Things to do in Streeterville

Sunday, Oct 11

Paul Marinaro Quintet - The Music of Nat 'King' Cole

Winter's Jazz Club

Enjoy the music of Nat 'King' Cole performed by Paul Marinaro and his quintet. Perfect for jazz lovers.

Sunday, Oct 11

SUNDAY OCTOBER 11: TIM SHROPSHIRE

The Comedy Bar

Join headliner Tim Shropshire for a night of laughs at The Comedy Bar in Chicago. A must-see for comedy enthusiasts.

Monday, Oct 12

SUNDAY OCTOBER 11: BARRY BREWER

The Comedy Bar

Headliner Barry Brewer brings laughs to The Comedy Bar in Chicago. A great choice for comedy fans looking for a fun night.

Tuesday, Oct 13

MONDAY OCTOBER 12: LATE NITE MIC WITH VIK PANDYA

The Comedy Bar

Join Vik Pandya and special guests for a night of comedy at The Comedy Bar in Chicago. Perfect for comedy lovers.

Wednesday, Oct 14

TUESDAY OCTOBER 13: TOMATO THROW SHOW

The Comedy Bar

Participate in an interactive comedy show at The Comedy Bar in Chicago. A unique night for comedy fans.

Wednesday, Oct 14

Michael Lerich Quartet - Swingin’ the Great American Songbook

Winter's Jazz Club

Experience the Michael Lerich Quartet performing the Great American Songbook at Winter's Jazz Club. Ideal for jazz enthusiasts.

Thursday, Oct 15

WEDNESDAY OCTOBER 14: CHICAGO'S BEST COMEDY SHOW

The Comedy Bar

Laugh the night away with Chicago's best comedians at The Comedy Bar. Enjoy pizza and great company in a lively atmosphere.

Thursday, Oct 15

2026 Sam Adams Stein Hoisting Contest!

Timothy O'Toole's Pub Chicago

Join the fun at the Sam Adams Stein Hoisting Contest at Timothy O'Toole's Pub. Compete for prizes in a spirited atmosphere.

Thursday, Oct 15

Jeremy Kahn Trio with guest Geof Bradfield - Chasin' the Trane: Celebrating John Coltrane's Centennial

Winter's Jazz Club

Join the Jeremy Kahn Trio for a special performance celebrating John Coltrane's centennial. A must for jazz enthusiasts.

Saturday, Oct 17

FRIDAY OCTOBER 16: JOEY BRAGG

The Comedy Bar

Join comedian Joey Bragg for a night of laughs at The Comedy Bar. Enjoy great humor in a fun atmosphere right off the Magnificent Mile.

Saturday, Oct 17

FRIDAY OCTOBER 16: CHICAGO'S BEST COMEDY SHOW

The Comedy Bar

Enjoy a hilarious night of stand-up comedy featuring Chicago's best comedians at The Comedy Bar. Perfect for a fun night out.

Saturday, Oct 17

SATURDAY OCTOBER 17: COMEDY BRUNCH! FEATURING BAD MOMZ OF COMEDY

The Comedy Bar

Enjoy a hilarious brunch with Orly K.G.'s Bad Momz of Comedy at The Comedy Bar. A fun event full of stand-up and laughs.

Sunday, Oct 18

SATURDAY OCTOBER 17: JOEY BRAGG

The Comedy Bar

Join comedian Joey Bragg for a night of laughs at The Comedy Bar. Enjoy a fun atmosphere right off the Magnificent Mile.

Sunday, Oct 18

Tatum Langley featuring Jeremy Kahn Quartet

Winter's Jazz Club

Enjoy a night of jazz with Tatum Langley and the Jeremy Kahn Quartet at Winter's Jazz Club. Perfect for jazz enthusiasts.

Sunday, Oct 18

SATURDAY OCTOBER 17: CHICAGO'S BEST COMEDY SHOW

The Comedy Bar

Enjoy a night of stand-up comedy featuring Chicago's best comedians at The Comedy Bar. Perfect for a fun night out.

Sunday, Oct 18

An Evening with Danny Sinoff and the Great American Songbook - Debut!

Winter's Jazz Club

Enjoy a night of jazz with Danny Sinoff and his band, perfect for jazz lovers and music enthusiasts.

Monday, Oct 19

SUNDAY OCTOBER 18: CALIMAR WHITE

The Comedy Bar

Enjoy a night of laughs with Calimar White at The Comedy Bar. A fun comedy event with pizza and nonstop humor.

Tuesday, Oct 20

MONDAY OCTOBER 19: LATE NITE MIC WITH VIK PANDYA

The Comedy Bar

Join Vik Pandya for a night of comedy at The Comedy Bar. Enjoy laughs and a free open mic session afterwards.

Wednesday, Oct 21

TUESDAY OCTOBER 20: TOMATO THROW SHOW

The Comedy Bar

Experience the interactive Tomato Throw Show at The Comedy Bar. Audience participation makes it a unique comedy night.

Wednesday, Oct 21

Ghouls Night Out Paint & Sip!

Timothy O'Toole's Pub Chicago

Enjoy a fun paint and sip night with art supplies included and themed drinks. A great evening for friends or date night.

Wednesday, Oct 21

Alex Austin Trio with guest vocalist Abigail Riccards

Winter's Jazz Club

Experience live jazz with the Alex Austin Trio featuring guest vocalist Abigail Riccards. A night for jazz lovers.

Thursday, Oct 22

WEDNESDAY OCTOBER 21: CHICAGO'S BEST COMEDY SHOW

The Comedy Bar

Enjoy a night of stand-up comedy with Chicago's top comedians and pizza. Perfect for a fun night out.

Thursday, Oct 22

Eric Jacobson Quintet - A Night in Tunisia: Dizzy Gillespie Birthday Celebration

Winter's Jazz Club

Celebrate Dizzy Gillespie's birthday with the Eric Jacobson Quintet performing a night of jazz.

Friday, Oct 23

THURSDAY OCTOBER 22: OHJAY LAMONT & FRIENDS

The Comedy Bar

Laugh along with OhJay Lamont and friends at The Comedy Bar for a night of comedy off the Magnificent Mile.

Saturday, Oct 24

FRIDAY OCTOBER 23: ZAR THE STAR

The Comedy Bar

Zar the Star headlines a comedy night at The Comedy Bar. Enjoy laughs and deep-dish pizza with friends.

Saturday, Oct 24

Abigail Riccards Quartet - Motown Gems: The Music of Stevie Wonder, Smokey Robinson, and Aretha Franklin

Winter's Jazz Club

Enjoy Motown gems performed by Abigail Riccards Quartet at Winter's Jazz Club. A must for jazz and soul fans.

Saturday, Oct 24

FRIDAY OCTOBER 23: ZAR THE STAR

The Comedy Bar

Zar the Star brings laughs to The Comedy Bar. Join for a night of comedy and delicious deep-dish pizza.

Saturday, Oct 24

Timmy's Tailgate For A Cause! With Noon Whistle & Sun Cruiser

Timothy O'Toole's Pub Chicago

Join Timmy's Tailgate for a Cause benefiting cancer research. Enjoy food and drinks while supporting a great cause in Chicago.

Sunday, Oct 25

SATURDAY OCTOBER 24: ZAR THE STAR

The Comedy Bar

Enjoy a night of laughs with Zar The Star at The Comedy Bar. A fun event for comedy lovers and fans of live performances.

Sunday, Oct 25

Ben Paterson Organ Trio featuring Bobby Broom

Winter's Jazz Club

Enjoy a night of jazz with the Ben Paterson Organ Trio at Winter's Jazz Club in Chicago.