BEST Things to Do in Chicago in May (From a Local!)

Searching for what to do in Chicago this May? Here are the best things to do in Chicago in May (from a local).

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.

I suggest bookmarking this blog post as I plan to update it regularly with any new events.

Things to Do in Chicago in May

Disclosure: This article contains affiliate links. I may make a small commission if you make a booking using my links at no extra cost to you. As an Amazon Associate I earn from qualifying purchases.

Take an Architecture River Cruise

Taking an architecture river cruise is a must when visiting Chicago. If the temperature not too cold you might enjoy a combination river and lake cruise.

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. Lake cruises depart from Navy Pier or the Michigan Avenue bridge.

Have Fun at Navy Pier

rides at Navy Pier Chicago
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.

Navy Pier is also the starting point for many boat rides and lake cruises.

Watch a Baseball Game

wrigley field Chicago

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.

You can also watch the Cubs from Wrigley View Rooftop.

Visit the Art Institute of Chicago

The Art Institute of Chicago is one of the best things to do in Chicago Illinois in May 2023
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.

When: Hours are Monday and Thursday–Sunday from 11 a.m.– 6 p.m. (10–11 a.m. for members). Closed on Tuesday–Wednesday.  (Click here to buy a skip the line ticket if you want to avoid long lines).

Where: 111 S Michigan Ave, Chicago, IL 60603

Cost:  $25 for adults, $19 for seniors, students and teens (14-17); 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 Garfield Park Conservatory’s Spring Flower Show

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. The Garfield Park Conservatory’s Spring Flower Show: Knock Knock (through May 9) features beautiful blooming flowers, including tulips, hydrangeas, daffodils, and hyacinth. Reservations required.

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)

Experience the Immersive Van Gogh Exhibit

From the creators of the blockbuster show at Atelier des Lumières seen by over 2 million visitors in Paris and Toronto and featured in Emily in Paris (one of my favorite travel shows on Netflix), the Immersive Van Gogh Exhibit, is a massive indoor digital presentation of Vincent Van Gogh’s artwork.

Where: Lighthouse ArtSpace at Germania Place, 108 W. Germania Pl, Chicago, IL

Cost:  Tickets start at $39.99 plus fees for off peak times. See https://www.vangoghchicago.com/ for full prices and to purchase tickets in advance.

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:  $25 for adults, $15 youth.

See the Tulips on Michigan Avenue

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. The Skydeck has implemented timed ticketing and they recommend reserving your tickets in advance to guarantee access. (Click here to buy a skip the line ticket if you want to avoid long lines).

Where: 233 S Wacker Dr, Chicago, IL 60606

Hours: Open daily from 9AM–10PM

Cost: Adult: $28-$35; kids age 3 to 11: $22-$26; and children under 3 are free. They also offer expedited entry for $55 and early bird for $65.

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.

Enjoy Lincoln Park Conservatory’s Spring Flower Show

Although not as large as the Garfield Park Conservatory, the Lincoln Park Conservatory is worth a visit and is more conveniently located for visitors. The Lincoln Park Conservatory’s Spring Flower Show, “Pillars of Spring” runs through May 8 and invites visitors to imagine gardens in a different way – vertically by planting from the ground upwards. Free registration is required for entry.  A limited number of pre-registered, timed-access tickets are released on a rolling basis two weeks prior to the visitation date.

Hours: Wednesdays through Sundays. Timed entry every 15-minutes from 10:00 am to 2:00 pm, all guests must exit by 3:00 pm.

Where: 2391 N Stockton Dr., Chicago, IL 60614

Cost: FREE
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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 in May include:

Candlelight: A Tribute to Taylor Swift
Candlelight: A Tribute to Adele
Candlelight: A Tribute to ABBA at Stan Mansion

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.

street art mural in Chicago

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.

Other neighborhoods that have a high concentration of street art include Pilsen as well as West Town.

Hang Out on the Riverwalk

best things to do chicago travel blog

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 the Mart in spring
Art on theMART is the largest permanent digital art projection in the world, projecting contemporary artwork across the 2.5-acre river-façade of theMART.

When: Twice nightly at 8:30 and 9 p.m.

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.

See Buckingham Fountain

Buckingham Fountain in Chicago opens in May
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, 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. The water is not on during the cooler months but is turned on in May every year during ComEd’s annual Switch on Summer celebration.

The official turning on of Buckingham Fountain is taking place on May 14 from 12-3pm with family friendly activities and entertainment including live music and free giveaways. You can even enter for a chance to flip the switch yourself here.

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.

Chicago Food Truck Festival

The popular Chicago Food Truck Festival kicks-off May 20 and will stay open for the next five months. The festival features a rotating selection of food trucks from around the city and is a great opportunity to support small businesses while bringing new and diverse lunch options to Chicago’s Loop. The changing list of weekly participants are shared on BACP’s social media accounts – @ChicagoBACP.
When: 11am – 3pm every Friday starting May 20

Where: Daley Plaza, 50 W. Washington Street

Admire Spring Flowers Outside

tulip fields in and near Chicago one of the best things to do in May 2022
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. Make sure to check out their outdoor art installation, Human+Nature by renowned South African artist Daniel Popper. The exhibition features 15- to 26-foot-tall sculptures in various locations across the Arboretum site to lead guests to areas they may not otherwise explore.

• 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.

Chicago May Events

In addition to the activities mentioned above, other May events include: Night Nation Run (May 7), Lincoln Park Uncorked: An Armitage-Halsted Wine Stroll (May 12), SAUCED Spring Night Market (May 13-14), Andersonville Wine Walk (May 15), American Writers Festival (May 15), Chicago Critics Film Festival (May 13-19), Illinois Craft Beer Week (May 13-20), AAPI Restaurants Week (May 13-22), Mayfest (May 20-22), Spring Tequila Tasting Festival (May 21), Anti-Cruelty Society’s Annual BARK (May 21), Helix Spring Artist Market (May 21), Spring Lincoln Roscoe Art & Craft Fair (May 21-22), Renegade Craft Fair (May 21-22), Paint the Town Red (May 26), Mole de Mayo (May 27-29), Belmont-Sheffield Music Festival (May 27-29), Mayfestiversary (May 28-29) and Sueños Music Festival (May 28-29).

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:



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