Searching for what to do in Chicago this May? Here are the best things to do in Chicago in May (from a local) – including the top attractions and the best May events and festivals.
I suggest bookmarking this blog post as I will be updating it regularly with new events and activities.
Chicago in May
May is usually a good month to visit Chicago. Temperatures are typically pleasant enough to enjoy Chicago’s many outdoor activities. Plus the popular attractions are less crowded before the busy tourist season starts around Memorial Day weekend.
For out of town visitors, please note that the weather in Chicago in May is very unpredictable and temperatures can vary greatly. Be prepared for winter, spring or summer like temperatures (sometimes all in one day!) as well as rain. Make sure to pack a travel umbrella, layers and check the weather right before your visit to know what to expect.
Things to Do in Chicago in May
Below are the top things to do in Chicago in May including all of the best May festivals and events.
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Take an Architecture River Cruise
Taking an architecture river cruise is a must when visiting Chicago.
Take a Lake Cruise
If you enjoy being on the water, a lake cruise is a fun activity whether in the day, around sunset and in the evening. While you don’t get to see the buildings up close like on a architecture river cruise, you do get to enjoy skyline views and a refreshing cool lake breeze.
If your time is short, you can do a combination river and lake cruise.
Have Fun at Navy Pier
Navy Pier is a must do if you are visiting Chicago with toddlers or kids. Fun attractions include a large Ferris wheel (click here to purchase a fast pass ticket and skip the long line), rides and games, restaurants, shops and the Chicago Children’s Museum.
Attend a Candlelight Concert
Chicago’s Candlelight Concerts is a series of special classical music concerts that take place in beautiful venues bathed in candlelight. Some of the concerts taking place this May include:
Candlelight: A Tribute to Pink
Candlelight: A Tribute to Adele
ABBA Under The Stars at AIRE
You can find the full list of candlelight concerts in Chicago here.
Look for Street Art
Chicago is full of street art and there are always new murals popping up.
One of the most famous Chicago murals is “Moose Bubblegum Bubble” (pictured above) by Jacob Watts located at 33 E. Ida B. Wells Drive (formerly 33 E. Congress Parkway). It is part of the Wabash Arts Corridor and is walking distance to Millennium Park, The Art Institute of Chicago and other tourist attractions.
Another famous mural is the Greetings From Chicago Mural at 2226 N Milwaukee Ave. You can see this mural and other street art on this street art tour.
Hang Out on the Riverwalk
The Chicago Riverwalk along the south bank of the Chicago River is one of the best spots in Chicago for people watching. There are restaurants, bars, shops and places to sit along the way. Many establishments open up in May for the season so this is a great month to enjoy the Riverwalk. You can find a map here.
See Digital Art Projections at Art on the Mart
Art on theMART is the largest permanent digital art projection in the world, projecting contemporary artwork twice nightly across the 2.5-acre river-façade of theMART.
Where: The Merchandise Mart, 222 W Merchandise Mart Plaza, Chicago, IL 60654. Spectators can watch the show from the jetty section of the Chicago Riverwalk on Wacker Drive between Wells Street and Franklin Street.
Cost: Free.
Go Kayaking in the River
A fun way to explore the city is to go kayaking in the Chicago River. There are several companies that offer kayaking tours in Chicago including Urban Kayaks, Kayak Chicago and Wateriders.
Please note that you will get a little wet so bring a waterproof case for your phone and water-resistant or quick-drying clothing.
Watch a Baseball Game
Chicago is known for their love of their sports teams, so if you are visiting in May you might want to attend a baseball game. To those unfamiliar, historic Wrigley Field is home to one of the city’s baseball teams – the Cubs. Whether a fan of the Cubs, baseball in general or just a fun atmosphere, a day at the 100 year old ballpark is a must for locals and tourists alike. You don’t need to enjoy baseball to enjoy a Cubs game – it is fun to just soak in the atmosphere.
You can find the Cubs schedule here and the Chicago White Sox schedule here.
Visit the Garfield Park Conservatory
The Garfield Park Conservatory is one of the largest and most stunning botanical conservatories in the US. Often referred to as “landscape art under glass,” it showcases thousands of plant species from around the world throughout eight indoor display gardens. Reservations required.
Through May 12, visitors can see this year’s Spring Flower Show, What’s in a Name?, which explains the history and science of botanical nomenclature alongside a beautiful flower show full of blooms.
Hours: Wednesday 10am-8pm; Thursday – Sunday 10am-5pm; Closed Monday and Tuesday
Where: 300 N. Central Park Ave., Chicago, IL 60624
Cost: FREE (suggested donation)
Visit the Lincoln Park Conservatory
Although not as large as the Garfield Park Conservatory, the Lincoln Park Conservatory is worth a visit and is more conveniently located for tourists. Advance online reservations are strongly recommended.
Through May 12, visitors can see this year’s “Sweet Gnome Chicago” Spring Flower Show.
Hours: Wednesdays through Sundays from 10am-5pm.
Where: 2391 N Stockton Dr., Chicago, IL 60614
Cost: FREE
Visit the Art Institute of Chicago
The Art Institute of Chicago is one of the oldest and largest art museums in the United States. In addition to its large permanent collection of art from around the world, you can see rotating exhibitions.
(Click here to buy a skip the line ticket if you want to avoid long lines).
Where: 111 S Michigan Ave, Chicago, IL 60603
When: Thursday 11am–8pm; Friday to Monday from 11am– 5pm. Closed on Tuesdays and Wednesdays.
