50 Chicago Pride Month events you’ll want on your calendar
Chicago’s LGBTQ+ community is celebrating Pride Month with dozens of events across the city—from major street festivals and the flagship parade to parties, sports gatherings, advocacy events and educational programs. Below is Windy City Times’ curated roundup of 50 LGBTQ+ Pride Month events happening across…
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Contestants give their all in IML and IMBB contests
The 2026 International Mister Leather (IML) and International Mister Bootblack (IMBB) contests continued at the Riviera Theatre, 4746 N. Racine Ave., with the Preliminary Contest Night. All 68 IML and all 4 IMBB contestants introduced themselves to the judges and the audience, showing off their personalities while modeling their most revealing leather wear. The event was emcee’d…
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Palm Springs’s Honey Davenport and Chicago’s Atlas Rose win leather competitions
International Mister Leather (IML) and International Mister Bootblack’s (IMBB) 48th year came to a close the evening of May 24 at the Riviera Theatre, 4746 N. Racine Ave. The winner of IML 2026 was Mr. Palm Springs Leather 2026, Honey Davenport. The winner of IMBB 2026 was Atlas Rose, Route 66 Bootblack 2025. IML’s first…
Nation & World
IN BRIEF Jason Collins, trans student stabbed, Warsaw’s pro-marriage move, Uganda drops bill, INK, Janet Jackson, Sally Field
NATIONAL Jason Collins—the NBA’s first openly gay player, who went on to become a pioneer for inclusion—died at age 47 after an eight-month battle with an aggressive form of brain cancer, according to media reports.…
Theater / Dance
THEATER Playwright McCraney probes the ethics of a ‘Windfall’ at Steppenwolf
Writer Tarell Alvin McCraney’s new drama Windfall, running now at Steppenwolf Theatre through May 31, is billed by its theater company as a story about “the spirit of activism versus money.” The play depicts a Chicago man whose son is killed in a violent police incident. When the father is offered a significant cash settlement, he…
Music
Chicago singers help Belting for Life reach new heights
On May 11, the 11th annual Belting for Life Concert reached a new milestone. The event, a fundraiser for AIDS Foundation of Chicago (AFC) was the most successful Belting for Life event yet, nearly selling out SPACE at 1245 Chicago Ave. in Evanston. Conceived, produced and curated by Christopher Pazdernik—and taking place on his birthday—Belting for…
Film / TV / Gossip
FILM The Chicago Critics Film Festival winds up with a Wilde week in the Windy City
The Chicago Critics Film Festival is curated by the Chicago Film Critics Association and is the only United States film festival programmed exclusively by critics. Founded in 1990, the Chicago Film Critics Association supports filmmaking and is an all-volunteer, not-for-profit organization. For its 13th edition, the CCFF was held from May 1-7 in 2026, at…
Books / Art
Trans
Chicagoan Caprice Carthans builds an enduring legacy of community care
Community advocate Caprice Carthans came of age among a generation of Black trans women who survived by taking care of one another. “It was a whole different set of dynamics back then because we were all unified,” Carthans said. “If you were in the life, folks scooped you up and nurtured you and trained you. It…
Lesbian
Owners of beloved lesbian bar ‘Dorothy’ open queer dive bar ‘Fathom’ in Lakeview
The owners of the popular lesbian bar Dorothy opened a new queer bar in Lakeview this week, with a more casual, “classic neighborhood dive bar” feel. Fathom, 1622 W. Belmont Ave., opened April 9 and was quickly at capacity, with a line of people waiting that stretched down the block. The new nautical-themed bar is designed to…