Are you looking for the best things to do in Chicago over Memorial Day Weekend? This is the guide for you!
Memorial Day Weekend in Chicago marks the start of summer with festivals, outdoor fun, and lakefront views.
It’s one of the best times to explore the city’s top attractions without the deep chill or high-season crowds. Here’s how to make the most of it.
There are special events over Memorial Day weekend, like three different parades and various festivals.
10 Best Things to Do in Chicago Over Memorial Day Weekend
1. Parades
1. Chicago Memorial Day Parade
The Chicago Memorial Day Parade is held on Monday, May 26, 2025, at 12:00 PM in Downtown Chicago.
It is one of the largest Memorial Day parades in the country!
The parade steps off from State Street between Lake and Van Buren Streets with a wreath-laying ceremony at 11:00 AM in Daley Plaza.
2. McKinley Park Memorial Day Parade
On the Southside, the McKinley Park Memorial Day Parade starts at 10:00 AM from McKinley Park Public Library (1915 W. 35th St.).
It features local veterans’ groups and marching bands.
3. Norwood Park Memorial Day Parade
Over in the Northwest Side, the Norwood Park Memorial Day Parade begins at 11:00 AM from Onahan School (6634 W. Raven St.).
It includes local schools, community groups, and veterans.
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2. Festivals
1. Mole de Mayo Festival
The Mole de Mayo Festival is a vibrant celebration of Mexican culture held over Memorial Day Weekend in Chicago’s historic Pilsen neighborhood.
In 2025, the festival will take place from Saturday, May 24, through Monday, May 26, at 18th Street between Halsted and Morgan Streets.
This free, family-friendly event features a mole cook-off where local chefs compete for the title of “Best Mole”.
It also features live music, lucha libre wrestling matches, and an open-air mercado showcasing local artisans and vendors.
2. Mayfestiversary
Mayfestiversary is a lively spring celebration hosted by Begyle Brewing and Dovetail Brewery in the Ravenswood neighborhood.
This family-friendly festival takes place on Saturday, May 24, 2025, from 11:00 AM to 10:00 PM, and Sunday, May 25, 2025, from 11:00 AM to 9:00 PM, at 1800 W Cuyler Ave, Chicago, IL 60613.
The event features live music performances, food trucks, and activities for all ages.
A suggested $5 donation supports the Friendship Center, a local food pantry.
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3. Belmont-Sheffield Music Festival
The Belmont-Sheffield Music Festival is a lively street festival held over Memorial Day Weekend in Chicago’s Lakeview neighborhood.
In 2025, the festival will take place from Friday, May 23, to Sunday, May 25, at 3200 N. Sheffield Avenue.
This free, family-friendly event features live music from tribute bands, local food vendors, and artisan booths. It’s located conveniently just steps from the Belmont El station.
3. Chicago Baseball Games
Seeing a Chicago Cubs or White Sox Game is a quintessential item on any Chicago summer itinerary.
The Chicago Cubs play the Colorado Rockies on Monday, May 26th.
Chicago White Sox play the Texas Rangers Friday, May 23rd – Sunday, May 25th
There are tons of things to do after the baseball games as well.
For example, Wrigley Field is located in the Wrigleyville neighborhood of Chicago. There are tons of restaurants, bars, and things to do around here.
4. Chicago Architecture Cruise
A Chicago Architecture Cruise is one of the best ways to see the city’s skyline.
You’ll glide down the Chicago River while a guide shares the stories behind the buildings.
It’s a relaxing, scenic break from the crowds and a perfect way to kick off summer sightseeing.
5. Chicago RiverWalk
The Chicago Riverwalk is a beautiful and scenic place to stroll, grab a bite at riverside cafes, or even rent a kayak.
It’s iconic on any Chicago Itinerary!
If you want to get off the beaten path a little bit, the Marketplace on Chicago’s Riverwalk is not very well known and considered a non-touristy activity in Chicago.
6. Free Walking Tour
Taking a free walking tour in Chicago over Memorial Day Weekend is an excellent way to explore the city’s rich history and vibrant neighborhoods.
Free walking tours are one of my favorite ways to get my bearings set in any new city!
7. Chicago Beaches Open
The city’s 26 miles of lakefront beaches are ready to welcome visitors over Memorial Day Weekend!
From Friday, May 23, 2025, at 11 a.m., lifeguards will be on duty daily from 11 a.m. to 7 p.m., ensuring safe swimming until Labor Day.
Popular spots like North Avenue Beach offer volleyball courts and vibrant beach bars, while Montrose Beach provides a spacious area with a designated dog-friendly section.
Chicago’s beaches provide a perfect setting to kick off the summer season!
8. Navy Pier Fireworks
Navy Pier’s free fireworks show kicks off summer on Saturday, May 24, 2025, at 10 PM.
This dazzling display lights up the lakefront with synchronized music and vibrant colors.
It’s a festive, family-friendly way to celebrate the holiday and enjoy Chicago’s skyline.
The show repeats every Wednesday at 9 PM and Saturday at 10 PM through Labor Day.
9. Chicago Farmer’s Markets
The city’s farmers markets open for the season on Saturday, May 17, 2025, with the Daley Plaza Market kicking off on Saturday, May 22, 2025.
These markets offer fresh produce, artisanal goods, and local specialties.
10. Skydeck
Skydeck Chicago is an amazing overview of the city. I love the new interactive museum exhibits you go through on the way to the elevator up!
Once at the top of the skydeck, you can spend as long as you would like enjoying the views.
Once you’re ready, you get in line for your 60 seconds to stand or sit in the glass box 1,300+ feet above the city. It’s a thrill!
Conclusion
Chicago is an excellent choice for a Memorial Day Weekend getaway.
From Navy Pier fireworks to walking the Chicago Riverwalk, lakefront biking to street fests like Mole de Mayo, the city buzzes with energy.
Whether you’re a first-timer or a local, it’s a weekend packed with classic Chicago vibes and summer kickoff magic.
