From legendary Sidetrack to late-night Hydrate, here are the best gay bars to party in Boystown — Chicago's historic LGBTQ+ heart.

Best Gay Bars in Boystown Chicago

The Best Gay Bars to Party in Boystown, Chicago

Chicago

Chicago Sugar Daddy is a shop in Chicago. Located at 3243 N Broadway, Chicago, IL 60657, USA.

Chicago Sugar Daddy

Cozy, laid-back mainstay featuring American bistro fare with global accents plus a full bar & patio.

Drew's on Halsted

Burgers & Tex-Mex eats pair with margaritas & house tequila drinks in cozy tavern digs with a patio.

D.S. Tequila Company

Quaint local bakeshop offering unique cakes, cupcakes, breakfast pastries, brownies & more.

Jennivee's Bakery

Upscale farm-to-table bar eats & a large beer & whiskey menu served in a traditional Irish pub.

Lady Gregory's Irish Bar & Restaurant

Rustic-chic bar offering elevated pub grub, including wood-fired pizzas, plus TVs & weekend brunch.

R Public House

Sfera is a restaurant in Chicago. Located at 5759 N Broadway, Chicago, IL 60660, USA.

Sfera

Stylish American hangout serving seasonal dishes and cocktails in architectural digs.

The Dearborn

The Lunchroom is a restaurant in Chicago. Located at 200 E Chestnut St, Chicago, IL 60611, USA.

The Lunchroom

American spot attached to a B&B offering Angus steaks & Sunday gospel brunch since 1985.

The Polo Inn

Cozy cafe featuring java drinks, light fare & Wi-Fi in a laid-back ambiance with comfy seating.

Two Hearted Queen

2Bears Tavern is a bar in Chicago. Located at 1140 W Wilson Ave, Chicago, IL 60640, USA.

2Bears Tavern

Upbeat, colorful LGBT-friendly bar with basic eats & weekend DJs amid art-lined walls.

Big Chicks

Western-themed Boystown bar & dance club with drag shows, karaoke, bingo & late-night hours.

Charlie's Chicago

Dorothy is a bar in Chicago. Located at 2500 W Chicago Ave, Chicago, IL 60622, USA.

Dorothy

Energetic gay dance club with theme nights & open very late.

Hydrate Nightclub

The Jeffery Pub is a bar in Chicago. Located at 7041 S Jeffery Blvd, Chicago, IL 60649, USA.

The Jeffery Pub

La Cueva Nightclub is a nightclub in Chicago. Located at 4153 W 26th St, Chicago, IL 60623, USA.

La Cueva Nightclub

Chic, low-lit lounge serving classic cocktails amid Toulouse-Lautrec-inspired decor.

Marty's Martini Bar

Meetinghouse Tavern is a bar in Chicago. Located at 5025 N Clark St, Chicago, IL 60640, USA.

Meetinghouse Tavern

Nobody's Darling is a bar in Chicago. Located at 1744 W Balmoral Ave, Chicago, IL 60640, USA.

Nobody's Darling

Industrial bar offering craft beers & seasonally inspired cocktails, plus a lounge with board games.

Rogers Park Social

Behomoth gay club drawing a diverse crowd, serving up slushy drinks & known for showtune nights.

Sidetrack

Neighborhood gay bar with games & theme nights in laid-back surrounds with a patio.

The SoFo Tap

Longtime, low-key gay sports bar with flat-screen TVs, darts, billiards & occasional karaoke.

North End

Laid-back gay bar with billiards, Wii & darts, plus theme nights & drink specials.

Cell Block

Classic & modern craft cocktails are hand-shaken in this small, stylish lounge with low lighting.

Elixir Lounge

Barks N' Rec is a shop in Chicago. Located at 1809 W Webster Ave, Chicago, IL 60614, USA.

Barks N' Rec

Thrift store selling clothing, furniture & books in support of the Howard Brown Health Center.

Brown Elephant Thrift Store

Store for designer men's casualwear with a large selection of underwear, plus bags & accessories.

CRAM Fashion

Early To Bed is a shop in Chicago. Located at 5138 N Clark St, Chicago, IL 60640, USA.

Early To Bed

Men's Room Chicago is a shop in Chicago. Located at 3343 N Halsted St, Chicago, IL 60657, USA.

Men's Room Chicago

Rattleback Records is a shop in Chicago. Located at 5405 N Clark St, Chicago, IL 60640, USA.

Rattleback Records

Refined boutique for women's & men's clothing, beauty & grooming, with home decor & accessories.

