Chicago transforms in May as warm temperatures, blooming gardens, and a packed calendar of outdoor events signal spring's arrival. From the city's most notable landmarks to seasonal festivals, here's your guide to experiencing the best things to do in Chicago in May.
Things To Do in Chicago in May: Attractions and Spring Events
May offers the perfect weather to explore things to do in Chicago without the summer crowds. With temperatures typically ranging from 50°F to 70°F, you'll enjoy comfortable conditions for both indoor cultural experiences and outdoor adventures. Chicago CityPASS® tickets provide access to the city's must-see attractions while saving you money on admission prices.
Discover Marine Life at Shedd Aquarium
The Shedd Aquarium offers a welcome respite if you encounter a rainy May day. Home to more than 32,000 aquatic animals, the aquarium features immersive exhibits like the Caribbean Reef, Amazon Rising, and the popular Abbott Oceanarium.
Don't miss the Jazzin' at the Shedd evening events, which usually begin in late May. These Thursday night events combine live music, cocktails, and after-hours access to exhibits with stunning lakefront views as the sun sets over Lake Michigan.
See the Stars at Adler Planetarium
May brings clearer night skies to Chicago, making it an excellent time to visit the Adler Planetarium. As America's first planetarium, this historic institution offers immersive sky shows in its three theaters along with interactive exhibits exploring space science. The planetarium's outdoor Skyline Walk provides one of the best vantage points for photographing Chicago's skyline against the backdrop of Lake Michigan.
Enjoy Views From Observation Decks
Spring visibility tends to be excellent from Skydeck Chicago, located on the 103rd floor of Willis Tower. After April showers clear the air, May often offers some of the year's most spectacular panoramic views stretching across four states.
For an unforgettable experience, step out onto The Ledge — glass balconies extending four feet outside the building, 1,353 feet above the ground. Morning visits typically offer smaller crowds, and sunset visits provide dramatic lighting over the city landscape.
For a different perspective of Chicago, make your way over to 360 CHICAGO at the top of the John Hancock Center. If you're feeling adventurous, make sure to give TILT a try. Both observation experiences are amazing additions to any May itinerary.
Millennium Park in Full Bloom
Every May, Millennium Park transforms into a botanical wonderland as gardens burst with colorful tulips, daffodils, and native wildflowers. Visit the iconic Cloud Gate sculpture (affectionately known as The Bean) for that perfect spring photo with Chicago's skyline reflected in its polished surface.
The Lurie Garden, spanning 2.5 acres at the park's southern end, reaches peak bloom in May with a stunning array of perennials and grasses. Free guided tours of the garden are typically offered on Thursday, Friday, and Sunday afternoons throughout May, providing insight into the garden's sustainable design and diverse plant species.
For music lovers, the Jay Pritzker Pavilion often hosts free concerts as part of the park's spring programming. Check the official schedule for specific dates and performances during your visit.
Stroll the Chicago Riverwalk
The Chicago Riverwalk comes alive in May as restaurants open their outdoor patios and river cruises resume regular schedules. This 1.25-mile pedestrian pathway offers beautiful views of the city's architectural landmarks while providing access to restaurants, bars, and public art installations.
Architecture enthusiasts can take advantage of a Shoreline Sightseeing Architecture River Tour. These 75-minute tours highlight significant buildings while explaining Chicago's influential role in modern architecture.
For a more active experience, rent kayaks from vendors along the riverwalk to paddle through the heart of downtown. As temperatures warm in May, these water activities become increasingly popular, so consider booking in advance.
Chicago Sports in May
Sports fans have plenty to cheer about in Chicago during May. The Chicago Cubs and Chicago White Sox both play home games throughout the month at Wrigley Field and Guaranteed Rate Field, respectively. The historic ivy on Wrigley's outfield walls typically begins turning green in May, adding to the iconic ballpark's charm.
The Chicago Fire FC soccer team plays home matches at Soldier Field, while the Chicago Red Stars women's soccer team competes at SeatGeek Stadium. Check team schedules and secure tickets in advance for these popular sporting events.
Enjoy Spring Festivals and Outdoor Fun
May marks the beginning of Chicago's renowned festival season with events celebrating everything from music to food to cultural heritage.
Belmont-Sheffield Music Fest
Usually held during Memorial Day weekend, this street festival features live music across multiple stages, food vendors, and artisan booths. Located in the Lakeview neighborhood near the Belmont Red Line station, the festival typically offers free admission with a suggested donation benefiting the Central Lakeview Merchants Association.
Bike or Walk the Lakefront Trail
Chicago's 18-mile Lakefront Trail provides a scenic route for walking, running, or cycling along Lake Michigan. Divvy bike-sharing stations located throughout the city offer convenient rental options for exploring the lakefront.
Several parks along the trail — including Grant Park, Burnham Park, and Lincoln Park — feature gardens that reach peak bloom in May. Pack a picnic to enjoy at one of the many designated areas along the route for a perfect spring afternoon.
Make the Most of Your Trip With CityPASS® Tickets
Maximize your Chicago experience while saving on admission to Chicago's top attractions with Chicago CityPASS® tickets. These tickets include entry to must-see destinations like Shedd Aquarium, Skydeck Chicago, and the Field Museum, allowing you to experience the best of Chicago without breaking your budget.
Chicago CityPASS® tickets provide flexibility for your May visit with a nine-day validity period, giving you plenty of time to explore at your own pace while enjoying the perfect spring weather. Start planning your adventure today!
Chicago Lodging
To get the most out of your stay in Chicago, we recommend finding lodging near Chicago's top attractions. Use this map to find the right lodging for you: