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Chicago Weekend Guide! Things to Do in Chicago This Weekend May 31-June 2

Chicago Weekend Guide! Things to Do in Chicago This Weekend May 31-June 2

  • Best events in Chicago this weekend March 22-24

The weekend is upon us and many of you are looking for a good time or at the least somewhere to go and have fun, maybe meet new people or cultivate a new hobby? Keep scrolling as we’ve curated a nice varied selection of things to do from events taking place in and around Chicago this special Memorial Day Weekend. You can have a basic weekend in Chicago or a great one when you tap in to our Chicago Weekend Guide.


WHERE:: Soldier Field | 1410 Special Olympics Drive 60605
WHEN:: May 24-26
WHY:: Experience the electrifying clash between Mexico and Bolivia. Cheer on your favorite team before they head to Copa América 2024.
COST:: Varies.  Click here for more info

WHERE:: Cadillac  Palace Theatre | 151 W. Randolph Street  60601 
WHEN:: through June 2 
WHY:: Madeline Ashton is the most beautiful actress (just ask her) ever to grace the stage and screen. Helen Sharp is the long-suffering author (just ask her) who lives in her shadow. They have always been the best of frenemies…until Madeline steals Helen’s fiancé away. As Helen plots revenge and Madeline clings to her rapidly fading star, their world is suddenly turned upside down by Viola Van Horn, a mysterious woman with a secret that’s to die for. Cast includes: Tony Award® nominees Megan Hilty (Wicked, “Smash”), Jennifer Simard (Company, Disaster!), and Christopher Sieber (Spamalot, Company), with Grammy® Award winner Michelle Williams (Destiny’s Child, Chicago), Death Becomes Her, based on the classic 1992 film, is a drop-dead hilarious new musical comedy about friendship, love, and burying the hatchet…again, and again, and again.
COST:: $35+ Click here for more info

WHERE:: Schaumburg Convention Center | 1551 Thoreau Drive North, Schaumburg, IL 
WHEN:: May 31-June 1
WHY:: NECANN’s Illinois Cannabis Convention will once again be the largest, most comprehensive gathering of the state’s cannabis industry and community, making it THE must-attend event for anyone who wants to be a part of this rapidly growing industry!
COST:: $50 Click here for more info

WHERE:: Navy Pier | 600 E Grand Avenue Chicago 60611 
WHEN:: through May
WHY:: Experience Chicago from a whole new perspective at Flyover. Follow your sense of adventure to Navy Pier and rediscover the feeling of absolute awe. Our exhilarating immersive journey connects you with Chicago like never before. Soar over iconic locations, dive into authentic stories and lose yourself to an adventure unlike any other.
COST:: $24.95 (Adult); $14.95(13 and under); $19.95 (military) Click here for more info

WHERE:: Gene Siskel Film Center | 164 N. State Street
WHEN:: May 31 through June 2
WHY:: The weekend’s lineup of films at the Siskel Film Center includes: “20,000 Species of Bees,”  Sidney Lumet’s classic “12 Angry Men,”  and “Kidnapped.”
COST:: Varies Click here for more info

WHERE:: Shops at Northbridge  | 520 N Michigan Avenue 60611 
WHEN:: May 31-June 23
WHY:: Attention Chicago! Discover pre-loved designer clothes, handbags, and more at up to 90% off original retail prices at Rent The Runway’s Chicago Sample Sale.
COST:: $50 Click here for more info


WHERE:: 51 E Ohio Street 60611
WHEN:: May 31-June 2 | 11AM – 7PM(Fri/Sat); 11AM – 5PM (Sun)
WHY:: Shop up to 70% off at the Acne Studios Chicago Sample Sale! Prices start at $20 for select items. Available runway apparel starts at $400+
COST:: $FREE to attend pay for items purchased. Click here for more info



WHERE:: Huntington Bank Pavilion at Northerly Island.
WHEN:: June 1-2| 12pm – 10pm
WHY:: The inaugural Chicago edition of Beyond Wonderland is an electronic dance festival organized by Insomniac Events. The two-day festival is poised to offer an immersive experience. 
COST:: $Varies Click here for more info


