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 from the best outdoor activities, festivals and events to the top indoor 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.

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What to Pack for Chicago for Memorial Day Weekend

For out of town visitors, 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.

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.

Join a Memorial Day Booze Cruise

Want to drink while enjoying being on the water? You can join several Memorial Day themed booze cruises including this daytime booze cruise or this sunset booze bruise.

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.

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 from 10:00 pm – 10:10 pm.

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

Another great option for watching the fireworks is a lake or river cruise which will stop on the water for passengers to enjoy the show.

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
Navy Pier is a must do if you are visiting Chicago with toddlers or kids. There are fun attractions at Navy Pier including a large Ferris wheel (click here to purchase a fast pass ticket and skip the long line), restaurants, shops and the Chicago Children’s Museum.

Starting on Memorial Day weekend, Navy Pier will be home to Pixar Putt, a summer pop-up, open-air 18-hole mini-golf course featuring characters from Disney and Pixar movies, including Toy Story, The Incredibles, Monsters, Inc., Finding Nemo, Coco, A Bug’s Life, Wall-E, and Inside Out.

Navy Pier is also the starting point for various sightseeing tours and cruises.

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 nightly at 9 pm and  9:30 pm. Spectators can watch the show from the jetty section of the Chicago Riverwalk on Wacker Drive between Wells Street and Franklin Street.

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.

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.

Other neighborhoods that have a high concentration of street art include Pilsen as well as West Town.

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

Experience the Immersive Van Gogh Exhibit

From the creators of the blockbuster show at Atelier des Lumières seen by over 2 million visitors in Paris and Toronto and featured in Emily in Paris (one of my favorite travel shows on Netflix), the Immersive Van Gogh Exhibit, is a massive indoor digital presentation of Vincent Van Gogh’s artwork.

Where: Lighthouse ArtSpace at Germania Place, 108 W. Germania Pl, Chicago

Cost:  Tickets start at $39.99 plus fees for off peak times. You can see full prices and purchase tickets in advance here.

Experience Frida: Immersive Dream

From the team behind the popular Immersive Van Gogh, Frida: Immersive Dream is a massive indoor digital presentation of Frida Kahlo’s artwork.

Where: Lighthouse ArtSpace at Germania Place, 108 W Germania Place, Chicago

Cost:  Timed tickets start at $29.99 plus fees for off peak times. You can see full prices and purchase tickets in advance here

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 is is usually turned on sometime in 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.

Free Millennium Park Summer Workout

Want to join free yoga (and other exercise classes) while also spending time outdoors? The Millennium Park Summer Workouts program begins on Saturday before Memorial Day weekend. The program offers series of free 45-minute workouts including Tai Chi, Yoga, Pilates and Zumba® on Saturday mornings at Millennium Park Great Lawn throughout summer.

8–8:45am – Tai Chi
9–9:45am – Yoga
10–10:45am – Pilates
11–11:45am – Zumba®

Where: Great Lawn at Millennium Park

Watch Classic Movies on a Rooftop

Want to watch classic movies against the backdrop of the Chicago skyline? Rooftop Cinema Club is opening its outdoor screening series to a rooftop in Fulton Market just in time for Memorial Day weekend.

Rooftop Cinema Club will be located on the fifth floor terrace of The Emily Hotel (311 N Morgan St). This will be 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.

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 4 baseballs games happening during Memorial Day weekend (including the Cubs and White Sox playing each other):

Saturday, May 28, 6:15 PM – Chicago White Sox vs. Cubs at Guaranteed Rate Field
Sunday, May 29, 1:10 PM – Chicago White Sox vs. Cubs at Guaranteed Rate Field
Monday, May 30, 12:05 PM – Chicago Cubs vs Milwaukee Brewers at Wrigley Field
Monday, May 30, 6:40 PM – Chicago Cubs vs Milwaukee Brewers at Wrigley Field

Chicago Memorial Day Weekend Events

In addition to the activities mentioned above, other festivals and events taking place on Memorial Day weekend include: Chicago Food Truck Fest (May 27), Friday Night Flights (May 27), Memorial Day Wreath Laying Ceremony and Parade (May 28), Belmont-Sheffield Music Festival (May 27-29), Mole de Mayo (May 27-29), Sueños Music Festival (May 28-29), Mayfestiversary (May 28-29), Live on the Lake (at Navy Pier) (May 28-30).

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:



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