Chicago Memorial Day Weekend - 10+ Fun Things to Do in May

Published: July 18, 2024
Chicago Riverwalk Tour

Memorial Day weekend marks the unofficial start of summer for many - so why not take advantage of the celebratory weekend and head to Chicago? Make the most of your long weekend in Chicago and explore the marvels of one of America's greatest cities where there's plenty to see and do in May. If you’re looking for Chicago Memorial Day Weekend ideas, check out some of these local activities, events and fun things do in Chicago including...

  • Navy Pier Fireworks
  • Hop aboard a Lake Cruise
  • Bike a car-free Lakeshore Drive
  • Enjoy one of the many street festivals
  • and more...

Save on Attraction Admission

Regular admission to a number of these attractions are included on the Go Chicago pass. Choose as you go from dozens of Chicago attractions and activities and save up to 55% off combined admission vs paying at the gate. See all available passes and Chicago attractions – learn more. Please note, some of these special May and Memorial Day weekend events may be separately ticketed and not included on the Go Chicago pass.

Navy Pier Fireworks and Fun

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Head over to the kid-favorite Navy Pier and spend the day riding the world famous Ferris wheel, walking the promenades, marveling at gardens and attractions, and popping into the many shops and eateries.

Memorial Day Weekend marks the start of the pier's summer fireworks schedule, so be sure to stick around in the evening for the show!

Plus, there are plenty of other things you can enjoy in the area, from world-class theater at the Chicago Shakespeare Theater, to the delightful fun at the Chicago Children's Museum.

Getting In: Navy Pier Centennial Wheel tickets and Chicago Children's Museum tickets are included with the Go Chicago pass.

See the City From Above

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If you want to explore the city without the time commitment of an actual tour, try an aerial view. Head to to observation deck at the top of the John Hancock Building, 360 CHICAGO.

There, you'll get amazing, unbeatable views of the city below, stretching from the shores of Lake Michigan out into the urban expanses of the city itself.

As the name implies, you'll get panoramic views that stretch for miles on a clear day, so don't forget that camera!

It's also conveniently located on the Mag Mile, so it's super easy to build in a quick visit here as part of a larger itinerary.

Getting In: 360 CHICAGO tickets are included with the Go Chicago pass.

Hop Aboard a Cruise

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For more fun things to do on Memorial Day weekend, consider taking the popular Classic Lake Tour. You and your family will embark on a 45 minute maritime excursion out onto Lake Michigan as you marvel at the breathtaking Chicago skyline and landmarks.

Other popular cruises include the historic Tall Ship Windy vessel, and the unbeatable Architecture River Cruise. The latter is especially important in a place like Chicago, where architectural styles and influences play such an important role in the history and character of the city.

Getting In: Classic Lake Tour tickets, Tall Ship Windy tickets, and Architecture River Cruise tickets are included with the Go Chicago pass.

Connect with Nature

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For some extra excitement, head over to the Lincoln Park Zoo to marvel at some exotic creatures and ride the animal-inspired thrill rides!

Our favorite ride is the lovely animal carousel. Lincoln Park is also just a beautiful space in which to appreciate the bounties of nature, nestled in an urban setting.

If you like parks but don't want to make the trek up to Lincoln Park from a hotel in the Loop, visit the expansive Millennium Park and the beautiful Lurie Gardens.

Or, if the animal encounters are what you love the best (and you feel up for a bit of a drive), head down to the Brookfield Zoo!

Getting In: Brookfield Zoo tickets and Lincoln Park Zoo Rides tickets are included with the Go Chicago pass.

Bike the Drive

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This Memorial Day Weekend, take advantage of a rare chance to bike on a completely car-free Lakeshore Drive.

Or, pedal where you please throughout the extensive system of Lakefront trails, including into the marvelous open park spaces.

There are of course also other bike paths throughout the city, and Millennium Park in particular is a popular expanse around which to bike.

Didn't bring a bike with you? It's super easy to rent one! As a bonus, your rental comes with a bike map to help your plan your route if you're unfamiliar with the city.

Getting In: Chicago Bike rental by Bike and Roll are included with the Go Chicago pass.

Chicago Memorial Day Parade

By Photo by U.S. Army Public Affairs - Midwest / soldiersmediacenter (Memorial Day Observance in Chicago) [CC BY 2.0], via Wikimedia Commons

Visited annually by about 10,000 Chicagoans, the parade begins promptly at noon and commemorates veterans and active duty personnel.

It starts at the intersection of State and Lake Street and continues down State Street to Van Buren. It begins with a wreath-laying ceremony, if you want to make sure you get a spot at the beginning.

