40 Fun Things to Do in Chicago in May

Once May hits, Chicagoans remember why they live here. This is the season we wait for all year. May is a great time to visit Chicago because there are tons of events happening with the return of festival season and nice weather, but we don’t have the bigger crowds of summer yet. I’ve lived in Chicago for nearly two decades, and I love May in Chicago because the weather isn’t too hot and humid yet and it’s still possible to visit popular attractions without a huge wait. Whether you’re visiting Chicago in May or you live in Chicagoland, here are 40 fun things to do in Chicago in spring.

Please note that this post contains affiliate links. I may earn a small commission for my honest recommendations, at no additional cost to you.

Fun Things to Do in Chicago in May

1. Celebrate Mother’s Day in Chicago

Mom deserves something unexpected this year. Whether she’s a music lover, art fan, or just needs a day to recharge, surprise her with one of these 9 Unique Ways to Celebrate Mother’s Day in Chicago.

2. See Chicago By Bike

With the return of spring weather, it’s the best time of year to go on a bike tour of Chicago. Bike tours are a great way to see the city’s iconic attractions because you can cover more ground quickly while admiring the views. Our 18-mile Lakefront Trail is a natural route to take in vistas of the skyline and Lake Michigan. There are many Chicago bike tours to choose from including a three-hour Ultimate City Bike Tour, or Lakefront Neighborhoods Bike Tour covering communities on the North Side. The Lincoln Park Bike Adventure gives you a deep dive into one neighborhood while the Signature Dishes Bike Tour lets you burn off Chicago pizza, hot dogs, brownies, and more while you learn. Need a boost? Try the Lakefront Electric Bike Tour.

3. Celebrate AAPI Month with a Chinatown Food Tour

May is Asian American and Pacific Islander Heritage Month, so it’s the perfect time to explore one of Chicago’s vibrant Asian communities in Chinatown. The Chinatown Food and Walking Tour will guide you through foods from various regions of China as well as the history of Chicago’s Chinatown. Taste your way from Sichuan to dim sum in this three-hour tour.

4. Mexico Fest at Navy Pier – May 2-4, 2025

Navy Pier teams up with the Consulado General de México en Chicago for a free festival celebrating Mexico. From traditional dance and music demonstrations to DJs and an artisan market, you’ll find many ways to honor the country’s vibrant culture.

5. Legions of Metal Fest at Reggie’s – May 2-3, 2025

Get ready to bang your head all weekend at Reggie’s for Legions of Metal Fest. More than 20 metal bands will be rocking out all weekend including Crimson Glory, Seven Spires, Sonja, and more. Don’t forget your ear plugs.

6. Stroll Through a Cemetery

Cemeteries aren’t just for spooky season. With beautiful landscaping and a peaceful setting, they are ideal places to admire Chicago’s spring blooms. Many cemeteries are also arboretums with flowering trees that attract countless bird species. During the pandemic, I even visited Graceland Cemetery on my birthday for a spring walk. Located in Lakeview, Graceland is a beautiful and historic place to ramble. Further north near Lincoln Square, Rosehill Cemetery is another scenic option known for attracting wildlife like deer. While you’re there, don’t miss the Shedd Memorial Chapel at Rosehill Cemetery.

7. Chicago Pickle Fest – May 3, 2025

Don’t be sour when you’re the only one not bar crawling through Wrigleyville with a pickle on a stick. The Chicago Pickle Fest takes you to more than a dozen venues around Lakeview for live music, pickley food (to purchase), and a whiskey shot with a pickleback. Who’s ready for a pickle party?

8. Ed Helms Shares Historic Screwups – May 3, 2025

Comedian Ed Helms, best known for his roles on The Office and The Hangover, shares his new book, SNAFU, with the Chicago Humanities Fest. Helms shares history’s greatest screwups from the 1950’s to the 2000’s. Laugh along as you hear hairbrained ideas like planting nukes on the moon to training felines as CIA spies.

