It’s in May when Chicago’s many parks and natural spaces reach their peak bloom. Tulips begin to line Michigan Avenue, Chicago’s best summer events begin announcing themselves sparking excitement for the months to come, and, despite the inevitable spring showers, days begin getting warmer.
While iconic Chicago activities like kayaking at the riverwalk, the spring Art on theMART projections, and firework shows at Navy Pier signal the beginning of Chicago’s most magical months, there is something in the air and atmosphere that tells Chicagoans it’s onwards and upwards from here!
From floral fun to captivating concerts, here are our top recommendations for the best things to do in Chicago this May.
1. Catch the cherry blossoms bloom
By early May Chicago is abloom with color and vibrancy across the city. One of the most magical moments of spring, however, is the emergence of the cherry blossoms which make a fleeting appearance in Chicago in only a couple of locations.
Due to their ephemerality one of the best things to do in Chicago in May is to start the month by heading down to Chicago’s Jackson Park around the Museum of Science and Industry and see the cherry blossoms while you can.
These unique flowers offer an ephemeral yet euphoric experience, especially when the sun is shining and Jackson Park can be enjoyed in all its glory.
Read our guide to seeing the cherry blossoms in Chicago.
2. Take in the tulips of Michigan Avenue
If you can’t get enough of floral flamboyance this time of the year another brilliant and simple May experience in Chicago is enjoying the tulips of Michigan Avenue.
Every fall the City of Chicago plants tens of thousands of tulip bulbs in the Michigan Avenue medians from Oak Street to Roosevelt Road and in late April these bulbs then begin shooting skyward, opening up and filling Michigan Avenue with a kaleidoscope of tulips.
3. Walk through tulip fields at Richardson Farm’s annual tulip festival
If Michigan Avenue’s tulips don’t quite fulfill your tulip craving an even larger tide of tulips can now be enjoyed out at Richardson Farm’s annual Tulip Festival.
Home to the world’s largest corn maze in the fall months, in spring the farm offers an incredible spectacle with over 30 different varieties and hues ranging from fiery coral to snowy white, pale yellow, and plum-drenched purple.
This year is the farm’s fourth annual tulip festival and millions of tulips have now pushed their way skyward prompting Richardson Farm to open early showing off their breathtaking ethereal elegance.
Read more about the Richardson Farm tulip festival.
4. Check out the ART on The MART spring projections
Back in the heart of Chicago, the ART on The MART projections have returned! One of the lights at the end of the tunnel every year comes in the form of artistic projections on the 2.5-acre river façade of the Merchandise Mart.
Holding the title of the largest permanent digital art projection in the world, ART on The MART attracts thousands to the Riverwalk every week by firing up 34 digital projectors and showcasing work from both renowned artists and local talent.
Every year it takes a few months off in winter before returning in mid-April to offer more scintillating spectacles for onlookers on the riverwalk.
The Spring 2024 Program is now running every night through June 5 featuring a commission by internationally acclaimed artist Nora Turato alongside the Chicago Public Schools projections “made in conjunction with the All-City Visual Arts program and featuring artwork by CPS seniors.”
Spectators can watch two free 30-minute programs of projections nightly from the jetty section of the Chicago Riverwalk on Wacker Drive between Wells Street and Franklin Street.
Read more about the ART On The MART spring schedule.
5. Kayak down the Chicago River
A truly unique May evening can be had by combining kayaking with the Art on the MART projections. After shutting down for the winter season, Urban Kayaks have reopened their Riverwalk and Lakefront locations kicking off the spring and summer seasons of kayaking.
Whether you’re down by the Chicago Riverwalk flanked on either side by the city’s famous highrise architecture or taking in the skyline from the protected waters of Monroe Harbour, kayaking in Chicago is a magical and truly unforgettable activity.
Read more about kayaking in Chicago.
6. Take to the water in an electric boat
With Chicago having emerged from winter, bridges are open and the city’s waterways are returning to life. Along with kayaking experiences, boat rentals are returning and Chicago Electric Boat Company, best known for its fleet of self-captained, eco-friendly vessels has now reopened for spring and summer.
From classic or luxury Duffy Boats to Party Barges, Cycleboats, Donut Boats, and now even rentable hot tub boats, Chicago Electric Boat Company has a range of fantastic captained or self-captained boating experiences for groups of up to 26 people all offering an unforgettable May activity in Chicago.
Read more about the Chicago Electric Boat Company.
7. Visit “Titanic: The Exhibition”
Talking of boats, an exhibition dedicated to the most famous ship to sail the seas has docked in Chicago and offers another great thing to do in Chicago in May.
Titanic: The Exhibition dives 2 ½ miles below the Atlantic’s surface to uncover the liner’s captivating story like never before and offering guests the chance to walk across the promenade deck of the world-renowned ship.
The exhibit follows the ship’s journey from its design in 1908 to its recovery in 1985. You’ll see hundreds of real artifacts from the Titanic, her sister ships, and films capturing the emotional tale. As you touch a take in stunning photography of the Titanic and step across the ocean floor strewn with relics, you’ll feel like you’re walking through history.
Read more about Titanic: The Exhibition.
8. Dive into the captivating world of Downton Abbey: The Exhibition
Delve deep into the post-Edwardian era with never-before-seen treasures, from original costumes to iconic props, and exclusive series footage in the latest stop of the acclaimed Downton Abbey: The Exhibition U.S. tour.
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.
With over 60 authentic costumes worn by the beloved characters, immerse yourself in the elegance and drama of this award-winning phenomenon.
Don’t miss out and get your tickets today for Downton Abbey: The Exhibition!
9. Check out the immersive ‘Bluey’ experience
Step into an episode of the Emmy Award-winning children’s show Bluey and meet fan-favorite characters at Chicago’s incoming “Bluey x Camp” experience.
Following a sold-out run in Los Angeles, the immersive “Bluey x Camp” experience is headed to Chicago offering fans a 5,000-square-foot recreation of Bluey’s house from the Emmy Award-winning children’s show.
Featuring photo ops, games, and meet-and-greet with the characters, the experience will debut in Chicago on May 24 running for several months through to the end of summer.
Read more about the Bluey Experience.
10. Go for a Mother’s Day brunch
While Bluey might make for a great experience for those with kids, it’s mothers who deserve to be spoilt a little this month. Celebrate your mom this Mother’s Day with decadent fluffy pancakes, mimosas galore, or whatever brunch tickles your fancy!
There are plenty of incredible brunch spots around Chicago and many offering Mother’s Day brunch specials for the May 14th holiday.
Read the full list of top brunch spots for this Mother’s Day in Chicago.
11. Send your senses soaring at a Dining in the Dark experience
Another phenomenal dining experience can be had courtesy of the Dining in the Dark event series.
Break away from routine and relearn how to use your taste buds on a unique night out with your vision temporarily suspended. Making for a memorable date night or a surreal experience with friends, the exclusive ‘Dining in The Dark’ dinner parties fully engage the senses by blindfolding guests and consequently heightening taste and smell to better focus on the exquisite food and wine pairings.
Grab tickets to a Dining in the Dark experience.
12-16. Be captivated by a Candlelight Concert
Chicago’s sublime Candlelight Concert series is providing an array of breathtaking spectacles in the Windy City. Talented musicians will be performing at extraordinary venues all over Chicago offering guests the chance to marvel at the enchanting combination of flickering candles and melodic sounds.
If you can’t decide on a concert but want to ensure you attend one or need to buy a gift for somebody special, Candlelight gift cards are really easy to use and valid for any Candlelight event in the U.S. making it a unique gift for both friends and family.
17. Channel your inner “Dancing Queen” at an ABBA tribute concert
Chicago’s Aire Rooftop Bar is reopening on May 19th, bringing you a stunning oasis with panoramic skyline views. Even better, the rooftop venue will host an ABBA-themed Concert Under the Stars on Sunday, May 26th. Complete with a full bar and light bites, this evening of talented musicianship will have you moving and grooving to each song. Snag tickets today while they last!
18. See live music at Lincoln Park’s Chicago Mayfest
Another place you can see music this month is at Lincoln Park’s Mayfest. The annual street party is back in May bringing live entertainment, food vendors, cover bands, and carnival games to Lincoln Park for another year.
Chicago Mayfest kicks off the summer festival season on Friday, May 17th through Sunday, May 19th on Armitage at Sheffield in the Historic District of Lincoln Park.
The event supports the local neighborhood with donations going to the historic Ranch Triangle area, the Lincoln Park Community, small businesses, and public schools in the area.
19. Head to Pilsen’s Mole de Mayo Street Festival
The following weekend in May another beloved neighborhood festival takes place from Friday, May 26th through Sunday, May 28th.
Pilsen’s annual street festival Mole de Mayo honors the traditional Mexican mole sauce featuring a range of tasty bites, wrestling competitions, traditional dances, performances, and, of course, plenty of delicious sauce!
20. Indulge in wings at Gallagher Way’s WingOut Chicago
If that’s made you hungry you might want to put Wing Fest in your calendar. Also taking place on Memorial Day Weekend, beginning the morning of Saturday, May 25th, WingOut Chicago is the ultimate chicken wing block party with Chicago’s best wing-slingers gathering to entertain with their recipes from traditional to the exotic and everything in between.
For the second year running, WingOut Chicago will take place at Wrigleyville’s Gallagher Way.
21. Celebrate the birth of house music
Mayor Brandon Johnson and Chicago’s Department of Cultural Affairs and Special Events (DCASE) in April announced a lineup of free House Music programming kicking off in late May and paying homage to House Music.
Four days of free events will culminate in the Chicago House Music Festival taking place in Millennium Park all in celebration of the popular genre that was born in Chicago in 1984.
The free events and activities include the Chicago Cultural Center hosting an Open House on Thursday, May 30th featuring DJs spinning house music throughout the historical building while arts programming and new visual art exhibitions take place from 4 p.m. through 8 p.m.
The next day on Friday, May 31st, the Chicago Cultural Center will then host the Chicago House Music Conference featuring engaging panels with house music world icons and experts in the industry.
Read more about the celebration in honor of house music’s 40th anniversary.
22. Check out the new Salt Shed Brewpub
Having closed its original Clybourn Avenue brewery at the end of 2023, ending a 35-year stay, Goose Island will soon be taking up residence in Chicago’s exciting new Salt Shed entertainment complex.
Located at 1357 N. Elston Ave—less than a mile from its original Clybourn Avenue address—the new brewpub will open on Friday, May 3rd, just across the river from the namesake island.
According to representatives, it will feature “both indoor and outdoor seating, a revamped menu, and an ever-changing beer list,” adding to the already astounding caliber of brewpubs and taprooms in Chicago.
Read more about the new Salt Shed Brewpub.
23. Ride Chicago’s brand-new ‘FlyOver’ experience
For those who may have missed it, unlikely as it is, Chicago’s much anticipated new attraction, the FlyOver experience, opened at Navy Pier at the start of March after more than $40 million and years of work. It remains one of our favorite things to do in Chicago in May.
Situated directly across from the Chicago Children’s Museum where the IMAX theater once stood, the exciting 48,000-square-foot immersive experience suspends riders above the city’s incredible skyline courtesy of a massive 65-foot spherical screen that surrounds riders as flight motion seats take them soaring from location to location.
Read more about the immersive ‘FlyOver’ experience.
24. Spend an evening at Shedd Aquarium for free
From the sky to the sea, another of Chicago’s main attractions, the Shedd Aquarium, is now offering a run of free admission every Tuesday evening of spring through to the end of June.
Illinois Residents can enter the beloved aquarium from 5 p.m. through to 9 p.m. on Tuesdays this May.
Read more about free Tuesday evenings at the Shedd Aquarium.
