Chicago Riverwalk Tour

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

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 ticketsTall 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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Things to do in West Loop, Chicago

Head to Chicago for your vacation and want to know what's good? Give West Loop a try. There's so much to do and see, you might never leave. Here's our list of the best things to do in West Loop, Chicago. Including: Street Markets Park walks Go bowling Get cultural Try climbing and more! Get Marketeering Let's start this shindig with a smattering of shopping. West Loop has an abundance of markets where you can pick up anything from fresh groceries to hand-crafted jewelry. If you're looking to wheel, deal, and shave a few bucks off your purchases, head over to Randolph Street Market. In the summer months, you'll find over one hundred vendors taking over the Chicago Journeyman Plumbers Union Hall parking lot. Within this bizarre bazaar, you'll discover stalls filled with antiques, old records, hand-crafted wonders, and other assorted knickknacks. Or, if food is your purchase of choice, give Chicago's French Market a go. You'll find myriad stalls with fresh produce from all corners of the world, and a host of pop-up restaurants and bakeries selling delicious bites. Rolling down the lanes Do you like balls? Do you hate pins? If you answered yes to both of these questions, this next entry will be for you. Punch Bowl Social has taken over West Loop. Their demands? Maximum fun. Their plan? 30,000ft of retro arcade, karaoke, fine dining, and more bowling lanes than you could shake a used pair of shoes at. Grab a drink, collect some fellows, and go throw some bowling balls down some bowling lanes to drop some bowling pins. It doesn't get much simpler than that. Then, when you're all bowled out, check all the other entertainment on offer, or grab some classic diner food from the on-site restaurant. Yee-haw. It's bowling time, or something. Park Life If the weather is good and you're so inclined, head to a park for a jolly good time! Thankfully, West Loop has some great green spaces, so if you're visiting Chicago, get that green in you. Perhaps its better-known park is Union Park, where the annual Pitchfork Music Festival brings farmers from all across America to get angry at things. Not really, it's a music festival, and a good one at that. However, if you don't make it in July, there's still loads to do. Pools to jump in, courts to play in, and that sweet grass to relax on. Or, if you want to entertain the little ones, stop by Mary Bartelme Park. It has an amazing children's playground with unique and exciting play equipment you won't find anywhere else. It's also good for dogs, if your little one walks on four legs. The Climb Picture the scene. You're a secret agent, climbing up a rocky cliff face. You receive a call on your sweet futuristic sunglasses. It's your secret spy agency, and they have a job for you. You choose to accept it, and throw the glasses off towards the camera as they self-destruct. Yeah! So if the climbing part of that interests you - and nothing else - head on over to Brooklyn Boulders. There, you'll find lots of surfaces to climb, which is what you want. If you're a seasoned pro, feel free to hit the walls and do some sweet flips, or whatever climbers do. If you're new to the climbing game, never fear. They have expert trainers on hand to teach you the tricks of the trade. And who knows, maybe they're secret agents too. Hiding in plain sight, at Brooklyn Boulders. Would you like to play a game? If you go to sleep listening to the distinctive cling of pinball tables and assorted beeps and boops of old arcade machines, you might like this next place. Take a running jump into Emporium Arcade Bar and fall into a world of old-school arcade action. With a slew of pinball-flicking, foosball-spinning, puck-slapping, and pool-shooting fun, it's a lovely place full of joy and smiles. If you have friends, bring them with you, and pump the fun up to stratospheric levels. After you've spent all your money on machines, take out a loan and go enjoy a refreshing cocktail or IPA at the bar. You will love it. Won't you? Yes. Culture! If all of that wasn't fun enough for you, how about a little learning and culture to take that fun factor to the next level? At the National Hellenic Museum in West Loop, you'll learn about Greek-American culture, and how Greek immigrants helped make Chicago the city it is today! Or, if you want to see some awe-inspiring art, check out the Kavi Gupta Gallery. Inside, you'll find artworks of all shapes and sizes to ponder over. Does it get any more cultural than that? No, it does not. State of the Union Station Want to see one of Chicago's most recognizable landmarks up close? West Loop has you covered with Union Station. Built back in the 1920s, it's the transport hub that brings many out-of-towers into the city. Its Art Deco stylings are so iconic that it's featured in heaps of Hollywood productions. The Untouchables, Catch Me If You Can, Blade Runner, and many, many more have shot iconic scenes in this very building. So go see it for yourself, and snap some sweet pics for your socials because you know you will. Grab a bite Phew, all the doing things and seeing stuff is bound to make you hungry. Thankfully, West Loop has plenty of places to refuel. In the mood for something meaty? Check out El Che Steakhouse for some prime cuts, refreshing drinks, and good times. Prefer your meat between two buns? Give Smyth and The Loyalist a go. Looking for something continental? Hit up avec for some Mediterranean delights. Grab a drink And finally, let's end our list on the drinks menu. West Loop has lots of bars and pubs to drown some suds. Head to Lone Wolf or Haymarket Pub for your craft beer needs, with plenty of local Chicago brews on tap. For some exotic cocktails, give Kumiko a try, which provides a Japanese twist on the usual mixer affair. If you want a variety of spirits, stumble to CH Distillery. And that's our list of things to do in West Loop, Chicago! Enjoy!
Dom Bewley
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Famous Chicago Landmarks & the Most Instagrammable Places to Take Pictures in Chicago