SPACE 519

Playful shop selling leather attire for men & women, including pants & underwear, plus accessories.

Leather64Ten

Veteran bookseller featuring a wide variety of general & children's literature plus LGBT titles.

Unabridged Bookstore

Indy-minded all-around bookshop known for its feminist & kid focus, with regular author appearances.

Women & Children First

Upmarket retailer specializing in cooking tools, gadgets & pots & pans plus culinary & wine classes.

The Chopping Block

Get in the Kitchen is a venue in Chicago. Located at 3617 N Broadway, Chicago, IL 60613, USA.

Get in the Kitchen

Educational & historical museum for adults offering exhibitions with wearable leather & kinky props.

Leather Archives & Museum

Pride Arts Center is a venue in Chicago. Located at 3656 N Halsted St, Chicago, IL 60613, USA.

Pride Arts Center

Windy City Times is a venue in Chicago. Located at 5315 N Clark St # 192, Chicago, IL 60640, USA.

Windy City Times

Barbara & Barbara Salon is a venue in Chicago. Located at 2925 W Diversey Ave, Chicago, IL 60647, USA.

Barbara & Barbara Salon

Chicago Male Salon is a venue in Chicago. Located at 3418 N Halsted St, Chicago, IL 60657, USA.

Chicago Male Salon

Landscape provider for residential & commercial areas, from design to maintenance & enhancements.

Christy Webber Landscapes

Han Training is a venue in Chicago. Located at 743 W Irving Park Rd, Chicago, IL 60613, USA.

Han Training

Salon Glow is a venue in Chicago. Located at 2766 N Lincoln Ave, Chicago, IL 60614, USA.

Salon Glow

Wish Me Luck Tattoo is a venue in Chicago. Located at 3323 W Armitage Ave, Chicago, IL 60647, USA.

Wish Me Luck Tattoo

Steamworks Chicago is a sauna and bathhouse in Chicago. Located at 3246 N Halsted St, Chicago, IL 60657, USA.

Steamworks Chicago

Psyche Fine Jewelry

Chicago's LGBTQ+ community is centered around Boystown (now officially called Northalsted), the first officially recognized gay village in the United States. The area features iconic venues like Sidetrack, Roscoe's Tavern, and The Closet. The city also has vibrant queer scenes in Andersonville, Lakeview, and the South Loop. Chicago Pride is one of the largest Pride celebrations globally, and the city hosts numerous LGBTQ+ events including Market Days and the Chicago International Film Festival's LGBTQ+ programming. The city's diverse queer community spans multiple neighborhoods and includes strong representation across all identities.

Bring your doggie and come grab a drink and treats.

Dog Day

A community event called Dog Day Afternoon at Sidetrack.

Join us for a festive Easter Sunday Buffet at The Polo Inn, featuring a variety of delicious dishes to celebrate the holiday. The event takes place on April 5, 2026, from 10:30 AM to 3:30 PM. Enjoy a special brunch menu in a welcoming atmosphere. For more details, visit the event page or contact The Polo Inn.

Easter Sunday Buffet

Celebrate Easter with Drew’s on Halsted.

Easter

Roscoe's Drag Brunch hosted by Batty Davis! Seatings at 12PM & 2PM. Serving brunch with a side of divalicious drag. $50 Bottomless Mimosas Bubbles & Brunch Package available. À La Carte options available as well.

Roscoe's Tavern

Saturday Drag Brunch

A drag brunch event featuring performances by drag artists with bottomless mimosas and brunch options.

This event explores the combination of impact play and erotic kinky hypnosis, highlighting how these elements can create deep and engaging scenes. Led by Leather Redux, the workshop covers a new topic each month, providing opportunities for learning and practicing new skills. The program is open to all genders, orientations, and experience levels.

LA&M Etienne Auditorium

Kink Klass w/ Master Leather Redux, Impact + Erotic Kinky Hypnosis = Hella Fun

This event explores the deep and interesting scenes that can be created by combining impact play and erotic kinky hypnosis. Participants will learn about the topics covered by Leather Redux, with a focus on consent and safety. The session is designed to be engaging and educational, open to all genders, orientations, and experience levels. It takes place in the LA&M Etienne Auditorium and is part of a monthly series held on the first Sunday of each month.

The Bi Wives Club is a comedy showcase for all outsiders who hide in plain sight. The show is a playful, intimate, and a reliably hilarious fan favorite. Audiences praise the humor, atmosphere, and the show’s sense of community and connection. It’s both one of the funniest and most energizing shows in town. This show will include ASL interpretation!

