Part of the Gay Chicago Guide — bars, events & things to do.
Friday, September 11, 2026
Test your trivia skills against drag queens in a fun, no-pressure showdown at this laid-back Uptown favorite. It's the perfect blend of competition and camaraderie—expect laughs, surprises, and the kind of friendly energy that makes 2Bears such a welcoming spot for the neighborhood queer scene. No cover, no attitude, just good times and a chance to prove your knowledge while hanging with some fabulous hosts. This event was imported by Out x Out. Please visit the venue link to verify details.
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Mon, 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.
Weekly
Mon, Sep 7
11:59 PM - 3:30 AM
2Bears Tavern Uptown, Chicago
Weekly Monday karaoke at 2Bears Tavern Uptown. Host the mic, connect with the community, and enjoy strong pours into the early morning.
Weekly
Tue, Sep 8
7:30 PM - 9:30 PM
2Bears Tavern Uptown, Chicago
Weekly Tuesday poker night at 2Bears Tavern Uptown. Casual game for all skill levels—meet neighbors, play cards, enjoy strong drinks in a laid-back gay bar.
Weekly
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.
WeeklyMon, 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.
WeeklyMon, 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.
WeeklyLet people know you're going, see who else is attending, and share the event with friends.
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