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				7 events 1 7 events, 1 2026-05-01 Chicago Leather Pride Weekend Chicago Leather Pride Weekend May 1 - May 3 Chicago Leather Pride Weekend Our second annual Weekend created to kick off Leather Pride... 2026-05-01 iEstrapped! iEstrapped! May 1 @ 11:00 pm - May 2 @ 12:00 am iEstrapped! ¡Mi gente lesbiana! Next month’s Strapped features an all latine... $14.11 1:00 pm The Missing Awareness Event@ Daley Plaza May 1 @ 1:00 pm The Missing Awareness Event@ Daley Plaza La Shann Walker Mother of 10 Years Missing Diamond &... Free, 1:00 pm Chicago May Day Rally & March May 1 @ 1:00 pm Chicago May Day Rally & March This May Day, a broad coalition of organizations are uniting... Free, 1:00 pm Petition in One of the Worst States for Ballot Access May 1 @ 1:00 pm Petition in One of the Worst States for Ballot Access Illinois is one of the WORST states for ballot access... + 2 More	4 events 2 4 events, 2 2026-05-01 Chicago Leather Pride Weekend 2026-05-01 iEstrapped! 10:30 am ChiPride Volunteering + Care For Real May 2 @ 10:30 am ChiPride Volunteering + Care For Real Join other LGBTQ+ and Ally volunteers as we assist Care... Free, 7:00 pm Artemis Singers Spring Concert – Power in Harmony May 2 @ 7:00 pm Artemis Singers Spring Concert – Power in Harmony Why "Power in Harmony"? Artemis Singers, Chicago’s Lesbian Feminist Chorus,... $20	3 events 3 3 events, 3 2026-05-01 Chicago Leather Pride Weekend 12:00 pm Spring Brunch & Fashion Show May 3 @ 12:00 pm Spring Brunch & Fashion Show The Spring Brunch & Fashion Show is Chicago House's fabulous..., 2:00 pm Old Gold feat. Good Girls DJs (30+) May 3 @ 2:00 pm Old Gold feat. Good Girls DJs (30+) It's Springtime Sensuality! Chicago's beloved all-vinyl day party for queer... $25
2 events 4 2 events, 4 8:00 am Prominent LGBTQ+ Addiction & Mental Health Program to Open in Chicago’s “Boystown” May 4 May 4 @ 8:00 am Prominent LGBTQ+ Addiction & Mental Health Program to Open in Chicago’s “Boystown” May 4 Chicago welcomes Los Angeles-based No Matter What Recovery (NMWR), a..., 6:00 pm Queer Fiber Artist Night at Dorothy May 4 @ 6:00 pm Queer Fiber Artist Night at Dorothy Bring your fiber work to Dorothy and join in a... Free	0 events 5 0 events, 5	1 event 6 1 event, 6 9:30 am LGBTQ+ Senior Resource Fair May 6 @ 9:30 am LGBTQ+ Senior Resource Fair Join Center on Halsted for the LGBTQ+ Senior Resource Fair... Free	3 events 7 3 events, 7 5:30 pm Citywide Pride Chicago Kickoff 2026! May 7 @ 5:30 pm Citywide Pride Chicago Kickoff 2026! We're delighted to invite you to Citywide Pride Chicago's annual..., 6:30 pm Mixed Media Mark Making May 7 @ 6:30 pm Mixed Media Mark Making Instructor: Sholo Beverly Let go of expectations and experiment with... $200, 7:00 pm Evolution of a Snake: The Showgirl Experience May 7 @ 7:00 pm Evolution of a Snake: The Showgirl Experience Hosted by Zachary Hourihane (Swiftologist) and Madeline Rubicam (The Lizard... $32	5 events 8 5 events, 8 6:00 pm Queer Nerd Meetup at Goblin Market May 8 @ 6:00 pm Queer Nerd Meetup at Goblin Market Hang out at an indie book shop and meet other... Free, 6:00 pm 6311Arts Invites the Public to Closing Reception for The Observed & The Imagined on May 8 May 8 @ 6:00 pm 6311Arts Invites the Public to Closing Reception for The Observed & The Imagined on May 8 CHICAGO — 6311Arts invites the public to a closing reception... Free, 6:30 pm Conversion Therapy Dropout Chicago Release Party with Tim Schraeder Rodriguez May 8 @ 6:30 pm Conversion Therapy Dropout Chicago Release Party with Tim Schraeder Rodriguez Join former Chicagoan Timothy Schraeder Rodriguez to celebrate the release... Free + 2 More	9 events 9 9 events, 9 2026-05-09 Sapphopalooza Sapphopalooza May 9 - May 31 Sapphopalooza Guest-programmed by Elizabeth Arnott, Music Box Films “Lesbian? Her birthday... 