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 in 2026 is Friday, May 22, through Monday, May 25.
The long weekend marks the unofficial start of summer in the city. Beaches reopen, neighborhood street festivals return, and parades honor fallen service members.
Chicago is literally one of my favorite cities in the entire world, so I write this post with my firsthand perspective on how much I love the Windy City.
I know, mildly dramatic, but I’m serious!
Visitors can spend the weekend watching fireworks at Navy Pier, exploring the Chicago Riverwalk, attending street festivals, or catching a Cubs or White Sox game. Play ball!
Whether you’re visiting Chicago for the first time or planning a holiday weekend getaway, these are the best Memorial Day weekend activities in Chicago for 2026.
Why Visit Chicago for Memorial Day Weekend
Memorial Day weekend is one of the best times to visit Chicago.
The weather warms up, lakefront beaches reopen, and the city begins its famous summer festival season.
What could be better than the official start to summer?!
Unlike July and August, crowds are slightly smaller, making it easier to experience popular attractions like the Chicago Riverwalk and Navy Pier.
Visitors can combine lakefront activities with Chicago’s world-class food scene, all in one perfect, long weekend.
10 Best Things to Do in Chicago Over Memorial Day Weekend
1. Attend a Memorial Day Parade
Chicago Memorial Day Parade: Downtown
The main Chicago Memorial Day Parade will take place this year on Saturday, May 23, 2026, in downtown Chicago.
The event begins with a wreath-laying ceremony at 11:00 AM in Daley Plaza, followed by the parade starting at 12:00 PM on State Street between Lake Street and Van Buren Street.
It is one of the largest Memorial Day parades in the United States, featuring military units, marching bands, veterans organizations, and civic groups.
McKinley Park Memorial Day Parade
The McKinley Park Memorial Day Parade takes place on Monday, May 25, 2026 at 10:00 AM.
The parade begins near the McKinley Park Public Library (1915 W. 35th Street) and features neighborhood organizations, veterans groups, and local marching bands.
This event offers a more community-focused Memorial Day celebration on Chicago’s South Side.
Norwood Park Memorial Day Parade
The Norwood Park Memorial Day Parade will be held on Monday, May 25, 2026 at 11:00 AM.
The parade typically begins at Onahan School (6634 W. Raven Street) and includes:
- local school groups
- veterans organizations
- community clubs
This long-running event is one of the most beloved Memorial Day traditions on Chicago’s Northwest Side.
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2. Visit Chicago’s Memorial Day Weekend Festivals
Memorial Day weekend marks the beginning of Chicago’s famous summer street festival season.
Neighborhoods across the city host lively outdoor festivals featuring live music, food vendors, craft beer, and local artisans.
Two popular early-summer events include:
Mayfestiversary
Mayfestiversary, hosted by Begyle Brewing and Dovetail Brewery, will take place Saturday, May 23 – Sunday, May 24, 2026.
The event is in Chicago’s Ravenswood neighborhood on the North Side.
The festival includes:
- live music
- craft beer from both breweries
- food trucks
- family-friendly activities
A suggested donation helps support the Friendship Center food pantry.
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Belmont-Sheffield Music Festival
The Belmont-Sheffield Music Festival is scheduled for Friday, May 22, through Sunday, May 24, 2026 in the Lakeview neighborhood.
The festival takes place along Sheffield Avenue near Belmont Avenue and features:
- live music from tribute bands
- food vendors
- craft booths
It’s conveniently located just steps from the Belmont CTA station.
3. Chicago Baseball Games
Seeing a Chicago Cubs or White Sox Game is a quintessential item on any Chicago summer itinerary!
Even for a long weekend.
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.
It’s also one of Chicago’s most lively neighborhoods!
There are tons of restaurants, bars, and things to do around here.
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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. Walk The 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 forever one of my favorite ways to experience Chicago. And 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 is 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 Opening for Summer (2026)
The city’s 26 miles of lakefront beaches officially open for summer over Memorial Day Weekend!
I have never seen a Chicago beach livelier than on Memorial 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
One of the highlights of Chicago Memorial Day weekend is the return of fireworks at Navy Pier!
The first summer fireworks show of 2026 is expected to take place on:
Saturday, May 23, 2026, at 10:00 PM
The show usually repeats every Wednesday at 9 PM and Saturday at 10 PM through Labor Day.
Navy Pier fireworks are by far one of the best free things to do in Chicago.
Especially amazing on the 4th of July!
9. Chicago Farmer’s Markets
Chicago’s outdoor farmers market season begins in mid-May, meaning several markets are open during Memorial Day Weekend 2026 (May 22–25).
One of the most popular is the Daley Plaza Farmers Market, which typically opens for the season in late May in downtown Chicago.
The market usually runs on Thursdays from 7:00 AM to 2:00 PM, making it a great stop if you’re exploring downtown before heading to other attractions like the Chicago Riverwalk or Millennium Park.
Visitors can browse a variety of local vendors selling:
- fresh Midwest produce
- artisan breads and baked goods
- flowers and plants
- specialty foods from Chicago vendors
I particularly love the Green City Market in Lincoln Park.
It’s surrounded by so much lush green space, and you’re just around the corner from the Lincoln Park nature trail and Chicago’s Lakefront Trail.
It’s easy to combine with a morning walk along Lake Michigan!
This market is open Saturdays from 7:00 AM to 1:00 PM and features dozens of local farmers and food producers.
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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!
Memorial Day Weekend Chicago Itinerary
If you’re visiting Chicago for the long weekend, here’s a mini itinerary to help you make the most of your trip.
Day 1
- Walk the Chicago Riverwalk (local personal favorite)
- Take a Chicago Architecture Cruise (highly rated among both locals and tourists)
- Dinner in West Loop
Day 2
- Morning at North Avenue Beach
- Chicago Cubs game at Wrigley Field
- Belmont-Sheffield Music Festival
Day 3
- Attend a Memorial Day Parade
- Visit Skydeck Chicago
- Watch fireworks at Navy Pier
FAQ: Chicago Memorial Day Weekend
1. When is Memorial Day Weekend in Chicago in 2026?
Memorial Day falls on Monday, May 25, 2026, with celebrations and events happening from Friday, May 22, through Monday, May 25.
2. Are Chicago beaches open on Memorial Day weekend?
Yes. Chicago’s lakefront beaches open for the season on Memorial Day weekend, with lifeguards typically on duty during opening beach hours through Labor Day.
3. Are there fireworks in Chicago on Memorial Day weekend?
Yes. Navy Pier typically launches its summer fireworks series during Memorial Day weekend.
And it’s always free!
Conclusion
Chicago is an excellent choice for a Memorial Day Weekend getaway. As a local, I guarantee you are in for an excellent trip.
From Navy Pier fireworks to walking the Chicago Riverwalk, lakefront biking to street fests, 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!
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