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Chicago Weekend Guide! Things to Do in Chicago This Memorial Day Weekend May 24-27

Chicago Weekend Guide! Things to Do in Chicago This Memorial Day Weekend May 24-27

  • 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:: 18th Street & Halsted Street 60608
WHEN:: May 24-26
WHY:: Since 2009, Mole de Mayo Festival strives to deliver a culturally dynamic and gastronomic outdoor festival in Chicago’s historic Pilsen neighborhood. Savor a variety of regional and specialty mole dishes from some of Pilsen’s popular eateries and the surrounding neighborhoods. Relish the sound at one of the two main music stages located at the entrances. Experience a variety of music styles from top local, national and international live acts. Take home a one-of-kind, hand-crafted piece of art, jewelry, or apparel from the many artisans, crafters and merchant booths lined up throughout the festival. The must-see festival highlight, lucha libre, will hold Saturday and Sunday from 3 p.m. to 5 p.m.
COST:: FREE Admission, $5 suggested donation.  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:: House of Blues Chicago | 329 N. Dearborn Street 
WHEN:: May 24
WHY:: Founded in 2010 by E.Z.Mo Breezy, GRITS & BISCUITS is a premiere entertainment concept that celebrates the southern experience through urban music, cultural connections and nightlife moves in a down home environment. Grits & Biscuits is a party for the people!
COST:: $20 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:: March 22 through March 24
WHY:: The weekend’s lineup of films at the Siskel Film Center includes: Ethan Hawke’s “WildCat,” Peterr Kass’ classic “Time of The Heathen,”  and “Smoking Tigers.”
COST:: Varies Click here for more info

WHERE:: 3200 N. Sheffield Avenue
WHEN:: May 24-26
WHY:: The unofficial start to summer is getting bigger starting Friday evening! Expect to have a blast at this popular 39th annual street happening on Sheffield Avenue in the heart of the Lakeview neighborhood (and just steps from the Belmont El station). Don’t miss top local tribute bands on the main stage (near Roscoe), great eats, libations (beer and wine) and artisans. Also expect an eclectic “community” entertainment stage near Belmont filled with fun neighborhood music acts, deejays and other performers. Headliners include Rod Tuffcurls & The Bench Press, Sixteen Candles, Trippin Billies.
COST:: $10 Click here for more info

WHERE:: Gallery Guichard | 436 East 47th Street 60653 
WHEN:: through May 19
WHY:: Mendel & Seton Classes of ’84 Presents The 1984 All Schools 40th Reunion Sneaker Ball.
COST:: $50 Click here for more info

WHERE:: North Avenue Beach | 1603 N. Lakeshore Drive
WHEN:: May 24-27 
WHY:: Castaways is synonymous with summertime in Chicago. The iconic boat house on North Avenue Beach features the best views in the city – overlooking the lakefront and the Chicago skyline. The newly reimagined Castaways Beach Club is the perfect blend of old and new. The classic charm of Castaways has been preserved while incorporating modern design elements, additional seating, and elevated food & beverage offerings. The result is a warm and inviting atmosphere that appeals to both loyal regulars and new customers alike. Come and experience the best of both worlds! .
COST:: $Free to attend, food + drinks on you Click here for more info


WHERE:: Grant Park
WHEN:: May 25 – 26 | 12pm – 10pm
WHY:: Sueños music festival, was first inaugurated in 2022, the festival mainly focuses on reggaeton and latin trap. As we step into Year 3 of El Festival Latino, we are excited to make it the best one yet. Lineup includes: Peso Pluma, Rauw Alejandro, Maluma, Ivan Cornejo, Bad Gyal, Elena Rose, Young Miko & many more.
COST:: $Varies Click here for more info


WHERE:: Wintrust Arena | 600 E. Grand Avenue 
WHEN::  May 25 | 7pm
WHY::  LIBERTY, BIBERTY, CEDRIC DIGGORY. The price has gone up and so has the vibe and hype. The Chicago Sky are ready to take on DeWanna Bonner and the Connecticut Sun.
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:: 1341 W. Randolph Street 
WHEN:: May 25 & 26 | 10am-5pm
WHY:: Find the best art, antiques and vintage decor, ephemera, vintage and indie designer fashion and jewelry, vinyl, global goods, fancy and fun foods – thousands of top-quality goods presented by dealers from around the country at this fancy European style flea market festival! Enjoy our market bars, cabana and air-conditioned beaux-arts building plus a continuous variety of live bands each day to make for an exceptionally fun shopping vibe — and the best people watching anywhere!
COST:: $12+ Click here for more info

WHERE:: Bamboo Club | 3505 N Clark St 
WHEN:: May 25 | 3 – 9pm 
WHY::Afrobeats Day Party Experience,
Memorial Holiday weekend Edition. DJ Diesel . DJ Hypeman . DJ Rymzy . DJ K.O. spinning the hottest Afrobeats . Amapiano . Hiphop & Dancehall. The Rooftop: This is by bottle service only. Limited access to Non-table holders. Sections on the rooftop will be first to sell out. Reserve yours now! 2nd Floor & Patio: Ceiling to floor window and Patio. Accessible to all attendees. Ready to party with other 400+ ravers… AC Blasting… GBEDU pumping!

