Things to do in Chicago

Thursday, Oct 22

24 Hours to Sketch Show

The Second City

Catch the 24 Hours to Sketch Show featuring original sketches by talented students. A great night of laughter and creativity awaits comedy fans.

Thursday, Oct 22

Rosa's Blues Jam hosted by David Levit

Rosa's Lounge

Join Rosa's Blues Jam hosted by David Levit for a night of live blues music. Perfect for blues fans looking for a lively atmosphere.

Thursday, Oct 22

Rosa's Blues Jam hosted by David Levit

Rosa's Lounge

Join Rosa's Blues Jam hosted by David Levit for a night of live blues music. Perfect for blues fans looking for a lively atmosphere.

Friday, Oct 23

Open Books & Laugh: A Standup Comedy Show for Literacy

Laugh Factory

Enjoy a night of stand-up comedy supporting literacy at Open Books & Laugh. Great for comedy fans and supporters of a good cause.

Friday, Oct 23

THURSDAY OCTOBER 22: OHJAY LAMONT & FRIENDS

The Comedy Bar

Laugh along with OhJay Lamont and friends at The Comedy Bar for a night of comedy off the Magnificent Mile.

Friday, Oct 23

Clued In Presents: Travel Can Be Murder

UP Comedy Club

Join the interactive improvised murder mystery at UP Comedy Club, inspired by classic detective stories.

Friday, Oct 23

Clued In Presents: Travel Can Be Murder

The Second City

Experience an improvised murder mystery at Second City’s UP Comedy Theatre. Engage with the cast and enjoy a unique show.

Friday, Oct 23

NATAN BADALOV presents: Community Service

RED ROOM Comedy Club

Join Natan Badalov for a night of edgy comedy at RED ROOM Comedy Club. Perfect for those who enjoy fresh talent.

Friday, Oct 23

Clued In Presents: Travel Can Be Murder

The Second City Training Center

Experience an improvised murder mystery inspired by Agatha Christie at The Second City. Perfect for mystery fans and comedy lovers.

Friday, Oct 23

Oscar Aydin is Dramatically Annoyed

The Lincoln Lodge

Catch Oscar Aydin, a vibrant comedian from New York, as he shares his humorous rants in Chicago.

Friday, Oct 23

My Best Friend Is Black Show

The Lincoln Lodge

Experience an all-Black live comedy variety show celebrating Blackness at The Lincoln Lodge in Chicago.

Friday, Oct 23

LIZ MANDEVILLE

Buddy Guy's Legends

Enjoy a night of live music featuring Liz Mandeville and an acoustic set by Matt Hendricks. Perfect for blues and jazz fans.

Friday, Oct 23

blackhawks at united center

Kaiser Tiger

Take advantage of the complimentary shuttle service to the United Center for the Blackhawks game.

Saturday, Oct 24

Nightmare at the Newport Pole Show

The Newport Theater

Experience a spooky pole show presented by Dahlia Dime and La Amazonian at The Newport Theater.

Saturday, Oct 24

Houston Dash at Chicago Stars FC

Fatpour McCormick: Ultimate Chicago Sports Bar

Catch the exciting match between Houston Dash and Chicago Stars at Fatpour Tap Works. Perfect for sports fans.

Saturday, Oct 24

FRIDAY OCTOBER 23: ZAR THE STAR

The Comedy Bar

Zar the Star headlines a comedy night at The Comedy Bar. Enjoy laughs and deep-dish pizza with friends.

Saturday, Oct 24

Ellen Harrold Headlines ONE NIGHT ONLY 10/23/26

The Lincoln Lodge

Comedian Ellen Harrold performs live at The Lincoln Lodge in Chicago for one night only.

Saturday, Oct 24

Trauma Dumping: A Hilarious Comedy Show!

The Lincoln Lodge

Enjoy a night of humor as top comedians share their worst experiences at The Lincoln Lodge in Chicago. Ideal for comedy lovers.

Saturday, Oct 24

AVERAGE JOEY

RED ROOM Comedy Club

Enjoy a night of laughs with AVERAGE JOEY at RED ROOM Comedy Club. Ideal for comedy lovers looking for something new.

Saturday, Oct 24

I Said What I Said: A Reality TV-Themed Comedy Show

The Lincoln Lodge

Experience a night of laughter with reality TV-themed comedy at The Lincoln Lodge in Chicago. Perfect for comedy fans.

Saturday, Oct 24

RAY FULLER

Buddy Guy's Legends

Enjoy live music from Ray Fuller at Buddy Guy's Legends. A great night for blues and jazz fans.

Saturday, Oct 24

FRIDAY OCTOBER 23: ZAR THE STAR

The Comedy Bar

Zar the Star brings laughs to The Comedy Bar. Join for a night of comedy and delicious deep-dish pizza.

Saturday, Oct 24

The Regulars

The Lincoln Lodge

Experience a unique candle-lit comedy show with The Regulars at The Lincoln Lodge. Ideal for comedy lovers.

Saturday, Oct 24

The Dollz Spectra (presented by Showdoll Heaux-ductions): OCTOBER 23

The Newport Theater

Experience a captivating burlesque performance at The Newport Theater, featuring Lady Ve'Lush and more.

Saturday, Oct 24

Wyatt Feegrado and Luke Abranches: The Sibling Rivalry Tour 10/23/26

The Lincoln Lodge

Enjoy a night of standup comedy with independent comedians Wyatt Feegrado and Luke Abranches in Chicago.

Sunday, Oct 25

History Shmistory

The Lincoln Lodge

Enjoy stand-up comics performing as historical figures in costume. A unique comedy experience for history buffs and comedy fans.

Sunday, Oct 25

SATURDAY OCTOBER 24: ZAR THE STAR

The Comedy Bar

Enjoy a night of laughs with Zar The Star at The Comedy Bar. A fun event for comedy lovers and fans of live performances.

Sunday, Oct 25

COREY DENNISON

Buddy Guy's Legends

Enjoy a night of jazz and blues with Corey Dennison at Buddy Guy's Legends. A vibrant evening for music lovers in Chicago.

Sunday, Oct 25

Brown Suga BackShots - A NEW BIPOC BURLESQUE COMP

The Newport Theater

Witness Chicago's premier all-BIPOC burlesque competition, Brown Suga BackShots, featuring talented artists from across the US.

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.