WHERE:: Soldier Field | 1410 Special Olympics Drive, 60605 
WHEN::  June 1| 7:30pm
WHY::The Chicago Fire FC’s Pride Night Celebration will take place during the Club’s Saturday, June 1 Match against the LA Galaxy. The Fire and Carvana will kick-off Pride Month with a celebration of unity and inclusivity, recognizing Chicago’s LGBTQIA+ community, their contributions to soccer, and beyond.
COST:: $Varies. Click here for more info 


WHERE:: Orland Square | 288 Orland Square Dr, Orland Park, 60462, United States
WHEN:: May 25 through June 9th
WHY:: Bounce, slide and dance your way through a surreal, candy-colored wonderland filled with laughter and unforgettable moments across the Bounce The City tour’s amazing inflatable attractions. Jump into City Xscape, where bouncing meets intergalactic adventure, race through The Giant’s neon obstacle course, slide down Skyscraper Slide’s towering thrills, and groove in The Silent Disco Dome.  A beloved sister of The Big Bounce America, this immersive family attraction is composed of four unique inflatables: the thrilling 600+ ft. long obstacle course The Giant; the intergalactic, extraterrestrial City Xscape; the towering, supersized Skyscraper Slide; and a silent Headphone Disco Dome with live DJs, lights, and special effects! From one end to the other, Bounce The City offers all kinds of inflatable fun for every age!
COST:: $24 Click here for more info

WHERE:: 4000 N. Milwaukee Avenue Portage Park
WHEN:: June 1-2 | 12pm – 10pm
WHY:: Some of Chicagoland’s favorite hot dog stands will compete for who has the best frankfurter at the 3rd annual Windy City Hot Dog Fest! And you get to be the judge! Plus, in addition to tasty dogs, patrons will get to listen to great local and regional acts on the event’s mainstage. Plus, don’t miss the kids’ area, arts & crafts vendors and a community stage!
COST:: Donation Click here for more info

WHERE:: Millennium Park| Enter at Michigan Ave. & Washington St., Michigan Ave. & Madison St., Randolph St. or Monroe St.  
WHEN:: June 1 | 4-9pm 
WHY::Kicking off Millennium Park’s 20th Anniversary Season, this FREE inspirational music festival brings audiences of all ages and backgrounds together to celebrate the power of music. 2024 features an all-star lineup headlined by the three-time GRAMMY® winning, highest-selling female gospel group in history, The Clark Sisters; Chicago’s own award-winning singer/songwriter Todd Dulaney; GRAMMY® winning contemporary gospel artist Chandler Moore; and three-time GRAMMY® nominated global recording artist Anita Wilson. Hosted by iHeartMedia Chicago’s Inspiration 1390’s Sonya Blakey, DeAndre Patterson and VaShawn Mitchell, the festival also showcases rising star Lena Byrd Miles and will bringaudiences to theirfeet with Choir Nation: A tribute to Chicago Church Choirs.
COST:: $FREE Admission Click here for more info

WHERE:: Division Street between Damen and Leavitt
WHEN::  May 31-June 2 | 12-10pm 
WHY:: The Festival features local restaurants, food trucks, food vendors, West Town retail vendors, corporate sponsors, local artists, and more.
COST:: “$10 Suggested Donation. Click here for more info

WHERE:: Museum of Contemporary Art Chicago Sylvia Neil and Daniel Fischel Galleries | 200 E. Chicago Avenue 60611
WHEN:: Open June 1 through March 2025 
WHY:: Across three decades, artist and filmmaker Arthur Jafa has developed a singularly dynamic practice comprising films and videos, photographs, and sculptures. Through his multidisciplinary work, Jafa seeks to encompass what he describes as “the full complexity, specificity, beauty, and potentiality of what Black folks have made and continue to make out of the bleak existential circumstance we’ve attended to over the past several hundred years.” Utilizing found imagery, music, and artistic techniques such as montage and collage, he has constructed an extensive assemblage of Black expression, layered and arranged in ways that reveal the diverse and complex realities of Black being. Lead support is provided by the Harris Family Foundation in memory of Bette and Neison Harris, the Zell Family Foundation, and Cari and Michael Sacks. Major support is provided by R. H. Defares and Agnes Gund. Generous support is provided by D. Elizabeth Price and Lou Yecies.
COST:: Museum admission $19 Click here for more info

