to the subject matter. 

Continue on to Edgewater, a lakefront community where you'll find the Bryn Mawr Historic District, indie shops and restaurants, the expansive Broadway Antique Market and exciting theaters such as Raven Theatre Company, Steep Theatre Company, and City Lit Theater Company.

Also part of Edgewater is Andersonville, a diverse neighborhood where vintage shops, home furnishings stores, and European eateries flourish. For fun, laid-back dining, stop by Hamburger Mary's, a popular burger joint with award-winning stage shows upstairs in Mary's Attic.

As Andersonville's main thoroughfare, Clark Street touts everything from bakeries to female-focused boutiques.

Not only does Women and Children First (5233 N. Clark St.) boast an expansive collection of titles, it's also a staunch advocate for female writers. With a mission to support the work of women authors, this popular Andersonville bookstore stays true to its name with more than 30,000 books by and about women, as well as a large selection of children's books.

Make time for a cabaret, musical theater, pop or jazz show by the Chicago Gay Men's Chorus or an adventurous, dialogue-spurring play by About Face Theatre


Related Listings

Yoshi's Cafe
3257 N. Halsted St.
Chicago, IL 60657
(773) 248-6160

Wood Restaurant
3335 N. Halsted St.
Chicago, IL 60657
(773) 935-9663

Ceres' Table
3124 N. Broadway St.
Chicago, IL 60657
(773) 922-4020

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LGBTQ Events

Chicago Diner
3411 N. Halsted St.
Chicago, IL 60657
(773) 935-6696

Bar Pastoral
2947 N. Broadway
Chicago, IL 60657
(773) 472-4781

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