In 2 weeks
Trans Umbrella — 2Bears Tavern Uptown
About the event
Trans Umbrella on Wednesday, November 4, 2026 at 2Bears Tavern Uptown in Chicago.
About the venue
2Bears Tavern Uptown is a small gay bar on West Wilson Avenue in Chicago's Uptown, north of the main Northalsted (Boystown) strip and near Andersonville. It is a neighbourhood bar with pinball machines and beer-and-shot deals, and reviews mention a relaxed, mixed crowd…
“Duckin' in from the rain on a weekday business trip, I found a really welcoming atmosphere here. The bartender was so friendly and made me feel right at home, even during a quiet afternoon. I’d happily return to this Chicago establishment.” — Cristobal, Google
“I love two bears! Truly an amazing neighborhood bar that is welcoming and accepting of all, with great bartenders taboot! Every neighborhood needs a two bears 💕” — Carly Norton, Google
Nearby Hotels
via Stay221140 West Wilson Avenue, Chicago, IL 60640 Open in Maps →
Our three picks · Chicago
via Stay22Victorian B&B on North Halsted in Northalsted (Boystown), with antique-filled themed suites steps from the gay bars.
Affordable chain hotel on North Broadway in the middle of Boystown, Chicago, walking distance to the Halsted Street gay bars.
32-storey glass Sofitel on East Chestnut Street, steps from the Magnificent Mile and the Museum of Contemporary Art.
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Last verified: 22 Oct 2026 Source: eventbrite.com Report an issue