What's on in Chicago this week?

44 events are listed in Chicago for this week (Oct 12–19), including SLIFT, Waitress (Chicago) and The Winter's Tale.

Are there free events in Chicago this week?

None of the 44 events listed for this week (Oct 12–19) are marked free. Free listings appear when a source says admission is free.

When is the next evntally digest?

The next weekly Chicago digest goes out Thursday October 15, with five picks matched to your taste. The first two digests are free with no card; continue for US$2.99/mo only if you choose.

This week · Chicago, IL · 44 events

Things to do in Chicago this week

Monday, October 12 to Monday, October 19 · 44 events

44 events are listed in Chicago, Illinois for this week (Oct 12–19), soonest first. The most common categories are arts & culture (11), live music (8) and comedy (8). None of the events listed are marked free.

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By vibe

Tuesday, October 13

SLIFT
Tue, Oct 13 · 6:30 p.m. CDT
Outset
Check price
Waitress (Chicago)
Tue, Oct 13 · 7:00 p.m. CDT
James M. Nederlander Theatre
Check price
The Winter's Tale
Tue, Oct 13 · 7:00 p.m. CDT
Chicago Shakespeare Theater
Check price
VOICEBOX w/ Cathy Richardson!
Tue, Oct 13 · 7:00 p.m. CDT
FITZGERALDS NIGHTCLUB
US$18.48
SONGWRITER'S CIRCLE w/ Host RON LAZZERETTI ft. guests David Hinske and Christine Melody
Tue, Oct 13 · 7:00 p.m. CDT
FITZGERALDS SIDEBAR
Check price
Play On!
Tue, Oct 13 · 7:00 p.m. CDT
Chicago Shakespeare Theater
Check price
Kokandy Productions Jekyll & Hyde (Chicago)
Tue, Oct 13 · 7:00 p.m. CDT
Broadway Playhouse at Water Tower Place
Check price
ChiTown Drive-In Presents - Beetlejuce (the Original)!
Tue, Oct 13 · 7:00 p.m. CDT
ChiTown Movies
Check price
Chicago Blackhawks vs. Pittsburgh Penguins
Tue, Oct 13 · 7:00 p.m. CDT
United Center
Check price
White Denim w. Arc Iris
Tue, Oct 13 · 7:30 p.m. CDT
SPACE
US$40.54
Vape! The Grease Parody
Tue, Oct 13 · 7:30 p.m. CDT
Apollo Theater
Check price
Celebrate CJE
Tue, Oct 13 · 7:30 p.m. CDT
George Van Dusen Theatre at North Shore Center
Check price
Jessie Ware: The Superbloom Tour
Tue, Oct 13 · 8:00 p.m. CDT
Aragon Ballroom
Check price
The Second City's: Pandemonium, Please Hold
Tue, Oct 13 · 8:00 p.m. CDT
Second City-Chicago: Mainstage
Check price
2026 MONSTA X WORLD TOUR [THE X : NEXUS] IN ROSEMONT
Tue, Oct 13 · 8:00 p.m. CDT
Rosemont Theatre
Check price
Lukas & Frank - Ages 21+
Tue, Oct 13 · 8:00 p.m. CDT
Subterranean
Check price
Will Varley, Mikey Harms
Tue, Oct 13 · 8:30 p.m. CDT
Reggies Music Joint
Check price

Wednesday, October 14

Thursday, October 15

Friday, October 16

Saturday, October 17

Sunday, October 18

Monday, October 19

ChiTown Drive-In Presents - Michael
Mon, Oct 19 · 7:00 p.m. CDT
ChiTown Movies
Check price

Questions about Chicago this week

What's on in Chicago this week?: 44 events are listed in Chicago for this week (Oct 12–19), including SLIFT, Waitress (Chicago) and The Winter's Tale.
Are there free events in Chicago this week?: None of the 44 events listed for this week (Oct 12–19) are marked free. Free listings appear when a source says admission is free.
When is the next evntally digest?: The next weekly Chicago digest goes out Thursday October 15, with five picks matched to your taste. The first two digests are free with no card; continue for US$2.99/mo only if you choose.

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Things to do in Chicago this week

Tuesday, October 13

SLIFT

Waitress (Chicago)

The Winter's Tale

VOICEBOX w/ Cathy Richardson!

SONGWRITER'S CIRCLE w/ Host RON LAZZERETTI ft. guests David Hinske and Christine Melody

Play On!

Kokandy Productions Jekyll & Hyde (Chicago)

ChiTown Drive-In Presents - Beetlejuce (the Original)!

Chicago Blackhawks vs. Pittsburgh Penguins

White Denim w. Arc Iris

Vape! The Grease Parody

Celebrate CJE

Jessie Ware: The Superbloom Tour

The Second City's: Pandemonium, Please Hold

2026 MONSTA X WORLD TOUR [THE X : NEXUS] IN ROSEMONT

Lukas & Frank - Ages 21+

Will Varley, Mikey Harms

Wednesday, October 14

Come from Away (Touring)

Music Theater Works Presents: Escape to Margaritaville

Joe Dombrowski

ChiTown Drive-In Presents -Coraline

Chicago Fire FC vs. Philadelphia Union (Beer Stein to 1st 5K)

Avery Cochrane - Ages 17+

Magenta Wave

Thursday, October 15

ALCS Home Game 1

Classic Stadium Tour

Damitas Histeria (En Español)

Chicago Blackhawks vs. Winnipeg Jets

Northwestern Wildcats Women's Volleyball vs. Nebraska Cornhuskers Womens Volleyball

ChiTown Drive-In Presents - Halloween (the 1978 Original!)

Friday, October 16

Illinois Product Expo

PFL Chicago

"Ghostbusters" at FITZGERALDS Fright Nights! **ft. a visit from a Ghostbusters Car!!**

Brent Morin

Brad Williams: The Tall Tales Tour

Feast A Da Funny

ChiTown Drive-In Presents - Obsession (2026)

Saturday, October 17

"The Rocky Horror Picture Show" at FITZGERALDS Fright Nights!

Ben Schwartz & Friends

Sweetest Day Comedy Jam

Sunday, October 18

La Mole (En Español)

Fred Armisen: Comedy For Musicians But Everyone Is Welcome

ChiTown Drive-In Presents - Night of the Living Dead

Monday, October 19

ChiTown Drive-In Presents - Michael

Questions about Chicago this week

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"Ghostbusters" at FITZGERALDS Fright Nights! ft. a visit from a Ghostbusters Car!!