Spring has sprung across Chicagoland and there many exciting events to fill your calendar! From family events to date night activities, there’s something for everyone—here are a few of our top picks to check out this weekend.
Make Every Mile Count at Race to the Flag 5K
Lace up for a 5K with heart. This community run supports the People’s Resource Center, which provides food, housing support, and job training to DuPage County residents. Whether you’re racing or walking, every step helps a neighbor in need.
Date: May 25
Time: 8AM-10AM
Cost: $17+
Location: Ty Warner Park, 800 Blackhawk Dr, Westmont
More Info: racetotheflag.org
Have Fun at the Memorial Weekend Carnival
Kick off summer with spinning rides, carnival games, and deep-fried everything at this weekend-long fest hosted by Windy City Amusements. From classics like the Ferris wheel to bumper cars and cotton candy stands, there’s plenty to keep families busy. Check online for daily ride specials.
Date: May 23-25
Time: Fri 6PM-10PM; Sat 1PM-10PM; Sun 1PM-9PM
Cost: Free
Location: Chestnut Court Shopping Center, 7511 Lemont Rd, Darien
More Info: darien.il.us
Shop for a Cause at the Spring Market
This pop-up market combines shopping and goodwill, with handmade goods, tasty food, and a silent auction benefiting small churches across Europe and the Midwest. Browse vendor booths for unique finds, grab a bite, and know your dollars are going toward a good cause.
Date: May 25
Time: 11:30AM-1:30PM
Cost: Free
Location: Timothy Christian Schools, 188 W Butterfield Rd, Elmhurst
More Info: facebook.com
Feel the Beat at Sueños
Chicago’s largest reggaeton and Latin music festival returns with a two-day lineup packed with global stars like Shakira, Peso Pluma, and Don Omar. Alongside the music, expect a full-on party in Grant Park with art installations, food vendors, and nonstop dancing.
Date: May 24-25
Time: 12PM-10PM
Cost: $199+
Location: Grant Park, 337 E Randolph St
More Info: suenosmusicfestival.com
Rock Out at the Belmont-Sheffield Music Festival
Now in its 40th year, this Lakeview fest unofficially kicks off Chicago summer with cover bands, food vendors, and neighborhood connection. Expect tribute acts on the main stage, plus local DJs, artisans, and a second stage near Belmont showcasing community performers.
Date: May 25-25
Time: Fri 5PM-10PM; Sat & Sun 11AM-10PM
Cost: Free
Location: 3200 N Sheffield Ave
More Info: chicagoevents.com
Raise a Glass at Mayfestiversary
Begyle Brewing and Dovetail Brewery team up again for this Memorial Day weekend bash featuring craft beer, live music, and local eats. It’s family and dog friendly, with activities for kids and a strong lineup of indie rock and funk acts.
Date: May 24-25
Time: Sat 11AM-10PM; Sun 11AM-11PM
Cost: $5 Suggested Donation
Location: N Ravenswood Ave and Belle Plaine Ave
More Info: mayfestiversary.com
Dive Into Flavor at Masala Memories: Celebrating South Asian Food in Chicago
Chefs and food journalists explore the city’s evolving South Asian cuisine scene in this evening panel moderated by author Colleen Taylor Sen. The discussion is followed by a tasting of street food from across the region; plus chai and beer from Azadi Brewing.
Date: May 24
Time: 3PM-5PM
Cost: $50
Location: South Asia Institute, 1925 S Michigan Ave
More Info: saichicago.org
Browse the Randolph Street Market
This indoor-outdoor vintage market in the West Loop kicks off its summer season with over 200 vendors selling everything from antiques to vinyl. Shop vintage fashion, home goods, and global finds while live bands and local eats round out the festive atmosphere.
Date: May 24-25
Time: 10AM-5PM
Cost: $12+
Location: 1341 W Randolph St
More Info: randolphstreetmarket.com
