Things to do in Chicago

Thursday, Sep 24

Willie Buck: A Chicago Blues Legend

Rosa's Lounge

Experience the Chicago blues legend Willie Buck live at Rosa's Lounge. A must-see for blues music fans.

Thursday, Sep 24

Willie Buck: A Chicago Blues Legend

Rosa's Lounge

Experience a night of Chicago blues with Willie Buck. Perfect for blues enthusiasts and live music lovers.

Thursday, Sep 24

Dario

Redhead Piano Bar

Enjoy an electrifying night with Dario at the Redhead Piano Bar. Perfect for late-night music lovers.

Thursday, Sep 24

Late Night Concert Series w/Marion Mallard

Andy's Jazz Club & Restaurant

Enjoy a late night concert featuring Marion Mallard at Andy's Jazz Club. Perfect for jazz lovers.

Thursday, Sep 24

2nd Set With Mario Abney

Andy's Jazz Club & Restaurant

Join the second set with Mario Abney at Andy's Jazz Club. Perfect for jazz enthusiasts.

Thursday, Sep 24

1st Set With Mario Abney

Andy's Jazz Club & Restaurant

Catch the first set featuring Mario Abney at Andy's Jazz Club. A must for jazz lovers.

Thursday, Sep 24

Sheryl Youngblood Band’s All-Music Jam Night

Rosa's Lounge

Join the Sheryl Youngblood Band for a lively jam session featuring blues, R&B, and more. Perfect for musicians and music fans alike.

Thursday, Sep 24

Thursday Drink Special: 1/2 Price Bottles & Carafes of Wine

Hopsmith Chicago

Thursdays are for wine lovers with half-price bottles and carafes. Perfect for unwinding after a long week.

Thursday, Sep 24

Trivia on the Lake

Navy Pier

Join Navy Pier for a summer-long trivia competition every Thursday evening. Perfect for trivia lovers and friends.

Thursday, Sep 24

Chicago White Sox at Kansas City Royals

Fatpour McCormick: Ultimate Chicago Sports Bar

Watch the White Sox take on the Royals at Fatpour Tap Works. A great spot for sports fans to enjoy the game.

Thursday, Sep 24

Miami Marlins at Chicago Cubs

Fatpour McCormick: Ultimate Chicago Sports Bar

Catch the Marlins vs. Cubs game at Fatpour Tap Works. Perfect for baseball fans looking for a great game day atmosphere.

Thursday, Sep 24

Happy Hour in Gold Coast at Hopsmith

Hopsmith Chicago

Enjoy daily drink specials and Happy Hour at Hopsmith. A great spot for after-work relaxation and socializing.

Thursday, Sep 24

Happy Hour

Woodie's Flat

Join us for Happy Hour at Woodie's Flat with drink and food specials. A great spot for sports fans and a fun night out.

Thursday, Sep 24

Thursday Specials: $5 House Tequila Shots and 1/2 Price Bottles of Wine

Fatpour McCormick: Ultimate Chicago Sports Bar

Enjoy $5 tequila shots and half-price wine bottles at Fatpour. A budget-friendly midweek treat.

Thursday, Sep 24

Washington Mystics vs. Chicago Sky

Fatpour McCormick: Ultimate Chicago Sports Bar

Watch the WNBA game between the Chicago Sky and Washington Mystics at Fatpour. Ideal for sports fans.

Thursday, Sep 24

Vibe Thursday - September 24, 2026

ROOF on theWit

Experience Vibe Thursday with DJs and an electrifying atmosphere high above the Chicago Loop.

Thursday, Sep 24

Dungeons & Dragons 18+

ERIS Brewery and Cider House

Join a weekly D&D session at ERIS Brewery for new and experienced players. A great way to immerse in fantasy gaming.

Thursday, Sep 24

Zachary Finnegan’s Timeless Quintet

Winter's Jazz Club

Enjoy a jazz performance by Zachary Finnegan's Timeless Quintet at Winter's Jazz Club in Chicago. A treat for jazz lovers.

Friday, Sep 25

Chicago Comedy Hour

The Second City

Experience the Chicago Comedy Hour at The Second City, featuring up-and-coming comedians in a variety show format.

Friday, Sep 25

Chicago Comedy Hour

The Second City Training Center

Experience a variety show of sketch, improv, and stand-up at The Second City. Perfect for comedy fans.

Friday, Sep 25

The Future of Comedy Showcase

The Lincoln Lodge

Catch the nation's longest running independent stand-up comedy showcase featuring up-and-coming talent at The Lincoln Lodge.

Friday, Sep 25

The Thursday Show: Chicago's Funniest Comedians with New Jokes!

The Lincoln Lodge

Catch Chicago's best touring comics testing new material at The Lincoln Lodge. Ideal for comedy enthusiasts.

Friday, Sep 25

The Uncanny Attic: Chapters I-L

The Newport Theater

Experience a dark comedy sequel through puppetry and live music at The Newport Theater. Perfect for theater enthusiasts.

Friday, Sep 25

Trickery Chicago Magic Show

Trickery

Experience Chicago's most entertaining magic show at Trickery. A great night out for magic enthusiasts and families alike.

Friday, Sep 25

Coached Ensembles

The Second City

Experience interactive improv with Coached Ensembles at The Second City. A night of laughter and creativity.

Friday, Sep 25

Bingeable: An Original Spin-off!

The Second City Training Center

Join us for a unique comedy show that creates a spin-off of your favorite comfort show. Ideal for comedy fans.

Friday, Sep 25

MICROFONO ABIERTO

RED ROOM Comedy Club

Join us for MICROFONO ABIERTO at RED ROOM Comedy Club in Chicago. A great opportunity for aspiring comedians and comedy fans.

Friday, Sep 25

Bingeable: An Original Spin-off!

UP Comedy Club

Join a hilarious show where audience ideas inspire a new spin-off episode. Great for comedy lovers and fans of improvisation.

Friday, Sep 25

Bingeable: An Original Spin-off!

The Second City

Enjoy a unique comedy show where audience suggestions create a new spin-off episode. Perfect for fans of improv and comedy.

Friday, Sep 25

All Star Comedy

Laugh Factory

Catch emerging comedians at the Thursday Night Stand Up Comedy show at Laugh Factory. Perfect for comedy fans.