Part of the Gay Chicago Guide — bars, events & things to do.
Monday, October 19, 2026
Grab the mic and belt out your favorites at this late-night karaoke experience hosted by Tyler Meyer, Andrew, and Tyler Hall. Running Monday nights into Tuesday mornings, SERVE! Vocal Edition brings a fun, unpretentious energy to 2Bears' welcoming room—no cover, no attitude, just strong pours and good vibes. Whether you're a karaoke regular or jumping in for the first time, it's the perfect low-key way to end your night in Uptown. 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
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
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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