9. Forest Preserve Spring Fest – May 4, 2025

Go touch grass in the Cook County Forest Preserve for Spring Fest. Head to Thatcher Woods from 12-3 p.m. for interactive nature programs, guided wildflower walks, fishing, and kids’ activities. The best part? There’s no admission cost to enjoy nature.

10. Andersonville Wine Walk – May 4, 2025

Cheers! The Andersonville Wine Walk returns for its 20th year. Choose from three different routes with ten stops each at local businesses throughout the North Side neighborhood.

11. Raise a Glass on the Chicago Riverwalk

Patio season has arrived my friends. In Chicago, we’re not limited to drinking on sidewalks, rooftops, and the lakefront. Our one-mile Riverwalk offers ample opportunities to sip, snack, and admire the downtown Chicago views. There’s something for everyone with beer at Chicago Brewhouse, wine at City Winery Riverwalk, and cider at the Northman. Make it a crawl and stop at favorites like Beat Kitchen on the Riverwalk and Tiny Tapp.

12. Lincoln Park Uncorked – May 8, 2025

‘Tis the season for wine walks. Lincoln Park Uncorked is your passport to tasting wine and bites at businesses along Armitage and Halsted. Twenty local businesses will host you on your wine journey along the North Side neighborhood.

13. Shop and Sip at Sauced Night Market – May 9-10, 2025

Since 2014, SAUCED has been popping up at various venues around Chicago spotlighting emerging chefs, artists, and artisans. The free Spring Night Market goes down near Lincoln Square at Half Acre Beer Co. from 5-10 p.m. Stock up on unique gifts, grab a bite from local restaurants, and have a beer.

14. Sounds of Progress Free Concert –  May 10, 2025

Enjoy a free community concert from the Chicago Opera Theater at the DuSable Black History Museum from 2-3:30 p.m. Sounds of Progress: Opera and the Civil Rights Movement blends storytelling and music to honor those who fought for equality.

15. Nils Frahm at Salt Shed – May 14, 2025

Zen out with the mesmerizing piano of Nils Frahm at the Salt Shed in partnership with Chicago Humanities Festival. Frahms compositions are both intimate and unconventional. His latest album, Day, was recorded in the summer of 2022 in complete solitude.

16. Get Outside

We’ve waited through a long winter, and now it’s time to get back outside and appreciate our surroundings. From Chicago’s urban nature spots like Promontory Point in Hyde Park and the Montrose Point Bird Sanctuary in Lakeview to nearby hikes like Matthiessen State Park or the Morton Arboretum, our region is bursting with natural beauty. For more ideas, check out my guide to the Best Places to Get Outside In and Around Chicago.

17. Marvel at Buckingham Fountain

Since 1927, Buckingham Fountain has dazzled visitors with its water and light displays. Celebrate its return—the fountain runs May through October—by stopping by from 9 a.m. to 10:35 p.m. for an awe-inspiring show. The sculptural fountain is one of the largest in the world. The major displays take place on the hour and last about 20 minutes, when you can see the water jet shoot to 150 feet high in one of Chicago’s most iconic sights.

18. Take a Chicago Architecture Center River Cruise

As a Chicagoan for the past 15 years, I still love taking an architectural boat tour every summer. No boat tour does it better than the Chicago Architecture Center‘s First Lady cruise. After all, what’s better than a dose of history with scenic city views and a bar? Your boat tour ticket includes admission to the Chicago Architecture Center, so don’t miss the opportunity to learn more about the iconic designs of the city that invented the skyscraper.

19. Windy City Margarita Festival – May 16-18, 2025

Did someone say margaritas? Once again, Pilsen is hosting Windy City Margarita Fest at Cermak and Canalport. Sample 15+ flavors of margaritas from mango to maracuyá to find your new fave. More than 30 bands and DJs will keep the party going all weekend.

