Things to do this weekend in Chicago

Saturday, Oct 3

Latina Comedy Festival Presents: The Buenotas Show

The Lincoln Lodge

Enjoy a night of bold laughs with confident comics at this comedy festival. Great for fans of diverse comedy.

Saturday, Oct 3

Diamondback

Broken Hearts

Experience a night of country and pop music with Diamondback at Broken Hearts in Chicago.

Saturday, Oct 3

FRIDAY OCTOBER 2: CHICAGO'S BEST COMEDY SHOW

The Comedy Bar

Join Chicago's best comedians for a night of stand-up and pizza at The Comedy Bar. Enjoy nonstop laughs in Streeterville.

Saturday, Oct 3

LIL ED

Buddy Guy's Legends

Join LIL ED for a night of electrifying music at Buddy Guy's Legends. Perfect for blues and jazz fans.

Saturday, Oct 3

Friday Night Fever Comedy Showcase

The Lincoln Lodge

Experience Chicago's hottest comedy show at The Lincoln Lodge, featuring a lineup of talented comedians.

Saturday, Oct 3

LowKey Funny Standup Comedy

Laugh Factory

Join us for a night of diverse stand-up comedy from local talents. Great for all comedy fans.

Saturday, Oct 3

Stephen Hull Experience

Rosa's Lounge

Join the Stephen Hull Experience for a night of blues and jazz at Rosa's Lounge in Chicago.

Saturday, Oct 3

BENDER

The Newport Theater

Join us for BENDER, an artistic exploration of gender and self at The Newport Theater. Perfect for those interested in diverse performances.

Saturday, Oct 3

Blackout Diaries

The Lincoln Lodge

Laugh along with comedians and regular folks sharing true drinking stories at Blackout Diaries. Great for comedy lovers.

Saturday, Oct 3

Late Night Concert Series w/Thaddeus Tukes

Andy's Jazz Club & Restaurant

Enjoy a late night concert featuring Thaddeus Tukes at Andy's Jazz Club. A great event for jazz lovers.

Saturday, Oct 3

Stephen Hull Experience

Rosa's Lounge

Experience a late-night blues set with the Stephen Hull Experience at Rosa's Lounge in Chicago.

Saturday, Oct 3

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, Oct 3

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, Oct 3

Ohio State Buckeyes at Iowa Game Day

Woodie's Flat

Watch the Ohio State game at Woodie's Flat with drink specials. Perfect for sports fans.

Saturday, Oct 3

Michigan State Spartans Football at Wisconsin

Hopsmith Chicago

Join fellow fans at Hopsmith in Chicago for the Michigan State Spartans football game. A great atmosphere for sports enthusiasts.

Saturday, Oct 3

Oktoberfest

The Boss Bar

Join us for an epic Oktoberfest celebration with food and drinks at The Boss Bar. Great for beer lovers.

Saturday, Oct 3

Standup Seminary // SATURDAYS // Oct 3-Nov 7

The Lincoln Lodge

Enroll in Standup Seminary for a foundation course in standup comedy. Ideal for new comedians.

Saturday, Oct 3

Ohio State Buckeyes at Iowa Game Day

Woodie's Flat

Join fellow fans for Ohio State football at Woodie's Flat with drink specials and great wings. Ideal for Buckeyes supporters.

Saturday, Oct 3

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, 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.