BEST Things do in Chicago on Memorial Day Weekend (From a Local)

Spending Memorial Day weekend in Chicago? Here are the best things to do in Chicago for Memorial Day weekend including the best Memorial Day weekend events and festivals to the top activities and attractions.

Chicago Memorial Day Weekend

Memorial Day weekend is a great time to visit Chicago. There are tons of fun things to do in Chicago on Memorial Day and even more during Memorial Day weekend.

Although summer does not start until June, Memorial Day weekend is considered the kick-off to Chicago’s summer season. Locals and visitors alike are excited to get outside and enjoy the warm weather. This means outdoor concerts, festivals and other events are in full swing until the end of summer.

You will also find plenty of great indoor attractions in case the weather is uncooperative or you prefer being indoors.

Disclosure: This article contains affiliate links. I may make a small commission if you make a booking using my links at no extra cost to you. As an Amazon Associate I earn from qualifying purchases.

What to Pack for Chicago for Memorial Day Weekend

For out of town visitors, please note that the weather in Chicago during Memorial Day weekend is unpredictable and temperatures can vary greatly.  Be prepared for either spring (rainy and mild temperatures) or summer weather (hot and humid).  Check the weather right before your visit to know what to expect.

Here are essentials things to pack for Chicago for Memorial Day weekend.

• Comfortable walking shoes – Chicago is a very walkable city so you will do a lot of walking
Reusable water bottle – It can be hot and humid Memorial Day weekend so it is important to stay hydrated
• Sunglasses
• A hat
• A travel umbrella
• Light sweater (and scarf) – For night, lake cruises, indoor places with cold AC
Waterproof case – For your phone if you plan to go kayaking or spend time in the water
External battery for your phone – To recharge your phone’s battery when you are outdoors
• Mosquito repellent – If you plan to be outside around dusk or at night.
• Sunscreen – A must if you will be spending a lot of time outside in the day
• Bathing suit and other beach essentials (if you are planning to spend time at the beach)

If you forget to bring something essential, don’t worry. There are many drugstores located close to the popular tourist attractions if you need to pick something up.

Things to Do in Chicago on Memorial Day Weekend

Here are the best things to do in Chicago on Memorial Day weekend.

Attend a Memorial Day Parade

There are a few Memorial Day parades taking place in Chicago on Memorial Day weekend:

Memorial Day Wreath Laying Ceremony and Parade – Saturday, May 25 in downtown Chicago. There is a Wreath Laying Ceremony at 11am at Daley Plaza (50 W. Washington St). The parade starts at noon on State Street from Lake St. to Van Buren St.

Norwood Park Memorial Day Parade – Monday, May 27 at 11:00 AM starting at Onahan School, 6634 W. Raven St.

McKinley Park’s Memorial Day Parade – Monday, May 27 at 10 a.m, starting from the McKinley Park branch of the Chicago Public Library, 1915 W. 35th St.

Join a Memorial Day Party Cruise

Join these Memorial Day themed booze cruises throughout the weekend and party on the “Summer Of George” boat with music and and a festive atmosphere:

Memorial Day Sunday Sunset Booze Cruise  – Sunday, May 26
Memorial Day Party Cruise  – Monday, May 27

Attend an Outdoor Festival

Memorial Day weekend is the start of the summer outdoor festival season. Outdoor festivals taking place during Memorial Day weekend include: Mole de Mayo (May 24-26), Belmont-Sheffield Music Festival (May 24-26), Mayfestiversary (May 25-26), Sueños Music Festival (May 25-26), Randolph Street Market Festival (May 25-26) and WingOut Chicago (May 25-26).

Take an Architecture River Cruise

Taking an architecture river cruise is a must on any Chicago bucket list.

Take a Lake Cruise

If you enjoy being on the water, a lake cruise is a fun activity whether in the day, around sunset and in the evening. While you don’t get to see the buildings up close like on a architecture river cruise, you do get to enjoy skyline views and a refreshing cool lake breeze. If your time is short, you can do a combination river and lake cruise. Lake cruises depart from Navy Pier or the Michigan Avenue bridge.

Powered by GetYourGuide

Go Kayaking

A fun way to explore the city is to go kayaking in the Chicago River or the lake. There are several companies that offer kayaking tours in Chicago including Urban Kayaks, Kayak Chicago and Wateriders.

