Part of the Gay Chicago Guide — bars, events & things to do.
Wednesday, October 14, 2026
Queers Gambit is a free chess night at 2Bears Tavern Uptown, open to every skill level from first timers to seasoned players. No pre signup needed, just show up and play. Every 2nd and 4th Wednesday, games start at 7PM. Free to play. 21+.
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Fri, Oct 16
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.
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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