9:30 am Trans Youth & Family Action Summit May 9 @ 9:30 am Trans Youth & Family Action Summit The Trans Youth & Family Action Summit at Center on... Free, 1:00 pm Chicago Queer History Walking Tours: Police, Gangsters, and Gay Bars May 9 @ 1:00 pm Chicago Queer History Walking Tours: Police, Gangsters, and Gay Bars The University of Chicago sociologist Ernest Burgess observed that the... Free, 5:00 pm Off the Grid: Action Camp Fundraiser May 9 @ 5:00 pm Off the Grid: Action Camp Fundraiser Join us for our 3rd Annual Action Camp Fundraiser: Off... $30 + 5 More	5 events 10 5 events, 10 2026-05-09 Sapphopalooza 3:00 pm Call Me Elizabeth May 10 @ 3:00 pm Call Me Elizabeth "Call Me Elizabeth," a one-woman show about the life of... $35, 3:00 pm PFLAG Loves Sidetrack Annual Fundraiser May 10 @ 3:00 pm PFLAG Loves Sidetrack Annual Fundraiser PFLAG is the nation's largest organization dedicated to supporting, educating,..., 5:00 pm Dear Momma II May 10 @ 5:00 pm Dear Momma II 🌼 Join Us for a Special Celebration! 🌼 Calling all... + 1 More
3 events 11 3 events, 11 2026-05-09 Sapphopalooza Sapphopalooza 7:30 pm Belting for Life May 11 @ 7:30 pm Belting for Life Chicago's favorite evening of big voices for a big cause,... $1 – $50, 7:30 pm Belting for Life May 11 @ 7:30 pm Belting for Life Chicago's favorite evening of big voices for a big cause,... $1 – $50	2 events 12 2 events, 12 2026-05-09 Sapphopalooza 6:00 pm Chicago Queer Wedding Show May 12 @ 6:00 pm Chicago Queer Wedding Show Get ready to celebrate love in all its forms at... $10	3 events 13 3 events, 13 2026-05-09 Sapphopalooza 7:00 pm Country Dancing at Whiskey Girl Tavern May 13 @ 7:00 pm Country Dancing at Whiskey Girl Tavern Join us for a fun night of FREE Country Dancing... Free, 7:00 pm Country Dancing at Whiskey Girl Tavern May 13 @ 7:00 pm Country Dancing at Whiskey Girl Tavern Join us for a fun night of FREE Country Dancing... Free	2 events 14 2 events, 14 2026-05-09 Sapphopalooza 7:00 pm Pitch Your Peeps May 14 @ 7:00 pm Pitch Your Peeps Take the stage to pitch your (35+) queer friend to...	2 events 15 2 events, 15 2026-05-09 Sapphopalooza 6:30 pm Lambda Legal’s Bon Foster Civil Rights Celebration May 15 @ 6:30 pm Lambda Legal’s Bon Foster Civil Rights Celebration We are thrilled to gather once again for the annual... $300	6 events 16 6 events, 16 2026-05-09 Sapphopalooza 2026-05-16 Ragbagalia Arts Fest Ragbagalia Arts Fest May 16 @ 2:00 pm - May 17 @ 1:00 am Ragbagalia Arts Fest As Chicago emerges from its winter burrow, a new cultural... $57.68 10:00 am Mobile City Hall: Shabbona Park May 16 @ 10:00 am Mobile City Hall: Shabbona Park We believe that City services should be accessible and available... Free, 11:00 am ChiPride Volunteering + Tree House Humane Society May 16 @ 11:00 am ChiPride Volunteering + Tree House Humane Society It’s kitten season! Volunteers will support Tree House during this..., 6:00 pm 6311arts Presents May Exhibition, Bringing Together Established Chicago Artists, Emerging Student Voices, and Inclusive Community Programming May 16 @ 6:00 pm 6311arts Presents May Exhibition, Bringing Together Established Chicago Artists, Emerging Student Voices, and Inclusive Community Programming CHICAGO — This spring, Edgewater community center 6311arts will present... Free + 1 More	7 events 17 7 events, 17 2026-05-09 Sapphopalooza 2026-05-16 Ragbagalia Arts Fest 10:00 am The Strut Lab – Modeling WERKshop May 17 @ 10:00 am The Strut Lab – Modeling WERKshop Confidence starts with your WALK — and we’re here to... $85, 2:00 pm David Sedaris in Chicago May 17 @ 2:00 pm David Sedaris in Chicago David Sedaris, renowned humorist and best-selling author, will perform at... $155, 5:00 pm The John Waters Screenplays: A Reading and Conversation May 17 @ 5:00 pm The John Waters Screenplays: A Reading and Conversation Join us for a reading and career-spanning conversation with legendary... + 2 More
