Events in Chicago , Illinois

Reality Detox: The Improv Experience

The Second City · Chicago

Thu, Oct 1

Idle Muse Theatre Company Presents “Witch”

The Edge Off Broadway Theatre · Chicago

Thu, Oct 1

Karaoke

Live Band Karaoke at Parlay

Brando's Lincoln Park · Chicago

Thu, Oct 1 · 8:00 PM

Get Tickets(opens in a new tab)

United Forces, Texas Toast Chainsaw Massacre, Insult To Injury

Reggies Music Joint · Chicago

Thu, Oct 1

Sir Thomas Madden Jr.

The Den Theatre · Chicago

Thu, Oct 1 · 8:00 PM

Thursday Night Stand Up Comedy at Laugh Factory Chicago

Laugh Factory Chicago · Chicago · From $21.41

Thu, Oct 1 · 8:00 PM

Latina Comedy Festival Presents: The Chingonas Show

The Lincoln Lodge · Chicago · $24.37

Thu, Oct 1

Get Tickets(opens in a new tab)

Lowspark

aliveOne · Chicago

Thu, Oct 1 · 8:00 PM

Nightlife

KEG Halloween Special - Ages 21+

Cole's Bar Chicago · Chicago

Thu, Oct 1

2nd Set With Mario Abney

Andy's Jazz Club & Restaurant · Chicago

Thu, Oct 1 · 8:30 PM

Do Chicago-Style Street Art - Paint and Sip in Chicago | Classpop!™

Studio W.I.P. · Chicago · $61.81

Thu, Oct 1

Sonic Soul

Buddy Guy's Legends · Chicago

Thu, Oct 1

Nightlife

30th Anniversary Thursdays

aliveOne · Chicago

Thu, Oct 1 · 9:00 PM

Latina Comedy Festival Presents: Las Jefas Show* (Spanish/español)

The Lincoln Lodge · Chicago · From $12.83

Thu, Oct 1 · 9:00 PM

Nightlife

Nigerian Independence Day @ RocBar Thursday, October 1st | 9PM–4AM

Rocbar · Chicago · From $23.11

Thu, Oct 1

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

Rosa's Lounge · Chicago

Thu, Oct 1 · 9:30 PM

Latina Comedy Festival Presents: The Patronas Show

The Lincoln Lodge · Chicago · $24.37

Thu, Oct 1

Blueprint

The iO Theater · Chicago

Thu, Oct 1

Late Night Concert Series w/The Chicago Experiment

Andy's Jazz Club & Restaurant · Chicago

Thu, Oct 1

The 11pm Show

The iO Theater · Chicago

Thu, Oct 1

Open World DJ Set with Hima-Ji

The Owl · Chicago

Fri, Oct 2

Schmid Celebration OPEN STUDIO (Extra Option)

The Palette & Chisel Academy of Fine Arts · Chicago

Fri, Oct 2

Festival

Fall Fest at Lincoln Park Zoo

Lincoln Park Zoo · Chicago · Free

Fri, Oct 2 · 8:00 AM

Chicago Handmade & Designer Market- Vendors Wanted

Millennium Park · Chicago · Free

Fri, Oct 2

Schmid Celebration 3-Day General Weekend Package

The Palette & Chisel Academy of Fine Arts · Chicago

Fri, Oct 2

Schmid Celebration 3-Day VIP Weekend Package

The Palette & Chisel Academy of Fine Arts · Chicago

Fri, Oct 2

Festival

Fall Fest

Lincoln Park Zoo · Chicago

Fri, Oct 2

Open Your Eyes: Chicago's Underground Pedway & Other Secrets of the Loop Walking Tour