The Bi Wives Club

Musical Monday, TGIF: Friday Afternoon, Sunday Funday.

Show Tunes

A party featuring live show tunes and musical performances at Sidetrack.

Join us for the Gospel Brunch at The Polo Inn on April 6, 2026, from 10:00 AM to 2:00 PM. Enjoy live organ music until 2 PM with a $1.50 per person entertainment cover. The event features a special Sunday Gospel Brunch menu. The Polo Inn is located at 3322 South Morgan Street, Chicago, IL 60608.

Gospel Brunch

Nat Nadha Vikitsreth will host an event to celebrate her book 'Raising Change Agents: Practicing Social Justice in Everyday Parenting'. She will be joined by Dorian A. Ortega for a conversation. The event will provide tools and strategies for busy parents to instill social justice values in their children through daily routines. Nat Vikitsreth, a decolonized therapist and activist, will discuss how to raise socially conscious kids, address triggers and trauma, and practice social justice in everyday parenting. The event includes a discussion on supporting long-term liberation work at home and is suitable for parents, practitioners, educators, and professionals working with children.

Raising Change Agents: Practicing Social Justice in Everyday Parenting

Sign up starts at 3PM every Monday by emailing events@roscoes.com

Roscoe’s Drag Race Sign Up

Kara Mel D’Ville & Ari Gato

A weekly drag show event hosted by Kara Mel D’Ville and Ari Gato at Roscoe's Tavern.

Free HIV testing in an affirming environment with wraparound community-centered, LGBTQ+ support services. Appointments available every Tuesday and Thursday from 10 am - 3:30 pm.

Brave Space Alliance

HIV Testing Appointments

Free HIV testing in a supportive environment with LGBTQ+ community services.

Hosted by Kara Mel D’Ville & Ari Gato along with the Kara Krew’s Mark & Hunter!

Roscoe’s Drag Race

A drag show hosted by Kara Mel D’Ville and Ari Gato at Roscoe's Tavern.

Join us EVERY Wednesday for Roscoe’s Dinner & Disney Musical Bingo hosted by Kimberly Summer.

Roscoe’s Dinner & Disney Musical Bingo

Kimberly Summer

A weekly dinner event featuring Disney musical-themed bingo hosted by Kimberly Summer.

Join the Unabridged Books' Speculative Book Club on Tuesday, April 7th, 2026, at 19:30 for a discussion of Margaret Atwood's dystopian novel, "The Handmaid's Tale." The event will take place at Unabridged Books, Inc., located at 3251 N. Broadway, Chicago, IL 60657. The club explores speculative fiction, including science fiction, fantasy, and horror, with a focus on engaging discussions and geeky enthusiasm. For questions, contact unabridgedbookstore@gmail.com.

Unabridged Books, Inc.

Speculative Book Club: "The Handmaid's Tale" by Margaret Atwood

Join us for Weekly Morning Storytime at Women & Children First in Chicago. Doors open at 10:15 a.m., and the program runs from 10:30 a.m. to 11:00 a.m. This half-hour session features stories, songs, and finger plays suitable for children aged 2 and up, but all ages are welcome. The event is led by a rotation of experienced readers and performers, including co-founder Miss Linda, teaching artist Miss Ruby, and musician Laura Doherty. Suggested donation is $3 per child.

Weekly Morning Storytime!

Workshop to educate community on the rights of sex workers and insights into maintaining safety and security in the field.

Sex Worker's Rights Workshop

A workshop to educate the community, especially trans people, about the rights of sex workers and how to stay safe in the field.

An event featuring designer Lizzie Fortunato and her team, including styling sessions and custom design experiences by appointment. The event takes place on April 8, 2026, from 3:00 PM to 7:00 PM at 200 E Chestnut St., Chicago, IL, and on April 9, 2026, from 11:00 AM to 4:00 PM at 1515 Sheridan Rd., Wilmette, IL. Attendees can RSVP via email at rsvp@space519.com.

Lizzie Fortunato Designer Appearance

Join us for Chicago's next Queer Soup Night at Babe's Sports Bar on April 8th, 2026, from 5:30 PM to 7:30 PM. Queer Chicago chefs will serve delicious soup for sliding scale donations ($5-$20), with all proceeds benefiting The Trevor Project, which provides crisis services and support to LGBTQ+ youth. The event features food, exclusive merchandise, and community gathering. Donations will be collected upon entry by cash or card. Babe's Sports Bar is wheelchair accessible, and masks will be available at the door.