Cost: Price varies; members and children under 14 are always free. Visit (Free admission on the first weekend in May for Bank of America credit or debit cardholders under the Bank of America Museums on Us program.)
Enjoy the Views from 360 CHICAGO Observation Deck
360 CHICAGO, the observatory on the 94th floor of the former John Hancock Building, has one of the best views of the Chicago skyline and Lake Michigan. (Click here to buy a skip the line ticket).
Where: 875 North Michigan Avenue, 94th floor, Chicago, IL 60611
Cost: Price varies.
See the Tulips on Michigan Avenue
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Every year thousands of tulip bulbs are planted in Michigan Avenue medians from Oak Street to Roosevelt Road. You can enjoy the tulips while shopping (or window shopping) on The Magnificent Mile (or The Mag Mile), an upscale section of Michigan Avenue, running from Oak Street to the Chicago River. Although a few stores on Michigan Avenue are pricey, it is totally free to window shop. Landmarks on the Mag Mile include the 360 Observation Deck, the historic Chicago Water Tower and the Tribune Tower. South of the Magnificent Mile you will find Millennium Park and the Art Institute of Chicago.
When: Tulips are usually in bloom from mid-April to mid-May but exact dates vary annually.
Where: Michigan Avenue from Oak Street to Roosevelt Road.
Cost: Free.
RELATED: Best Places to See Tulips in and near Chicago
Enjoy the Views from Skydeck Chicago
Skydeck Chicago in Willis Tower offers spectacular views spanning up to four states. Make sure to visit The Ledge, a glass balcony extending four feet outside the 103rd floor of Willis Tower.
Where: 233 S Wacker Dr, Chicago, IL 60606
Hours: Open daily from 9AM–8PM
Cost: Prices vary. Click here to buy a skip the line ticket if you want to avoid long lines.
Visit the Field Museum
The Field Museum is one of the largest natural history museums in the world. Inside the museum you will see Maximo, the Titanosaur, the largest dinosaur that ever lived. (Click here to purchase an Early Access VIP Tour if you want to avoid crowds).
When: Open daily 9am to 5pm (last admission at 4pm)
Where: Chicago’s Museum Campus, 1400 S Lake Shore Dr, Chicago, IL 60605 (detailed directions and parking information is available here)
Cost: Prices vary.
Tip: If you are visiting a few museums and indoor attractions, consider purchasing a Chicago CityPASS or Go Chicago Card to save money on entrance fees.
See Buckingham Fountain
Buckingham Fountain, a well known Chicago landmark in the center of Grant Park, is one of the largest fountains in the world. When the water is turned on (in mid-May), it produces a major water display for 20 minutes every hour with a center jet shoots water to a height of 150 feet into the air. Beginning at dusk, a spectacular light and music display accompanies the major water display.
When: Water is turned in mid-May for the season with the Switch on Summer & Night Out Kick-Off.
Hours: 8 a.m. to 11:00 p.m. daily
Visit Local Farmers Markets in Chicago
Most farmers markets start opening up for the season in May. These markets are a great place to buy healthy, local, farm-fresh foods. Two of the best farmers markets in Chicago include the Green City Market in Lincoln Park and the Logan Square Farmers Market. You can see the list and schedule of all Chicago farmers markets here.
Admire Spring Flowers Outside
There are many places in and near Chicago to admire beautiful spring flowers in May. Some of the best spots to see flowers in the city and suburbs outside include:
• Lurie Garden is a 2.5-acre garden located at the southern end of Millennium Park. The garden is a combination of perennials, bulbs, grasses, shrubs and trees and offers great skyline views.
• Morton Arboretum (in Lisle about 26 miles west of downtown) is home to more than 4,000 different types of trees among 1,700 acres and publishes a weekly bloom report.
• The Chicago Botanic Garden (in suburban Glencoe about 24 miles north of downtown) is one of the world’s great living museums and conservation science centers with 27 gardens and four natural areas, situated on 385 acres on and around nine islands, with six miles of lake shoreline. You can check their seasonal bloom chart here to see what’s in bloom during your visit.
Attend an Outdoor Festival
May is the start of the outdoor festival season. The best outdoor festivals taking place in May include: Chicago Mayfest (May 17-19), Mole de Mayo (May 24-26), Belmont-Sheffield Music Festival (May 24-26), Mayfestiversary (May 25-26), Sueños Music Festival (May 25-26), Randolph Street Market Festival (May 25-26), WingOut Chicago (May 25-26), Maifest (May 30-31), Do Division (May 31) and Lincoln Park Greek Fest (May 31).
Chicago May Events
In addition to the activities mentioned above, other May events include: Illinois Craft Beer Week, Beer Under Glass (May 3), Cinco de Mayo Parade (May 5), Chicago Cabaret Week (May 10-19), Night Nation Run (May 11), Switch on Summer & Night Out Kick-Off at Buckingham Fountain (May 11), Chicago Margarita Fest (May 17-19), Renegade Craft Fair (May 18-19), Spring Lincoln Roscoe Art & Craft Fair (May 18-19), American Writers Festival (May 19), Paint the Town Red (May 23), Memorial Day Wreath Laying Ceremony and Parade (May 25), Norwood Park Memorial Day Parade (May 27) and Chicago House Music Conference (May 31).
As you can see there are many things to do in Chicago in May.
Planning a trip to Chicago? Check out my Chicago guides and itineraries:
