Things to do in Chicago

Sunday, Oct 25

John Primer & The Real Deal Blues Band

Rosa's Lounge

Join us for a night of blues with John Primer & The Real Deal at Rosa's Lounge. Perfect for blues enthusiasts and late-night music lovers.

Sunday, Oct 25

Joke Sistas Chicago

The Lincoln Lodge

Laugh out loud with the funniest women in comedy at The Lincoln Lodge. Perfect for comedy lovers looking for a fun night out.

Sunday, Oct 25

House of Improv

UP Comedy Club

Enjoy a showcase of top improv teams at UP Comedy Club. A fun night for comedy lovers in Chicago.

Sunday, Oct 25

Uncensored Comedy - Chicago’s most unfiltered late night comedy show

The Lincoln Lodge

Uncensored Comedy features touring stand-up comics sharing their wildest material. Perfect for those who enjoy unfiltered humor.

Sunday, Oct 25

Nightmoves

The California Clipper

Join residents Ross Kelly & Jesse Sandwich for a night of House, Boogie, Funk, and more at The California Clipper.

Sunday, Oct 25

John Primer & The Real Deal Blues Band

Rosa's Lounge

Enjoy a night of blues music with John Primer and his band at Rosa's Lounge. Ideal for blues lovers and late-night music fans.

Sunday, Oct 25

blackhawks at united center

Kaiser Tiger

Catch the Blackhawks game with a complimentary shuttle service from Kaiser Tiger. Perfect for sports fans looking for an easy game day experience.

Sunday, Oct 25

Sunday Brunch Stand Up Comedy

Laugh Factory

Enjoy a fun Sunday brunch with stand up comedy at Laugh Factory. Ideal for comedy lovers.

Sunday, Oct 25

Old Town School's Blues Band showcase

Rosa's Lounge

Experience a showcase of blues music from Old Town School students. Great for music lovers and fans of blues.

Sunday, Oct 25

Bobbi Wilsyn & Company - The Divine One: Sassy Miss Sarah Vaughan

Winter's Jazz Club

Enjoy an evening of jazz with Bobbi Wilsyn and her talented ensemble at Winter's Jazz Club. Perfect for jazz enthusiasts.

Sunday, Oct 25

Wild and Sublime LIVE in Chicago - EIGHTH ANNIVERSARY SHOW 10/25/26

The Lincoln Lodge

Celebrate eight years of Wild & Sublime with a night of sex-positive comedy and storytelling in Chicago.

Monday, Oct 26

CYNTHIA & FRIENDS

RED ROOM Comedy Club

Enjoy a night of laughter at the RED ROOM Comedy Club with the Cynthia & Friends comedy showcase.

Monday, Oct 26

Brett Goldstein

The Chicago Theatre

See Brett Goldstein's Sex, Death & Small Talk Tour at The Chicago Theatre. A must for comedy fans.

Monday, Oct 26

SUNDAY OCTOBER 25: CHICAGO'S BEST COMEDY SHOW

The Comedy Bar

Join top comedians for a night of laughs and pizza at The Comedy Bar. Perfect for comedy fans looking for a fun night out.

Monday, Oct 26

Lauren Hall

Redhead Piano Bar

Enjoy an evening of live music with Lauren Hall at The Redhead Piano Bar in Chicago. Perfect for jazz and soul music lovers.

Monday, Oct 26

Baddieville's Got Talent: Standup, Drag, Music & More

The Lincoln Lodge

Chicago's wildest talent show featuring standup, drag, and live music at The Lincoln Lodge. A unique experience.

Monday, Oct 26

Cole de Genova

The California Clipper

Enjoy live jazz and blues with Cole de Genova at The California Clipper in Chicago.

Tuesday, Oct 27

MONDAY OCTOBER 26: LATE NITE MIC WITH VIK PANDYA

The Comedy Bar

Enjoy a night of comedy hosted by Vik Pandya with special guests and an open mic. Perfect for comedy fans and aspiring comedians.

Tuesday, Oct 27

An Evening with Tedeschi Trucks Band

The Chicago Theatre

Experience the Future Soul Tour with Tedeschi Trucks Band at The Chicago Theatre. A must-see for live music fans.

Wednesday, Oct 28

TUESDAY OCTOBER 27: GUY'Z NITE COMEDY SHOW

The Comedy Bar

Join Guy Reuven for a night of comedy featuring surprise headliners at The Comedy Bar in Chicago.

Wednesday, Oct 28

Halloween Singo - Music Bingo!

Timothy O'Toole's Pub Chicago

Join Halloween SINGO Music Bingo at Timothy O'Toole's Pub for a fun twist on bingo. A festive night for music lovers and bingo fans.

Thursday, Oct 29

Father Mike Schmitz

The Chicago Theatre

See Father Mike Schmitz for Parables: A Time of Reflection at The Chicago Theatre. Ideal for those interested in inspirational talks.

Thursday, Oct 29

WEDNESDAY OCTOBER 28: CHICAGO'S BEST COMEDY SHOW

The Comedy Bar

Experience an interactive stand-up show at Crowd Work Wednesday, hosted by Pat Bolduc & John Gasper at The Comedy Bar.

Thursday, Oct 29

Noir at the Bar

ERIS Brewery and Cider House

Join local authors for a thrilling night of crime novels at ERIS Brewery and Cider House. A unique literary experience.

Thursday, Oct 29

Who All Gone Be There…. AGAIN?!

The Lincoln Lodge

Join Jillian for a live taping of her stand-up special at The Lincoln Lodge. Great for fans of comedy and live performances.

Thursday, Oct 29

The Bootleggers

Broken Hearts

Join The Bootleggers for a lively night of country music at Broken Hearts in Chicago.

Thursday, Oct 29

Class! With Sara Benincasa & Chad the Bird

The Lincoln Lodge

Enjoy a night of mildly educated comedy with Sara Benincasa and Chad the Bird at The Lincoln Lodge in Chicago.

Thursday, Oct 29

Italoween

The California Clipper

Celebrate Italoween with Nolia & Pen Pals, featuring Italo Disco and more. A great night for dance music fans.

Thursday, Oct 29

Nate Manos Band – Pro-Jam

Rosa's Lounge

Join Nate Manos Band for a late-night blues jam session featuring special guests at Rosa's Lounge in Chicago.

Thursday, Oct 29

Nate Manos Band – Pro-Jam

Rosa's Lounge

Join Nate Manos Band for a late-night blues jam session featuring special guests at Rosa's Lounge in Chicago.