Singles in Chicago
Low-pressure mixers, social nights, and ways to actually meet someone.

Haunted Hotel Halloween Ball
Mega Halloween costume dance party at Congress Plaza. Multi-room DJ stages, theatrical decor, bottle service.

Big Irish Jay at Riddles Comedy Club
Big Irish Jay Hollingsworth headlines Riddles Comedy Club for a full weekend of stand-up. $25 cash cover, two-drink minimum.

Cruising The Waves Yacht Party
You're floating down the Chicago River and out onto Lake Michigan while a top-shelf open bar keeps the good times flowing—and then Navy Pier's fireworks explode across the skyline right in front of you. This inaugural yacht experience pairs live DJs, dinner, and unobstructed water views with the kind of vantage point landlubbers will never have.

Drew Thomas at Riddles Comedy Club
Drew Thomas headlines Riddles Comedy Club. Two nights of stand-up at 7:30 PM and 10 PM. $25 cash cover, two-drink minimum.

Blue Violet Late-Night Social
High-energy Latin and Afrobeat social at Hubbard Inn in River North. Weekly recurring Friday midnight track with elite cocktail mixology and VIP table

Black Yacht Weekend: Juneteenth Kickoff Party
Launch Juneteenth weekend at Vertiport Chicago's massive hangar venue with a headline performance by ODeal, blending culture, music, and community in one of the city's most unique event spaces.

Son Little
With special opening act Tonina. All sales are final, no refunds/exchanges permitted, but tickets may be transferred through your TM Account. Garcia's is fully ADA compliant featuring wheelchair lifts and ramps between the various levels of the venue, assisted listening devices upon request, and allows official service animals. Premium Table seating is located closest to the stage offering the most intimate music experience for guests and includes table service. Reserved Table seating is located on our main floor, behind the Premium section, and also includes table service. Both Premium and Reserved table seating is cabaret style which means you may be sitting with other fans. Private Booths are available and depending on the booth seats 1 to 4, 5, or 6 guests. General Admission/Standing Room is located around the sides of the room on an elevated level for quality viewing and easy bar access. 21 & Over Show. Must be 21+ with a valid ID to purchase alcohol. At Garcia's Chicago.

THRILLER — The Michael Jackson Dance Party
Step into the iconic world of Thriller at Chop Shop in Wicker Park as the city's most electrifying dance party pays tribute to the King of Pop. Don yo

Harlem Hayfield, Margo MacEro, Little Victory, Joel Gragg
At Reggies Music Joint.

Jeremy Piven
At Chicago Improv - Schaumburg.

Pleasantries, When We Was Kids, Middle Seat
Pleasantries, When We Was Kids, and Middle Seat take over Reggies Music Joint on June 12.

Augustana + Phantom Planet
Mid-2000s indie rock reunion at Lincoln Hall. Augustana (Boston) and Phantom Planet (California) share a nostalgic bill.

Nando de La Gente: En Espanol
Nando de La Gente brings his En Espanol show to Chicago Improv in Schaumburg on June 6.

After Dark at Punch Bowl Social
Free late-night events at Punch Bowl Social, Fulton Market. Multiple dates.

Soul Solidarity — Heart of Chicago Soul Club
Two crews bringing their rarest wax to Color Club—expect the kind of deep soul cuts that make you understand why people still chase vinyl. You'll feel the difference in how these DJs mix: intentional, unhurried, built for dancing that lasts all night.

LGBTQIA+ Craft Cocktail Social Hour at Nobodys Darling
Inclusive craft cocktail social at the award-winning Nobody's Darling. Acclaimed artisan cocktails featuring independent BIPOC-owned spirit labels. We

Jennifer Hartswick and Nick Cassarino Duo
Jennifer Hartswick and Nick Cassarino bring their duo show to Garcia's Chicago on June 5.

Comedy Is Dead with Marcella Arguello
Marcella Arguello brings her sharp, no-filter comedy to the Den Theatre's intimate stage in Wicker Park—expect the kind of set that makes you simultaneously uncomfortable and unable to stop laughing. She's got that rare ability to dismantle social niceties while keeping you completely engaged, turning observations about identity and culture into comedy that actually lands.

Megan Moroney: The Cloud 9 Tour
Megan Moroney brings The Cloud 9 Tour to United Center on June 2.

Adam Addis at Zanies
Adam Addis hits the Zanies stage for a night of stand-up comedy that's smart, sharp, and guaranteed to leave you sore from laughing. Doors at 6 PM, sh

Karaoke Night at Louie Lous
Open mic karaoke every Friday and Saturday. Cheap drinks, no cover, and a crowd that cheers for everyone. Wicker Park vibes.

The First Date — Live Dating Comedy Show at Laugh Factory
Chicago's funniest stand-up comedians hit the stage while a lucky audience member gets picked for a live first date. You'll hear the jokes but can't s

House Music is Home at Navy Pier
Chicago's house music scene takes over Navy Pier for the summer's most ambitious lakefront takeover—think multiple stages pumping four-on-the-floor beats with Lake Michigan as your backdrop, because nothing hits like dancing with that breeze rolling off the water. You'll navigate a sprawling pier carnival atmosphere packed with enough stages and sound systems to keep you discovering new sounds all night, all completely free if you RSVP ahead.