Inside Chicago Walking Tours · Chicago

Fri, Oct 2

American Prophets: Writers, Religion, and Culture

American Writers Museum · Chicago

Fri, Oct 2

Family

Castle

Chicago Children's Museum · Chicago

Fri, Oct 2

Flyway City: Architecture for a Flourishing Ecosystem

Chicago Architecture Center · Chicago

Fri, Oct 2

Family

Book Builders

Harold Washington Library · Chicago

Fri, Oct 2

Mini Zoom Room

Chicago Children's Museum · Chicago

Fri, Oct 2 · 10:00 AM

The Chicago School Alumni Impact Summit

The Chicago School · Chicago · From $10

Fri, Oct 2

Open Play Time

West Lawn Branch Library · Chicago

Fri, Oct 2

Serial Killer: The Exhibition

Cinespace · Chicago

Fri, Oct 2

Chicago Greeter Riverwalk InstaGreeter Walk

Vietnam Veteran's Memorial · Chicago · Free

Fri, Oct 2

Food & Drink

Rooftop Oasis Hours

Offshore Rooftop · Chicago

Fri, Oct 2

Chicago Greeter – Loop InstaGreeter

Chicago Cultural Center · Chicago · Free

Fri, Oct 2

Mäkelä Conducts Mahler 9

Orchestra Hall, Symphony Center · Chicago

Fri, Oct 2

Mahjong Club

Clearing Branch Library · Chicago

Fri, Oct 2

Sports

DePaul Athletics Men's Soccer

Wish Field · Chicago · Free

Fri, Oct 2

Teen Checkers Open Play

Back of the Yards Branch Library · Chicago

Fri, Oct 2 · 3:00 PM

Smoke Square Shop · Chicago

Fri, Oct 2

Haunted by Our Dark Side: Chicago Ghosts, Gangsters, and True Crime Tour

Inside Chicago Walking Tours · Chicago

Fri, Oct 2

Food & Drink

Natties and Patties Food Pop Up

Central Park Bar · Chicago

Fri, Oct 2 · 4:30 PM

Get Tickets(opens in a new tab)

Hard Country Honky Tonk with The Hoyle Brothers

Empty Bottle · Chicago

Fri, Oct 2 · 5:00 PM

Conference

HomeDadCon - Chicago 2026 (Oct.2-3)

Embassy Suites Chicago - Downtown · Chicago

Fri, Oct 2 · 6:00 PM

FashionBar THE SHOWS: October 2026 - The Trans Media Fashion Show

Water Tower Place, Level 3 · Chicago · From $28.52

Fri, Oct 2

Wicker Park Bucktown's “First Fridays” Art Walk

Jackson Junge Gallery · Chicago · Free

Fri, Oct 2

Cutting and Pasting a World: The Paper Craft of Henry Darger

Intuit Art Museum · Chicago

Fri, Oct 2 · 6:00 PM

Still She Rise… But God

Kennedy-King College · Chicago · From $55.20

Fri, Oct 2

Sports

FashionBar THE SHOWS: October 2026 – The Trans Media Fashion Show

WATER TOWER PLACE – Level 4, Michigan Ave. · Chicago

Fri, Oct 2 · 6:00 PM

Bridge Performance Incubator Showcase

Hyde Park Art Center · Chicago · Free

Fri, Oct 2

1st Set With The Pamoja Project

Andy's Jazz Club & Restaurant · Chicago

Fri, Oct 2

Friday Night Chess Club

Rizal Center · Chicago · Free

Fri, Oct 2

Pandemonium, Please Hold

The Second City · Chicago

Fri, Oct 2 · 6:30 PM

Latina Comedy Festival Presents: The Bebesitas Show

The Lincoln Lodge · Chicago · $24.37

Fri, Oct 2

The Infinite Wrench

The Neo-Futurist Theater · Chicago

Fri, Oct 2

Jekyll& Hyde

Broadway Playhouse at Water Tower Place · Chicago

Reality Detox: The Improv Experience

The Second City

Chicago, IL

Reality Detox: The Improv Experience

The Second City

Chicago, IL

Idle Muse Theatre Company Presents “Witch”

Thu, Oct 1Theater

Idle Muse Theatre Company Presents “Witch”

The Edge Off Broadway Theatre

Chicago, IL

Idle Muse Theatre Company Presents “Witch”

Thu, Oct 1Theater

Idle Muse Theatre Company Presents “Witch”

The Edge Off Broadway Theatre

Chicago, IL

Thu, Oct 1Karaoke

Live Band Karaoke at Parlay

Brando's Lincoln Park

Chicago, IL

Thu, Oct 1Karaoke

Live Band Karaoke at Parlay

Brando's Lincoln Park

Chicago, IL

Get Tickets via TicketWeb →

United Forces, Texas Toast Chainsaw Massacre, Insult To Injury

Thu, Oct 1 · 8:00 PMMusic

United Forces, Texas Toast Chainsaw Massacre, Insult To Injury

Reggies Music Joint

Chicago, IL

TicketWeb

Get Tickets via TicketWeb →(opens in a new tab)

United Forces, Texas Toast Chainsaw Massacre, Insult To Injury

Thu, Oct 1 · 8:00 PMMusic

United Forces, Texas Toast Chainsaw Massacre, Insult To Injury

Reggies Music Joint

Chicago, IL

Get Tickets →(opens in a new tab)

Sir Thomas Madden Jr.

The Den Theatre

Chicago, IL

Sir Thomas Madden Jr.

