Things to Do in Chicago for Memorial Day Weekend

With Memorial Day coming up fast, you probably want to plan the perfect weekend-long celebration in Chicago. Memorial Day lands on the last Monday of May every year and has been a federal holiday since 1971. Memorial Day gives us the chance to slow down and take time to honor those who’ve died while serving in the United States military. It’s our opportunity to celebrate the freedom they afforded us and acknowledge the sacrifices our soldiers made and continue to make today.

To many, the Memorial Day weekend also kicks off the summer season, and it’s the time of year to welcome sunshine and warmer weather with open arms. A lot of people have off of work on Memorial Day to celebrate American heroes and enjoy a weekend of fun with their family, friends and community.

Memorial Day Weekend In Chicago

Although winter months in Chicago can get pretty chilly, May temperatures are pleasantly balmy with an average high of 65 and an average low of 50. By June, you can expect temperatures to rise into the mid-70s. It’s usually not too hot or too cold around Memorial Day, making it comfortable weather for enjoying outdoor festivities.

Chicago comes alive during the Memorial Day weekend, offering tons of ways to celebrate. In this post, we’ll give you ideas to help you plan a fun and memorable Memorial Day weekend in Chicago. Put on your sunglasses, dust off the grill and get ready for fun in the sun Chicago-style. Here are the best things to do for Memorial Day weekend in Chicago!

Tour With Bobby’s Bike Hike

Whether you’re new to the city or a lifelong Chicagoan, our famous tours of Chicago are bound to create an experience you’ll never forget. Our biking and walking tours take you behind the scenes, so to speak, for a view of Chicago that you won’t find on a bus or boat tour. You’ll experience firsthand the energy of the city and what makes every neighborhood unique.

Memorial Day weekend is a great time to show friends and family members, who’ve never been to Chicago, the charming neighborhoods, parks and landmarks on a guided tour. On our Lakefront Neighborhoods Bike Tour, you’ll go off the beaten path to bike Chicago neighborhoods, as well as, take a ride through must-see areas like North Avenue Beach.

Foodies will adore our Bike, Bites and Brews bike and food tour, where you’ll sample all the classic foods Chicago is known for from deep-dish pizza to some of the best cupcakes you’ll ever sink your teeth into. And of course, let’s not forget the samples of refined and refreshing craft beer.

We also offer family friendly and kid-friendly tours. This super easy, two-hour-long bike tour is perfect for little ones excited to check out the free Lincoln Park Zoo or stand next to a giant Abraham Lincoln statue.

Our bike tours are the perfect way to learn about Chicago’s rich past and new flavors, with an intimate, fun and safe journey led by a knowledgeable bike guide. If you’re a Chicagoan, there’s no better way to show your visiting friends and family around town. Plus, all levels and ages are welcome. What could be a better way to get the party started?

Watch the Memorial Day Parade

Chicago’s Memorial Day Parade typically takes place on State Street. This annual parade has been gracing Chicago streets since 1870 and is one of the largest Memorial Day parades in the country.

Make sure to get there early to get a seat, as this parade attracts thousands of spectators each year. Enjoy the floats, music, dancing and more to set the stage for a weekend of fun while honoring those who’ve fought for our country.

If you wish, you can get a head start and attend the Wreath Laying Ceremony at Daley Plaza. All are invited to this free event that honors the soldiers who dedicated their lives to our freedom.

Visit the Pritzker Military Museum and Library

Learn about military and war history as we celebrate our soldiers with a trip to the Pritzker Military Museum and Library. Explore war posters, photographs, icons, maps, manuscripts and original art pieces for an in-depth look at military culture over the years. 

pritzker military museum chicago

The library features more than 62,000 volumes covering all cultures, countries, eras and U.S. military branches. Start your Memorial Day weekend with a deeper understanding of what it means to serve this great country we call home.

Attend a Music Festival During Memorial Day Weekend in Chicago

Chicago is home to tons of annual festivals, from music festivals to food festivals and everything in between. Chicagoans love to celebrate with their neighbors and enjoy a vibrant arts and cultures scene.

