Want to know what’s happening this weekend in Chicago? Look no further. There’s a whole calendar of exciting events, exhibits, and activities taking place all over the city this month in Chicago.

This summer weekend in Chicago is jam-packed with artisan markets, jaw-dropping art exhibits, riveting live theatre, family-friendly fun, exciting Pride events, Juneteenth celebrations, and so much more.

Check out just a few of the top things to do this weekend in Chicago, June 20 – 22, 2025.

Chicago Pride Fest 2025
June 21 – 22
Chicago Pride Fest 2025

Chicago Pride Fest® is a two-day street festival on June 21-22, 2025; the weekend before the Chicago Pride Parade (June 29, 2025). The 24th annual Chicago…

June 21 – 22, 2025
Northalsted
Halsted Street from Addison to Grace Streets
Black Yacht Weekend – Juneteenth Weekend
Jun 19 – Jun 22
Black Yacht Weekend – Juneteenth Weekend

Black Yacht Weekend 2025 is the ultimate summer event celebrating community, culture, and the luxury of life on the water. Set against the stunning backdrop…

Thursday June 19, 2025 — Sunday June 22, 2025
The Playpen
500 N Lake Shore Dr
Summer Nature Fest
June 20
Summer Nature Fest

Explore the museum inside and out after hours! Join us for an evening of summer fun featuring: Live Animals! Live Music! Outdoor Nature Play! Nature…

June 20, 2025
House of Burlesque Chicago – Pride Show
Jun21
House of Burlesque Chicago – Pride Show

Join Hot Tawdry for Chicago's most intimate monthly Burlesque and Drag Show! This June 21st we celebrate Pride on our stage with an ICONIC line-up!…

Saturday June 21, 2025
House of Blues | Chicago
329 N Dearborn St
WNDR Pride Month Mixer featuring Chicago’s Haus of Paint
Jun22
WNDR Pride Month Mixer featuring Chicago’s Haus of Paint

WNDR Chicago is proud to be collaborating with the iconic queer collective “Haus of Paint.” Composed of 7 incredible artists, the Haus of Paint has…

Sunday June 22, 2025
wndr museum
1130 W Monroe St.
Pride with The Neo-Futurists: 30 Queer Plays in 60 Straight Minutes
June 20 – 22
Pride with The Neo-Futurists: 30 Queer Plays in 60 Straight Minutes

The Neo-Futurists' annual Pride tradition returns! Join us for 30 glow'd up, sweat-soaked, lipstick-smeared, gender-euphoric, gay-panic-inducing plays in 60 minutes -- all in the name…

June 20 – 22, 2025
The Neo-Futurist Theater
5153 N. Ashland Ave.
The Deep Pockets Of Graceland Cemetery Walking Tour
June 21
The Deep Pockets Of Graceland Cemetery Walking Tour

Dive into this captivating journey through the hallowed grounds of Chicago’s Graceland Cemetery. As we stroll amidst the stunning and serene beauty of historic resting…

June 21, 2025
Graceland Cemetery
4001 N. Clark Stree
Gold Coast Greek Festival
June 20 – 22
Gold Coast Greek Festival

Chicago's Gold Coast Greek Festival is back! Offering Chicagoans and visitors a taste of authentic Greek food, live music and dancing, Greek DJ sets, and…

June 20 – 22, 2025
Annunciation Greek Orthodox Cathedral
1017 N LaSalle Drive
Forest Preserves of Cook County’s 12th annual ‘Juneteenth Jubilee’
June 21
Forest Preserves of Cook County’s 12th annual ‘Juneteenth Jubilee’

The Forest Preserves of Cook County invites residents to celebrate freedom, family and country with activities, presentations, performances and exhibits that highlight Black history, arts…

June 21, 2025
Sand Ridge Nature Center, 15891 Paxton Ave in South Holland
15891 Paxton Ave
Chicago Greeter InstaGreeter Walks of the Riverwalk
June 21
Chicago Greeter InstaGreeter Walks of the Riverwalk

