Things to do in Chicago

Sunday, Sep 27

BLEED LOCAL | Blood Drive & Open Mic

RED ROOM Comedy Club

Participate in the BLEED LOCAL blood drive and open mic event at RED ROOM Comedy Club in Chicago.

Sunday, Sep 27

Trickery Chicago Magic Show

Trickery

Experience Chicago's most entertaining magic show at Trickery. A fun night out for magic enthusiasts and comedy lovers.

Sunday, Sep 27

Spider Saloff Quintet - Chet Baker: The Cool Jazz of the 50’s

Winter's Jazz Club

Spider Saloff - vocals; Pete Benson - piano; Art Davis - trumpet; Rob Kassinger - bass; Alex Hall - drums

Sunday, Sep 27

The Future of Comedy Showcase

The Lincoln Lodge

Enjoy a special comedy showcase featuring Chicago's up-and-coming talent at The Lincoln Lodge.

Sunday, Sep 27

Hot 5 Comedy Show

The Lincoln Lodge

Laugh with five of Chicago's hottest comedians at this entertaining comedy show.

Sunday, Sep 27

1st Set With Russ Phillips Quartet

Andy's Jazz Club & Restaurant

Experience the Russ Phillips Quartet at Andy's Jazz Club for an evening of jazz music in a cozy setting.

Sunday, Sep 27

SUNDAY SEPTEMBER 27: JAY WASHINGTON

The Comedy Bar

Comedian Jay Washington headlines a weekend of laughs at The Comedy Bar in Chicago.

Monday, Sep 28

WGCI comedy showcase: new name same vibe!

Laugh Factory

Enjoy laughs at the WGCI Comedy Showcase, featuring a lineup of comedians in Chicago. A fun night for comedy enthusiasts.

Monday, Sep 28

Edie Arnold is a Loser

UP Comedy Club

Watch Edie Arnold is a Loser, a fast-paced comedy about a punk band of misfits. Ideal for fans of irreverent theater in Chicago.

Monday, Sep 28

Edie Arnold is a Loser

The Second City

Experience Edie Arnold is a Loser, a fast-paced comedy show at The Second City in Chicago. Ideal for fans of irreverent theater.

Monday, Sep 28

Sunday Night Stand Up Comedy

Laugh Factory

Catch up-and-coming comedians at Laugh Factory in Chicago. A fun night for comedy enthusiasts.

Monday, Sep 28

Edie Arnold is a Loser

The Second City Training Center

Catch Edie Arnold is a Loser, an irreverent comedy about a punk band, at The Second City in Chicago. A must-see for theater fans.

Monday, Sep 28

Jeopardy Bar League

Trader Todd's

Join the Jeopardy Bar League for a fun trivia night at Trader Todd's. Ideal for quiz enthusiasts.

Monday, Sep 28

Sunday Best

The Lincoln Lodge

Enjoy a 90-minute showcase featuring top Chicago comedians. A great way to spend a Sunday evening with laughter and fun.

Monday, Sep 28

Comedians That Are Gay

The Lincoln Lodge

Experience a comedy show featuring talented queer comedians. A must-see event for comedy lovers in Chicago.

Monday, Sep 28

Who’s Waldo?

The Lincoln Lodge

Enjoy a comedy variety show where everyone is Waldo at The Lincoln Lodge. A night of laughs and surprises.

Monday, Sep 28

Sara Bareilles

The Chicago Theatre

See Sara Bareilles perform live at The Chicago Theatre as part of The Good Grief Tour. A must for pop music fans.

Monday, Sep 28

2nd Set With Russ Phillips Quartet

Andy's Jazz Club & Restaurant

Experience live jazz with the Russ Phillips Quartet at Andy's Jazz Club. A perfect night for jazz lovers.

Monday, Sep 28

SUNDAY SEPTEMBER 27: MIKE SAMP

The Comedy Bar

Enjoy a night of laughs with Mike Samp headlining at The Comedy Bar, a great spot for comedy lovers in Chicago.

Monday, Sep 28

C Mikhail & Reckless Darling - Live

Skylark

Enjoy a live performance by C Mikhail and Reckless Darling at Skylark. A blend of unique musical styles awaits.

Monday, Sep 28

Surfin' Bird - Live

Skylark

Enjoy Surfin' Bird at Skylark, a lively music event capturing summer vibes. Perfect for those wanting a fun night out in Chicago.

Monday, Sep 28

NICHOLAS ALEXANDER

Buddy Guy's Legends

Enjoy a night of live music featuring Nicholas Alexander and a jazz set by Lynn Hilton at Buddy Guy's Legends in Chicago.

Monday, Sep 28

Sunday Night Stand Up Comedy

Laugh Factory

Enjoy a night of comedy at Laugh Factory in Chicago. A great way to unwind and laugh.

Monday, Sep 28

Humboldt Aboreal - HAFters

The California Clipper

Enjoy a night of music with the Humboldt Arboreal DJs at The California Clipper. Perfect for fans of house and disco music.

Monday, Sep 28

Too Gold // Garry Princeton & the Flyover Country

Broken Hearts

Join us for a night of country rock with Too Gold and Garry Princeton at Broken Hearts Bar in Chicago.

Monday, Sep 28

Late Night Concert Series w/Andrew Toombs

Andy's Jazz Club & Restaurant

Enjoy a late-night concert featuring Andrew Toombs in a cozy jazz club. Ideal for jazz lovers and night owls.

Monday, Sep 28

Jeremy Bell

Redhead Piano Bar

Experience an exciting night with Jeremy Bell at the Redhead Piano Bar, perfect for late-night entertainment.

Monday, Sep 28

Emily Popli

Redhead Piano Bar

Join Emily Popli for a late-night performance at The Redhead Piano Bar in Chicago, featuring captivating music.

Monday, Sep 28

Tony Hays

Redhead Piano Bar

Join us for an electrifying night with Tony Hays at The Redhead Piano Bar, filled with great music and drinks.

Monday, Sep 28

Sundays and Mondays - Open for Special Events Only

Rosa's Lounge

Rosa's Lounge is open for special events on Sundays and Mondays. Contact us for event inquiries.