20. AAPI Restaurants Week – May 16-25, 2025

Asian American, Native Hawaiian and Pacific Islander Heritage Month is a great time to taste some of the best AAPI-owned restaurants in Chicago. Celebrate the 4th annual AAPI Restaurants Week at local favorites like Tandoor Char House, Aloha Eats, Saigon Sisters, and more!

21. Go on a Chicago Record Store Crawl

Chicago is a music city, so it’s no surprise that we boast a number of internationally recognized record stores. Some neighborhoods even have several places to flip through vinyl, making a mini crawl a fun way to spend an afternoon. In West Town, don’t miss Reckless Records and their in-store shows, Dusty Groove’s vintage jazz, funk, and soul selection, and Shuga Records which also has its own record label. Head to Logan Square for nostalgic punk and garage recordings at Bric-A-Brac, Signal Records from the owner of the Chicago Research label, and Record Breakers for hardcore and metal LPs. Don’t miss Lakeview’s Gramophone which draws electronic fans from far and wide.

22. Wright Plus Architectural Housewalk – May 17, 2025

Chicago is a town of architecture nerds, and one of coolest architecture experiences you can have is held annually next door in Oak Park. The Wright Plus Architectural Housewalk invites you inside eight private residences designed by Frank Lloyd Wright and his contemporaries for a tour. This insider opportunity only comes once a year!

23. Shop and Eat at Maxwell Street Market – May 18, 2025

Maxwell Street Market was an iconic place for Chicagoans to haggle, eat, and hear live music for decades before moving to its current location in the 1990s. The market on the Near West Side is still a fun place to browse a myriad of household products, clothing, and more from 10 a.m. to 3 p.m. Fill up on food from local vendors Jim’s Original Hot Dog and Lalo’s Mexican Restaurant. 

24. Stroll the Magnificent Mile

Sure, the Mag Mile lost some of its luster and storefronts following the pandemic. Yet the Near North Side thoroughfare of Michigan Avenue is still a fun place to stroll, shop, and snack as you admire city views and spring blooms. Hit the malls at 900 North Michigan Shops, Water Tower Place, and the Shops at North Bridge or shop luxury at Ikram’s striking red storefront or Burberry’s plaid building. Dine at the chic RL Restaurant, savor high-end tapas at the Purple Pig, or eat French-Vietnamese cuisine in style at Le Colonial. Don’t forget to head under the Mag Mile for a bite at the Billy Goat and admire the collection of famous rocks embedded in the Tribune Tower.

25. Mole de Mayo Street Festival – May 24, 2025

Who doesn’t love a good mole? Get your fill at Mole de Mayo Fest at 18th Street and Ashland Avenue in Pilsen. In addition to Mexican cuisine you can expect art, music, and lucha libre!

26. Sueños Music Festival – May 24-25, 2025

Latin artists rule at Sueños Music Festival in Grant Park. Sing along with headlining artists like Shakira (!), Peso Pluma, Don Omar, Grupo Frontera, Wisin, and dozens more. Round out the weekend with art installations, Latin food, and a Ferris wheel ride.

27. Admire the Chicago Cultural Center

Many visitors pass by this stately building on Michigan Avenue in the Loop without knowing that it’s full of dazzling free attractions. The Chicago Cultural Center is home to the world’s largest Tiffany stained-glass dome in Preston Bradley Hall. Don’t miss another gorgeous dome in the recently restored Grand Army of the Republic (G.A.R.) Hall and Rotunda. It’s also home to free art exhibitions, a learning lab, and free public events. Stop at the Buddy gift shop on the ground floor to purchase gifts made exclusively by Chicago artists.

@urbnexplorer Want to shop local? Buddy only stocks items created by Chicago artists, including my book Secret Chicago! 📕Here’s how to find the store hidden in the Chicago Cultural Center.🕵️‍♀️ #chicago #secretchicago #shoplocalbusiness ♬ Afrobeat – FASSounds

28. Admire Navy Pier’s Fireworks –  May 24-August 30, 2025

One of the sure signs of Chicago summer is the fireworks displays blasting off at Navy Pier on Wednesday and Saturday nights. Even if you’re not at the pier, you can admire the fireworks display from many locations around town, especially on the lakefront. The show launches every Wednesday at 9 p.m. and Saturday at 10 p.m.