The Den Theatre

Chicago, IL

Thu, Oct 1 · 8:00 PMFrom $21.41Comedy

Thursday Night Stand Up Comedy at Laugh Factory Chicago

Laugh Factory Chicago

Chicago, IL

Thu, Oct 1 · 8:00 PMFrom $21.41Comedy

Thursday Night Stand Up Comedy at Laugh Factory Chicago

Laugh Factory Chicago

Chicago, IL

Thu, Oct 1 · 8:00 PM$24.37Comedy

Latina Comedy Festival Presents: The Chingonas Show

The Lincoln Lodge

Chicago, IL

Thu, Oct 1 · 8:00 PM$24.37Comedy

Latina Comedy Festival Presents: The Chingonas Show

The Lincoln Lodge

Chicago, IL

Lowspark

aliveOne

Chicago, IL

Lowspark

aliveOne

Chicago, IL

Get Tickets via Ticketmaster →

Thu, Oct 1 · 8:00 PMNightlife

KEG Halloween Special - Ages 21+

Cole's Bar Chicago

Chicago, IL

Ticketmaster

Get Tickets via Ticketmaster →(opens in a new tab)

Thu, Oct 1 · 8:00 PMNightlife

KEG Halloween Special - Ages 21+

Cole's Bar Chicago

Chicago, IL

Get Tickets →(opens in a new tab)

2nd Set With Mario Abney

Andy's Jazz Club & Restaurant

Chicago, IL

2nd Set With Mario Abney

Andy's Jazz Club & Restaurant

Chicago, IL

Thu, Oct 1 · 8:30 PM$61.81Art

Do Chicago-Style Street Art - Paint and Sip in Chicago | Classpop!™

Studio W.I.P.

Chicago, IL

Thu, Oct 1 · 8:30 PM$61.81Art

Do Chicago-Style Street Art - Paint and Sip in Chicago | Classpop!™

Studio W.I.P.

Chicago, IL

Sonic Soul

Buddy Guy's Legends

Chicago, IL

Sonic Soul

Buddy Guy's Legends

Chicago, IL

30th Anniversary Thursdays

Thu, Oct 1Nightlife

30th Anniversary Thursdays

aliveOne

Chicago, IL

30th Anniversary Thursdays

Thu, Oct 1Nightlife

30th Anniversary Thursdays

aliveOne

Chicago, IL

Thu, Oct 1 · 9:00 PMFrom $12.83Comedy

Latina Comedy Festival Presents: Las Jefas Show* (Spanish/español)

The Lincoln Lodge

Chicago, IL

Thu, Oct 1 · 9:00 PMFrom $12.83Comedy

Latina Comedy Festival Presents: Las Jefas Show* (Spanish/español)

The Lincoln Lodge

Chicago, IL

Thu, Oct 1 · 9:00 PMFrom $23.11Nightlife

Nigerian Independence Day @ RocBar Thursday, October 1st | 9PM–4AM

Rocbar

Chicago, IL

Thu, Oct 1 · 9:00 PMFrom $23.11Nightlife

Nigerian Independence Day @ RocBar Thursday, October 1st | 9PM–4AM

Rocbar

Chicago, IL

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

Rosa's Lounge

Chicago, IL

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

Rosa's Lounge

Chicago, IL

Thu, Oct 1 · 9:30 PM$24.37Comedy

Latina Comedy Festival Presents: The Patronas Show

The Lincoln Lodge

Chicago, IL

Thu, Oct 1 · 9:30 PM$24.37Comedy

Latina Comedy Festival Presents: The Patronas Show

The Lincoln Lodge

Chicago, IL

Blueprint

The iO Theater

Chicago, IL

Blueprint

The iO Theater

Chicago, IL

Late Night Concert Series w/The Chicago Experiment

Andy's Jazz Club & Restaurant

Chicago, IL

Late Night Concert Series w/The Chicago Experiment

Andy's Jazz Club & Restaurant

Chicago, IL

The 11pm Show

The iO Theater

Chicago, IL

The 11pm Show

The iO Theater

Chicago, IL

Open World DJ Set with Hima-Ji

Open World DJ Set with Hima-Ji

The Owl

Chicago, IL

Open World DJ Set with Hima-Ji

Open World DJ Set with Hima-Ji

The Owl

Chicago, IL

Schmid Celebration OPEN STUDIO (Extra Option)

The Palette & Chisel Academy of Fine Arts

Chicago, IL

Schmid Celebration OPEN STUDIO (Extra Option)

