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Gay Chicago

Chicago's Monthly LGBTQ Storytelling Event!
OUTspoken! LGBTQ Stories

First Tuesdays, 7-9pm (doors at 6pm) at Sidetrack. Welcoming new storytellers to the OUTspoken! stage; unique first hand tales from across our diverse community. Inspired, inspiring, funny, heartbreaking - like life…with friends all around you. Typically there will be 6 storytellers and one intermission.
Come workout with us!
Chicago Dragons Rugby Football

Every Tuesday + Thursday 7-9pm practice at Clarendon Park Community Center, 4501 N Clarendon Ave. Social and fundraising events at Replay, Sidetrack, Hydrate and other venues - see their facebook page for upcoming events.
Ongoing monthly events at Chicago's Leather Bar since 1977
Coming up at Touché

First FRI M.A.F.I.A Club Night and CD4 POZ socials/ postive-minded men. First SAT Bear Night w/ 12am pizza. Second FRI Chicago Leather Women's Cruise. Second SAT Dungeon Master Night w/ midnight S/M demo. Third SAT BLUF Leather, Rubber, Uniform Dress Code Gear Night w/ barber + bootblack. Fourth FRI ONYX Club Nights. Fourth SAT Ripe Party w/ Deep Beats, Dim Lights, Hot Go-Go Dudes.
A Rock/Punk/Experimental/New Wave queer night
Glitter Creeps

When they feel like it Rock/Punk/New Wave queer night hosted/ co-curated by Donnie + Madison Moore of ABSOLUTELY NOT. New/exciting local bands from Chicago/ beyond perform onstage. Previously 3rd Wednesdays - now "held WHENEVER THE #$%! WE FEEL LIKE IT! So get pumped for STACKED bills, SIQQ hosts, and of course MORE GLITTER! Keep your eyes peeled and brows on fleek!"
The longest running musical comedy in Chicago
Cupid Has a Heart On

Saturdays 8pm at Stage 773, 1225 W. Belmont.. Fast paced, musical sketch show; hilarious, irreverent, and a raunchy good time. For belly laughs about body image and relationships this is sure to deliver with comedic wit to spare. Created by Stage 773 Creative Director, Brian Posen, who directs and plays accompaniment.
Galleries of contemporary art
The New Contemporary

Ongoing at Art Institute. 44 iconic works by artists such as Andy Warhol, Roy Lichtenstein, and Jasper Johns. These paintings, sculptures, and photographs transform the museum’s presentation of contemporary art, bringing new depth and perspective to the Art Institute’s already strong holdings, making this collection the strongest of any encyclopedic art museum in the world.
A sexy love story unlike anything you have seen

Ongoing through June 2, 2019, 8pm. Exploring the emotional, intellectual, and physical connections between three men. Josh and Alex, a married couple in an open relationship, invite Darius to share their bed one night. When a new intimate connection begins to form, all three men must come to terms with their individual definitions of love, loyalty, and trust. Features full male nudity.
Chicago's Leather Bar Since 1977
Touché May

May 3-5, 2019, Cinco de Mayo Weekend: FRI M.A.F.I.A. Club Night; SAT Bear Night w/ midnight pizza; SUN Beer Bust w/ free taco buffet/raffles. May 11th, 10pm-4am Riot Bear - Rip It Up - Hard/ Heavy/ Outside the Mainstream w/ DJ Germ. May 24th, 3rd Annual Pig Daddy w/ Trenton Ducati; Pig Pen Pileup Stars Devin Franco, Leo Forte, Riley Mitchel, Silver Steele, Aleks Buldocek, Lorenzo Flexx.
Get Sidetrack'd Cinco De Mayo Sunday Funday!
Cinco De Mayo Sunday Funday Tea Dance

