Things to do in Chicago, IL

803 events · Comedy, Food & Drink, Nightlife, Parks & Outdoors

Friday, September 25

Nightlife

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Fri · Sep 25 · 8:00 PM

JEFF NEWELL'S NEW TRAD OCTET

Green Mill Cocktail Lounge

$16

Fri · Sep 25 · 8:30 PM

Rat Johnson Persian Cowboy Waterpennies

Cole's Bar

Fri · Sep 25

Saturday June with Jami Dawn and Dave & Gabe

Uncommon Ground

Fri · Sep 25

Melody Angel: The Dreamcatcher Tour

Rosa's Lounge

Saturday, September 26

Nightlife

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Sat · Sep 26 · 1:00 AM

RIGHTEOUS ROOSTER ORGAN TRIO

Green Mill Cocktail Lounge

Free↻ Recurring

Sat · Sep 26 · 8:30 AM

Movie - Indiana Dunes: Nature's Masterpiece - Visitor Center

Indiana Dunes National Park

Parks & Outdoors

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Sat · Sep 26 · 10:00 AM

The Oracle of Evergreen: A BLACK PLANT IT EXHIBITION 2026

Garfield Park Conservatory Alliance

Parks & Outdoors

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Sat · Sep 26 · 10:00 AM

Soul of the Stone

Garfield Park Conservatory Alliance

Parks & Outdoors

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Sat · Sep 26 · 10:30 AM

U of I Extension Ask a Master Gardener

Garfield Park Conservatory Alliance

Parks & Outdoors

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Sat · Sep 26 · 11:00 AM

Budding Botanist

Garfield Park Conservatory Alliance

Parks & Outdoors

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Sat · Sep 26 · 11:00 AM

Sensory Play Workshop with Luna Y Cielo Play Cafe.