All vacations are essentially about the experience – the sights, sounds, and tastes of the attractions you visit and the streets you walk. The way you felt at the top of the Ferris wheel, or the awe you experienced looking down from the top of a 96-story building. Beautiful memories, but all memories fade. You want the pictures you take to be the kind of shots you might frame, the ones you’ll treasure years later. To help you out on your quest to find the perfect photography subjects, we put together a list of the top places to take pictures in Chicago. Best Ways to See Famous Chicago Landmarks There’s plenty of great places to snap the perfect instagram photo of famous Chicago landmarks during your trip. Here are a few fun ways to help you get around while sightseeing... Hop On Hop Off Chicago Bus Tour Architecture River Cruise Bike Rental from Bike and Roll Chicago Here's some more info on fun Chicago sightseeing tours. Many of the photo opps we listed below are located near some of the top attractions in the Chicago – so you can combine the best sights with the best things to do. See all available passes, attractions & prices – Learn more. Best Places to Take Pictures in Chicago 3. The Picasso sculpture in Daley Plaza An icon of twentieth century art innovation, Picasso is known for his use of abstract shapes and re-interpretation of form. This untitled sculpture (usually just called the Chicago Picasso) was actually commissioned specifically by the architects of the Daley Center and has never been displayed anywhere else. For this reason alone, you need to snap a shot of this one-of-a-kind statue. Plus, how many museums let you take photos of Picasso’s work? Daley Plaza is on the Loop, near a number of popular Chicago attractions, so it’s a good central place to start your day. 9. Wrigley Field As the second-oldest baseball stadium in the country, Wrigley Field is a historical institution and a must see Chicago landmark. It has been home to the Chicago Cubs since 1916, and much of the exterior architecture reflects its heritage. Of course, a lot of the interior has been updated very recently to accommodate modern MLB standards, but plenty of historical elements remain -- including the old fashioned scoreboard on the side, proclaiming your presence in Wrigley Field. Even if you’re not a Cubs fan, it’s an iconic building in American professional sports. Let's Recap While this list is by no means exhaustive, it does contain a bunch of our favorite places to take pictures in Chicago. From the most popular attractions to skyline views and scenic parks, there’s something to suit every taste when it comes to Chicago photo opportunities. Remember, a number of these famous Chicago landmarks and attractions are available with the Go Chicago Card, where you can save on combined admission prices vs. paying at the gate.
Katie Sagal
Things to do in Old Town Chicago
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Things to do in Old Town Chicago