May 5, 2019, 1-5pm. Join Dixie Lynn Cartwright + Team Sidetrack for Party Music in all bars, Show Tunes 5-10pm Downstairs w/ Dixie Lynn Cartwright and Fun on the Rooftop all day. 5pm Taco Bar by Blue Agave-K Station, while they last. 10pm Sunday Funday After Dark featuring favorite Latin Pop Stars. Drag from Jasmine Phoenix + Evah Envy - get on stage to win Fun Prizes.
It takes one HUGE screen & dozens more to truly deliver all the Realness!
Chicago's RuPaul's Drag Race Season 11 Viewing Party

May 9, 2019, 8pm-2am. Chicago's RPDR Viewing Party. Watch and Win with Team Sidetrack hosts Dixie Lynn Cartwright + DiDa Ritz + the Sidetrack Pit Crew. After Ru, don't miss the Celebration of Chicago Drag: Shantay You Stay! w/ Danika Bone't. Bring Charisma, Uniqueness, Nerve, Talent and we'll Start Your Engines with games, RuPaul's Drag Race swag + fun surprises!
Not you Mother's 80s night
Cruisin' - 80s with Moose the DJ

May 10, 2019, 11pm-4am. Moose the DJ Cruisin' series: darker, danker, dirtier spin on 80s night w/ mix of vintage 80s Chicago House, HINRG, UK Synthpop, Industrial, late 80s vocals and deeper mixes of 80s favorites each 2nd Friday/ month. The Hole at The Jackhammer Complex will pump w/ Djjerry Featherston for your contemporary fix (or making new friends). Upstairs Vintage 80s porn.
Midnight Movies at the Music Box
The Rocky Horror Picture Show

May 11, 2019, midnight cult classic screenings: The Rocky Horror Picture Show features the Midnight Madness shadowcast, with audience participation of course! At The Music Box, 3733 N Southport Ave. See schedule for more midnight movies at their website:
At The Hole inside The Jackhammer Complex
SINglet Sundays in The Hole

May 12, 19, 26, 2019, 10pm Sundays through Dec 23rd at The Hole/ Jackhammer Complex. Join the regulars on the wrestling mats with everyone’s favorite bartender, Dan, playing all your alternative-electro-industrial music favorites. The event will also feature pop-up fetish demonstrations. FB
Live for the Applause, celebrate the opening of the Enigma Residency...
All Things Gaga

May 15, 2019, 9pm-2am. Get on stage as if A Star Is Born. Lip sync favorite Lady Gaga songs to win Fun Prizes w/ hostess Dixie Lynn Cartwright. Gaga-inspired Party Music mix to Just Dance to all night long. A Perfect Illusion: Gaga tribute drag performances by Chicago Queens Krissy Feetface, Alex Kay, Maxine LaQueene and Jadè Shade. You were Born This Way for Gagariffic FUN!
A grand week of Chicago premieres!
Chicago Critics Film Festival 2019

May 17-23, 2019, the Chicago Film Critics Association week-long selection of films including recent festival favorites and as-yet-undistributed works from a wide variety of filmmakers. The only major film critics group hosting its own festival. Features works from around the globe and offers viewers an eclectic blend of raunchy comedy, introspective drama and mind-blowing fantasy.
In the heart of Boystown each month friends come together to dance
May Queer Contra

May 18, 2019, 6:30-9:30pm at Second Unitarian Church of Chicago, 656 W Barry Ave. Live music - uniquely queer, inclusive dance - bring your friends! Band: Stringtime Boys (Emily Lorraine and Tim Macdonald). Caller TBA. 6:30pm lesson. 7-9:30pm dance. Beginners welcome/ encouraged. Suggested donation $10 at the door.
Hosted by Sidetrack The Video Bar
Special Edition Men's Room Wednesday

May 22, 2019, 9pm-2am. Team Sidetrack is geared-up and ready to Party! Special edition of the (usually) first Wednesday of the month event featuring naughty games to win fun prizes with Dixie Lynn Cartwright! As always, our friends from Men's Room Chicago will be here with an awesome Pop-Up Shop and cool giveaways! No Cover…it's Sidetrack.
Leather, uniform, & fetish men from around the world
International Mr Leather 2019