Babe's Sports Bar

Queer Soup Night @ Babe's Sports Bar

Join Venusian Visions for a monthly pop-up tarot event held at Dorothy on April 8, 2026. The event runs from 18:00 to 22:00, offering attendees a chance to explore tarot readings in a vibrant setting.

Venusian Visions: a monthly pop up tarot event at Dorothy

Join us EVERY Wednesday for Roscoe’s Dinner & Disney Musical Bingo hosted by Kimberly Summer

A drag event featuring dinner and Disney-themed musical bingo.

Join us for Social Hour on April 8, 2026, from 19:00 to 20:00. This event provides an opportunity to connect and socialize with others in the community.

Social Hour - April 8

Queer Social: Curated Events for LGBTQ People

Join the weekly virtual Social Hour to build friendships and community among LGBTQ+ peers across the US.

Social Hour - Online

Join the Unabridged Books' Speculative Book Club on Wednesday, April 8th, 2026, at 19:30 for a discussion of Margaret Atwood's dystopian novel, "The Handmaid's Tale." The event takes place at Unabridged Books, Inc., located at 3251 N. Broadway, Chicago, IL 60657. The club explores speculative works across science fiction, fantasy, and horror, fostering engaging conversations and geek-outs. For more information, visit the event page or contact the bookstore via email.

Free HIV testing in an LGBTQ+ friendly environment with support services.

A screening of episodes 1 and 2 of 'The Lovers', an independent queer series set in 2020 Los Angeles, exploring themes of love and identity. The event features a viewing of the episodes with writer, director, and star Daviel Shy, followed by an open viewing at Dorothy, a venue that is 21+ and ADA accessible. Doors open at 6:00 PM, with screenings starting at 7:00 PM, and the venue remains open until 11:00 PM.

The Lovers Screening at Dorothy

A vibrant celebration of diverse cuisines featuring local vendors, live music, and family-friendly activities.

Millennium Park

Food Festival 2026

Chicago Foodies Association

Join us for a celebration of the best burgers in Chicago! Enjoy tasting different burger styles, live music, and family-friendly activities.

Burger Fest Chicago

Chicago Food Events

Join us for a vibrant celebration of music, food, and community. Featuring local bands and artists.

Spring Music Festival

Chicago Arts Council

An art gallery opening event at Center on Halsted, showcasing new artworks. Further details are not provided.

Center on Halsted

Art Gallery Opening

An art gallery opening showcasing two artists exploring identity, growth, and imagined worlds.

Join us on Friday, April 10, 2026, at Women & Children First in Chicago for an event celebrating Megan Milks' essay collection 'Mega Milk.' Megan Milks will be in conversation with Vera Blossom. The event will explore themes such as the dairy industry, queer intimacy, family, fluidity, whiteness, and cows through a series of essays. Masks are required for attendance, and the venue is wheelchair accessible. Seating is on a first-come, first-serve basis, with options for reserved seats and accommodations upon request.

MEGA MILK by MEGAN MILKS

Join us for the Howard Brown Health Annual Gala to support LGBTQ+ health initiatives. Enjoy an evening of entertainment, dinner, and fundraising activities.

Howard Brown Health Center

Howard Brown Health Annual Gala

Howard Brown Health

Join us for a night celebrating The Beatles with live tribute performances, classic hits, and Beatles-themed activities.

The Beatles Tribute Night

Join us for the Roscoe's RuPaul's Drag Race Season 18 Viewing Party with hosts Naysha Lopez, Batty Davis, and Kara Mel D’Ville along with special guests Raja Gemini and Thorgy Thor. Roscoe's opens at 4PM for cocktails, snacks, and dinner. Doors open for standing room & cover begins at 6PM. 21+ only.

Roscoe's RuPaul's Drag Race Season 18 Viewing Party

Naysha Lopez, Batty Davis, Kara Mel D'Ville

A watch party to view RuPaul's Drag Race Season 18 with hosts and special guests at a drag-themed bar.

A vibrant drag queen event featuring special guests Raja Gemini and Thorgy Thor, hosted by Batty Davis, Naysha Lopez, and Kara Mel D'Ville.

Roscoe's Drag Queen Party

Join us for a fabulous evening of Bingo with a drag queen host, fun games, and entertainment.

Queer City Guides for Chicago

The Best Gay Bars to Party in Boystown, Chicago

Where Things Are Happening

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