Garfield Park Conservatory Alliance

Parks & Outdoors

Free↻ Recurring

Sat · Sep 26 · 1:00 PM

Daily Ranger Guided Tours

Pullman National Historical Park

Sat · Sep 26 · 3:00 PM

Ian Rosenberg - "Terrible Stuff Damaging Everybody" - Samantha Chatman

Seminary Co-op Bookstore

Nightlife

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Sat · Sep 26 · 3:00 PM

PAPER MACHETE

Green Mill Cocktail Lounge

Nightlife

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Sat · Sep 26 · 8:00 PM

JEFF NEWELL'S NEW TRAD OCTET

Green Mill Cocktail Lounge

$16

Sat · Sep 26 · 8:30 PM

Dravin and the Ravens Friendly Faces Jack Moony & The Sun Drops

Cole's Bar

Sat · Sep 26 · 9:00 PM

Bricktown Sound

Hungry Brain

Sat · Sep 26

Stephen Hull Experience

Rosa's Lounge

Sat · Sep 26

The Chain Links with Al Day and Victor Sanders

Uncommon Ground

Sunday, September 27

Free↻ Recurring

Sun · Sep 27 · 8:30 AM

Movie - Indiana Dunes: Nature's Masterpiece - Visitor Center

Indiana Dunes National Park

Parks & Outdoors

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Sun · Sep 27 · 10:00 AM

The Oracle of Evergreen: A BLACK PLANT IT EXHIBITION 2026

Garfield Park Conservatory Alliance

Parks & Outdoors

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Sun · Sep 27 · 10:00 AM

Soul of the Stone

Garfield Park Conservatory Alliance

Sun · Sep 27 · 12:00 PM

Burning Bush Fall Fest '26

Burning Bush Brewery

Parks & Outdoors

Free↻ Recurring

Sun · Sep 27 · 1:00 PM

Daily Ranger Guided Tours

Pullman National Historical Park

Nightlife

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Sun · Sep 27 · 4:00 PM

CHICAGO JAZZ COMPOSERS COLLECTIVE

Green Mill Cocktail Lounge

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Sun · Sep 27 · 5:30 PM

Open Mic Night

aliveOne

Nightlife

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Sun · Sep 27 · 8:00 PM

SOUL MESSAGE

Green Mill Cocktail Lounge

Nightlife

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Sun · Sep 27 · 9:00 PM

Open Mic Night

My Buddy's

Nightlife

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Sun · Sep 27 · 10:00 PM

Open Mic Night

Reed's Local

Sun · Sep 27

Shure Sponsored Open Mic Grand Finale

Uncommon Ground

Monday, September 28

Free↻ Recurring

Mon · Sep 28 · 8:30 AM

Movie - Indiana Dunes: Nature's Masterpiece - Visitor Center

Indiana Dunes National Park

Mon · Sep 28 · 6:30 PM

Old St. Pat's Book Club

The Book Cellar

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Mon · Sep 28 · 7:00 PM

Trivia Night

Guinness Open Gate Brewery

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Mon · Sep 28 · 7:00 PM

Trivia Night

Pilot Project Brewing - Logan Square

Free↻ Recurring

Mon · Sep 28 · 7:00 PM

MissSpoken

Cole's Bar

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Mon · Sep 28 · 7:00 PM

Trivia Night

Fatpour Tap Works - Wicker Park

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Mon · Sep 28 · 8:00 PM

Open Mic Night

Riddles Comedy Club

Mon · Sep 28

Super Six

Zanies Comedy Club Chicago

Nightlife

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Mon · Sep 28

JOEL PATERSON & FRIENDS

Green Mill Cocktail Lounge

Tuesday, September 29

Free↻ Recurring

Tue · Sep 29 · 8:30 AM

Movie - Indiana Dunes: Nature's Masterpiece - Visitor Center

Indiana Dunes National Park

Tue · Sep 29 · 5:30 PM

Thant Myint-U, "Peacemaker"

The Book Cellar

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Tue · Sep 29 · 7:00 PM

Trivia Night

Sheffield's Wine & Beer Garden

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Tue · Sep 29 · 7:00 PM

Trivia Night

Timothy O'Toole's Pub Chicago

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Tue · Sep 29 · 7:00 PM

Trivia Night

Butch McGuire's

Nightlife

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Tue · Sep 29 · 7:00 PM

Trivia Night

Jake Melnick's Corner Tap

Nightlife

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Tue · Sep 29 · 7:00 PM

Open Mic / Blues Jam

Gallery Cabaret

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Tue · Sep 29 · 7:00 PM

Trivia Night

Roscoe Village Pub

Nightlife

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Tue · Sep 29 · 7:00 PM

Trivia Night

Punch Bowl Social Chicago

$15.77

Tue · Sep 29 · 7:30 PM

Ruth Theodore Damsel. Sgt. Starling

Cole's Bar

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Tue · Sep 29 · 7:30 PM

Open Mic Comedy

Harrigan's

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Tue · Sep 29 · 8:00 PM

Open Mic Night

Emerald Isle

Nightlife

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Tue · Sep 29 · 8:00 PM

CHICAGO CELLAR BOYS

Green Mill Cocktail Lounge

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Tue · Sep 29 · 9:00 PM

Open Mic Night

Vaughan's Pub

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Tue · Sep 29 · 9:00 PM

Open Mic Night

Laugh Factory Chicago

Tue · Sep 29

Dave Herrero Feat. Pete Galanis special guest Adam Hernacki

Rosa's Lounge

Wednesday, September 30

Free↻ Recurring

Wed · Sep 30 · 8:30 AM

Movie - Indiana Dunes: Nature's Masterpiece - Visitor Center

Indiana Dunes National Park

Parks & Outdoors

↻ Recurring

Wed · Sep 30 · 10:00 AM

The Oracle of Evergreen: A BLACK PLANT IT EXHIBITION 2026

Garfield Park Conservatory Alliance

Parks & Outdoors

↻ Recurring

Wed · Sep 30 · 10:00 AM

Soul of the Stone

Garfield Park Conservatory Alliance

Parks & Outdoors

Free↻ Recurring

Wed · Sep 30 · 1:00 PM

Daily Ranger Guided Tours

Pullman National Historical Park

Wed · Sep 30 · 7:00 PM

Never Too Old: The YA Book Club

The Book Cellar

Nightlife

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Wed · Sep 30 · 7:00 PM

Geeks Who Drink Trivia

Fado Irish Pub

Parks & Outdoors

Wed · Sep 30 · 7:00 PM

Healing Roots: Medicinal Plants and Ancestral Memory | Raices que Sanan: Plantas Medicinales y Memoria Ancestral