You can also rent a kayak at Ohio beach here.

Please note that you will get a little wet so bring a waterproof case for your phone and water-resistant or quick-drying clothing.

Watch Free Fireworks

Memorial Day is the start of firework season in Chicago. Navy Pier puts on free summer fireworks shows starting on Saturday night before Memorial Day weekend.

While you can watch the fireworks show from Navy Pier, you can also watch it from various spots along the Lakefront.

A great way to watch the fireworks is to join a lake or river cruise which will stop on the water for passengers to enjoy the show.

Powered by GetYourGuide

Spend Time at the Beach

Chicago beach season starts Friday before Memorial Day. Oak Street Beach and Ohio Street Beach are conveniently located close to the major tourist attractions. Popular North Avenue Beach is located close to Lincoln Park but is also the most crowded.

Swimming is permitted at beaches when lifeguards are on duty from 11 am – 7 pm daily. You can check swimming conditions here.

You can also rent kayaks, jet skis and boats at various beaches to get out on the lake.

Walk or Bike the Lakefront Trail

Chicago lakefront

Chicago’s Lakefront Trail is a paved path on a 18-mile-long stretch along Lake Michigan. During Memorial Day weekend, the lakefront will be packed with locals and visitors walking, running and riding bikes. Walking or biking all or part of the trail is a great way to see the Chicago skyline, people watch and get some exercise. Here is a map of the trail as well as its access points.

Have Fun at Navy Pier

rides at Navy Pier Chicago

Fun attractions at Navy Pier include a large Ferris wheel (click here to purchase a fast pass ticket and skip the long line), other rides and games as well as the new Flyover Chicago.

Visitors can also enjoy free live music at Navy Pier during Memorial Day weekend. Listen to DJs playing house & dance music at the Wave Wall Performance Platform on Saturday evening. You can also catch Live on the Lake!, a free outdoor live music series in the Navy Pier Beer Garden.

Navy Pier is also home to the Chicago Children’s Museum which is perfect for toddlers and younger kids.

Hang Out on the Riverwalk

best things to do chicago travel blog

The Chicago Riverwalk along the south bank of the Chicago River is one of the best spots in Chicago for people watching. There are restaurants, bars, shops and places to sit along the way -see a map here.

Watch Digital Art at Art on theMart

Art on the Mart
Looking for a unique thing to do at night? Check out Art on theMART, the largest permanent digital art projection in the world, projecting contemporary artwork across the 2.5-acre river-façade of theMART. Free 30-minute program of projections are shown twicenightly. Spectators can watch the show from the jetty section of the Chicago Riverwalk on Wacker Drive between Wells Street and Franklin Street.

Look for Street Art

Moose Bubblegum Bubble by Jacob Watts one of the most famous street art murals in Chicago

Looking for a unique thing to do for Memorial Day weekend? Walk around Chicago looking for street art.

One of the most famous Chicago murals is “Moose Bubblegum Bubble” by Jacob Watts which located at 33 E. Congress (South Wall).  This famous mural is part of the Wabash Arts Corridor and is walking distance to Millennium Park, The Art Institute of Chicago and other well known tourist attractions.

Another famous mural is The Greetings From Chicago Mural at 2226 N Milwaukee Ave, in Chicago’s Logan Square neighborhood. You can see this mural and other street art on this street art tour.

See Buckingham Fountain

Buckingham Fountain in Chicago
Buckingham Fountain, a well known Chicago landmark in the center of Grant Park, is one of the largest fountains in the world. The water is not on during the cold months but it will be turned on by mid-May.

When the water is turned on, it produces a major water display for 20 minutes every hour with a center jet shoots water to a height of 150 feet into the air. Beginning at dusk, a spectacular light and music display accompanies the major water display.

Watch a Baseball Game

wrigley field Chicago

Chicago is known for their love of sports, including baseball. You don’t need to be a baseball fan to enjoy a game – it is fun to just soak in the atmosphere.

There are several Chicago White Sox baseball games in Chicago happening during Memorial Day weekend.

Friday, May 24 – Chicago White Sox vs. Baltimore Orioles at Guaranteed Rate Field (with post game fireworks)
Saturday, May 25 – Chicago White Sox vs Baltimore Orioles at Guaranteed Rate Field
Sunday, May 26 – Chicago White Sox vs Baltimore Orioles at Guaranteed Rate Field
Monday, May 27 – Chicago White Sox vs. Toronto Blue Jays at Guaranteed Rate Field

Watch Classic Movies on a Rooftop

Want to watch classic movies against the backdrop of the Chicago skyline? Check out Rooftop Cinema Club outdoor screening series to a rooftop in Fulton Market.

Rooftop Cinema Club is located on the fifth floor terrace of The Emily Hotel (311 N Morgan St) and is a high end movie experience complete with tropical decor, lawn games, state-of-the-art LED screens, individual wireless headphones and a range of seating options including lounge chairs and loveseats. Guests can also order drinks and snacks. You can purchase tickets in advance here.

So far I have covered outdoor activities and attractions but there are also plenty of indoor attractions and activities if you need a break from being outside or the weather is still cool and rainy.

Dinos Alive: An Immersive Experience

The Dinos Alive: An Immersive Experience will only be in Chicago for a limited time. Dinos Alive is a dinosaur exhibition featuring life-size animated replicas in an immersive Jurassic venue. This immersive experience brings you face-to-face with the fearsome and spectacular dinosaurs that dominated the animal world for 140 million years. From the turkey-sized Velociraptors to the mighty T-rex, interact with life-sized, moving animatronics of a large variety of species, and see these magnificent creatures in their natural Jurassic habitat. Kids can enjoy a “Budding Experts” interactive space, where they can become paleontologists and tame the most iconic dinosaurs. Children ages 3 and under enter free of charge.

Where: Exhibition Hub Art Center Chicago, 2367 W Logan Blvd, Chicago, IL 60647

Cost: Price varies. Click here for full prices and to purchase tickets in advance.

Visit the Art Institute of Chicago

The Art Institute of Chicago in one of the best Chicago indoor attractions

The Art Institute of Chicago (111 S Michigan Ave) is one of Chicago’s best indoor attractions and one of top museums in the world.

Click here to buy a skip the line ticket if you want to avoid long lines.

Enjoy the Views from 360 CHICAGO Observation Deck

360 CHICAGO, the observatory on the 94th floor of the former John Hancock Building, has one of the best views of the Chicago skyline and Lake Michigan.

(Click here to buy a skip the line ticket).

Where: 875 North Michigan Avenue, 94th floor, Chicago, IL 60611

Downton Abbey: The Exhibition

Downton Abbey: The Exhibition just started its limited time run in the Chicago area. Delve deep into the post-Edwardian era with never-before-seen treasures, from original costumes to iconic props, and exclusive series footage. Traverse the grandeur of the Crawley estate, from the bustling kitchen to the opulent dining room. Explore British society, culture, and fashion amidst historical upheavals.

Where: 4963 Old Orchard Shopping Center, Skokie, IL 60077 (about 17 miles from downtown Chicago)

Cost: Price varies. Click here for full prices and to purchase tickets in advance.

Titanic: The Exhibition

Titanic: The Exhibition has extended its limited time run in the Chicago area for a few more weeks. This interactive experience allows you to step inside recreations of the Titanic’s interior. Immerse yourself in the stories of its passengers, see hundreds of artifacts, and discover the tale of the design, creation, launch, maiden voyage, and tragedy of the historic ship.

Where: 4963 Old Orchard Shopping Center, Skokie, IL 60077 (about 17 miles from downtown Chicago)

Cost: Price varies. Click here for full prices and to purchase tickets in advance.

Chicago Memorial Day Weekend Events

In addition to the festivals and activities mentioned above, other events taking place on Memorial Day weekend include: Chicago Food Truck Fest (May 24), Soldier Field 10 Memorial Day Run (May 24, 2025), Millennium Park Summer Workout (May 25), AirOtic Soirée: A Sensual Cirque Cabaret! (May 25) and Concert Under The Stars: ABBA Under The Stars at AIRE (May 26).

As you can see there are many things to do in Chicago on Memorial Day weekend.

Planning a trip to Chicago? Check out my Chicago guides and itineraries:



Leave a Reply

Your email address will not be published. Required fields are marked *

CommentLuv badge

This site uses Akismet to reduce spam. Learn how your comment data is processed.