2 events 18 2 events, 18 2026-05-09 Sapphopalooza Sapphopalooza 6:00 pm 6311arts Presents May Exhibition, Bringing Together Established Chicago Artists, Emerging Student Voices, and Inclusive Community Programming May 18 @ 6:00 pm 6311arts Presents May Exhibition, Bringing Together Established Chicago Artists, Emerging Student Voices, and Inclusive Community Programming CHICAGO — This spring, Edgewater community center 6311arts will present... Free	2 events 19 2 events, 19 2026-05-09 Sapphopalooza 6:00 pm 6311arts Presents May Exhibition, Bringing Together Established Chicago Artists, Emerging Student Voices, and Inclusive Community Programming May 19 @ 6:00 pm 6311arts Presents May Exhibition, Bringing Together Established Chicago Artists, Emerging Student Voices, and Inclusive Community Programming CHICAGO — This spring, Edgewater community center 6311arts will present... Free	4 events 20 4 events, 20 2026-05-09 Sapphopalooza 6:00 pm 6311arts Presents May Exhibition, Bringing Together Established Chicago Artists, Emerging Student Voices, and Inclusive Community Programming May 20 @ 6:00 pm 6311arts Presents May Exhibition, Bringing Together Established Chicago Artists, Emerging Student Voices, and Inclusive Community Programming CHICAGO — This spring, Edgewater community center 6311arts will present... Free, 6:00 pm Law at the Library: LGBTQIA+ and the Law: Transgender Rights May 20 @ 6:00 pm Law at the Library: LGBTQIA+ and the Law: Transgender Rights The Chicago Bar Association (CBA), along with partners at the... Free, 7:30 pm Leftist political commentator Lily Eagla joins Chicago’s Late Night Talk Show May 20 @ 7:30 pm Leftist political commentator Lily Eagla joins Chicago’s Late Night Talk Show Get the late night talk show experience without heading to... $15	8 events 21 8 events, 21 2026-05-09 Sapphopalooza 2026-05-21 GRABBY Awards GRABBY Awards May 21 - May 23 GRABBY Awards The annual GRABBYS Award Show highlighting top talent and performances... 2026-05-21 LGBTQ+ Advocacy Day with Equality Illinois LGBTQ+ Advocacy Day with Equality Illinois May 21 LGBTQ+ Advocacy Day with Equality Illinois Our community is under attack, and we need your voice... Free 6:00 pm Planting Power and Perseverance: Partners in Dignity Soiree 2026 May 21 @ 6:00 pm Planting Power and Perseverance: Partners in Dignity Soiree 2026 Join us for the 2026 Partners in Dignity Soiree: Planting..., 6:00 pm Coochies May 21 @ 6:00 pm Coochies Coochies: The OG Hoochie Cabaret 🐾 The Sapphic Freaknik of... $12, 6:00 pm Legends of Chicago Drag Celebration May 21 @ 6:00 pm Legends of Chicago Drag Celebration The Costume Council of the Chicago History Museum is turning... + 2 More	8 events 22 8 events, 22 2026-05-09 Sapphopalooza 2026-05-21 GRABBY Awards 2026-05-22 About Face presents Re/Generation Studio 2026 About Face presents Re/Generation Studio 2026 May 22 @ 5:30 pm - May 23 @ 6:00 pm About Face presents Re/Generation Studio 2026 Join About Face Theatre and Chicago LGBTQ+ creatives to build... Free 2026-05-22 About Face presents Re/Generation Studio 2026 About Face presents Re/Generation Studio 2026 May 22 @ 5:30 pm - May 23 @ 6:00 pm About Face presents Re/Generation Studio 2026 Join About Face Theatre and Chicago LGBTQ+ creatives to build... Free 10:00 am Lori Cannon Way – Street Naming Ceremony May 22 @ 10:00 am Lori Cannon Way – Street Naming Ceremony Join us in honoring the life and legacy of Lori... Free, 6:00 pm 6311arts Presents May Exhibition, Bringing Together Established Chicago Artists, Emerging Student Voices, and Inclusive Community