Getting In: The Chicago Memorial Day Parade is free and open to the public.

Hit Up the Beach

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Although "beach town" isn't the first label one puts to Chicago, there certainly are some wonderful beaches that dot the shores of Lake Michigan.

Memorial Day Weekend marks the official opening of the beaches in Chicago, so grab a towel and head out there!

Keep in mind that the water will still be chilly, though, so maybe just concentrate on hoping for a nice day with good bright sun (you might want to bring a frisbee).

Getting In: It's free to stroll and swim at Chicago beaches.

Visit a Conservatory

Enjoy some nature in an urban setting. Two of Chicago's most popular conservatories are the Garfield Park Conservatory and The Lincoln Park Conservatory. You can even "visit" tropical climates within different areas of the conservatories. This is the perfect way to step away from the crowds and take in some natural beauty. Getting In: the Garfield Park Conservatory and the Lincoln Park Conservatory are both free and open to the public.

Belmont-Sheffield Music Festival

Kicking off Chicago’s outdoor street fest, this music festival is located just steps from the Belmont Red Line ‘El’ stop.

The lineup gets better every year, featuring delightful cover bands and unique local music.

No tickets are required, but donations are strongly encouraged to benefit the Central Lakeview Merchants Association.

There are actually a bevy of festivals to choose from on Memorial Day Weekend in Chicago, from Irish-themed events to EDM concerts. Check out the events calendars for more ideas and ticketing info.

Getting In: The Belmont-Sheffield Music Festival is separately ticketed and is not included with the Go Chicago pass.

Shopping (& Window Shopping)

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Of course, Memorial Day Weekend wouldn't be the same without a bit of shopping.

It's often a time of year with the best sales and deals, and its a good chance to scope out stores you wouldn't normally spend time in.

Be sure to stroll down the Magnificent Mile for some exciting shopping opportunities that range from fast fashion to haute couture, or pop into Water Tower Place Mall for some more fun choices, including a LEGO® store!

Remember to Save on Attraction Admission

There you go - plenty of fun ideas for things to do in Chicago in May to help you plan your Memorial Day weekend itinerary. Remember, many of these great ideas are included on the Go Chicago pass, where you can save up to 55% on combined admission vs paying at the gate. We really hope you consider adding a few of these popular options to your upcoming plans. Enjoy!

Katie Sagal
Go City Travel Expert

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The Ferris Bueller Guide to Chicago

Visiting Chicago and want to experience your very own day off, Ferris Bueller style? We’ve put together a Ferris Bueller’s Day Off Chicago itinerary so you can walk in the footsteps of Ferris, Cameron, and Sloane as they enjoy the best sights and attractions Chicago has to offer. As Ferris said: “Life moves pretty fast. If you don't stop and look around once in a while, you could miss it.” So make the most of your Chicago vacation and visit the best attractions the city has to offer, including... SkyDeck Chicago The Art Institue of Chicago Wrigley Field And more! Save on admission Remember, many of these popular Chicago attractions are included with the Go Chicago pass. You could save up to 55% on admission vs gate price. SkyDeck Chicago The Art Institute of Chicago Wrigley Field Chicago sights While exploring Chicago, keep an eye out for other famous locations from Ferris Bueller’s Day Off, including... Chicago Mercantile Exchange Daley Plaza 22 West Schiller Street See the Chicago Mercantile Exchange where they watch the trading pit in action. Stroll down Daley Plaza, where Ferris joined the Von Steuben Day Parade. And although the restaurant they go to for lunch doesn’t exist, you can see the exterior at 22 West Schiller Street. In summary We hope this guide has helped you plan your very own Ferris Bueller-inspired Chicago day off. Remember, many of these popular Chicago attractions are included with the Go Chicago pass. You could save up to 55% on admission vs gate price. Share your trip with us Follow us on Facebook and Instagram, and share your adventure with us. Tag us at @GoCity and use #GoCityPass on your travel photos to keep us up to date with your vacation!
Seren Morris
things to do in gold coast chicago
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Things to do in Gold Coast, Chicago

