Out x Out Logo
EventsVenuesBlog
Get the App
Out x Out Logo

Discover LGBTQ+ events, venues, and community in cities across the country.

InstagramFacebookTikTokTwitterBluesky

Explore

  • Events
  • Venues
  • Gay Bars Near Me
  • Gay Bathhouse Near Me
  • Gay Clubs Near Me
  • Blog
  • Newsletter

Company

  • Advertise
  • List Your Services
  • Resources
  • Contact Us

Get the App

Download on the
App Store
Get it on
Google Play

© 2026 PAXST LLC. All rights reserved.

TermsPrivacyCommitmentAttributions

Made with ♥ for the LGBTQIA+ community

Home/Events/Chicago/Tonight

Gay Events Tonight in Chicago

Find out where the gay scene is heading tonight in Chicago. We track LGBTQ+ parties, drag shows, and nightlife across Chicago, Illinois so you can see exactly what's on this evening and plan your night out.

All events →Today →This Weekend →Venues →

Never miss a night out when traveling or at home

Free on iOS and Android

App StoreGoogle Play

Monday, June 29

Make Mondays Suck Less

Make Mondays Suck Less

5 PM - 2 AM

The SoFo Tap, Chicago

Monday night gay bar in Chicago with cold beer, friendly bartenders, and a dog-friendly patio. Laid-back neighborhood vibe for the queer community.

Weekly
Sapphic Serenade: Dorothy's Karaoke Night hosted by E.

Sapphic Serenade: Dorothy's Karaoke Night hosted by E.

7 PM - 11 PM

Dorothy, Chicago

Sapphic Serenade: monthly queer karaoke hosted by E at Dorothy's underground lounge. Final Monday of each month. Community, laughter, and live performances.

ABC Bingo

ABC Bingo

7 PM - 11 PM

Charlie's, Chicago

Free drag bingo every Monday at Charlie's Chicago with hosts Aurora and Bella. Drink specials, 21+. Gay nightlife in Chicago.

Weekly
Mario Kart Mondays

Mario Kart Mondays

7 PM - 2 AM

Replay Lakeview, Chicago

Weekly Mario Kart tournament at queer-owned Replay Lakeview in Boystown. Compete for $50, play arcade, enjoy happy hour specials. Sign-ups at 7 PM.

Weekly
Squabble: A Game of Queeries

Squabble: A Game of Queeries

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
Musical Monday: Show Tunes at Sidetrack

Musical Monday: Show Tunes at Sidetrack

8 PM - 2 AM

Sidetrack, Chicago

Weekly show tunes night at Sidetrack in Chicago. Sing along to Broadway hits, dance, and enjoy frozen cocktails with the LGBTQ+ community.

Weekly
Monday MiXXXer

Monday MiXXXer

8 PM - 2 AM

Cell Block, Chicago

Weekly gay leather and fetish night at Cell Block. Dancing, backroom bar, and judgment-free vibes every Monday in Chicago's intimate club space.

Weekly
Tube Bears, Big Bears, Hot Bears - Pride Sunday

Tube Bears, Big Bears, Hot Bears - Pride Sunday

9 PM - 2 AM

The SoFo Tap, Chicago

Join the bear community for Pride Sunday at SoFo Tap. No cover, cold drinks, and a laid-back gay atmosphere. Every Sunday in Chicago.

Charlie's Chicago Live with Reggay Boots

Charlie's Chicago Live with Reggay Boots

11 PM - 2 AM

Charlie's, Chicago

Weekly Monday open stage talent showcase at Charlie's Chicago. Perform or watch for $50 prize, drink specials, and live entertainment.

Weekly
SERVE! Vocal Edition - Karaoke

SERVE! Vocal Edition - Karaoke

11:59 PM - 3:30 AM

2Bears Tavern Uptown, Chicago

Weekly Monday karaoke at 2Bears Tavern Uptown. Hosted by Tyler Meyer, Andrew, and Tyler Hall. Late-night singing in a welcoming gay space.

Weekly
Free newsletter

Events x City Guides Delivered Weekly

Catch your city's vibe or the global LGBTQ+ scene.

No spam, unsubscribe anytime.

Out x Out venue preview

From the Blog

View all →
Chicago Gay City Image
City Guides

LGBTQ+ Guide to Chicago 2026: Gay Bars, Events, Neighborhoods & More

Your complete guide to LGBTQ+ Chicago — the best gay bars, annual events, neighborhoods, hotels, and things to do in the Windy City.

Robbie S.Robbie S.
March 16, 2026
Chicago Black Pride 2026: Pride South Side, Parties & Black LGBTQ+ Chicago
Events & Festivals

Chicago Black Pride 2026: Pride South Side, Parties & Black LGBTQ+ Chicago

Pride South Side, holiday-weekend parties, and the Black & Brown LGBTQ+ bars that carry the scene year-round — your Chicago Black Pride 2026 guide.

Robbie S.Robbie S.
June 26, 2026
Gay Andersonville: A Local's Guide to Chicago's Quieter Gayborhood (2026)
Neighborhoods

Gay Andersonville: A Local's Guide to Chicago's Quieter Gayborhood (2026)

Andersonville is Chicago's brunch-and-boutiques gayborhood — residential, queer-women-friendly, and built around independent shops, not bottle service. Here's the local's guide.

Robbie S.Robbie S.
June 26, 2026
Recommend an Event·Share us with a LGBTQ+ or Friendly Business