Things to do in Chicago

Sunday, Oct 25

SATURDAY OCTOBER 24: ZAR THE STAR

The Comedy Bar

Join Zar The Star for a night of comedy and deep-dish pizza at The Comedy Bar. Ideal for fans of live comedy shows.

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

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

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

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.

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.

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: CROWD WORK WEDNESDAY

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

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.

Thursday, Oct 29

Jam Sandwich

UP Comedy Club

Enjoy a night of spontaneous improv comedy at The Second City with Jam Sandwich. A fun experience for comedy lovers.

Thursday, Oct 29

From Lava to Vine: A Volcanic Wine Dinner

The Village

Explore volcanic wines with a curated dinner at The Village. Perfect for wine enthusiasts and food lovers.

Friday, Oct 30

Lev Fer ONE NIGHT ONLY

The Lincoln Lodge

Enjoy a night of hilarious standup comedy with Lev Fer at The Lincoln Lodge. A great option for comedy fans.

Friday, Oct 30

THURSDAY OCTOBER 29: OHJAY LAMONT & FRIENDS

The Comedy Bar

Enjoy a night of laughs with OhJay Lamont and friends at The Comedy Bar, a must-see comedy event in Chicago.

Friday, Oct 30

Exotic Erotic presented by Gender F*cked Productions and KazMo Universe

The Newport Theater

Celebrate culture and community through burlesque and performance art at Exotic Erotic in Chicago. A unique night of entertainment.

Friday, Oct 30

Brew Comedy: New Material Night

Laugh Factory

Catch new material from comedians at Brew Comedy night at Laugh Factory. Ideal for comedy enthusiasts.

Friday, Oct 30

NIGEL MACK

Buddy Guy's Legends

Experience an electrifying performance by Nigel Mack at Buddy Guy's Legends. A great night for live music enthusiasts.