29. Make Your Own Fragrance

Have you ever wanted to blend your own fragrance? Whether it’s for yourself, a gift, or a fun activity with a friend, a Perfume Making Class is a memorable experience. The guided experience in Streeterville will introduce you to fragrance notes, teach you how to blend them, and help you make a fragrance all your own. 

30. Belmont Sheffield Fest – May 23-25, 2025

You’ve been waiting all winter to sing along to a cover band. Enter Belmont Sheffield Music Fest, a classic Chicago summer street fest in Lakeview. Local favorites like 16 Candles and Rod Tuffcurls & the Bench Press take the stage, while another stage brings Trader Todd’s karaoke outside.

31. Downtown Chicago Memorial Day Parade – May 24, 2025

Honor the men and women who made the ultimate sacrifice defending our country by marking Memorial Day. The wreath laying ceremony begins at 11 a.m. at Daley Plaza. It’s followed by a parade starting at noon and proceeding south on State Street from Lake Street to Van Buren Street.

32. Try a Viral Croissant for a Cause

Visit Daisies in Logan Square all May starting at 7 a.m. to try its special croissant collaboration with Milk Bar. Daisies pastry chef Leigh Omilinsky and Milk Bar founder Christina Tosi created the Bake Sale Croissant stuffed with a brownie and two types of cookies and topped with vanilla mousse, more cookies, and sprinkles. A portion of proceeds benefit Cookies for Kids’ Cancer.

33. Take a Selfie at Cloud Gate

Since it was unveiled in 2006, Cloud Gate, aka “The Bean,” has become a Chicago icon. After 17 years in Millenium Park, the Bean and surrounding plaza underwent a 10-month renovation. If it’s been a while since you’ve bean there, stop by to admire the skyline reflection, find yourself in the myriad reflections underneath, and snap that selfie. You know it’s fun.

34. C.R.D. Southside Memorial Day Parade – May 26, 2025

In addition to the downtown parade, the Annual Commander Robert Davis Southside Memorial Day Parade pays homage to community veterans in Auburn Gresham. The event starts with a wreath laying ceremony including speakers and a live band at 77th and Emerald Ave. It’s followed by a parade that will start and end at that location.

35. Lincoln Square Maifest – May 29-June 1, 2025

Welcome spring in German style at Maifest in Lincoln Square. You may have noticed Lincoln Square’s maypole, now you can dance around it in traditional European fashion along with dancers in lederhosen and dirndls. Music, beer, pretzels, and other German favorites will be available across from the Old Town School of Folk Music.

36. Windy City Hot Dog Fest – May 30-June 1, 2025

Decide once and for all who has the best hot dog in Chicago at the Windy City Hot Dog Fest. Don’t expect boring dogs at the Portage Park festival. Local vendors put a spin on the traditional dog with Indian, Polish, and Asian-inspired variations. Don’t miss crafts, live music, and a hot dog eating contest, naturally.

37. Do Division Street Festival – May 30-June 1, 2025

One of Chicago’s best summer street festivals returns with more than 30 music acts and dozens of food and craft vendors for Do Division. This year, the Wicker Park festival’s headliners include Illuminati Hotties, Gustaf, Y La Bamba, the Wedding Present, Shing02, and ShiAx And The Hatchetmen.

38. Hit a Pickleball Court in Chicago

As Ed Helms noted on a recent visit to Chicago, we have a lot of pickleball. You’ll find the largest pickleball option at SPF in Lincoln Park. Big City Pickle has three locations to choose from in Fulton Market, the Gold Coast, and Lincoln Park. You can find free pickleball courts in Chicago parks like Grant Park in the Loop, Warren Park Field House in West Ridge, Mandrake Park Pickleball and Tennis Courts in Oakland, and Gwendolyn Brooks Park in North Kenwood.

