Things to do in Streeterville

Wednesday, Sep 23

Bobby Lewis Quintet - 90th Birthday Tour!

Winter's Jazz Club

Experience live jazz with Bobby Lewis and his quintet at Winter's Jazz Club in Chicago. A night of great music awaits.

Wednesday, Sep 23

Abigail Riccards & Friends - A Night of Soul / Jazz / Blues Favorites

Winter's Jazz Club

Experience a night of soul, jazz, and blues with Abigail Riccards and her band. Ideal for jazz enthusiasts.

Thursday, Sep 24

Comedians You Should Know: Chicago's Funniest Stand-Up. No Joke.

Timothy O'Toole's Pub Chicago

Enjoy rotating lineups of top comedians at Timothy O'Toole's Pub in Chicago. Great for comedy lovers and casual nights out.

Thursday, Sep 24

WEDNESDAY SEPTEMBER 23: WHATS FUNNY COMEDY FESTIVAL

The Comedy Bar

Join Chicago's best comedians for a night of stand-up at The Comedy Bar during the What's Funny Comedy Festival.

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

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

THURSDAY SEPTEMBER 24: WHATS FUNNY COMEDY FESTIVAL

The Comedy Bar

Join Chicago's best comedians for a night of stand-up at The Comedy Bar during the What's Funny Comedy Festival.

Friday, Sep 25

Live on the Lake

Navy Pier

Enjoy a weekend of live music by the lake featuring various bands. Great for music fans and outdoor lovers.

Saturday, Sep 26

Chicago Soul Jazz Collective with LaShera Ellis

Winter's Jazz Club

Catch the Chicago Soul Jazz Collective featuring LaShera Ellis at Winter's Jazz Club. A must for jazz enthusiasts.

Saturday, Sep 26

Bosman Twins Quintet

Winter's Jazz Club

Enjoy a night of jazz with the Bosman Twins Quintet at Winter's Jazz Club. Perfect for jazz enthusiasts and live music lovers.

Saturday, Sep 26

Better Together - Music to Move Your Soul!

Winter's Jazz Club

Experience an evening of soulful music with Better Together at Winter's Jazz Club. A perfect night for jazz 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.

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

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

Live on the Lake

Navy Pier

Experience outdoor live music featuring Chicago's best bands at Live on the Lake. Great for music enthusiasts.

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

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

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.

Wednesday, Sep 30

TUESDAY SEPTEMBER 29: TOMATO THROW SHOW

The Comedy Bar

Participate in the interactive Tomato Throw Show at The Comedy Bar, where the audience decides the funniest performer.

Wednesday, Sep 30

Wednesdays Half Price Wine Bottles!

Timothy O'Toole's Pub Chicago

Ladies, enjoy half price wine bottles every Wednesday at O'Toole's. A perfect midweek treat for wine lovers.

Wednesday, Sep 30

Mondays Half Price Wine Bottles!

Timothy O'Toole's Pub Chicago

Ladies, enjoy half price wine bottles every Monday at O'Toole's. A perfect midweek treat for wine lovers.

Wednesday, Sep 30

Patricia Barber

Winter's Jazz Club

Experience the smooth sounds of Patricia Barber at Winter's Jazz Club. A delightful evening for jazz lovers in Chicago.

Thursday, Oct 1

WEDNESDAY SEPTEMBER 30: CROWD WORK WEDNESDAY

The Comedy Bar

Join Crowd Work Wednesday at The Comedy Bar for an interactive comedy experience hosted by Pat Bolduc & John Gasper.

Thursday, Oct 1

Spotlight On: Alfonso Ponticelli

Winter's Jazz Club

Experience an intimate performance by guitarist Alfonso Ponticelli, featuring an onstage interview with Howard Reich. Ideal for jazz enthusiasts.

Saturday, Oct 3

FRIDAY OCTOBER 2: DAUOOD NAIMYAR

The Comedy Bar

Enjoy laughs with headliner Dauood Naimyar at The Comedy Bar. A great night of comedy awaits in Streeterville.

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.

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

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

SATURDAY OCTOBER 3: 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.

Sunday, Oct 4

Mad-Good - Songbird Series - Celebrating Signature Voices of Jazz: Nancy Wilson

Winter's Jazz Club

Enjoy a night of jazz celebrating the iconic Nancy Wilson. A must for jazz lovers and music enthusiasts in Chicago.