So, you've chosen your vacation destination. The Windy City. Chi-Town. The real-life Metropolis, minus the superheroes. Chicago is a fantastic getaway destination, full of great food, fun nights out, and plenty of top-level entertainment. But it's a big old town, with multiple districts and areas that crisscross throughout its gargantuan layout. With so many to choose from, which one is right for you? Well, don't let choice paralysis get the better of you! We've done all the research necessary, so you don't have to. Give Gold Coast a go. It's as simple as that. With a wealth of entertainment on offer, it's the perfect vacation spot. Here are our picks for the best things to do in Gold Coast, Chicago! Including: Oak Street Beach Playboy Mansion Broadway Playhouse Washington Square Park Drake Hotel Bar and more! Hit the Beach Why not ease into your trip with a spot of lounging? After all, you've got the rest of your vacation to go see the sights. Lucky for you, the Gold Coast lives up to its namesake. Head there, and you'll find Oak Street Beach. Of course, you'll find heaps of golden sand, clean sea, and (hopefully) glistening sun - that's what the beach is all about, after all. However, Oak Street Beach is also perfectly placed to visit at any time during the day, as it's just a stone's throw from the city itself. Take a dip in the ocean, go grab an ice cream for the kids - or yourself, who are you kidding - and then check out the nearby patio bar for a cool, refreshing drink. Easily one of the best things to do in the Gold Coast when you visit Chicago. Feel like a Playboy Yes, really. Though you probably know the Playboy Mansion as the once celebrity-laded party mansion near Beverly Hills, it wasn't always there. In fact, the original Playboy Mansion was bought right here on the Gold Coast back in the '50s. The rather less impressive original is well over 100 years old at this point, and has changed hands multiple times. First, Hefner donated it to the School of the Art Institute of Chicago when he moved into his legendary LA pad. Then, the institute sold it to a redevelopment firm, and it's now been converted into condos in a rather typical fashion. However, if you want to see a piece of 20th-century American history in the flesh, you owe it to yourself to go and bask in the extravagant opulence of the original Playboy Mansion. Just don't plan on buying one of the condos, unless you've got a few mill to spare. Broadway, baby! If the weather takes a turn, or you just want a couple of hours out of the sun, why not retreat to the bright lights and comfort of broadway? Yes, even in Chicago, you can get a taste of the New York performance mile thanks to Broadway Playhouse! A stone's throw from the coast, you'll find a host of great plays and musicals being shown throughout the year, from all-time classics to the new shows on the block. You might even stumble upon a one-man show, or local play before it gathers steam. Walk in the Park Are you a fan of the color green? Do you like walking? Is the prospect of breathing in fresh air, mingling with trees, shrubs, and grass appealing to you? Answer us these questions three, and we'll give you a place you want to be. At. A park, of course! Gold Coast has you covered in flowers and grass, thanks to Washington Square Park. Go there for the giant 19th-century fountain, stay for the delightful green spaces, picnic opportunities, or simply for a stroll. So, what are you waiting for? Get Risky When you're in Gold Coast, why not grab a drink at a Hollywood monument? Sort of, at least. Featured in the '80s Tom Cruise classic Risky Business, the Drake Hotel is one of Chicago's most recognizable landmarks! But we're not talking about the room service here. We're talking about the Hotel's bar, called the Coq d'Or. This lavish hotel lounge has been warming customers' cockles since the dark Prohibition days. Head inside and find a wealth of drinks, a menu to die for, and enough comfort you'll feel like a marshmallow. A pampered marshmallow. Best Pizza in town Wow, all that doing things, seeing things, and experiences must have made you hungry. Well, Chicago is famous for one thing in the food department, and that's deep dish. The Chicagoan take on the Italian classic is known worldwide for its deliciousness, thanks to its unusual sauce-over-cheese twist. So why not go get some and see if it lives up to its reputation? Lou Malnati's, right in Gold Coast, is arguably the best in town. The name is a staple of the Chicago style, having helped pioneer it in the early 20th century. So go grab a slice of delight and take your tastebuds to pizzatown. Or something. Go Shopping Let's end this list on a shopping, surely many of our readers' favorite pastimes. Thankfully, Gold Coast is full of shops of all shapes and sizes, so no matter what item you seek, you're sure to find it there. However, for those of you with expensive tastes, you'll be looking for The Magnificent Mile. Head there, and you'll find a shopper's paradise. Over 400 stores line the 'Mile', including the likes of Chanel, Louis Vitton, and Tiffany. So, if you're looking for some dear deals and have the cash to splash, you'll be right at home. On top of all that shopping, you'll also find a slew of gourmet restaurants, snug cafes, and much more. So, if that all sounds like heaven to you, go on down and see what's cracking! And that's our list of the best things to do in Gold Coast, Chicago! If you want to know about the other areas of Chicago, check out our thoughts here. Heading to Chicago at the tail end of winter? The beaches might be a no-go, but there's plenty more to do and see!
Dom Bewley

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