Things to do in Chicago

Saturday, Oct 3

Latina Comedy Festival Presents: The Marathon Show

The Lincoln Lodge

Experience fast and funny comedy with tight 5-minute sets from various comics. Perfect for comedy lovers looking for a lively night out.

Saturday, Oct 3

Keep Coming Back

The Lincoln Lodge

A comedy variety show focused on recovery themes. Great for those interested in comedy and personal stories.

Saturday, Oct 3

JaxxSway - October 3, 2026

ROOF on theWit

Join JaxxSway for an electrifying night of music and dancing at ROOF on theWit. Ideal for nightlife lovers.

Saturday, Oct 3

Latina Comedy Festival Presents: The Mamacitas Show

The Lincoln Lodge

Enjoy a night of humor from Latina comedian moms sharing relatable stories and laughs. A must-see for fans of diverse comedy.

Saturday, Oct 3

Newport Theater Camp: Winter Act Development Courses

The Newport Theater

Join the Newport Theater Camp to learn and create a burlesque or cabaret act in Chicago.

Saturday, Oct 3

1st Set With The Pamoja Project

Andy's Jazz Club & Restaurant

Experience live jazz with The Pamoja Project at Andy's Jazz Club, perfect for jazz lovers.

Saturday, Oct 3

420 Frankenstein

The Second City Training Center

Experience a unique twist on Mary Shelley's classic with 420 Frankenstein at The Second City Training Center.

Saturday, Oct 3

Latina Comedy Festival Presents: The Lotería Show

The Lincoln Lodge

Join the fun with a comedy/game show that combines laughter and games. Perfect for those seeking a unique entertainment experience.

Saturday, Oct 3

doja cat at united center

Kaiser Tiger

Experience Doja Cat live at the United Center with shuttle service available from Kaiser Tiger.

Saturday, Oct 3

Trickery Chicago Magic Show

Trickery

Experience the most entertaining magic show in Chicago at Trickery. A fun night for magic enthusiasts and families.

Saturday, Oct 3

Hecklers’ Happy Hour Comedy Show

The Lincoln Lodge

Join the Hecklers’ Happy Hour Comedy Show at The Lincoln Lodge for a fun night of comedy in Chicago.

Saturday, Oct 3

420 Frankenstein

The Second City

Experience a unique twist on Mary Shelley's classic with 420 Frankenstein at The Second City.

Saturday, Oct 3

420 Frankenstein

UP Comedy Club

Join the fun with 420 Frankenstein, a comedic take on a classic story at UP Comedy Club.

Sunday, Oct 4

Little Miss Anthropes: All Drag Comedy Showcase

The Lincoln Lodge

Experience a pageant of stand-up drag performers with a rotating theme at The Lincoln Lodge.

Sunday, Oct 4

SATURDAY OCTOBER 3: DAUOOD NAIMYAR

The Comedy Bar

Join us for laughs with headliner Dauood Naimyar at The Comedy Bar. A great night of comedy in Streeterville.

Sunday, Oct 4

Clued In

The Second City Training Center

Enjoy a unique comedy experience where the audience helps solve a mystery. Perfect for fans of interactive theater.

Sunday, Oct 4

Newport Peek-Easy: Burlesque, Drag, and Variety Show

The Newport Theater

Enjoy a weekly cabaret show featuring burlesque, drag, and variety acts. Perfect for fans of arts and culture.

Sunday, Oct 4

Saturday Night Stand Up Comedy

Laugh Factory

Catch up-and-coming comedians at Laugh Factory's Saturday night stand-up. Perfect for comedy lovers.

Sunday, Oct 4

Bill Burr Live

The Chicago Theatre

Catch comedian Bill Burr performing live at The Chicago Theatre on select dates. A must-see for comedy fans.

Sunday, Oct 4

Latina Comedy Festival Presents: The Nenas Show

The Lincoln Lodge

Spotlight on rising Latina comics delivering bold jokes and energy. A great night for comedy fans looking for fresh talent.

Sunday, Oct 4

Latina Comedy Festival Presents: The Señoras Show

The Lincoln Lodge

Enjoy bold and hilarious perspectives from experienced Latina comics. Perfect for those who appreciate diverse comedy styles.

Sunday, Oct 4

Rami Gabriel

The California Clipper

Experience live music with Rami Gabriel at The California Clipper. A night of blues, jazz, and more.

Sunday, Oct 4

RED ROOM COMEDY

RED ROOM Comedy Club

Catch today's hottest up-and-coming comedians at the RED ROOM Comedy Club in Chicago. A great night for comedy lovers.

Sunday, Oct 4

Champian Fulton Trio - Celebrating Billie Holiday and Dinah Washington

Winter's Jazz Club

Enjoy a night of jazz with Champian Fulton and her trio. Perfect for jazz lovers and music enthusiasts.

Sunday, Oct 4

Trickery Chicago Magic Show

Trickery

Experience the most entertaining magic show in Chicago at Trickery. A fun night for magic enthusiasts and families.

Sunday, Oct 4

Latina Comedy Festival Presents: The Meras Meras Show

The Lincoln Lodge

Experience top-tier comedy with a fierce lineup at The Meras Meras Show. Ideal for fans of high-energy performances.

Sunday, Oct 4

Bill Larkin

Redhead Piano Bar

Enjoy an evening of music with Bill Larkin at Redhead Piano Bar. A lively atmosphere for those seeking entertainment and fun.

Sunday, Oct 4

2nd Set With The Pamoja Project

Andy's Jazz Club & Restaurant

Catch The Pamoja Project for a lively jazz performance at Andy's Jazz Club in Chicago. Perfect for jazz lovers.

Sunday, Oct 4

Best of The Second City

The Second City

Experience the best sketch comedy and songs from The Second City. Perfect for fans of comedy and entertainment.

Sunday, Oct 4

Chill AF Presents

The Second City

Enjoy a night of comedy with top Chicago comedians at The Second City. Ideal for comedy lovers and fans of live performances.