Memorial Day kicks off the summer festival season with a variety of fun festivals you can take friends or family to. For example, the Belmont-Sheffield Music Fest has been celebrating the Memorial Day weekend for over 30 years. Gather your friends for this musical shindig which showcases local tribute bands, tons of food, drinks and regional art.

Or you can head to Chicago’s Millennium Park — the hot spot for summer-long musical festivities. Dance your way into summer at the Chicago House Music Festival, which will feature disc jockeys and live performances.

You also have the option to take a road trip to Three Sisters Park in Chillicothe to attend the Summer Camp Music Festival. Spend your Memorial Day weekend grooving to seven stages of musical talent. So many festivals, so little time!

Eat and Shop at the Randolph Street Market Festival

Get ready to browse over 300 vendors at the Randolph Street Market Festival over the Memorial Day weekend. Enjoy live bands, an abundance of delicious food and the chance to search for vintage, antique and global treasures.

Kids 12 and under are free, and there’s plenty for the entire family to enjoy. From tasty sweet treats to make the young ones smile, to unique vintage decor to add to your home, there’s truly something for everyone at the Randolph Street Market.

food in chicago on memorial day

Have a Chicago Craft Beer Outdoors

Celebrate the start of summer with a trip to one of Chicago’s many patios, beer gardens or rooftops bars. It’s tough to choose which to visit with so many options, but we’ll share a few ideas to help you get started.

For example, you might try Kaiser Tiger for their 200-seat beer garden and traditional treats like jumbo Bavarian pretzels, fresh-cut Belgian-style fries and Schnitzel sandwiches. Kaiser Tiger is one of Chicago’s best beer gardens according to Zagat and has a large patio that can handle the Memorial Day weekend crowds without a problem.

To take advantage of a seasonal spot, head to the Miller Lite Beer Garden on Navy Pier. From May to October, you can enjoy a gorgeous view, live outdoor music, choose tasty drinks from an extensive beer and cocktail menu and indulge in classics like beer-soaked bratwurst and hand-tossed pizza. It’s an ideal place for families too with plenty of options for kids. Plus, there’s no fee to enter.

If you want to plan a Memorial Day celebration at a bar or restaurant that offers comfortable outdoor seating, you shouldn’t have any trouble finding an establishment that works for you. You may want to call and make reservations ahead of time depending on where you plan to go, but we have to say — choosing a place out of all the many options will be the toughest part!

Bike the Lakefront Trail 

Memorial Day weekend is the perfect time to get outside and enjoy the spring weather — whether you want to explore yourself with a bike rental or want to see what guided bike tour of Chicago entails.

If you’re new to biking in the city, we’ve got you covered with everything you need to know about biking in Chicago. From e-bikes to comfort bikes, to The Lakefront Trail to The 606 Trail, we’ll set you on the right path to exploring the city.

Hit the Beach

Many Chicagoans can’t wait to pack away winter scarves and sweaters, put on their swimwear and head to one of Chicago’s lakeside beaches. Pack a cooler, grab some beach towels and head out for fun in the sun over the Memorial Day weekend when Chicago’s 26 miles of beaches are open and free to the public.

You might go to North Avenue Beach, one of Chicago’s most popular destinations, to lounge in the sun or enjoy a beachside burger at Castaways Bar and Grill. Or take the kids to Lane Beach where lifeguards are on duty, and a nearby playground gives kids a chance to play while you enjoy the view of Lake Michigan.

Take the Kids to a Butterfly Release at Peggy Notebaert Nature Museum (2:00pm – 2:30pm)

Chicago is a magical city in more ways than one, including being home to a Memorial Day weekend butterfly release. Enjoy this magical release with the family at the Peggy Notebaert Nature Museum. Watch newly emerged butterflies flutter their colorful wings in the Judy Istock Butterfly Haven. The First Flight Butterfly Release takes place May 30, 2022 from 2pm to 2:30pm.

