Things to Do in Chicago and DuPage – Weekend Guide (May 22 – May 24, 2026)
Chicago Weekend Highlights
Chicago is heading into Memorial Day weekend with an exciting lineup of festivals, markets, immersive experiences, food tours, live performances, and major sporting events happening across the city. From the colorful return of Fleurs de Villes FLORA and Sueños Music Festival to neighborhood farmers markets, Cubs baseball, and guided food adventures through Pilsen and the West Loop, there’s no shortage of ways to kick off summer in Chicago. Here are 15 events worth checking out this weekend.
May 22, 2026 – Friday Picks
Ink & Outrage: 18th-Century Satirical Prints in London & Dublin
Explore rare political satire artwork and historic prints at the Driehaus Museum through this fascinating cultural exhibition.
Fleurs de Villes FLORA at 900 North Michigan Shops
See stunning floral mannequins and large-scale botanical art installations displayed throughout 900 North Michigan Shops.
Minecraft Experience: Villager Rescue
Step into an immersive Minecraft-inspired world filled with interactive challenges, scavenger hunts, and live adventure gameplay.
Chicago Cubs vs. Houston Astros
Catch the Cubs at Wrigley Field as they take on the Houston Astros during a weekend series in Chicago.
Chicago Greeter – Loop InstaGreeter
Discover downtown Chicago through a free guided walking experience featuring architecture, local history, and hidden city gems.
May 23, 2026 – Saturday Picks
Division Street Farmers Market
Shop fresh produce, flowers, local foods, and artisan products at one of Chicago’s longest-running outdoor markets.
Daley Plaza Farmers Market
Spend the morning downtown browsing seasonal produce, prepared foods, and locally made goods in the Loop.
Millennium Park Summer Workouts
Join free outdoor fitness classes in Millennium Park with energetic group workouts in the heart of downtown Chicago.
Thinking Through Tapestry | American Tapestry Alliance at Evanston Art Center
Explore contemporary textile art and creative tapestry works featured in this unique Evanston exhibition.
Excerpts of Imagination | Louis De Guzman
Experience colorful contemporary artwork and imaginative visual installations from Chicago artist Louis De Guzman.
May 24, 2026 – Sunday Picks
Sueños Music Festival 2026
Celebrate Latin music and culture at Grant Park with major performances, food vendors, and festival experiences throughout the weekend.
Street Foods of Pilsen Food Tour
Taste authentic Mexican cuisine while exploring the murals, restaurants, and culture that make Pilsen one of Chicago’s top food neighborhoods.
Gateway to The West Loop Food Tour
Discover Chicago’s famous West Loop dining scene through guided tastings at some of the neighborhood’s most talked-about restaurants.
Chicago Cubs vs. Houston Astros
Wrap up the holiday weekend with another Cubs home game at iconic Wrigley Field.
The Hula-Hoopin’ Queen
Enjoy a family-friendly theatrical performance based on the beloved children’s book at Greenhouse Theater Center.
DUPAGE WEEKEND HIGHLIGHTS
Memorial Day weekend is bringing a packed lineup of family-friendly events, outdoor activities, festivals, exhibits, live entertainment, and dining experiences across DuPage County. From mini golf at The Morton Arboretum and climbing adventures in Wheaton to blues festivals, brunch outings, and immersive museum exhibits, there’s something happening all weekend long throughout the western suburbs. Here are the top DuPage County events to check out this weekend.
May 22, 2026 – Friday Picks
Perfect Game Windy City Memorial Day Classic
Watch competitive youth baseball teams from around the region compete during this major Memorial Day weekend tournament in New Lenox.
Wonder Woods Mini Golf
Enjoy a nature-themed mini golf experience surrounded by colorful outdoor art installations at The Morton Arboretum in Lisle.
America 250 Summer Art Banner Exhibit
Explore patriotic-themed public art banners celebrating America’s 250th anniversary throughout Downtown West Chicago.
America250 Elmhurst
Celebrate America’s upcoming 250th anniversary with community-wide exhibits, installations, and special programming across Elmhurst.
Cabinet of Curiosities Exhibit
Discover unusual artifacts, historic treasures, and fascinating local history at the DuPage County Historical Museum in Wheaton.
May 23, 2026 – Saturday Picks
Vivid Creatures
Experience larger-than-life animal sculptures and interactive art displays throughout The Morton Arboretum in Lisle.
We The People: Naperville and the American Story Exhibit
Learn about Naperville’s historical connection to America’s evolving story through engaging exhibits and local artifacts at Naper Settlement.
“A Noteworthy Crime” Dinner Detective
Solve a live interactive murder mystery while enjoying dinner during this entertaining detective-themed experience in Lisle.
Blues, Brews & BBQ
Spend the evening enjoying live blues music, barbecue favorites, and local craft beer at The Forge in Lemont.
Family Climbing Tower
Challenge yourself on a towering outdoor climbing wall experience at Lincoln Marsh in Wheaton.
May 24, 2026 – Sunday Picks
Family Style Sundays
Gather for a relaxed Italian-style dining experience featuring shareable dishes and family-friendly specials in Downers Grove.
Weekend Wrap-Up
Chicago and DuPage County are set for another busy spring weekend filled with entertainment, outdoor activities, cultural experiences, live performances, family-friendly attractions, food events, and seasonal festivals. Across the city and suburbs, residents and visitors can explore everything from immersive exhibits and neighborhood experiences to brunch outings, markets, sporting events, music, and interactive activities. With Memorial Day weekend approaching, the lineup reflects the start of summer across Chicagoland, giving people plenty of ways to enjoy the warmer weather throughout both downtown Chicago and the western suburbs.
Also Read: Tickets Now Available for the Obama Presidential Center Ahead of June Opening
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