25. Dive deep beneath the waves at Field Museum’s new interactive ‘Unseen Oceans’ exhibition
For more underwater fun, an exciting new exhibition launched last month at Chicago’s Field Museum. “Unseen Oceans” takes guests to “a whole world hidden beneath the waves of the ocean” inviting them to marvel at life-sized projections of bizarre and bewildering deep sea creatures very rarely seen by the human eye.
From exploring an immersive underwater cavern to jumping inside an interactive deep-sea submersible and piloting through the depths alongside ocean creatures, guests can experience the unworldly realms of the ocean’s darkest corners from the comfort of inside the Field Museum’s walls.
Read more about the Field Museum’s Unseen Oceans exhibit.
26. Enjoy free admission to the Field Museum on a Wednesday
On the topic of the Field Museum, at the start of the year, the museum announced a new regular free admission day for all of 2024.
The most popular museums and attractions in Chicago have nearly always announced random free days throughout the year, especially during the months that are quiet for Chicago’s tourism industry.
This year, however, the Field Museum is doing things a little differently and the iconic museum invites Illinois Residents to enjoy free admission every Wednesday in 2024.
Read more about Field Museum’s free Wednesdays.
27. Check out the Museum of Science and Industry’s new James Bond exhibit
Chicago’s Museum of Science and Industry, which holds the title of the largest science museum in the Western Hemisphere and one of the largest science museums in the world, launched a brand new exhibition recently.
Titled 007 Science: Inventing the World of James Bond, the new exhibit spotlights the world of none other than history’s most famous fictional spy and is the first-ever official exhibition to focus on the science and technology behind the world’s longest-running movie franchise.
Read more about the 007 Science: Inventing the World of James Bond exhibit.
28. Revel in one of Chicago’s best speakeasies
If James Bond has you feeling secretive, one of the best things to do in Chicago in May is head to this electric speakeasy. One of our top picks is in Fulton Market upstairs at Nisos.
The hidden cocktail lounge (hint: look for the bookshelf) is tucked away on the second floor of Nisos Prime. The 2,000-square-foot room offers a wondrous, carefree late-night experience full of energy and music and transports guests to the nightlife of the Mediterranean.
Read more about Chicago’s best speakeasies.
29. Try an escape room in Chicago
While at speakeasies the challenge can be getting in, at Chicago’s escape rooms the challenge is getting out. A great plan for families, friends, or work events, escape rooms put your problem-solving skills to the test with puzzles, clues, and tasks designed for groups or all ages to enjoy.
Luckily, Chicago has an array of exciting escape rooms from which to choose!
30. Buckel up for a Drunk Shakespeare show
Another brilliant Chicago experience comes in the form of a live Drunk Shakespeare show.
On a stage in a hidden speakeasy behind the Chicago Theater, guests will find a glam cocktail bar and library with over 10,000 books. Five classically-trained actors meet as members of “The Drunk Shakespeare Society.” One of them has had at least five shots of a strong spirit, and then they (quite over-confidently) attempt to perform a major role in a Shakespearean play!
Hilarity and mayhem ensue while the four sober actors try to keep the script on track. Every show is different depending on who is drinking… and what they’re drinking!
Grab tickets to a Drunk Shakespeare show.
31. Chuckle away at Chicago comedy show
If you’re looking for more laughs, there’s no place better for that than at a Chicago comedy show. Famous for its production of funny guys and girls, Chicago has some of the best places to see a comedy show in the country.
At Laugh Factory Chicago, some of today’s biggest names and local comedians are delivering something for every taste and style throughout the year.
Grab tickets to a show at Laugh Factory Chicago.
32. Gaze at the stars at the Adler Planetarium for free
Talking of theatrical experiences, Chicago’s Adler Planetarium is currently offering a new Afrofuturistic multiverse experience in its Grainger Sky Theater titled Niyah and the Multiverse.
Perfect for those with kids, it takes guests on a visually stunning journey as a curious Chicago pre-teen travels through the multiverse.
