Things to do in Chicago

Saturday, Sep 26

Laughter Hours: Late Night Jazzy-Themed Comedy Show

The Lincoln Lodge

Experience a late-night jazzy-themed comedy show featuring top comedians and live jazz at The Lincoln Lodge.

Saturday, Sep 26

Rocket Force Comedy - September Edition

Laugh Factory

Enjoy a late-night comedy lineup at Laugh Factory Chicago. Perfect for comedy lovers seeking a good laugh.

Saturday, Sep 26

Chris Heroldt

Redhead Piano Bar

Catch Chris Heroldt live at Redhead Piano Bar for a late-night performance filled with great music and drinks.

Saturday, Sep 26

Saturday Drink Special: Bottomless Bloody Marys, Bud LIght, Or Mimosas

Woodie's Flat

Enjoy bottomless Bloody Marys, Bud Light, or mimosas during our Saturday special. Perfect for a leisurely weekend.

Saturday, Sep 26

Newport Theater Camp - Fall/Winter Classes 2026

The Newport Theater

Explore classes in burlesque, bellydance, comedy, and more at Newport Theater Camp this fall.

Saturday, Sep 26

Ohio State Buckeyes vs Illinois Game Day

Woodie's Flat

Watch Ohio State take on Illinois at Woodie's Flat with drink specials and wings. A must for Buckeyes fans.

Saturday, Sep 26

Michigan State Spartans Football vs Nebraska

Hopsmith Chicago

Watch the Michigan State Spartans take on Nebraska at Hopsmith Chicago. Perfect for sports fans and game day gatherings.

Saturday, Sep 26

CHAOS Oktoberfest

CHAOS Brew Club

Join a unique Oktoberfest with German beers, food, and fun activities. A great outing for beer enthusiasts and festival lovers.

Saturday, Sep 26

Live on the Lake

Navy Pier

Experience outdoor live music featuring top bands at Navy Pier. Enjoy a variety of genres with friends by the lakeside.

Saturday, Sep 26

blackhawks at united center (preseason)

Kaiser Tiger

Catch the Blackhawks preseason game with a complimentary shuttle to the United Center from Kaiser Tiger. A fun outing for sports fans.

Saturday, Sep 26

Keep Coming Back

The Lincoln Lodge

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

Saturday, Sep 26

Ryan Paradise Sep 26

ROOF on theWit

Experience an electrifying night with DJ Ryan Paradise at ROOF on theWit. Enjoy Chicago nightlife with skyline views.

Saturday, Sep 26

Trickery Chicago Magic Show

Trickery

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

Saturday, Sep 26

1st Set With Mallard and Hedez

Andy's Jazz Club & Restaurant

Enjoy a night of jazz with Mallard and Hedez at Andy's Jazz Club. Ideal for jazz enthusiasts.

Saturday, Sep 26

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, Sep 26

Colorado Rockies at Chicago White Sox

Fatpour McCormick: Ultimate Chicago Sports Bar

Watch the Rockies face the White Sox at Fatpour Tap Works for an ultimate game day experience.

Saturday, Sep 26

Chicago Cubs at Boston Red Sox

Fatpour McCormick: Ultimate Chicago Sports Bar

Catch the Cubs vs. Red Sox at Fatpour Tap Works for a great sports viewing experience.

Saturday, Sep 26

Chicago Fire FC at Charlotte FC

Fatpour McCormick: Ultimate Chicago Sports Bar

Catch the Chicago Fire FC match against Charlotte FC at Fatpour Tap Works for an exciting sports experience.

Sunday, Sep 27

Menace To Sobriety

The Lincoln Lodge

Enjoy a hilarious comedy show benefiting The Lincoln Lodge, featuring top talent. Perfect for comedy lovers looking for a fun night out.

Sunday, Sep 27

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, Sep 27

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, Sep 27

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, Sep 27

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, Sep 27

Bassem Youssef

The Chicago Theatre

Experience Bassem Youssef's The Belly of The Beast Tour at The Chicago Theatre. Ideal for fans of comedy and live performances.

Sunday, Sep 27

SATURDAY SEPTEMBER 26: CHICAGO'S BEST COMEDY SHOW

The Comedy Bar

Join Chicago's top comedians for a night of stand-up and pizza at The Comedy Bar.

Sunday, Sep 27

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, Sep 27

Powerpoint Night Live!

The Lincoln Lodge

Enjoy an evening of slide-based edutainment at The Lincoln Lodge. Perfect for those looking for a unique and fun night out.

Sunday, Sep 27

Trickery Chicago Magic Show

Trickery

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

Sunday, Sep 27

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, Sep 27

The Future of Comedy Showcase

The Lincoln Lodge

Experience a comedy showcase featuring Chicago's up-and-coming talent. Ideal for comedy fans looking for fresh performances.