With long days and warm nights, summer weekends are made for exploring. Whether you’re staying local or venturing out, here are a few events worth adding to your calendar.
Shop Small at the Kids Flea Market
Young sellers take center stage at this pint-sized market where kids run their own booths filled with gently used books, toys, clothes, and handmade goods. The event doubles as a crash course in entrepreneurship for the sellers and a treasure hunt for the rest of us. Whether you’re shopping for bargains or just in it for the cuteness overload, this market promises plenty of both.
Date: June 28
Time: 9AM-3PM
Cost: Free
Location: Joseph C. Vallez Activity Center, 1529 Harlem Ave, Berwyn
More Info: nbpd4fun.org
Catch the Glow at the Evening Firefly Walk
Experience the quiet magic of summer nights on this guided firefly walk through the forest preserves. Timed for twilight, the stroll offers a gentle way to connect with nature as thousands of fireflies flicker in the growing dark. Designed for families, it’s a peaceful way to slow down and soak up the season.
Date: June 27
Time: 8PM-9PM
Cost: Free with Registration
Location: Trailside Museum of Natural History, 738 Thatcher Ave, River Forest
More Info: fpdcc.com
Feel the Energy at the XXV American Sokol Set
This massive, multi-day celebration of fitness and Czech heritage brings together athletes of all ages for gymnastics competitions, a pickleball tournament, fitness challenges, youth programming and more. But it’s not all sweat; there’s also a local brewery tour, a Chicago-style social, and a big celebration dance to close out the festivities.
Date: June 27-29
Time: Various Times
Cost: Various Pricing
Location: Various Locations
More Info: calendarwiz.s3.amazonaws.com
Dance All Weekend at Back lot Bash
What started as a neighborhood block party has grown into one of Pride weekend’s biggest celebrations. Now in its 21st year, Back Lot Bash brings two days of high-energy music and community to Andersonville. Saturday’s lineup includes DJ Kid Riot, PINK Squeeze Band, and Too Much Molly, while Sunday welcomes headliner JoJo Siwa and a packed roster of performers and DJs. Expect drag, dancing, and a whole lot of fun!
Date: June 28-29
Time: 3PM
Cost: $25+
Location: Cheetah Gym Parking Lot, 5248 N Clark St
More Info: backlotbashchicago.com
Shop Original Work at Millennium Art Festival
Surround yourself with color and creativity at this outdoor art fest in the heart of downtown. With 110 artists showing everything from sculpture and photography to jewelry and painting, there’s something for every taste. Enjoy live music, face painting, food trucks, and interactive demos-and maybe even bring home a one-of-a-kind piece. The best part? It’s free to attend and just steps from Millennium Park.
Date: June 28-29
Time: 10AM-5PM
Cost: Free
Location: 180 N Stetson Ave
More Info: amdurproductions.com
Eat Local at the Chicago Food Truck Festival
A who’s who of Chicago’s mobile food scene rolls into the South Loop for two days of outdoor dining. Over 40 trucks dish out crowd favorites like tacos, lobster rolls, and deep-fried sweets, with drinks and live music. Whether you’re a foodie or just looking for a laid-back bite in the sun, this fest hits the spot. General admission is free, but VIP packages include drink tickets and early access.
Date: June 28-29
Time: 10AM-8PM
Cost: Free
Location: 2300 S Indiana Ave
More Info: chicagofoodtruckfestival.com
Celebrate at the Chicago Pride Parade
The 54th annual Pride Parade kicks off with bold floats, big energy, and a message that’s as timely as ever. This year’s theme, United in Pride, centers on community, resilience, and the power of showing up. The route winds through Uptown and Lakeview, and draws hundreds of thousands of spectators. Look for our own float in the lineup and come celebrate love, identity, and progress with us!
Date: June 29
Time: 11AM-2PM
Cost: Free
Location: 3900 N Broadway
More Info: pridechicago.org
Sip and Stroll at Craft Brews
Sip your way through one of the city’s most scenic beer festivals. This adults-only night at Lincoln Park Zoo features 100+ craft beers and ciders, with tasting stations set against lush gardens and animal habitats. Bonus perks include a souvenir cup, access to the carousel, lawn games, and live music by SideStreets. It’s one part zoo, one part beer garden-and completely unique.
Date: June 28
Time: 7PM-10PM
Cost: $57+
Location: Lincoln Park Zoo, 2001 N Clark St
More Info: lpzoo.org