Adler Planetarium is always worth a visit and makes for a great April activity before sunset gets later and later. Illinois residents can enter for free every Wednesday evening from 4-10 pm provided they bring proof of residency and enjoy access to the largest public telescope in the Midwest as well as a range of exciting astronomy events and activities.
More information and tickets can be found at adlerplanetarium.org.
33. Try an indoor skydiving experience
For dare devils and fun seekers, you might be interested in testing your skydiving skills in one of Chicago’s state-of-the-art indoor skydiving centers this April.
One of the best things you can do in Chicago this month is head to iFly Indoor Skydiving Center in Lincoln Park or iFly Indoor Skydiving Center in Rosemont..
Kids and adults can experience the same sensation you’d get 12,000 feet up in the sky. If you feel you have what it takes, you can test your vertigo above Chicago’s iconic skyline at Skydive Chicago, one of the world’s largest skydiving resorts.
Read more about the indoor skydiving experience.
34. Head out of the city and see Illinois’ natural spectacles
Ok, we know this one isn’t strictly in Chicago but with so much going on in the city, one of the best things to do in Chicago in May is escape to the quiet of Illinois’ natural beauty and explore the natural spectacles a short journey from the city.
Though our state may not boast wonders with the universal magnitude of the Grand Canyon nor the grandiose reputation of Niagra Falls, Illinois is teeming with diverse ecological landscapes that transform into incredible natural paradises this time of the year.
From monolithic marvels to cascading waterfalls, we’ve selected seven natural wonders of Illinois that you can visit during their spring transformation:
Read the full article to discover our seven natural wonders of Illinois.
35. Stay in a Starved Rock Getaway cabin
For an even more prolonged experience in nature, Getaway House is a chain of tiny cabin hideaways that helps people in big, bustling cities like Chicago, DC, LA and NYC disconnect from their busy city lives with restorative stays in the middle of nature.
One of the aforementioned spots, Starved Rock State Park, has a selection of minimalistic cabins with floor-to-ceiling windows allowing guests to wake up fully immersed in the wilderness.
Located in lush landscapes and with minimalist yet comfortable designs, they offer the perfect escape for those wanting to disconnect from busy city lives with restorative stays in the middle of nature.
Read more about Getaway experiences.
36. Discover the Windy City’s small pockets of Eden
Of course, you don’t have to leave the Windy City to find natural escapes. One of the best things to do in Chicago in May is take in the nature all around you; there are many places you can get back in touch with Mother Nature right here in the city, and there is no better time than the start of spring.
The Lakefront, lush parks, and incredible hiking trails offer great natural experiences, but Chicago also has numerous secret gardens hidden across the city.
Read our full article on 10 of the best spots around the city to stop and smell the roses.
37. Check out Brazilian samba dancers, jugglers, and aerialists while enjoying dinner and drinks at Copa Carnivale
Add a little excitement to your Thursday night on May 9th by attending Carnivale’s thrilling Copa Carnivale experience. This 90-minute disco-themed party will feature a live band, Brazilian samba dancers, juggling, aerialists, alongside a menu of delicious dinner and drinks! Choose from two seatings, 6 p.m. and 8:30 p.m. If you miss it, be sure to add Carnivale to your list of restaurants to check out. Enjoy live performances every Thursday, or catch their samba dancers in the Rumba Lounge every Friday.
38. Warm up and revitalize at Chicago’s most unique spas
After battling through the bleak of winter, one of the best things to do in Chicago in May is head to a spa. You’ve got to consider your well-being after these hostile months, especially if you’re spending time outdoors exploring nature or doing extreme sports.
Luckily Chicago is full of answers and there’s no better place to relax and unwind than at Chicago’s many serene spas and bathhouses.
From places like River North’s lavish AIRE Ancient Baths inspired by the traditional Roman, Greek, and Ottoman ancient experience of bathing to the unique PIVA Beer Spa offering huge larch wooden tubs filled with near 100-degree beer, herbs, and hops there are so many options in Chicago.
Head to our Secret Chicago list of Chicago’s best spas for an informative guide.
[Featured image from Shutterstock]