The Palette & Chisel Academy of Fine Arts

Chicago, IL

Fri, Oct 2FREEFestival

Fall Fest at Lincoln Park Zoo

Lincoln Park Zoo

Chicago, IL

Fri, Oct 2FREEFestival

Fall Fest at Lincoln Park Zoo

Lincoln Park Zoo

Chicago, IL

Fri, Oct 2 · 8:00 AMFREECommunity

Chicago Handmade & Designer Market- Vendors Wanted

Millennium Park

Chicago, IL

Fri, Oct 2 · 8:00 AMFREECommunity

Free · Eventbrite →

Chicago Handmade & Designer Market- Vendors Wanted

Millennium Park

Chicago, IL

Schmid Celebration 3-Day General Weekend Package

The Palette & Chisel Academy of Fine Arts

Chicago, IL

Schmid Celebration 3-Day General Weekend Package

The Palette & Chisel Academy of Fine Arts

Chicago, IL

Schmid Celebration 3-Day VIP Weekend Package

The Palette & Chisel Academy of Fine Arts

Chicago, IL

Schmid Celebration 3-Day VIP Weekend Package

The Palette & Chisel Academy of Fine Arts

Chicago, IL

Fall Fest

Fri, Oct 2Festival

Fall Fest

Lincoln Park Zoo

Chicago, IL

Fall Fest

Fri, Oct 2Festival

Fall Fest

Lincoln Park Zoo

Chicago, IL

Open Your Eyes: Chicago's Underground Pedway & Other Secrets of the Loop Walking Tour

Inside Chicago Walking Tours

Chicago, IL

Open Your Eyes: Chicago's Underground Pedway & Other Secrets of the Loop Walking Tour

