Things to do in Streeterville

Thursday, Oct 1

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, Oct 1

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, 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.

Friday, Oct 2

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, 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

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, Oct 3

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, 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

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, 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

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, 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.

Sunday, Oct 4

SUNDAY OCTOBER 4: KEVIN WILLIAMS

The Comedy Bar

Enjoy a night of laughs with Kevin Williams at The Comedy Bar. Perfect for comedy fans looking for a fun night out.

Monday, Oct 5

SUNDAY OCTOBER 4: JUSTIN WHITEHEAD

The Comedy Bar

Laugh the night away with Justin Whitehead at The Comedy Bar. A must-see for comedy enthusiasts in Chicago.

Tuesday, Oct 6

MONDAY OCTOBER 5: LATE NITE MIC WITH VIK PANDYA

The Comedy Bar

Join Vik Pandya for a night of comedy and open mic at The Comedy Bar. Ideal for comedy lovers and aspiring comedians.

Wednesday, Oct 7

TUESDAY OCTOBER 6: TOMATO THROW SHOW

The Comedy Bar

Experience the interactive Tomato Throw Show at The Comedy Bar. A unique comedy event where the audience decides the fun.

Wednesday, Oct 7

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, Oct 7

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, Oct 7

Carmen Stokes Quartet - Under the Influence: Exploring the Musical Influences of Roberta Flack

Winter's Jazz Club

Enjoy an evening of jazz with Carmen Stokes Quartet at Winter's Jazz Club. Great for jazz lovers and music enthusiasts.

Thursday, Oct 8

WEDNESDAY OCTOBER 7: CHICAGO'S BEST COMEDY SHOW

The Comedy Bar

Experience a night of stand-up comedy and pizza at The Comedy Bar. Perfect for comedy fans in Chicago.

Thursday, Oct 8

Hinda Hoffman Quartet

Winter's Jazz Club

Enjoy a night of jazz with Hinda Hoffman Quartet at Winter's Jazz Club. Perfect for jazz lovers looking for a cozy setting.

Saturday, Oct 10

FRIDAY OCTOBER 9: PAUL ELIA

The Comedy Bar

Join comedian Paul Elia for a night of laughter at The Comedy Bar in Chicago, perfect for comedy fans.

Saturday, Oct 10

Dee Alexander featuring the Jeremy Kahn Quartet

Winter's Jazz Club

Experience the soulful vocals of Dee Alexander at Winter's Jazz Club. A night of jazz not to be missed.

Saturday, Oct 10

FRIDAY OCTOBER 9: PAUL ELIA

The Comedy Bar

Catch comedian Paul Elia for a night of laughs at The Comedy Bar in Chicago, a great spot for comedy lovers.

Saturday, Oct 10

SATURDAY OCTOBER 10: THE RUNNING GAME SHOW

The Comedy Bar

Enjoy niche comedy with fellow running enthusiasts at The Comedy Bar in Chicago, perfect for runners and comedy fans.

Sunday, Oct 11

SATURDAY OCTOBER 10: PAUL ELIA

The Comedy Bar

Join Paul Elia for another night of comedy at The Comedy Bar in Chicago, a must-see for laughter lovers.

Sunday, Oct 11

Thaddeus Tukes Quartet featuring Jeremy Kahn and special guest Angel Spiccia

Winter's Jazz Club

Enjoy live music from Jah Ollin at Tiki Bar. A night of great vibes and entertainment awaits.

Sunday, Oct 11

SATURDAY OCTOBER 10: PAUL ELIA

The Comedy Bar

Don't miss comedian Paul Elia at The Comedy Bar in Chicago for a night filled with laughter and fun.