Out × Out Weekly: This Week In Gay Life

Welcome to the inaugural Out × Out Weekly. Each issue covers what's actually happening in queer life — drag, news, travel, and a different city we're spotlighting every week. This is Issue 01: April 29, 2026.

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The Briefing

Six things worth knowing from gay life this week:

RuPaul drops the All Stars 11 cast and it's stacked. Joey Jay, Crystal Methyd, Kennedy Davenport, Salina EsTitties — 18 returning queens are back for a Tournament of All Stars bracket battle, premiering on Paramount+ May 8. PinkNews

Provincetown CabaretFest unveils its 2026 schedule. Faith Prince gets the Lifetime Achievement Award at the June 8-14 run at Post Office Cabaret and Gifford House, with Sally Mayes, Anthony Murphy and Nicolas King among the headliners — a reason to extend your early-summer Cape trip. BroadwayWorld

Lady Gaga and Doechii drop the gayest video of the year. "Runway" — directed by Parris Goebel for The Devil Wears Prada 2 — landed Tuesday with high-fashion choreography that already sent the song to No. 1 on Billboard's Dance Digital chart. The Source

Tribeca rolls out one of its queerest lineups ever. For the festival's 25th anniversary, Lilly Wachowski returns for a 30th-anniversary screening of Bound, Lux Pascal headlines the feature Summer War, and a Shanghai-set lesbian love story called Ephemera screens June 3-14. The Queer Review

Portland's Gayborhood plans a comeback. A new queer bar called Camp is taking over the legendary Scandals space on Harvey Milk Street, eyeing a June opening that — paired with city-backed streetscape work — could finally restart foot traffic in the Burnside Triangle after years of closures. Hoodline Portland

Kehlani drops a self-titled fifth album on her 31st birthday. 17 tracks of queer R&B firepower including the Grammy-winning "Folded" plus features from Cardi B, Missy Elliott, Brandy and Lil Wayne — Kehlani uses she/they and the record leans hard into sexual fluidity. Rated R&B

Visit Gay Chicago — Our City of the Week

Chicago is the Midwest's queer capital — a long-weekend's worth of nightlife packed into a few square miles. Boystown (officially Northalsted) is the heart of it: high-energy clubs like Sidetrack and Splash, drag brunches and dinners at Kit Kat, naughty nights at Jackhammer or Cell Block, and a Pride parade that pulls a million people every June.

A few stops up the L line, the scene spreads out — Andersonville's lesbian bars and intimate cocktail spots, Edgewater's leather and dance bars, and Uptown's bear-friendly hangouts. Over 100 gay-friendly venues across the city, walkable in pockets, easy to bar-hop in pairs.

Top Venues

Sidetrack. The Boystown institution — show tunes nights, frozen cocktails, multi-level patio. Open every night. View on Out × Out

Jackhammer. Edgewater's anything-goes leather and dance bar. Two floors, themed parties, late-night energy. View on Out × Out

Dorothy. Andersonville's beloved lesbian speakeasy — expert cocktails, intimate red-door vibe, weekly DJ residencies. View on Out × Out

Kit Kat Lounge. The Lakeview drag-dinner cabaret. Sunday MarTEAni Dance with $9 specials and gogo dancers is a Chicago staple. View on Out × Out

Plan your visit: browse Chicago's gay scene or book your trip on Expedia.

Get Out of Town

Six flight deals from major US hubs to popular gay travel destinations this May:

PHX → Puerto Vallarta, MX from $312. Roundtrip on Alaska Airlines, May 7–May 11. Book on Expedia

DFW → Cabo San Lucas, MX from $131. Roundtrip on American Airlines, May 19–May 26. Book on Expedia

SFO → New York, NY from $148. Roundtrip on Frontier Airlines, May 11–May 18. Book on Expedia

BOS → Miami, FL from $164. Roundtrip on Frontier Airlines, May 13–May 20. Book on Expedia

SEA → Las Vegas, NV from $73. Roundtrip on Frontier Airlines, May 4–May 7. Book on Expedia

BNA → New Orleans, LA from $172. Roundtrip on Southwest Airlines, May 20–May 25. Book on Expedia

Prices, dates, and availability are subject to change without notice. Final pricing displayed at checkout. Some routes may carry carrier restrictions, baggage fees, or seasonal blackouts.

Want flight deals every week? Try Dollar Flight Club free — they spot cheap fares the moment they drop, international and domestic.

This was Issue 01 of Out × Out Weekly. New issues every week — subscribe or share this with a friend who needs more gay in their inbox.