COST:: $Varies Click here for more info

WHERE:: Gallagher Way  | 3635 N Clark Street 60613
WHEN::  May 25-26 | 12-9pm 
WHY:: WingOut Chicago returns to its iconic new home at Gallagher Way!! On the footsteps of Wrigley Field, patrons can indulge in all the flavors from Chicago’s top vendors while also enjoying cold beverages and live music.From Classic Buffalo, Honey Chili, Jerk, Wood Smoked, Sweet and Spicy, Spicy Garlic, Buffalo Blue, Asian Ginger, Southern BBQ, Habanero Hot and more … Dozens of varieties will be represented in all for patrons to try! 2024 Vendor Lineup to Include Names Such As:
Jake Melnick’s Corner Tap, Bub City, Base Hit BBQ, Hangry’s, El Campeon, Woodie’s Flat, Prime Tacos, The Wild Hare, Jokers Cajun Smokehouse, Smoke Daddy, Max & Leo’s, Parlay (Lincoln Park), Rizzo’s Bar & Inn and More. Musical Lineup To Include: Marlon and The Shakes, Golden Street Reggae Band, Vibe Music LIVE, and Your DJs: Terry Cloth and KRLS1.
COST:: “Pre-Sold Tickets for WingOut are 100% SOLD OUT. Walk-Ups are possible. Click here for more info

WHERE:: Wreath Laying Ceremony, Daley Plaza (50 W. Washington St) | Parade, State Street from Lake St. to Van Buren St. at Noon
WHEN:: May 25 | 11am- 
WHY:: Chicago’s Memorial Day Parade honors all men and woman who made the ultimate sacrifice in defense of our country. The Wreath Laying Ceremony will begin at 11am at Daley Plaza (50 W. Washington Street). The Parade will step off at noon and proceed south on State Street from Lake Street to Van Buren Street. Rear Admiral Zeita Merchant, U.S. Coast Guard will serve as this year’s Parade Grand Marshal. Rear Admiral Merchant, who was born in Chicago, recently made history by becoming the first African American female promoted to flag rank in U.S. Coast Guard history. This year’s Major General John A. Logan Patriot Award will honor André Richardson King; and the City of Chicago will acknowledge two Junior Reserve Officers’ Training Corps (JROTC) students with the Cadets of the Year Award: C/LTC Lorena Mozo of Farragut Career Academy and C/Capt Fernando Gonzalez of Marine Leadership Academy. During the Wreath Laying Ceremony and Parade, the City of Chicago honors fallen heroes and Gold Star family members who have lost a loved one in the United States Armed Forces to combat operations or while on active duty.
COST:: Free to attend Click here for more info


See Also
Photo image of the downtown landscape of chicago featuring tall buildings and the famous chicago cloud gate aka the bean in Millennium Park

WHERE::  Lincoln Park | Tribe Supper Club | 1239 West Lake Street
WHEN:: May 25 | 12 – 8pm
WHY::Come join us for a day of delicious food and good vibes. BRUNCH & BOUNCE, is the perfect way to start your weekend with a bang. Indulge in a scrumptious brunch spread while BOUNCING to some of the Best music by Southern Artist, curated by some of Chicago’s hottest DJ’s. Round up your friends or show up to make some new ones. Mark your calendars and get ready to Brunch and Bounce with us.
COST:: $10 suggested donation for entry; Click here for more info

WHERE:: Soldier Field | 1410 Special Olympics Drive Chicago 60605
WHEN:: May 25 | 7am
WHY:: Soldier Field 10 celebrating its 20th Memorial Day run through the heart of Chicago! Remember the brave soldiers who made the ultimate sacrifice for our country on the 10K or 10-Mile course after a pre-race playing of taps and a military salute. Enjoy the spectacular skyline views and beautiful scenery like Lake Michigan before you cross the finish line ON Soldier Field! The Post-Race Tailgate will be waiting for you in the Stadium Green with complimentary beer (21+), live music, and much more! The Soldier Field 10 courses highlight the city’s biggest attractions including Soldier Field, the Museum Campus and the beautiful shores of Lake Michigan! Our 10-Mile and 10K courses follow the same routes with the 10K runners taking an earlier turnaround..
COST:: $89  Click here for more info

WHERE:: SeatGeek Stadium | 7000 South Harlem Avenue, Bridgeview
WHEN:: May 25 | 6:30pm
WHY:: The Chicago Red Stars are a professional women’s soccer club and a founding member of the National Women’s Soccer League (NWSL), which they have played in since 2013. This historic team features a diverse set of world-class players and is committed to advancing women’s soccer and building a championship culture on and off the pitch. .
COST:: $Varies  Click here for more info


WHERE:: Harold Washington Library | 400 S. State Street 
WHEN:: May 19 | 11am-5pm
WHY:: The second American Writers Festival on May 19, 2024 in Chicago is presented by the American Writers Museum and Chicago Public Library. The free literary festival will be held at multiple stages inside the Harold Washington Library Center and feature a number of leading contemporary authors, poets, artists, and playwrightsThe Festival will feature in depth conversations with diverse writers including sci-fi authors, game writers and designers, journalists and poets. From labor history to true crime thrillers to jazz music, the Festival will celebrate the past, promote the present and inspire the future of American writing. Children’s storytimes, photo booths, literary crafts and mini writing workshops get adults and kids into the written word, and authors will sign books for sale.
COST:: $FREE. All programs are entirely free to attend and no prior registration is required. Click here for more info



WHERE:: Cindy’s at Chicago Athletic Hotel | 12 S. Michigan Avenue
WHEN::  May 19 | 6pm-10pm 
WHY::  Night Brunch was created to celebrate food, music, and friends. This is a common culture of people that know it takes all 3 elements to make a memorable moment. Who says we have to do brunch, like everyone else, we just want great food, dope people, and to set the vibes. Come thru. Music by Jay Illa.
COST:: Registration required. Click here for more info


Featured image credit: Ozzie Stern via Unsplash

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