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13 things to do over Memorial Day weekend in Chicago

Celebrate the unofficial start to summer in Chicago at these music festivals, street fairs and more.

Lauren Brocato
Written by
Lauren Brocato
Things To Do Editor, Time Out Chicago
Downtown Chicago
Photograph: Courtesy George Bakos/Unsplash | Downtown Chicago
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The weekend we’ve been waiting for is finally here. This Memorial Day weekend marks the unofficial start of summer, when the city comes alive once again.

There’s a lot to do over the three-day weekend, but luckily, there's time to fit in a little bit of everything. Read on for the best Memorial Day events in Chicago. 

1. Attend the Memorial Day Parade and wreath-laying ceremony

Sat

After a wreath is laid at the eternal flame in Daley Plaza at 11am in remembrance of those who died serving in the U.S. armed services, Chicago's annual Memorial Day Parade marches down State Street (from Lake to Van Buren streets) beginning at noon. Crowds line the street waving flags and paying their respects as part of this Chicago tradition, which dates all the way back to 1870.

2. Watch the Navy Pier fireworks show

Sat

fireworks
Photograph: ShutterstockFireworks

During the summer, the Chicago attraction hosts twice-weekly fireworks shows (on Wednesdays at 9pm and Saturdays at 10pm) from Memorial Day weekend through Labor Day weekend, with stunning views available from across Navy Pier’s public spaces. During the winter months, the pyrotechnics return for a much-needed encore. If you're feeling weary of crowds, you can also take in the show from nearby beaches or while cruising along the Lakefront Trail.

3. Run the Soldier Field 10

Sat

You may never get to enter the gridiron with the Chicago Bears, but you can take off on a 10-mile run from the team's home turf. The Soldier Field 10-Mile begins and ends at the stadium, sending participants on a scenic jaunt down the Lakefront Trail. Everyone who registers receives a Chicago jersey tee and a stadium blanket, and finishers get a medal memorializing their achievement. Stick around afterwards for a beer at the post-race tailgate.

4. Or jam out at Sueños Music Festival

Sat, Sun 

suenos music festival
Photograph: Jesus J. MonteroSuenos Music Festival

This two-day extravaganza returns to Grant Park over Memorial Day weekend. Taking place on a single stage in Grant Park's Hutchinson Field, Sueños will feature headlining sets from Kali Uchis, Fuerza Regida, J Balvin and more. In addition to two days of music, you can try food from some of Chicago's best Latin restaurants, a host of art installations and experiential activations, and a Ferris wheel in the park that you can ride between (or during) sets. 

5. Enjoy free admission at the Pritzker Military Museum & Library

Sat

This small yet comprehensive military library and museum is offering free admission on Saturday, May 23 in honor of Memorial Day. Visit to check out The War of 1812: Countering Peril on the High Seas and at Home, an exhibit chronicling the conflict between the U.S. and the U.K.

6. Break a sweat at a free fitness class in the park

Sat

Spin classes and weight lifting can wait for the winter. This summer, jump-start your weekend with free cardio kickboxing, yoga, pilates and Zumba classes on Millennium Park’s Great Lawn and in Wrigley Square every Saturday from May through August.

7. Then sample craft beers at Mayfestiversary

Sat, Sun

Ravenswood Corridor neighbors Dovetail and Begyle return this year for their annual Memorial Day weekend street fest on Malt Row, where attendees can sip beer from both breweries and grab bites from Beard and Belly, Donerman, Happy Lobster and more. Catch live music and consider tossing in a donation, which will benefit neighborhood food pantry The Friendship Center. 

8. Treasure hunt at Randolph Street Market

Sat, Sun

Get ready to hunt for some new (and old) treasures! The beloved Randolph Street Market Festival is back with two days of curated, European-style vintage and antique shopping. Browse wares from hundreds of vendors, or grab a cocktail and bite to eat from local restaurants while tapping your toes to live music. 

9. Discover new indie artists at The Salt Shed’s music festival

Sat, Sun

The Chicago skyline and the Morton Salt building in the foreground
Photograph: Sandra SteinbrecherThe Salt Shed

Returning for its second year, The Salt Shed’s flagship music festival promises a weekend of left-of-center sounds and alternative icons. This year’s lineup features Aussie singer-songwriter Courtney Barnett, electronic luminary Toro y Moi, and noise-pop pioneers The Jesus and Mary Chain. Beyond the music, attendees can explore the quirky Oddball Market and a studio sale curated by the Chicago nonprofit Arts of Life.

10. Watch the sunset from a rooftop bar

Sat-Mon

Want to know what's even better than a frozen cocktail on a hot day? A frozen cocktail on a rooftop on a hot day. Cool off all Memorial Day weekend long with drinks at these sky-high watering holes—just be prepared to make a reservation or brave a wait for walk-ins. 

11. Cruise down the river on a boat tour

Sat-Mon

Not brave enough to take a dip in Lake Michigan yet? Get out on the water with one of the city's best boat tours, from mesmerizing architecture tours along the Chicago River to wind-whipping speedboat cruises on the lake. You can even rent a small electric boat and be your own captain for a day, if you're feeling adventurous. 

12. Bike the Lakefront Trail

Sat-Mon

Lakefront Trail
Photograph: Neal O'Bryan for Time OutLakefront Trail

Stretching from Hollywood Avenue on the North Side to 71st Street to the south, the Lakefront Trail is a great way to experience one of Chicago's crown jewels: Lake Michigan. It also serves as a reminder for residents of why our city, edged by sparkling blue water, is a pretty nice place to live. 

13. Or escape the city for a hike

Sat-Mon

If you're to dodge the long-weekend crowds, put on your best boots and hit the trails at some of the best places for hiking near Chicago. Thankfully, you don't need to go too far to escape the urban jungle because there's no shortage of great spots for hiking within driving distance.

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