May is a lovely time in Chicago, as the city’s parks and public spaces come alive with vibrant blooms. Tulips start to line Michigan Avenue, summer events are gearing up, and the Riverwalk restaurants buzz with activity—there’s a palpable energy in the air. Here are our top recommendations for the best things to do in Chicago this May.
Get tickets early for one of the biggest movies of the year, From the World of John Wick: Ballerina
From the World of John Wick: Ballerina sets the Keanu Reeves-helmed franchise into a lethal new direction. It stars Ana de Armas as Rooney, a trained assassin raised in the ballet-drenched Ruska Roma underworld. The film opens June 6 and tickets are on sale now—click here for more info.
🍿 Release date: Jun. 6, 2025
Catch the cherry blossoms bloom
By early May, Chicago bursts into bloom with vibrant colors throughout the city. One of the most enchanting moments of spring is the arrival of the cherry blossoms, which bloom for a brief period in only a few select locations around Chicago. Due to their fleeting nature, one of the best things to do in Chicago in May is to visit Jackson Park, near the Museum of Science and Industry, to see the cherry blossoms while you still can.
Take in the tulips of Michigan Avenue
If you love floral beauty this time of the year, one brilliant and simple experience in Chicago is to enjoy the tulips along Michigan Avenue, from Oak Street to Roosevelt Road. By early May, these bulbs begin to sprout and bloom, transforming Michigan Avenue into a vibrant display of colorful tulips.
Walk through tulip fields at Richardson Farm’s annual tulip festival
If the tulips on Michigan Avenue leave you wanting more, you can visit Richardson Farm’s annual Tulip Festival for an even more impressive display. Known for hosting the world’s largest corn maze in the fall, the farm transforms in spring with an incredible array of over 30 different varieties of tulips, available in vibrant hues that range from fiery coral to snowy white, pale yellow, and rich plum.
Check out the ART on The MART spring projections
The ART on The MART projections have returned! One of the highlights of May is the artistic projections on the 2.5-acre river façade of the Merchandise Mart. As the largest permanent digital art projection in the world, ART on The MART attracts thousands of visitors to the Riverwalk each week. The display features 34 digital projectors that showcase works from both renowned artists and local talent.
Experience a DIY Facial Bar
Kayak down the Chicago River
Experience a truly unique evening in May by combining kayaking with the Art on the MART projections. Urban Kayaks has reopened its Riverwalk and Lakefront locations, marking the start of the spring and summer kayaking season. Whether you’re paddling along the Chicago Riverwalk, surrounded by the city’s iconic high-rise architecture, or enjoying the skyline from the sheltered waters of Monroe Harbour, kayaking in Chicago is a magical experience.
Sail on the Chicago River
As Chicago emerges from winter, the bridges are open, and the city’s waterways are coming back to life. Along with kayaking opportunities, boat rentals are also resuming. The Chicago Electric Boat Company, renowned for its fleet of self-captained, eco-friendly vessels, has reopened for the spring and summer seasons.
They offer a variety of boating experiences, ranging from classic and luxury Duffy Boats to Party Barges, Cycleboats, Donut Boats, and even rentable hot tub boats. With options for groups of up to 26 people, Chicago Electric Boat Company provides unforgettable boating activities this May in Chicago.
Go for a Mother’s Day brunch
Celebrate your mom this Mother’s Day with delicious fluffy pancakes, mimosas galore, or whatever brunch delights you! There are numerous amazing brunch spots in Chicago, many offering Mother’s Day brunch specials for the May 11th holiday.
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.
Be captivated by a Candlelight Concert
Candlelight Concert series offers a stunning array of performances in the city. Talented musicians will play at extraordinary venues, allowing guests to enjoy the enchanting blend of flickering candlelight and melodic sounds. If you’re unsure which concert to attend but still want to experience this magical event, or if you need a special gift for someone, Candlelight gift cards are a convenient option. They are valid for any Candlelight event in the U.S., making them a unique gift for both friends and family.
See live music at Lincoln Park’s Chicago Mayfest
You can enjoy live music this month at Lincoln Park’s Mayfest. This annual street party returns in May, featuring live entertainment, food vendors, cover bands, and carnival games at Lincoln Park.
Chicago Mayfest marks the beginning of the summer festival season, running from Friday, May 16, to Sunday, May 18, at Armitage and Sheffield in the historic Lincoln Park District. The event supports the local community, with donations benefiting the historic Ranch Triangle area, the Lincoln Park community, small businesses, and public schools in the region.
The Budweiser Concert at Gallagher Way
On Saturday, May 24, Dawes will perform LIVE at Gallagher Way as part of the Budweiser Concert Series, featuring special guest Lily Kershaw! Join us for an exciting evening of live music and fun under the stars. Gates will open at 7:00 p.m., and the concert will begin at 7:30 p.m.
Spend an evening at Shedd Aquarium for free
Chicago’s Shedd Aquarium, one of the city’s main attractions, is now offering free admission every Tuesday evening from spring until the end of June. Illinois residents can visit the beloved aquarium from 5 p.m. to 9 p.m. on Tuesdays throughout May.
Enjoy free admission to the Field Museum on a Wednesday
At the beginning of the year, the Field Museum announced a new initiative for 2025: regular free admission days. While many popular museums and attractions in Chicago typically offer random free days throughout the year, particularly during the quieter months for tourism, the Field Museum is taking a different approach this year. They invite all Illinois residents to enjoy free admission every Wednesday throughout 2025.
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 to visit this vibrant speakeasy. One of our top picks is located 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. This 2,000-square-foot space offers a lively late-night experience filled with energy and music, transporting guests to the nightlife of the Mediterranean.
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.
Gaze at the stars at the Adler Planetarium for free
The Adler Planetarium is always worth a visit, especially as we approach the longer days of spring. Illinois residents can enjoy free admission every Wednesday evening from 4:00 to 10:00 PM, provided they bring proof of residency. Visitors can also explore the largest public telescope in the Midwest and participate in a variety of exciting astronomy events and activities.
Stay in a Starved Rock Getaway cabin
