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 iconic events like the Chicago House Music Festival, top neighborhood festivals, artisan markets, jaw-dropping art exhibits, riveting live theatre, family-friendly fun, exciting cultural events, and so much more.
Check out just a few of the top things to do this weekend in Chicago, Aug. 22 – 24, 2025.
Chicago House Music Festival and Conference
The Chicago House Music Festival is an annual celebration of Chicago house music that has revolutionized dance music globally. Held in Millennium Park every summer, this joyous event celebrates the Chicago-born genre and attracts house fans from across the globe to hear today’s top DJs and up-and-coming talent.
Sangria Festival Chicago
Sangria Festival Chicago returns to Humboldt Park for a weekend celebration like no other — where sangria takes center stage!
Get ready to sip, savor, and celebrate at Chicago’s only festival dedicated to the art of sangria, expertly paired with Latin-inspired cuisine, live music, dancing, and outdoor fun. This festive gathering is your passport to flavor, culture, and community.
Lakeview Taco Fest
With its eclectic mix of trendy stores, charming boutiques, and delectable restaurants, the Southport Corridor is one of Chicago’s most sought-after destinations. This August, it gets even hotter as tacos take center stage at the 12th Annual Lakeview Taco Fest, a celebration of flavor, fun, and community.
Chicago Triathlon
Cheer on elite athletes over two days as they swim, bike, and run along Chicago’s scenic lakefront. Voted the Best Sprint Triathlon in the USA, the Chi Tri is one of the world’s largest and most accessible triathlons.
EEEEEATSCON Chicago
EEEEEATSCON Chicago 2025 Details Tickets: On sale July 1 at 10 a.m. CT at eeeeeatscon.com exclusively for Chase cardholders. When: August 23-24, 2025 Chase Sapphire…
Chicago International Boat Show
Chicago International Boat Show August 21–24, 2025 | Navy Pier Marina & Festival Grounds The Chicago International Boat Show launches this summer with an all-new…
MJ
Back by overwhelming demand, the multiple Tony Award®-winning musical MJ is making a victorious return to Chicago. Created by Tony Award-winning Director/Choreographer Christopher Wheeldon and…
Glenwood Sunday Market in Rogers Park
The nonprofit Rogers Park Business Alliance (RPBA) announces 23 local vendors for the 16th anniversary season of the Glenwood Sunday Market, which will operate every…
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…
The Lawndale Route 66 Festival
The Lawndale Route 66 Festival, taking place on Sunday, August 24, 2025, from 10:00 AM to 7:00 PM, along a historic stretch of Route 66…
Summer Wine Down at Gallagher Way
On Saturday, August 23, Gallagher Way transforms into wine country with a laid-back tasting event featuring plenty of wines to sample, live music, floral bouquet…
Guardians of the Earth and Sky
Come on an adventure with the Four Celestial Guardians: the White Tiger of the West, the Black Tortoise of the North, the Azure Dragon of…
Thirsty Ears Festival
The Thirsty Ears Festival, now in its tenth year, is Chicago's only classical music street festival. For two days we close Wilson Ave. to feature…
Cumbia Catedral
Get ready for an unforgettable "Cumbia Catedral" at The Epiphany in Chicago!Join us for a night of high-energy rhythms, featuring a special national live performance…
Tikka Masala
Tikka Masala: The Indian Improv Comedy Game Show. Get ready for a laugh-out-loud night of unscripted chaos, cultural flavor, and spicy twists! Tikka Masala is…
Escape the Museum at Griffin MSI
Escape the Museum is back and better than ever. After a sold-out weekend in 2024, Griffin MSI is hosting 12 nights of "The Wandering Alchemist."…
Simple Plan – Bigger Than You Think! Tour
Pop-punk veterans Simple Plan are celebrating their 25th anniversary as a band in a big way, announcing a headlining Summer 2025 US tour with support…
Alexander Nate (Live in Technicolor) at Thalia Hall
With a captivating blend of soulful melodies and deeply heartfelt lyrics, Alexander Nate has carved out a distinct space for himself in the music world.…
Zoo Uncorked: Wines & Vines
Sip, savor, and explore at Wines & Vines, Brookfield Zoo Chicago’s exclusive 21+ event featuring the grand opening of our breathtaking Tropical Forests habitat! Enjoy a…
Englewood Village Market
Grow Greater Englewood's 6th Annual Englewood Village Market kicks off on Saturday, June 14th to connect residents with Black-owned businesses and activities rooted in Black…
Goose Island Bike Tour
Join us for a relaxing and informative bike tour of Goose Island on Aug. 23rd fom 10 a.m. to noon. We'll meet at Passion House…
Living in the Shade: Open Space and Public Housing
This exhibition at the National Public Housing Museum explores the role of open space—large lawns and tenant gardens, paved paths and play spaces, shady seating…
The Messi Experience Chicago
The Messi Experience is an immersive and interactive multimedia exhibition inspired by the life and career of Lionel Messi. As part of its world tour,…
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…
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…
Chicago Greeter InstaGreeter Walks of the Loop
InstaGreeter Downtown walks Looking for a quick and easy way to see downtown Chicago's top sights? Let InstaGreeter take you on a free hour-long guided…
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…
Explore our events calendar for more Chicago events and happenings.
Please note that all events are subject to change.