May 23-27, 2019, Memorial Day Weekend at the Congress Plaza Hotel, 520 S Michigan Ave. Thousands converge to party, network/ select International Mr Leather. Four-day Leather Market leather/fetish artisans/ retailers; erotic attractions, body enhancement specialists. FRI Party. SAT APEX ONYX dance. SUN IML Competition + IML Victory Celebration Party. MON Black and Blue Ball. More info:
Hosted by Grrr it's Friday at The SoFo Tap and The SoFo Tap
Grrr Kinky Bear with DJ RONS

May 24, 2019, 9pm-2am. Come out and play with the bearded, the burly and their admirers at Chicago's Best Bear Night, this Friday. DJ RONS on the decks with your favorites. No cover, no attitude, it's a fun-fur-all. A BIG BEAR welcome to our friends from out of town and visiting for both IML and Memorial Day Weekend. The PATIO BAR WILL BE OPEN!
Jock Party by Joe Whitaker
FuKR Chicago IML Kickoff - Domination

May 24, 2019, 10pm-5am. Joe Whitaker/ The Dilf Party Present Hot House Music Beats by DJs TBA. The F*kr Party For Men! The Hottest USA Jock Party is back to kick off the IML Weekend. Encouraged: jockstraps, harnessess, suspender straps. Get Strapped + Geared Up for Fun! Hot Dirty House Music + Hot Dirty Fun - Only at the World Famous Jackhammer! Clothes Check Available.
Jamie Babbit's creative feature debut follows Megan Bloomfield
But I'm a Cheerleader

May 24 + 25, 2019, midnight. A highschool cheerleader, sent to gay conversion therapy camp when her parents suspect her to be a lesbian, meets a girl named Graham who challenges camp ideals and what it means to be gay. Filled with clever innuendos, colorful imagery, and witty characters to make you smile and laugh as it offers a satirical look at queer identity issues/ gender roles.
Erotic Video Awards
The Grabbys XX

May 25, 2019, Memorial Day weekend with the hottest male porn stars in the business. Saturday awards bash, plus parties with the guys at Hydrate, Sidetrack, Lucky Horseshoe, and Charlies; Sunday Recovery Brunch at North End. Host hotel (this past year): The Fairmont Chicago, Millennium Park. See website for updates, nominees, interviews, and more:
at The SoFo Tap: Hosted by D.I.L.F. - Celebrating its EIGHTH year
DILF: IML w/ Mark Saltzman + Muffy Fishbasket

May 25, 2019, 9pm-3am. Chicago's biggest monthly party for men over 35 and the guys who want to get with them. The annual IML Memorial Day Weekend Daddyfest with hosts Leatherman Mark Saltzman + Muffy Fishbasket, welcoming all hot leather and kink daddies. Moose the DJ will be mixing his signature retro-remixed sound with synthpop from the past and present with deep cuts to thrill.
IML Saturday Night
Neverland presents My Coach

May 25, 2019, 11pm-5am. A celebration of the locker rooms, the uniforms, and the DILFS that dominated our adolescent fantasies. MUSIC by DJ PAULO (Los Angeles) and DJ Alex Cabot (Neverland Resident). LIGHTS by Joe Gillan.
A great time on our awesome patio — with a side of bears, cubs and otters!
GROWLr BBQ Bear Beer Blast Sunday

May 26, 2019, 1-3pm. Memorial Day weekend isn't complete unless you have a great BBQ. FREE! Burgers, Brats, Hot Dogs and Veggie Burgers with all the fixins will be waiting for you to devour! Drink specials.
Hosted by Organized Grime Crew
CUN - Tea - IML 41

May 26, 2019, 5-10pm. International Mr Leather Weekend... C U Next Tea! with Karsten Sollors (Black & Blue Ball), Dan Darlington (BRÜT / NY), and Dom Brown (Resident). Sponsored by: Steamworks Chicago. FREE Clothes Check. People of any color, size, body type, gender, gender expression(s), and sexual orientation are welcome. Next date: June 30th - Pride.
IML Weekend - Hosted by Neverland Events and Artist Management
Happily Never Afters