Garfield Park Conservatory Alliance

Parks & Outdoors

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Wed · Sep 30 · 7:30 PM

Whimsy Wednesday

Garfield Park Conservatory Alliance

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Wed · Sep 30 · 7:30 PM

Geeks Who Drink Trivia

Commonwealth Tavern

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Wed · Sep 30 · 8:00 PM

Geeks Who Drink Trivia

Dante's Tavern

Nightlife

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Wed · Sep 30 · 8:00 PM

Karaoke Night

Sidekick's Entertainment Lounge

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Wed · Sep 30 · 8:00 PM

Trivia Night

George Street Pub

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Wed · Sep 30 · 8:00 PM

Trivia Night

Burwood Tap

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Wed · Sep 30 · 8:00 PM

Comedy Open Mic

Cole's Bar

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Wed · Sep 30 · 8:00 PM

Karaoke Night

Rabbit Hole Wrigley

Nightlife

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Wed · Sep 30 · 8:00 PM

ALFONSO PONTICELLI

Green Mill Cocktail Lounge

Wed · Sep 30 · 9:00 PM

Beisel Jesalva Wagster Zerang

Hungry Brain

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Wed · Sep 30 · 9:00 PM

Karaoke Wednesdays

Replay Lakeview

Wed · Sep 30

Sheryl Youngblood Band’s All-Music Jam Night

Rosa's Lounge

Wed · Sep 30

Lynn Live Vocals with Mikey Harms and Phin Gleber

Uncommon Ground

Thursday, October 1

Parks & Outdoors

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Thu · Oct 1 · 10:00 AM

Soul of the Stone

Garfield Park Conservatory Alliance

Parks & Outdoors

↻ Recurring

Thu · Oct 1 · 10:00 AM

The Oracle of Evergreen: A BLACK PLANT IT EXHIBITION 2026

Garfield Park Conservatory Alliance

Parks & Outdoors

Free↻ Recurring

Thu · Oct 1 · 1:00 PM

Daily Ranger Guided Tours

Pullman National Historical Park

Nightlife

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Thu · Oct 1 · 5:00 PM

ANDY BROWN

Green Mill Cocktail Lounge

Nightlife

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Thu · Oct 1 · 7:00 PM

Open Mic Night

Whiskey Girl Tavern

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Thu · Oct 1 · 7:30 PM

Jeopardy! Bar League

Guthries Tavern

Nightlife

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Thu · Oct 1 · 8:00 PM

ALAN GRESIK'S SWING ORCHESTRA

Green Mill Cocktail Lounge

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Thu · Oct 1 · 8:00 PM

Trivia Night

Bucktown Pub

Thu · Oct 1

Nat Lefkoff

Uncommon Ground

Thu · Oct 1

Thursday Night Live Blues: Feat. Lil’ Ed Williams w/ Sumito Ariyoshi

Rosa's Lounge

Friday, October 2

Nightlife

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Fri · Oct 2 · 1:00 AM

GREEN MILL JAM SESSION with MARQUIS HILL

Green Mill Cocktail Lounge

Parks & Outdoors

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Fri · Oct 2 · 10:00 AM

The Oracle of Evergreen: A BLACK PLANT IT EXHIBITION 2026

Garfield Park Conservatory Alliance

Parks & Outdoors

↻ Recurring

Fri · Oct 2 · 10:00 AM

Soul of the Stone

Garfield Park Conservatory Alliance

Parks & Outdoors

Free↻ Recurring

Fri · Oct 2 · 1:00 PM

Daily Ranger Guided Tours

Pullman National Historical Park

Nightlife

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Fri · Oct 2 · 5:00 PM

Chris Foreman

Green Mill Cocktail Lounge

$16

Fri · Oct 2 · 7:30 PM

Good Morning Bedlam, Winter TV, Sam Roethgen

Cole's Bar

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Fri · Oct 2 · 8:00 PM

Open Mic Night

O'Donnell's

Nightlife

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Fri · Oct 2 · 8:00 PM

HINDA HOFFMAN QUARTET

Green Mill Cocktail Lounge

Fri · Oct 2

Zakhoury and Matt Krahula

Uncommon Ground