Inside Chicago Walking Tours

Chicago, IL

American Prophets: Writers, Religion, and Culture

American Writers Museum

Chicago, IL

American Prophets: Writers, Religion, and Culture

American Writers Museum

Chicago, IL

Castle

Chicago Children's Museum

Chicago, IL

Castle

Chicago Children's Museum

Chicago, IL

Flyway City: Architecture for a Flourishing Ecosystem

Chicago Architecture Center

Chicago, IL

Flyway City: Architecture for a Flourishing Ecosystem

Chicago Architecture Center

Chicago, IL

Book Builders

Harold Washington Library

Chicago, IL

Book Builders

Harold Washington Library

Chicago, IL

Mini Zoom Room

Chicago Children's Museum

Chicago, IL

Mini Zoom Room

Chicago Children's Museum

Chicago, IL

Fri, Oct 2 · 10:00 AMFrom $10Community

The Chicago School Alumni Impact Summit

The Chicago School

Chicago, IL

Fri, Oct 2 · 10:00 AMFrom $10Community

The Chicago School Alumni Impact Summit

The Chicago School

Chicago, IL

Open Play Time

West Lawn Branch Library

Chicago, IL

Open Play Time

West Lawn Branch Library

Chicago, IL

Serial Killer: The Exhibition

Cinespace

Chicago, IL

Serial Killer: The Exhibition

Cinespace

Chicago, IL

Chicago Greeter Riverwalk InstaGreeter Walk

Vietnam Veteran's Memorial

Chicago, IL

Chicago Greeter Riverwalk InstaGreeter Walk

Vietnam Veteran's Memorial

Chicago, IL

Rooftop Oasis Hours

Offshore Rooftop

Chicago, IL

Rooftop Oasis Hours

Offshore Rooftop

Chicago, IL

Chicago Greeter – Loop InstaGreeter

Chicago Cultural Center

Chicago, IL

Chicago Greeter – Loop InstaGreeter

Chicago Cultural Center

Chicago, IL

Mäkelä Conducts Mahler 9

Orchestra Hall, Symphony Center

Chicago, IL

Mäkelä Conducts Mahler 9

Orchestra Hall, Symphony Center

Chicago, IL

Mahjong Club

Clearing Branch Library

Chicago, IL

Mahjong Club

Clearing Branch Library

Chicago, IL

Fri, Oct 2FREESports

DePaul Athletics Men's Soccer

Wish Field

Chicago, IL

Fri, Oct 2FREESports

DePaul Athletics Men's Soccer

Wish Field

Chicago, IL

Teen Checkers Open Play

Back of the Yards Branch Library

Chicago, IL

Teen Checkers Open Play

Back of the Yards Branch Library

Chicago, IL

Fri, Oct 2 · 3:00 PMMusic

Smoke Square Shop

Chicago, IL

Fri, Oct 2 · 3:00 PMMusic

Smoke Square Shop

Chicago, IL

Haunted by Our Dark Side: Chicago Ghosts, Gangsters, and True Crime Tour

Inside Chicago Walking Tours

Chicago, IL

Haunted by Our Dark Side: Chicago Ghosts, Gangsters, and True Crime Tour

Inside Chicago Walking Tours

Chicago, IL

Natties and Patties Food Pop Up

Natties and Patties Food Pop Up

Central Park Bar

Chicago, IL

Natties and Patties Food Pop Up

Natties and Patties Food Pop Up

Central Park Bar

Chicago, IL

Get Tickets via TicketWeb →

Hard Country Honky Tonk with The Hoyle Brothers

Fri, Oct 2 · 4:30 PMMusic

Hard Country Honky Tonk with The Hoyle Brothers

Empty Bottle

Chicago, IL

TicketWeb

Get Tickets via TicketWeb →(opens in a new tab)

Fri, Oct 2 · 4:30 PMMusic

Hard Country Honky Tonk with The Hoyle Brothers

Empty Bottle

Chicago, IL

Get Tickets →(opens in a new tab)

Fri, Oct 2 · 5:00 PMConference

HomeDadCon - Chicago 2026 (Oct.2-3)

Embassy Suites Chicago - Downtown

Chicago, IL

Fri, Oct 2 · 5:00 PMConference

HomeDadCon - Chicago 2026 (Oct.2-3)

Embassy Suites Chicago - Downtown

Chicago, IL

Fri, Oct 2 · 6:00 PMFrom $28.52Art

FashionBar THE SHOWS: October 2026 - The Trans Media Fashion Show

Water Tower Place, Level 3

Chicago, IL

Fri, Oct 2 · 6:00 PMFrom $28.52Art

FashionBar THE SHOWS: October 2026 - The Trans Media Fashion Show

Water Tower Place, Level 3

Chicago, IL

Fri, Oct 2FREEArt

Wicker Park Bucktown's “First Fridays” Art Walk

Jackson Junge Gallery

Chicago, IL

Fri, Oct 2FREEArt

Wicker Park Bucktown's “First Fridays” Art Walk

Jackson Junge Gallery

Chicago, IL

Cutting and Pasting a World: The Paper Craft of Henry Darger

Intuit Art Museum

Chicago, IL

Cutting and Pasting a World: The Paper Craft of Henry Darger

Intuit Art Museum

Chicago, IL

Fri, Oct 2 · 6:00 PMFrom $55.20Theater

Still She Rise… But God

Kennedy-King College

Chicago, IL

Fri, Oct 2 · 6:00 PMFrom $55.20Theater

Still She Rise… But God

Kennedy-King College

Chicago, IL

Fri, Oct 2Sports

FashionBar THE SHOWS: October 2026 – The Trans Media Fashion Show

WATER TOWER PLACE – Level 4, Michigan Ave.

Chicago, IL

Fri, Oct 2Sports

FashionBar THE SHOWS: October 2026 – The Trans Media Fashion Show

WATER TOWER PLACE – Level 4, Michigan Ave.

Chicago, IL

Fri, Oct 2 · 6:00 PMFREEArt

Bridge Performance Incubator Showcase

Hyde Park Art Center

Chicago, IL

Fri, Oct 2 · 6:00 PMFREEArt

Free · Eventbrite →

Bridge Performance Incubator Showcase

Hyde Park Art Center

Chicago, IL

1st Set With The Pamoja Project

Andy's Jazz Club & Restaurant

Chicago, IL

1st Set With The Pamoja Project

Andy's Jazz Club & Restaurant

Chicago, IL

Fri, Oct 2FREETrivia & Games

Friday Night Chess Club

Rizal Center

Chicago, IL

Fri, Oct 2FREETrivia & Games

Friday Night Chess Club

Rizal Center

Chicago, IL

Fri, Oct 2Comedy

Pandemonium, Please Hold

The Second City

Chicago, IL

Fri, Oct 2Comedy

Pandemonium, Please Hold

The Second City

Chicago, IL

Fri, Oct 2 · 6:30 PM$24.37Comedy

Latina Comedy Festival Presents: The Bebesitas Show

The Lincoln Lodge

Chicago, IL

Fri, Oct 2 · 6:30 PM$24.37Comedy

Latina Comedy Festival Presents: The Bebesitas Show

The Lincoln Lodge

Chicago, IL

The Infinite Wrench

The Neo-Futurist Theater

Chicago, IL

The Infinite Wrench

The Neo-Futurist Theater

Chicago, IL

Jekyll& Hyde

Broadway Playhouse at Water Tower Place

Chicago, IL

Jekyll& Hyde

Broadway Playhouse at Water Tower Place

Chicago, IL