Part of the Gay Chicago Guide — bars, events & things to do.
Friday, September 4, 2026
Get ready to test your trivia skills against some fierce drag queens at this hilarious game show showdown. Compete for prizes while the queens keep the laughs coming in this fun, interactive night that's equal parts brain power and entertainment. It's the perfect blend of friendly competition and community vibes—whether you're a trivia champion or just here for the drag performances and good times, you'll fit right in at this weekly favorite. This event was imported by Out x Out. Please visit the venue link to verify details.
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Mon, Aug 31
7:30 PM - 9:30 PM
2Bears Tavern Uptown, Chicago
2Bears Tavern Uptown's free feud-style game night every Monday at 7:30pm, hosted by Pup Figaro — teams compete on LGBTQ+ poll questions for prizes.
Weekly
Mon, Aug 31
11:59 PM - 3:30 AM
2Bears Tavern Uptown, Chicago
Weekly Monday karaoke at 2Bears Tavern Uptown. Hosted by Tyler Meyer, Andrew, and Tyler Hall. Sing your heart out in a laid-back, lively gay bar atmosphere.
Weekly
Tue, Sep 1
7:30 PM - 9:30 PM
2Bears Tavern Uptown, Chicago
Weekly Tuesday poker night at 2Bears Tavern Uptown. Casual, social card games for all skill levels in a welcoming gay neighborhood bar.
Weekly
Thu, Sep 3
10 PM - 3:30 AM
2Bears Tavern Uptown, Chicago
Weekly Thursday open mic at 2Bears Tavern Uptown. No cover, no judgment—bring your voice or cheer on performers in a laid-back gay bar.
Weekly
Fri, Sep 4
11 PM - 1:30 AM
2Bears Tavern Uptown, Chicago
Monthly gay game night at 2Bears Tavern Uptown. Join Deanie and Ruff for drinks, friendly competition, and community in a laid-back bear-friendly space.
MonthlyMon, Sep 7
7:30 PM - 9:30 PM
2Bears Tavern Uptown, Chicago
2Bears Tavern Uptown's free feud-style game night every Monday at 7:30pm, hosted by Pup Figaro — teams compete on LGBTQ+ poll questions for prizes.
WeeklyLet people know you're going, see who else is attending, and share the event with friends.
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