See Also


WHERE::  City Winery Chicago | 1200 West Randolph Street
WHEN:: June 1& 2
WHY:: Not that he’d wish it on anyone, but it was during his ten-year sentence in prison that Lyfe Jennings developed his honest sound, thanks to isolation and Erykah Badu. It was an arson charge that put the Toledo, Ohio native in prison. His musical aspirations started in the church choir and grew up in the Dotsons, a teenage group that Lyfe formed with his brother and a couple cousins. Prison made his music deeper, according to Lyfe, and when a copy of Erykah Badu’s Baduizm ended up in his cell in 1997, he was inspired and had the feeling that this introspective edge to his music was worth developing. 
COST:: $Varies; Click here for more info

WHERE:: Soldier Field | 1410 Special Olympics Drive Chicago 60605
WHEN:: June 1 -June 2 | 10am-5pm
WHY::Kick off the summer at the first major art fair of the season, located in the beautiful Hyde Park neighborhood on the South Side of Chicago. The 57th Street Art Fair is THE place to buy art, whether you’re a seasoned collector or new to the art scene. Meet friends, bring your family, enjoy the day at this historic, welcoming, fun event. All artists exhibiting at the Fair are stationed in their booths throughout the weekend to discuss their work.
COST:: $FREE  Click here for more info

WHERE:: Shedd Aquarium | 1200 S. DuSable Lake Shore Drive 60605
WHEN:: June 1 | 6pm-10:30pm
WHY:: Join Shedd Aquarium and A Queer Pride in celebrating our vibrant and creative LGBTQ+ community! Kick off Pride Month festivities in style with a memorable Pride Night at Shedd featuring multiple DJs and an ocean-themed drag showcase. Discover the wonders of the aquatic animal world in an environment that welcomes and embraces all identities, all while making new friends and reconnecting with old ones. Don’t miss out on this unique opportunity to convene together to embrace the diversity of our community!
COST:: $14.95(Members); $19.95(Chicago residents); $39.95 (Non-Chicago resident);   Click here for more info



WHERE:: Millennium Park, Multiple stages | Michigan Ave. & Washington St 
WHEN:: June 2 | 10am-9pm
WHY:: The Chicago House Music Festival is an annual celebration of the Chicago-born genre that has revolutionized dance music globally. This year’s event celebrates the 40th anniversary of house music with four days of free events culminating in the main event on Sunday. House Fest will feature a lineup of local and international DJs including Tony Touch, ANANÉ, Ash Lauryn, Andrew Emil,Microdot, Dj Slugo, Luis Baro, Karizma, Wayne Williams and Alan King of the Chosen Few DJs and more.
COST:: $FREE. All programs are entirely free to attend and no prior registration is required. Click here for more info

WHERE:: Tacotlan | 4312 W. Fullerton 
WHEN:: June 2 | 12-5pm
WHY:: Club de Chingonas was founded by Jessica Perjes, one of the owners of Tacotlan. This group was created to help empower women and to help each other navigate this crazy, and definitely difficult, business world. Each year, Tacotlan holds a place for these women to come together to promote and sell their products. It’s a free event for the women to participate. This year we received help from Alderman Felix Cardona and his team and we were approved for a permit to hold our event on the entire sidewalk in front of Tacotlan, from Kildare to Lowell. This is an event that you won’t want to miss. There will be a DJ, 20+ women entrepreneurs selling their products, amazing food from Tacotlan, and a raffle prize!
COST:: $FREE. Click here for more info

Featured image credit: Ozzie Stern via Unsplash

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