Need Big Plans For Memorial Day Weekend In Chicago? Here are 14 Amazing Things To Do

Taylor Justin The Haute Seeker sitting on a pontoon boat on Lake Michigan in Chicago

The unofficially official kick-off to the summer season starts this weekend in Chicago. Memorial Day is a three-day long weekend that commences the summer season with outdoor events, cookouts, family gatherings, and more.

If you are visiting Chicago or are a local and just need something fun to do, check out this guide of amazing things to do and cool events to check out this holiday weekend.

Why do we celebrate Memorial Day?

Memorial Day unofficially marks the beginning of the summer season. But what does the holiday mean to Americans? According to, Memorial Day is an American holiday, honoring the men and women who died while serving in the U.S. military. Many Americans observe Memorial Day by visiting cemeteries or memorials, holding family gatherings, and participating in parades. The holiday was originally known as Decoration Day, it originated in the years following the Civil War and became an official federal holiday in 1971.

Mole de Mayo Festival // Image by Taylor Justin

Fun Things to Do during Memorial Day Weekend

  1. Get out on the water by renting a pontoon, sailboat, yacht, or even jet ski.
  2. Catch fireworks at Navy Pier for free. Catch the best views from the Ferris Wheel with this discounted admission from The Haute Seeker.
  3. Grab some friends and hit up your favorite Chicago beach.
  4. Check out popular festivals in the city and suburbs. Including one of our favorites, Mole de Mayo.
  5. Host a cookout and ask others to bring their favorite side dishes.
  6. Take in the breath taking views on a rooftop. Check out the map of our favorites.
  7. Freshen up your summer wardrobe and shop at a trendy boutique.
Taylor Justin The Haute Seeker sitting on a pontoon boat on Lake Michigan in Chicago

Memorial Day Events Around Chicago

Memorial Day Wreath laying ceremony & parade

Saturday, May 28th // 11:00 a.m.

Cost: Free Admission

Chicago’s Memorial Day Parade honors all men and woman who made the ultimate sacrifice in defense of our country.

Wine Fest on the Beach – Wine Tasting at North Ave. Beach

Friday, May 27th // 6:00 p.m. – 9:00 p.m.

Cost: $50 – $60

Grab your closest friends and enjoy this beachfront getaway while sipping a variety of different wines at the Shore Club. Tickets to the event include three hours of tastings, giveaways, and more! Taste a variety of wines while hanging out at Shore Club on North Avenue Beach.

Cubs vs White Sox

Saturday, May 28th – Sunday, May 29th // Time Varies

Cost: $47 – $900

Root for your favorite Chicago baseball team during Memorial Day weekend in Chicago. The Cubs take on the White Sox at Guaranteed Rate Field. You couldn’t ask for a better matchup!

Memorial Day Weekend Cruises at DuSable Harbor

Sunday, May 29th – Monday, May 30th // Time Varies

Cost: $12.50 – $20

Spring is in full swing and Chicago is at its most beautiful, so this Memorial Day weekend come celebrate with a relaxing cruise on Lake Michigan. Hop aboard a beautiful yacht and glide past the picturesque Chicago skyline, enjoying great views and the cool breeze on the deck or taking in the sights from inside the yacht. You can sip cocktails from the cash bar while enjoying great music and a laidback vibe.


Friday, May 27th // 5:00 p.m. & 8:00 p.m.

Cost: Free Admission; $25 – $30 for flight samples

In partnership with Choose Chicago, Chicago Friday Night Flights will kick off its sixth season at Gallagher Way this Memorial Day Weekend. The evening will feature local food and 25+ breweries from neighborhoods across the city, as well as Friday Night Flights’ resident DJ spinning records throughout the night. Get ready for a great night of Chicago beer, local food, and music.

A Dope Art Show ft. Plant Shop Chicago & Birria TaTaTacos

Monday, May 30th // 2:00 p.m. – 8:00 p.m.

Cost: Free Admission; Donations are appreciated

Head to Ludlow Liquor this Memorial Day weekend for the Dope Art Show. The art show features over a dozen local artists from the Chicagoland area. For its 4-year anniversary, the show is going all out by collaborating with Plant Shop Chicago, Birria Ta-Ta-Tacos, and Ludlow Liquor for an all day celebration.

Sueños Chicago Music Festival

Cost: $275 – $1500

Saturday, May 28th – Sunday, May 29th // 12:00 p.m.

A brand new festival is taking over Grant Park this Memorial Day weekend. Sueños Chicago will feature over 15 talented Reggaeton & Latin artists. From the giants to the best of the up-and-coming artists, this lineup is going to bring an unforgettable weekend to Grant Park.

Interested in more things to do this weekend in Chicago? Check out our events calendar for a list of popular events taking place around Chicagoland.

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