39. Play High Tech Shuffleboard at Electric Shuffle

If you thought you knew bar shuffleboard, think again. London-based Electric Shuffle just opened a location in River North with vintage house party vibes and an outdoor patio. Play shuffleboard complete with camera vision technology with up to 20 friends!

40. Laugh at an Improv Comedy Show

Improv was invented right here in Chicago by “Mother of Improv” Viola Spolin. Countless comedy legends have had their start in Chicago’s comedy scene, and the legacy continues today. Steve Carell, Bill Murray, and Tina Fey all got their start at the Second City in Old Town. The iO Theater (short for improv Olympic) in Lincoln Park boasts Amy Poehler and Chris Farley among its alumni. Don’t miss the Revival in the South Loop which has been on the scene since 2015.

Visiting Chicago in May FAQ

Is May good time to visit Chicago?

May is a great time to visit Chicago. The city is blooming, the sun is shining, and the events calendar is full of festivals. There is so much culture, sports, and restaurants to enjoy across Chicago before the summer heat and crowds hit the city. Warmer spring temperatures bring Chicagoans out of hibernation, yet you can still snag cheaper flights and hotel deals than other times of year. Book popular restaurant reservations in advance as well as tickets to Chicago’s top attractions like the Shedd Aquarium, the Museum of Science and Industry, or Navy Pier.

How cold is Chicago in May?

May in Chicago welcomes the sunshine, but can still be chilly. According to the National Weather Service, the average temperatures in Chicago in May range from a high of 70 degrees to a low of 50 degrees. Expect sunshine and blue skies interrupted by spring rain showers and cool breezes. With rapidly shifting weather, be sure to check the forecast before you visit Chicago in the spring.

What should I wear to Chicago in May?

If you’re wondering what clothes to wear to Chicago in May, expect spring weather with a chill. Sunny days can still have a cool breeze, especially near the lake. I recommend wearing layers to be prepared for warm days followed by cool nights. Rain is always a possibility during spring in Chicago. Check the weather forecast before you visit Chicago in May so you can pack appropriately.

After nearly two decades of living in Chicago, here are my recommendations for what to wear in Chicago in the spring.

• Chicago is a walking town, so pack comfortable shoes like sneakers or boots.  
• Dress in layers so you can adjust to the different temperatures indoors and outdoors. You may want to layer with a women’s flannel or men’s flannel.
• A classic button-down Oxford or chambray shirt is great for traveling, and I’ve never met a striped Breton shirt that I didn’t like.
• In spring, I typically layer a lighter trench coat, leather jacket, or bomber jacket over my outfit.
• It doesn’t hurt to pack a beanie in case it gets chilly at night and a windproof travel umbrella for rainy spring days.

Where to Stay in Chicago in May

Wondering where to stay overnight in Chicago in the spring? My favorite hotel views are from the Chicago Athletic Association overlooking Millennium Park and the boats on Lake Michigan and the LondonHouse with jaw-dropping views of the Chicago River from the rooftop bar. I love the views of Grant Park from the Blackstone Hotel and the Hilton Chicago.

Click here for a full list of Chicago hotels!

If you want to research hotels and vacation rentals for your Chicago visit, this map can help you compare the available options. It’s set to show hotels and rentals in downtown Chicago, but you can view any neighborhood where you’d like to stay.

I hope this helps you have fun when you visit Chicago in May!

Need more information on what to do while you’re in Chicago? Check out all of my Chicago articles and don’t miss my Chicago books Secret Chicago: A Guide to the Weird, Wonderful, and Obscure and Chicago Scavenger!

Find out what to do in Chicago throughout the year:

• Fun Things to Do in Chicago in January
• Fun Things Do in Chicago in February
• What to Do in Chicago in March
• Fun Things to Do in Chicago in April