Ahoy there, sailor! Are you taking the old steamboat over to the growing Metropolis they call Chicago? I do declare, you may be delighted by the city's Old Town district. There's plenty to do and see there, partner. Want to know what? Well, we'll tell you right now. Here are some of the best things to do in Old Town, Chicago! Including: Stand up A little history The beach Immersive art The theater and more! Second City Let's kick things off with the best medicine. We're talking about laughter, of course! What if we told you that Old Town is where some of the best and brightest comics strutted their stuff before becoming famous? You might think that's nonsense. But believe us, it is not. Many of the comic greats you see on your screens today cut their teeth at Second City, America's premier improv club. Through the years, comedy legends such as Bill Murray, Alan Alda, John Belushi, and Mike Myers have called it home, and you'll always find hilarious hijinks going on there. So go check it out! Who knows, maybe you'll stumble upon the next big thing in comedy when you visit? If you like to laugh and you're visiting Chicago, Second City is easily one of the best things to do in Old Town! Chicago History Museum If you're visiting Chicago, you might not know much about the city or its history. Would you like to know more? Well, never fear, because the Chicago History Museum is here! Step inside, and discover the city's rich history from a number of exhibits. At the Crossroads of America exhibit, you'll get to relive the most significant events in the city's history, meet Chicago's most renowned leaders, and learn how culture shaped Chi-Town throughout the centuries. Step into Sensing Chicago, and appreciate the city with all five senses! Hop on a high-wheel bike, hear the roar of the Great Fire of Chicago, smell the unique scents of the Union Stock Yard, and catch a fly ball at Cominsky Park! Perfect for big and little kids alike. Enter the Abraham Lincoln exhibit and learn all about the life and struggles of one of the country's best presidents! See how his leadership shaped the Civil War, and the events that led up to his assassination. And finally, check out Facing Freedom in America, which charts the struggle of many people's efforts to achieve freedom in the country. These interactive displays will open your mind to the plights of many peoples, from suffrage to the civil rights movement. North Ave Beach Need to relax? Unwind? Lacking a little Vitamin D and want to get tanning? Then you'll want to hit the beach. Thankfully, Old Town has North Avenue Beach, which not only offers many opportunities for you to lounge or wade into the water, but also activities too! Head there in summer, and you'll find a slew of volleyball tournaments, bikes to rent, and opportunities to try out watersports like paddleboarding and kayaking. So, if you need a little sun, sea, and sand when you're in Chicago, go check it out! The Moody Church Whether you're religious or not, you may be partial to a grand spectacle. If the thought of grandiose architecture and awe-inspiring craftsmanship gets you giddy, go check out the Moody Church in Old Town. This grand place of worship was completed back in the 1920s, and stands as a testament to design. Go get your pray on, or simply attend to look around. You're sure to find someone on hand to talk you through the construction of the building, and the goings-on within over the years. Either way, it's a great stop on your travels through Chicago's Old Town! A Red Orchid Theatre Do you want to supplant your visit with dramatics? Go check out A Red Orchid Theatre. Widely considered to be one of the best theaters in the country, Red Orchid is comprised of multiple writers, actors, and directors, including Hollywood's Michael Shannon. Every year, their shows break new ground in the theater world, telling edgy, gut-wrenching stories that are performed with finesse. So, why not go check out one of their critically-acclaimed performances when you're in Old Town? Eat, of course! All that reading and planning your trip to Old Town has probably left you hungry. Let's fix that. Thankfully, Old Town has a whole host of delightful restaurants and cafes for you to visit! Want to start your morning just right? Try Kanela Breakfast Club, a Chicago eatery with spots all over the city. Omelets, eggs, grilled cheese, and much more await you on their diverse menu. If you want some delicious cocktails to wash down a hearty meal, head to Happy Camper. During the day, you'll pair authentic pizzas with a host of drinks. During the night, you'll get to enjoy one of the best bars in the city! Want to sample barbecue that delighted the late, great Frank Sinatra? Then stop by Twin Anchors, which has quality ribs on offer all year round. Are you feeling continental? Try La Fournette, a traditional French bakery right in the heart of Old Town. Alongside the usual suspects of baguettes, croissants, and sweet pastries, they also have salads, soups, and much more behind the counter. So, whatever you feel like eating, Old Town's got you covered! Get immersive with Van Gogh And finally, let's end this rowdy route through Old Town's best bits with something different. If you've dipped your toe into the world of art, you know about Vincent Van Gogh. The Dutch Post-Impressionist painter is one of the most critically-lauded artists in the world. His paintings sell for millions, and his best works hang in the most fabulous galleries on Earth. You might know of Van Gogh, but you've never seen his work like this. At the Immersive Van Gogh experience, you'll see his works come to life with animation. Walk through his most famous works, like Starry Night, Sunflowers, and The Potato Eaters. It's an illuminating experience, and with over 2 million visits to its original Paris installation, it's a easily one of the best things to do in Old Town when you visit Chicago! And that's our list of the best things to do in Old Town, Chicago! Enjoy your visit!
Dom Bewley

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