Things to do in Chicago

Wednesday, Sep 30

Blazed and Confused Wednesday Movie Trivia with $7 THC Beverages + $6 Willies Cocktails

Woodie's Flat

Enjoy a fun trivia night with THC beverages at Woodie's Flat. Ideal for trivia lovers looking for a unique experience.

Wednesday, Sep 30

Salsa Dancing

From Here On Food Hall

Join us for a lively Salsa Dancing evening with a beginner lesson and social dancing. Great for dance enthusiasts.

Wednesday, Sep 30

lionel richie at united center

Kaiser Tiger

Enjoy a complimentary shuttle service to the United Center for the Lionel Richie concert. A convenient option for attendees.

Wednesday, Sep 30

Bulls at United Center

Kaiser Tiger

Complimentary shuttle service to and from the Bulls game at the United Center.

Wednesday, Sep 30

Sip, Sketch & Socialize

ERIS Brewery and Cider House

Join us for Sip, Sketch & Socialize at ERIS Brewery for a creative night of art and drinks. Ideal for art lovers.

Wednesday, Sep 30

Abigail Riccards & Friends - A Night of Soul / Jazz / Blues Favorites

Winter's Jazz Club

Experience a night of soul, jazz, and blues with Abigail Riccards and her band. Ideal for jazz enthusiasts.

Wednesday, Sep 30

Patricia Barber

Winter's Jazz Club

Experience the smooth sounds of Patricia Barber at Winter's Jazz Club. A delightful evening for jazz lovers in Chicago.

Thursday, Oct 1

WEDNESDAY SEPTEMBER 30: CROWD WORK WEDNESDAY

The Comedy Bar

Join Crowd Work Wednesday at The Comedy Bar for an interactive comedy experience hosted by Pat Bolduc & John Gasper.

Thursday, Oct 1

Thirst for Adventure! A Dungeons & Dragons Live Comedy Show

The Lincoln Lodge

Enjoy an epic Dungeons & Dragons live comedy show featuring top Chicago comedians. Perfect for fans of tabletop games and comedy.

Thursday, Oct 1

Bill Burr Live

The Chicago Theatre

See comedian Bill Burr perform live at The Chicago Theatre. A must-see event for comedy fans in Chicago.

Thursday, Oct 1

Dancing People presented by Jean Wildest

The Newport Theater

Join the Rhinestone Cowboy at The Newport Theater for a unique cabaret experience filled with entertainment.

Thursday, Oct 1

Comedy Royalty: A Chicago Comedy Showcase

The Lincoln Lodge

Enjoy an epic night of laughs with Chicago's top comedians at The Lincoln Lodge. Great for comedy fans looking for a night of entertainment.

Thursday, Oct 1

Windy City Cowboy Club

Broken Hearts

Enjoy line dance lessons and great music at the Windy City Cowboy Club. A fun night for dance enthusiasts.

Thursday, Oct 1

RIFF CITY STANDUP COMEDY SHOW

The Lincoln Lodge

Enjoy a unique stand-up comedy experience where the jokes are all about you at Riff City.

Thursday, Oct 1

RED ROOM OPEN MIC

RED ROOM Comedy Club

Join us for an open mic night at RED ROOM Comedy Club. A chance for comedians to showcase their talents in a welcoming environment.

Thursday, Oct 1

Mike Brumfield

Redhead Piano Bar

Join us for an evening with Mike Brumfield at Redhead Piano Bar for great music and entertainment. Ideal for a night out in Chicago.

Thursday, Oct 1

Sir Thomas Madden Jr.

The Den Theatre

Join Sir Thomas Madden Jr. for a night of sketch comedy at The Den Theatre, featuring unique humor.

Thursday, Oct 1

Wednesday Night Stand Up Comedy

Laugh Factory

Catch new comedians at Wednesday Night Stand Up Comedy. Ideal for comedy fans.

Thursday, Oct 1

Comedians You Should Know: Chicago's Funniest Stand-Up. No Joke.

Timothy O'Toole's Pub Chicago

Enjoy rotating lineups of top comedians at Timothy O'Toole's Pub in Chicago. Great for comedy lovers and casual nights out.

Thursday, Oct 1

Hush Hush Stand Up Comedy Show

The Lincoln Lodge

Enjoy an intimate stand-up comedy showcase featuring headliners and local favorites at The Lincoln Lodge. Perfect for comedy fans.

Thursday, Oct 1

Jasmine Ellis LIVE in Chicago - 09/30/26

The Lincoln Lodge

Catch Jasmine Ellis performing standup comedy for one night only at The Lincoln Lodge. A night of laughter awaits.

Thursday, Oct 1

Late Night Concert Series w/Kevin Nabors Jr.

Andy's Jazz Club & Restaurant

Join Kevin Nabors Jr. for a late-night jazz concert at Andy's Jazz Club. Ideal for jazz lovers and night owls.

Thursday, Oct 1

Spotlight On: Alfonso Ponticelli

Winter's Jazz Club

Experience an intimate performance by guitarist Alfonso Ponticelli, featuring an onstage interview with Howard Reich. Ideal for jazz enthusiasts.

Friday, Oct 2

Latina Comedy Festival Presents: The Lots of Locas Show

The Lincoln Lodge

Experience wild and hilarious performances by top Latina comics at The Lots of Locas Show. A night of laughter and fun.

Friday, Oct 2

Steelers at Cleveland Browns Game Day — Thursday Night Football

Hopsmith Chicago

Watch Steelers vs Browns on Thursday Night Football at Hopsmith Tavern. A great atmosphere for sports fans.

Friday, Oct 2

Latina Comedy Festival Presents: The Cabronas Show

The Lincoln Lodge

Experience raw and unfiltered comedy at The Cabronas Show featuring bold Latina comics. A night of laughter and truth.

Friday, Oct 2

Insecure: The 10th Anniversary Tour

The Chicago Theatre

Join Issa Rae for Insecure: The 10th Anniversary Tour at The Chicago Theatre. A special event for fans of the series.

Friday, Oct 2

Thursday Night Stand Up Comedy

Laugh Factory

Catch the latest talent at Thursday Night Stand Up Comedy. A fun night for comedy enthusiasts.

Friday, Oct 2

Latina Comedy Festival Presents: The Chingonas Show

The Lincoln Lodge

Experience bold Latina comedians at The Chingonas Show, featuring sharp punchlines and nonstop laughs.

Friday, Oct 2

SONIC SOUL

Buddy Guy's Legends

Join SONIC SOUL for an electrifying night of music at Buddy Guy's Legends. Perfect for jazz and blues enthusiasts.