May 27, 2019, 7am-1pm. Neverland's signature afterhours brand, no-frills dance party that executes music, lighting, and sound with surgical precision. No dancers, no hosts, no drama, no attitude, no one bothering you, and no fucks given. DJ Alex Cabot from 7am Monday morning until 1pm or later. Got a flight out? Bring your bags and we'll put you in an uber to the airport.
The most anticipated party of IML weekend
IML Black and Blue Ball

May 27, 2019, 9pm. The official closing party of IML weekend returns to Chicago’s historic House Of Blues w/ Matthew Harvat + team to transform the venue into an exciting space specifically for the event. Show for ages 21+ w/ DJ Karsten Sollors (CHI) and International Superstar DJ/Producer Tom Stephan (LON) headlining, bringing their bass and drum beats to the dance floor.
Hosted by Pride Films and Plays
Desire in a Tinier House

May 30 - June 29, 2019, 7:30pm (22 dates). Trevin has chased his ex-boyfriend all the way to Colorado, only to fall madly in love with his ex’s friend Carlos. Trevin seduces Carlos into a trailer-bound life where they weather disasters and dystopia in their sexual island. But can their love-home outlast jealous intruders and time itself?
"..not just admission to the films but admission to a subculture” - Roger Ebert
Chicago Underground Film Festival

June 5-9, 2019, at Logan Theatre. Annual 5-day film showcase: 25 screenings, 4 Bar Talk discussions, 5 After-Parties. independent features, shorts, documentaries + experimental films from around the world. Innovative/ unique programming from lowbrow entertainment of John Waters, Doris Wishman and Coffin Joe to fine art avant-garde films and videos.
For young adults with student ID or proof of age
Out! on a School Night by Pride Films & Plays

June 6, 2019, 7:30pm - Desire in a Tinier House. Also July 18th, 7:30pm - Casa Valentina. High school and college students come to experience a PFP production at no cost. A program to provide young adults with free, theatrical productions dealing with LGBTQ+ themes in a safe, open, and educational space. An ongoing program see updates on upcoming productions.
A Chicago Swedish mid-summer bash

June 8, 2019, the 54th annual Andersonville summer street festival; around 50,000 people fill Clark Street each year, from Foster to Catalpa for music for cutting-edge bands, ethnic dance troupes, lots of food, and vendor wares. Born out of Andersonville’s Swedish heritage, Midsommarfest will transport you back to old-world Swedish traditions.
Prestigious outdoor art fair - the 45th year
Wells Street Art Festival

June 8-9, 2019, on N Wells St, between North Ave and Division St. Glass and ceramics, to pencil drawings and oil paintings - a diverse mix of nearly 200-plus juried artists + free educational workshops + tasty cuisine from the neighborhood’s eclectic restaurants and cool music stage acts. A treasure trove of creativity in Chicago’s historic Old Town neighborhood.
A Celebration of Sir Noel Coward - his knighthood 50th anniversary
Mad About the Boy, with Robert Rodi

June 16, 2019, 7:30pm. Theatrical legend. Jazz Age pioneer. Gay icon. A look back on the extraordinary career of Noel Coward; trailblazing style, enduring influence, and songs rivaling Cole Porter for their emotional range and irresistible melody: Mad Dogs and Englishmen; A Room with a View; If Love Were All - from the swooningly romantic to the shamelessly ribald.
Hosted by Pride Films and Plays and Pride Arts Center
50 Years of Pride - A Cabaret

June 23, 2019, 7:30-10:30pm. Join the best singers in Chicago for a rousing celebration of 50 years of Pride! Daniel Washelesky directs.
Hosted by Matt Bearracuda and Bearracuda Worldwide
Bearracuda Chicago Gay Pride 2019!