The Peggy Notebaert Museum is part of the Chicago Academy of Sciences. Having opened its doors in 1869, the Academy was Chicago’s first public museum. You’ll have plenty of opportunities to have fun and connect with nature at the Academy of Sciences, whether you attend one of the events, explore one of the many fascinating exhibits or walk the outdoor nature trails. It offers the perfect opportunity to prepare for the warm days spent with the trees and animals, right in the city.

Go to Red, White, and Bar-B-Q on Memorial Day Weekend

One way to let your patriotic spirit shine is to eat as much barbecue as your belly can handle at this family-friendly Memorial Day festival. Located in Ty Warner Park in Westmont, this barbecue frenzy features three days and nights of live music, entertainment, an all-ages carnival, crafts, beer and of course — the best barbecue one can find. Why trouble yourself with Memorial Day cooking and cleanup when you can relax and enjoy a day of family fun at Red, White and Bar-B-Q?

Catch the Fireworks at Navy Pier

memorial day fireworks in chicago

End the perfect Memorial Day celebration with an awe-inspiring firework display at Navy Pier. Throughout the summer, you can watch firework shows, synchronized to music, over Lake Michigan.

Navy Pier is open year-round, and there is no admission fee to enter. There are plenty of activities at the pier that, while they may have admission costs, are tons of fun.

For example, you can take your family for a ride on the famous Centennial Wheel for magnificent views of the Chicago skyline and Lake Michigan. Or you can watch fireworks from aboard a cruise. Enjoy a dinner buffet, entertainment and the best view of fireworks from the rooftop deck on a Mystic Blue Fireworks Dinner Cruise, open on Memorial Day weekend.

MB Bike the Drive

Typically held on Memorial Day weekend in Chicago, Bike the Drive has been moved to September 4, 2022

The MB Bike the Drive event offers a way to see Chicago that’s only available once a year. This year’s Bike The Drive falls on September 4, 2022 instead of Memorial Day weekend has it has in year’s past. For almost five whole hours you can ride your bike down Lake Shore Drive, one of Chicago’s busiest roadways, without a care in the world and not a car in sight.

Take your family on an unforgettable journey to celebrate a love of biking with other Chicagoans during this special annual event. All proceeds support the Active Transportation Alliance which fights to make hiking, biking and public transportation more accessible and safer for city residents and visitors. Experience spectacular views and bike-riding freedom like never before.

Bobby’s Bike Hike offers exclusive discounts on anything you may need for Bike the Drive! Reserve your bike rental for Bike the Drive from Bobby’s Bike Hike.

Start Planning Your Memorial Day in Chicago, Explore with Bobby’s Bike Hike

As the biggest city in the Midwest, Chicago has a character and history so rich and colorful you won’t want to miss a thing. One great way to explore the history, art, culture and unmatched personality of this great American city is by bike or foot. What better way is there to take in the aromas wafting from a world-class eatery or enjoy the breeze of Lake Michigan on your skin?

If you’re looking for a way to make the most out of your Memorial Day weekend, consider Bobby’s Bike Hike. We don’t like to brag, but we’ve been consistently rated as the number one bike tour service in Chicago on TripAdvisor. Unlike a bus tour, our guided bike tours of Chicago give you an intimate insider’s view of the city we love to call home, plus biking is a great way to enjoy the kickoff to summer during Memorial Day weekend!

Chicago is one of America’s best cities to walk or bike in, due to its flat geography and sophisticated network of trails and sidewalks. No matter what your biking or hiking abilities are, our tours move at a pace anyone can handle so you can enjoy a look at Chicago no other tour can provide.

All of our guides share one thing in common — a passion for Chicago and an even stronger desire to share that passion. We want to help you explore all that this city has to offer, from its delicious restaurants and breweries to its fascinating neighborhoods. We’ll help you navigate the city and learn all about its hidden treasures as well as its most famous attractions on a safe and unforgettable bike tour.

Ready to book your tour with friends or family? Reach out to Bobby’s Bike Hike today and get rolling, or book a guided Chicago tour online!