Best Things to Do in Chicago in May

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 enought 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

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 cruise

Taking an architecture river cruise is a must when visiting Chicago.


Hang out at Navy Pier

rides at Navy Pier Chicago
Navy Pier can be somewhat of a tourist trap but it 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.


The 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,” the Garfield Park Conservatory showcases thousands of plant species from around the world throughout eight indoor display gardens. 

Hours: Wednesday 10am-8pm; Thursday – Sunday 10am-5pm; Closed Monday and Tuesday

Where: Garfield Park Conservatory, 300 N. Central Park Ave., Chicago, IL 60624

Cost: FREE but donations appreciated

Watch digital art 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: 30-minute program of projections are shown nightly

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.

Visit the Museum of Illusions Chicago

The Museum of Illusions Chicago offers an interactive, immersive and fun experience for both adults and kids. Visitors can engage in over 80 astonishing and mind-bending exhibits that will teach you about vision, perception, the human brain and science.

When: Sunday – Thursday: 10am – 8pm Friday – Saturday: 10am – 9pm

Where: 25 E Washington St, Chicago, IL 60602

Cost:  Adult (ages 18+): $21; Child (ages 5 – 12): $15; Child (ages 4 and under): FREE;
Student (ages 13+), Teachers, Military / First responders and Senior Citizens (ages 60+): $18​ with ID; Family (2 adults + 2 children): $65

Enjoy the views from 360 CHICAGO Observation Deck

360 CHICAGO, the observatory on the 94th floor of the former John Hancock Building, has the best views of the Chicago skyline and Lake Michigan.

Where: 875 North Michigan Avenue, 94th floor, Chicago, IL 60611

Cost:  $25 for adults, $15 youth.


Shop (or window shop) on the Magnificent Mile

Join the throngs of visitors and locals shopping (or window shopping) on The Magnificent Mile. The Magnificent Mile (or The Mag Mile), is an upscale section of Michigan Avenue, running from Oak Street to the Chicago River. Although some of the 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. Michigan Avenue is the most picturesque in the spring (until approximately mid-May) when the tulips planted along the sidewalk and in the medians are in full bloom.

Enjoy the views from Skydeck Chicago

Skydeck Chicago in Willis Tower has returned with a transformed experience that will allow you to see, hear & be immersed in Chicago from street to sky. Skydeck 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.

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.

Get Some Culture at The Field Museum

The Field Museum is a natural history museum in Chicago, Illinois, and is one of the largest such 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. Click here to see prices and purchase tickets online in advance. Illinois residents get free admission on free admission days.

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.

Visit the Art Institute of Chicago

The Art Institute of Chicago is one of the best things to do in Chicago Illinois in May 2021
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. Must purchase tickets online in advance. (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 their website to purchase tickets in advance. (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.)

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.

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. The water is not on during the cold months but is is usually turned on sometime in May.

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. 

Admire Spring Flowers

tulip fields in and near Chicago one of the best things to do in May 2021
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 five 15- to 26-foot-tall sculptures which will be 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 at the Chicago Botanic Garden during your visit.

Richardson Adventure Farm (in Spring Grove about 65 miles northwest of downtown Chicago) will be hosting its second Tulip Festival from mid-April to mid-May. They have planted 5 acres of tulips with 300,000 bulbs in 30 different varieties. RELATED: Best Places to See Tulips in and near Chicago

As you can see there are many things to do in Chicago this May.

Planning a trip to Chicago? Check out my Chicago guides and itineraries:



One Comment

Leave a Reply

Your email address will not be published. Required fields are marked *

This site uses Akismet to reduce spam. Learn how your comment data is processed.