Part of the Gay Chicago Guide — bars, events & things to do.
Friday, October 16, 2026
Put your trivia skills to the test in this interactive game show hosted by drag queens at 2Bears' laid-back Uptown spot. Compete for prizes while enjoying strong pours and good company in a no-cover, no-attitude environment that's perfect for a fun Friday night out. Whether you're a trivia buff or just here for the laughs and entertainment, it's the kind of low-key event that keeps people coming back to this welcoming neighborhood bar. This event was imported by Out x Out. Please visit the venue link to verify details.
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Wed, Oct 14
7 PM - 8:30 PM
2Bears Tavern Uptown, Chicago
Free LGBTQ+ chess night at 2Bears Tavern Uptown in Chicago, every 2nd and 4th Wednesday at 7pm. All skill levels, no signup needed.
Monthly
Mon, Oct 19
11:59 PM - 3:30 AM
2Bears Tavern Uptown, Chicago
Weekly Monday karaoke at 2Bears Tavern Uptown. No cover, strong pours, hosted by Tyler Meyer and Andrew. Low-key late-night fun for everyone.
Monthly
Tue, Oct 20
7:30 PM - 9:30 PM
2Bears Tavern Uptown, Chicago
Weekly Tuesday poker night at 2Bears Tavern Uptown. No cover, laid-back vibe. Test your skills against fellow players in a friendly, unpretentious gay bar.
MonthlyFri, Oct 23
7 PM - 10 PM
2Bears Tavern Uptown, Chicago
Weekly drag queen trivia at 2Bears Tavern Uptown. Test your skills, win prizes, and enjoy strong drinks in a no-cover, welcoming gay bar. Fridays.
MonthlyMon, Oct 26
11:59 PM - 3:30 AM
2Bears Tavern Uptown, Chicago
Weekly Monday karaoke at 2Bears Tavern Uptown. No cover, strong pours, hosted by Tyler Meyer and Andrew. Low-key late-night fun for everyone.
MonthlyTue, Oct 27
7:30 PM - 9:30 PM
2Bears Tavern Uptown, Chicago
Weekly Tuesday poker night at 2Bears Tavern Uptown. No cover, laid-back vibe. Test your skills against fellow players in a friendly, unpretentious gay bar.
MonthlyLet people know you're going, see who else is attending, and share the event with friends.
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