Part of the Gay Chicago Guide — bars, events & things to do.
Friday, September 18, 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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Thu, Sep 10
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.
WeeklyFri, Sep 11
7 PM - 10 PM
2Bears Tavern Uptown, Chicago
Weekly drag queen trivia at 2Bears Tavern Uptown. Test your skills, laugh with fabulous hosts, no cover. Friday nights in Chicago's gay scene.
Weekly
Mon, Sep 14
7:30 PM - 9:30 PM
2Bears Tavern Uptown, Chicago
Weekly Feud-style game show night at 2Bears Tavern Uptown. Teams compete in trivia and strategy rounds with queer humor. No cover, strong drinks, Mondays.
Weekly
Mon, Sep 14
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.
Weekly
Tue, Sep 15
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.
WeeklyThu, Sep 17
10 PM - 3:30 AM
2Bears Tavern Uptown, Chicago
Weekly Thursday open mic at 2Bears Tavern Uptown. No cover, no pretense—perform or enjoy local artists in a friendly gay bar crowd.
WeeklyLet people know you're going, see who else is attending, and share the event with friends.
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