June 29, 2019, 9pm-2am. Dance party for bears, beards, cubs, pups, daddies, furballs, beefcakes, otters, and other wildlife. PRIDE SATURDAY with very special guest from Sydney - Paul Goodyear; and from Bearracuda LA - Ryan Jones! Hot Go-Go's and 700+ guys await you. Clothes check available.
A month of festivities
Chicago Pride 2019

June, 2019 Pride Month events, with two day Pride Fest, and final Sunday Parade June 30th, from N Halsted at Belmont to Lincoln Park by way of Broadway & Diversey. The Pride Street Festival, takes place on N Halsted, with music, food, vendors. Dozens more social, cultural, athletic & political events. See website for 2018 media + 2019 updates:
Advance tickets: 5 supersized events for $50
Windy City Black Pride

July 4-8, 2019. FRI Urbano Blackout Party at Fantasy w/ DJs X-Tasy, Trouble (ATL) and Gavin T (MIA); SAT Wet n Wild Pool Party at Holiday Inn Chicago O'Hare + Black Party at Metro w/ DJs Unknown (NYC), Trouble (ATL) and X-Tasy (CHI); SUN Closing Party at Club Escape w/ DJ Ron Carroll + XXX Dancers. FRI-MON nights at Club Escape. Host hotel: Holiday Inn Chicago O'Hare.
The largest two-day street fair in the Midwest
Northalsted Market Days

August 10-11, 2019, 11am-10pm. Celebrating its 38th anniversary, the annual street fair on 6 blocks of N Halsted, between Belmont and Addison; many musical acts, multiple stages; hundreds of food, arts and crafts vendors. Dozens of gay bars, dance clubs, restaurants, stores and a bathhouse surround the festival site. A crowd of over 180,000 people arrives from across the globe.
Chicago’s leading jazz artists
Chicago Jazz Festival

August 23 - September 1, 2019, Labor Day Weekend in Millennium Park Cultural Center, Von Freeman Pavilion (S Promenade), the Jazz and Heritage Pavilion (N Promenade), the Jay Pritzker Pavilion, the Chicago Cultural Center (78 E Washington), and other venues. A favorite Labor Day Weekend tradition of free, quality live musical performances since 1979.
37 years of queer film
Reeling: Chicago LGBTQ+ International Film Festival

September 19-29, 2019. Award-winning international feature films, social documentaries & experimental shorts. Past year: 65 screening at six venues around town, including: Landmark's Century Centre, 2828 N Clark St; Instituto Cervantes, 31 W Ohio; Chicago Filmmakers, 5243 N Clark St; ShowPlace ICON, 150 W Roosevelt Rd.
Because Everybody Loves Movies
Chicago International Film Festival

October 16-27, 2019, 12 days at AMC River East 21, 322 E Illinois St. Oldest competitive North American film festival, founded in 1964 to provide an alternative to commercial Hollywood movies that dominated city theaters. 12-day world-renowned annual event with the best in international cinema, new talents, and windows to a world of film previously or otherwise unavailable in Chicago.
Outrageous and imaginative costumes!
Haunted Halsted Halloween 2019

October 31, 2019. The 23rd Annual Halloween Parade, 5-10pm up N Halsted from Belmont, to Addison, with cash prize awards and live entertainment. Registration on Halsted just north of Belmont near The Playground Theater, 5-7pm for Costume Contest in one of five categories.
23rd Annual
Mr International Rubber

November 8-10, 2019. The Center on Halsted registration, Kink Market, Social, Gear Sale. Past year included: Touché Welcome Party. Contest at The Center, Brût Party at Fantasy, Strict Rubber Dress Code Party at Leather Rose Assn, The Rubber Ball, Steamworks and Cell Block events. Contest at MCA + Galleria Domain 2 + Jackhammer events. SUN Closing at Sidetrack.
Black Alphabet Film Festival
BAFF 2019 Chicago

Mid-November, 2019. Affirming diversity in gender/ sexual expression within the Black LGBTQ community, and celebrating stories of Black LGBTQ-identified people through the art of film. Two days of screenings at The Reva and David Logan Center. Tickets and line up details at website:
The 31st Annual
Rhinoceros Theater Festival 2020

January - February, 2020. Annual month-long multi-arts non-narrative, multidisciplinary fringe festival; new theatrical works by invited artists/ companies. The longest-running multi-arts fringe festival in Chicago, the Rhino features works in theater and performance from Chicago companies and national artists alike.