Things to do in Chicago

Monday, Oct 19

Tales from the $trip

The Newport Theater

Enjoy true stories told by $trippers at The Newport Theater in Chicago.

Monday, Oct 19

Dyke Country

The Lincoln Lodge

Enjoy a comedy show featuring Lee Robinson & Kate Strobel at The Lincoln Lodge. A fun night for comedy fans.

Monday, Oct 19

Marital Bed & Chris Coleslaw Band - Live

Skylark

Enjoy a night of unique live music with Marital Bed and Chris Coleslaw Band. Ideal for fans of quirky and post-punk sounds.

Monday, Oct 19

ELEVATION BAND – LITTLE WALTER FOUNDATION

Buddy Guy's Legends

Join the Elevation Band for a lively performance supporting the Little Walter Foundation. Great for blues and jazz lovers.

Monday, Oct 19

Sips x Z Bar - October 19

Z Bar

Join Sips at Z Bar for a curated cocktail evening. Ideal for cocktail enthusiasts and social gatherings.

Tuesday, Oct 20

MONDAY OCTOBER 19: LATE NITE MIC WITH VIK PANDYA

The Comedy Bar

Join Vik Pandya for a night of comedy at The Comedy Bar. Enjoy laughs and a free open mic session afterwards.

Tuesday, Oct 20

Breast in Show 8

The Newport Theater

Support breast cancer survivors at Breast in Show 8, a burlesque event raising funds for charity at The Newport Theater.

Wednesday, Oct 21

TUESDAY OCTOBER 20: TOMATO THROW SHOW

The Comedy Bar

Experience the interactive Tomato Throw Show at The Comedy Bar. Audience participation makes it a unique comedy night.

Wednesday, Oct 21

The Counterpoint Theatre Launch Party

The Newport Theater

Join the cabaret fundraiser for the launch of The Counterpoint Theatre. Perfect for arts enthusiasts and community supporters.

Wednesday, Oct 21

Ghouls Night Out Paint & Sip!

Timothy O'Toole's Pub Chicago

Enjoy a fun paint and sip night with art supplies included and themed drinks. A great evening for friends or date night.

Wednesday, Oct 21

A Chillingly Chic Pumpkin Paint Night

ERIS Brewery and Cider House

Join us for a fun pumpkin painting night at ERIS Brewery and Cider House. A creative evening with friends awaits.

Wednesday, Oct 21

Alex Austin Trio with guest vocalist Abigail Riccards

Winter's Jazz Club

Experience live jazz with the Alex Austin Trio featuring guest vocalist Abigail Riccards. A night for jazz lovers.

Thursday, Oct 22

24 Hours to Sketch Show

The Second City Training Center

Watch talented students perform original sketches in just 24 hours at Donny's Skybox Theater. A night of laughter awaits.

Thursday, Oct 22

24 Hours to Sketch Show

UP Comedy Club

Experience the 24 Hours to Sketch Show with fresh comedic content by aspiring comedians. Ideal for those who enjoy innovative and funny performances.

Thursday, Oct 22

WEDNESDAY OCTOBER 21: CHICAGO'S BEST COMEDY SHOW

The Comedy Bar

Enjoy a night of stand-up comedy with Chicago's top comedians and pizza. Perfect for a fun night out.

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

Chicago's Late Night Talk Show: The Not That Late Show

The Lincoln Lodge

Catch Chicago's Not That Late Show for comedy and live performances. A fun night for fans of variety shows and local talent.

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.

Thursday, Oct 22

Eric Jacobson Quintet - A Night in Tunisia: Dizzy Gillespie Birthday Celebration

Winter's Jazz Club

Celebrate Dizzy Gillespie's birthday with the Eric Jacobson Quintet performing a night of jazz.

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

Jenny & Brad

Redhead Piano Bar

Join Jenny & Brad for an evening of live music in a lively atmosphere, perfect for a night out.

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

Oliver Scott Ensemble

The California Clipper

Enjoy a night of live jazz music with the Oliver Scott Ensemble. Ideal for jazz lovers and music enthusiasts.