Explore the Chicago Riverwalk with our knowledgeable volunteers! InstaGreeter walks take you on a free hour-long guided walk of the Riverwalk, without the need to…

June 21, 2025
Vietnam Veteran’s Memorial
The Joffrey Ballet’s Alice’s Adventures in Wonderland
June 20 – 22
The Joffrey Ballet’s Alice’s Adventures in Wonderland

Experience this Chicago premiere with The Joffrey Ballet, the first American ballet company to bring Wheeldon’s Wonderland to life. Plunge down the rabbit hole into…

June 5 – 22, 2025
Lyric Opera of Chicago
20 N. Wacker Dr. , Chicago, IL, 60606
Big Bus Tours’ Sunset Live Tour
June 20 – 22
Big Bus Tours’ Sunset Live Tour

Big Bus Tours, the global leader in open-top bus sightseeing, invites visitors to experience the enhanced Sunset Live Tour in Chicago. Available May 8 through…

June 20 – 22, 2025
618 N Clark St.
618 N. Clark St
Chicago Cubs vs. Seattle Mariners
June 20 – 22
June 20 – 22, 2025
Wrigley Field
1060 West Addison Street
Titanique
June 20 – 22
Titanique

Broadway In Chicago presents the Porchlight Music Theatre production of TITANIQUE All aboard NYC’s must-sea musical comedy! When the music of Céline Dion makes sweet Canadian…

March 26 – July 13, 2025
Broadway Playhouse at Water Tower Place
175 E. Chestnut St .Chicago, IL 60611
An Iliad
June 20 – 22
An Iliad

A timely and gripping retelling of Homer’s epic poem, An Iliad returns to Court’s stage, illuminating the human cost of conflict with breathtaking urgency. Timothy Edward Kane reprises his…

June 14 – 29, 2025
Court Theatre
5535 S. Ellis, Chicago, IL, 60637
Chicago Greeter Neighborhood PopUp Series
June 21
Chicago Greeter Neighborhood PopUp Series

Join the Chicago Greeter Neighborhood PopUp Series for FREE guided walks through the city's vibrant neighborhoods - led by friendly local volunteers! Come explore, connect, and experience Chicago…

May 24 – Aug. 30
Navy Pier
June 21
Navy Pier Summer Fireworks

Navy Pier is known for its spectacular summer fireworks displays, which kick off on Memorial Day weekend. This year, the Memorial Day weekend fireworks show at Navy Pier will be held on Saturday, May 24 at 10 p.m.

Saturday May 24, 2025 Saturday August 30, 2025

600 E. Grand Avenue

Millennium Park Summer Workouts
June 21
Millennium Park Summer Workouts

The workout program takes place on the Great Lawn in Millennium Park on Saturdays, May 17 to August 30, 8-11:45 a.m. with a series of…

May 17 – Aug. 30, 2025
Millennium Park
201 E Randolph St
You Will Get Sick
June 20 – 22
You Will Get Sick

A young man with a secret. An older woman who will listen. A predatory flock of birds. An upcoming audition for The Wizard of Oz. Welcome…

June 5 – July 13, 2025
Frida Kahlo
June 20 – 22
Frida Kahlo’s Month in Paris

Don’t miss the first-ever exhibition of Kahlo’s work at one of the most renowned art museums in the world.

Saturday March 29, 2025 Sunday July 13, 2025

Art Institute of Chicago

Dressed in History: A Costume Collection Retrospective
June 20 – 22
Dressed in History: A Costume Collection Retrospective

What do a red sequin burlesque costume, a pair of original Air Jordan 1s, a baby’s wool bathing suit, and an enormous white tulle Christian…

Nov. 8 – July 27, 2025
Chicago History Museum
1601 N. Clark St.

Explore our events calendar for more Chicago events and happenings.

Please note that all events are subject to change.