Programming May 22 @ 6:00 pm 6311arts Presents May Exhibition, Bringing Together Established Chicago Artists, Emerging Student Voices, and Inclusive Community Programming CHICAGO — This spring, Edgewater community center 6311arts will present... Free, 7:00 pm Transcendent Souls IV May 22 @ 7:00 pm Transcendent Souls IV Transcendent Souls IV is an all-cello concert of works by... Free + 1 More	8 events 23 8 events, 23 2026-05-09 Sapphopalooza 2026-05-21 GRABBY Awards 2026-05-22 About Face presents Re/Generation Studio 2026 2026-05-22 About Face presents Re/Generation Studio 2026 2026-05-23 Zentrø Zentrø May 23 @ 9:00 pm - May 24 @ 2:00 am Zentrø Zentrø, our Global Kink and Leather Main Event alongside Brüt,... 1:00 pm Chicago Queer History Walking Tours: May 23 Sex and Rebellion May 23 @ 1:00 pm Chicago Queer History Walking Tours: May 23 Sex and Rebellion It's IML weekend, and to commemorate this week is all... Free, 6:00 pm 6311arts Presents May Exhibition, Bringing Together Established Chicago Artists, Emerging Student Voices, and Inclusive Community Programming May 23 @ 6:00 pm 6311arts Presents May Exhibition, Bringing Together Established Chicago Artists, Emerging Student Voices, and Inclusive Community Programming CHICAGO — This spring, Edgewater community center 6311arts will present... Free, 7:30 pm Jibz Cameron: Hell in a Handbag May 23 @ 7:30 pm Jibz Cameron: Hell in a Handbag A freaks freak, artist Jibz Cameron, best known for her... Free	6 events 24 6 events, 24 2026-05-09 Sapphopalooza 2026-05-24 Global Kink and Leather Closing Party Global Kink and Leather Closing Party May 24 @ 9:00 pm - May 25 @ 4:00 am Global Kink and Leather Closing Party Join us as we finish the inaugural Global Kink and... 2026-05-23 Zentrø 9:00 am ChiPride Volunteering + Friends of the Forest Preserves – LaBagh Woods May 24 @ 9:00 am ChiPride Volunteering + Friends of the Forest Preserves – LaBagh Woods Join LGBTQ+ and Ally Volunteers as we partner with Friends... Free, 6:00 pm May’s Queer Swing Dance! May 24 @ 6:00 pm May’s Queer Swing Dance! We're nearly a year in now and we're looking forward..., 6:00 pm 6311arts Presents May Exhibition, Bringing Together Established Chicago Artists, Emerging Student Voices, and Inclusive Community Programming May 24 @ 6:00 pm 6311arts Presents May Exhibition, Bringing Together Established Chicago Artists, Emerging Student Voices, and Inclusive Community Programming CHICAGO — This spring, Edgewater community center 6311arts will present... Free
4 events 25 4 events, 25 2026-05-09 Sapphopalooza Sapphopalooza 2026-05-24 Global Kink and Leather Closing Party Global Kink and Leather Closing Party 6:00 pm 6311arts Presents May Exhibition, Bringing Together Established Chicago Artists, Emerging Student Voices, and Inclusive Community Programming May 25 @ 6:00 pm 6311arts Presents May Exhibition, Bringing Together Established Chicago Artists, Emerging Student Voices, and Inclusive Community Programming CHICAGO — This spring, Edgewater community center 6311arts will present... Free, 7:00 pm Queer Speed Dating May 25 @ 7:00 pm Queer Speed Dating Meet other cutie queers in a space that’s easy, fun,... $13 – $25	3 events 26 3 events, 26 2026-05-09 Sapphopalooza 2:00 pm Mezcla’s Writers Group Meetup May 26 @ 2:00 pm Mezcla’s Writers Group Meetup A quarterly meetup for writers in the Chicagoland area to... Free, 6:00 pm 6311arts Presents May Exhibition, Bringing Together Established Chicago Artists, Emerging Student Voices, and Inclusive Community Programming May 26 @ 6:00 pm 6311arts Presents May Exhibition, Bringing Together Established Chicago Artists, Emerging Student Voices, and Inclusive Community Programming CHICAGO — This spring, Edgewater community center 6311arts will present... Free	6 events 27 6 events, 