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
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…
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…
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…
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!…
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…
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…
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…
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…
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…
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…
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…
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…
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…
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…
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…
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.
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…
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…
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.
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…
Explore our events calendar for more Chicago events and happenings.
Please note that all events are subject to change.
