The Haute Seeker

Need Big Plans For Memorial Day Weekend 2023 In Chicago? Here are 14 Amazing Things To Do

Memorial Day is the unofficially official kick-off to the 2023 summer season, and it starts this weekend in Chicago. The three-day long weekend commences “SummertimeChi” with fun outdoor events, festivals, community activities, and more.

If you are visiting Chicago or are a local needing 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.

Chicago Weather During Memorial Day Weekend 2023

Whether you are visiting or live in the area, the biggest question beyond what to do in Chicago during the holiday weekend is how the weather will be. Generally, the temperatures in Chicago during May are usually low and can range between 53°F and 66°F. This weekend, the weather will range between the high 60s to mid-70s. This is great weather to get outdoors and enjoy many of the events and activities that Chicago has to offer. It’s a good idea to dress in layers or bring a jacket just in case you get caught in the cooler temperatures at night or in the early morning.

Mole de Mayo Festival // Image by Taylor Justin

Things to Do Memorial Day Weekend Chicago

There are many fun and interesting things to do in Chicago during Memorial Day weekend. Here are a few of the best things to do around the city.

  1. Check out one of many neighborhood and city-wide festivals—this is your ultimate list of 2023 Chicago Festivals.
  2. Get out on the water by renting a pontoon, sailboat, yacht, or even jet ski.
  3. Catch fireworks at Navy Pier for free. Catch the best views from the Ferris Wheel with this discounted admission from The Haute Seeker.
  4. Grab some friends and hit up your favorite Chicago beach.
  5. Eat, drink, and shop like a local—I’ve got a list of all of their favorite spots.
  6. Host a cookout and ask others to bring their favorite side dishes.
  7. Take in the breathtaking views with this easy guide to the best rooftops in the city.
  8. Freshen up your summer wardrobe and shop at a trendy boutique.
  9. Explore a Chicago museum and see what’s new from the past, present, or future. Check out this roundup of the best museum exhibitions to see in 2023.
chicago cityscape
Photo by Pixabay on

Memorial Day Events Around Chicago

There are plenty of activities, festivals, and annual events that take place during Memorial Day weekend. Check out this list of the unique events taking place over the holiday weekend.

Sueños Music Festival in Grant Park

Saturday, May 27th – Sunday, May 28th // 12 p.m. – 10 p.m.

Cost: $199 – $1,499

Sueños is bringing the biggest Latin lineup Chicago has ever seen. The music festival will feature live performances by 20+ Reggaeton & Latin artists, delicious food from local vendors, art, activities, and more!

SummerSalt Market: A Special Memorial Day Weekend Edition

Saturday, May 27th – Sunday, May 28th // 12 p.m. – 5 p.m.

Cost: Free

SummerSalt Market is back and bigger this weekend in Chicago. The market features vintage, vinyl, furniture, and more, plus some of the best food & drinks Chicago offers. Hangout out on the fairgrounds of Chicago’s newest music venue and discover something new.

Memorial Day Weekend Cruises

Saturday, May 27th // 7:15 p.m.

Cost: $69.95

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. Enjoy a luxurious night aboard the Anita Dee for the biggest Memorial Weekend yacht cruise. Tickets include an open bar, 2 DJs, 3 Decks + Fireworks Show!

Memorial Day Wreath Laying Ceremony & Parade

Saturday, May 27th // 11:00 a.m.

Cost: Free Admission

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

5th Anniversary: A Dope Art Show

Monday, May 29th // 12:00 p.m. – 5:00 p.m.

Cost: Free Admission; Donations are appreciated

Head to Ludlow Liquor this Memorial Day weekend for the Dope Art Show. This year the art show will showcase 50+ artists from the Chicagoland area. The collaborative event will also feature local food vendors and shops like Plant Shop Chicago, Birria Ta-Ta-Tacos, and Ludlow Liquor for an all-day celebration.

For more things to do in Chicago, check out the daily events calendar.


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