27 2026-05-09 Sapphopalooza 8:00 am Pride Trivia Night May 27 @ 8:00 am Pride Trivia Night Kick off Pride season with Sip, Slay, Solve: HRC Chicago... $15 – $60, 5:30 pm Community Dialogue: Stories of Pride May 27 @ 5:30 pm Community Dialogue: Stories of Pride Join us for a free community dialogue about LGBTQ+ Pride... Free, 5:30 pm Community Dialogue: Stories of Pride May 27 @ 5:30 pm Community Dialogue: Stories of Pride Join us for a free community dialogue about LGBTQ+ Pride... Free + 2 More	3 events 28 3 events, 28 2026-05-09 Sapphopalooza 4:30 pm OUT OF THE OFFICE Kick off Pride Month in Chicago May 28 @ 4:30 pm OUT OF THE OFFICE Kick off Pride Month in Chicago THE 25th ANNUAL OUT OF THE OFFICE Kick-Off Pride Month... $1 – $50, 6:00 pm 6311arts Presents May Exhibition, Bringing Together Established Chicago Artists, Emerging Student Voices, and Inclusive Community Programming May 28 @ 6:00 pm 6311arts Presents May Exhibition, Bringing Together Established Chicago Artists, Emerging Student Voices, and Inclusive Community Programming CHICAGO — This spring, Edgewater community center 6311arts will present... Free	4 events 29 4 events, 29 2026-05-09 Sapphopalooza 2026-05-29 Go Girl, Saugatuck! Go Girl, Saugatuck! May 29 - May 31 Go Girl, Saugatuck! Go Girl! Saugatuck is an inclusive-of-all on the female spectrum... 6:00 pm 6311arts Presents May Exhibition, Bringing Together Established Chicago Artists, Emerging Student Voices, and Inclusive Community Programming May 29 @ 6:00 pm 6311arts Presents May Exhibition, Bringing Together Established Chicago Artists, Emerging Student Voices, and Inclusive Community Programming CHICAGO — This spring, Edgewater community center 6311arts will present... Free, 7:30 pm Chicago Repertory Ballet’s Spring Series May 29 @ 7:30 pm Chicago Repertory Ballet’s Spring Series MAY 29 - 31 \| RUTH PAGE CENTER FOR THE... $40	9 events 30 9 events, 30 2026-05-09 Sapphopalooza 2026-05-29 Go Girl, Saugatuck! 11:30 am Dim Sum & Drag: Avatar The Last Brunch Bender May 30 @ 11:30 am Dim Sum & Drag: Avatar The Last Brunch Bender Dim Sum & Drag presents Avatar The Last Brunchbender! Join... $44.29, 2:00 pm Centering Queer Identities & Experiences: A Model of Affirming Medical Care May 30 @ 2:00 pm Centering Queer Identities & Experiences: A Model of Affirming Medical Care Join Out With Purpose and RUSH Hospital for a presentation... Free, 6:00 pm 6311arts Presents May Exhibition, Bringing Together Established Chicago Artists, Emerging Student Voices, and Inclusive Community Programming May 30 @ 6:00 pm 6311arts Presents May Exhibition, Bringing Together Established Chicago Artists, Emerging Student Voices, and Inclusive Community Programming CHICAGO — This spring, Edgewater community center 6311arts will present... Free + 4 More	6 events 31 6 events, 31 2026-05-09 Sapphopalooza 2026-05-29 Go Girl, Saugatuck! 2026-05-31 City in a Garden: Queer Art and Activism in Chicago City in a Garden: Queer Art and Activism in Chicago May 31 City in a Garden: Queer Art and Activism in Chicago City in a Garden: Queer Art and Activism in Chicago is... 6:00 pm 6311arts Presents May Exhibition, Bringing Together Established Chicago Artists, Emerging Student Voices, and Inclusive Community Programming May 31 @ 6:00 pm 6311arts Presents May Exhibition, Bringing Together Established Chicago Artists, Emerging Student Voices, and Inclusive Community Programming CHICAGO — This spring, Edgewater community center 6311arts will present... Free, 6:00 pm T’was the Night Before PRIDE May 31 @ 6:00 pm T’was the Night Before PRIDE A Queer Mixer for everyone to come out, get to... $15, 7:30 pm Chicago Repertory Ballet’s Spring Series May 31 @ 7:30 pm Chicago Repertory Ballet’s Spring Series MAY 29 - 31 \| RUTH PAGE CENTER FOR THE... $40