What to do in May in Chicago (2019)

This post lists top things to do in Chicago in May, updated for 2019, as well as things to do at night, free activities and family-friendly events. Be sure to read about things to do all year round!




This section covers our top ten list for May. When possible, we’ve noted activities that are free or kid-friendly. 

Some of the items listed in this post are included for free with the purchase of a tourist discount pass

1. Take a Sightseeing Tour

Take advantage of the springtime weather and get out with a sightseeing tour!

Of course, we have pay-what-you-like walking tours, which cover Chicago architecture, history, new neighborhoods, and ghost stories.



If walking tours aren’t your thing, you can get a ride on one of Chicago’s bus tours to cover more ground.

You can also take to the water with a boat tour. Our boat tours page covers water taxis, cruises with or without dinner, and sailboat and kayaking tours.

2. Catch a Concert

From the House of Blues and the Vic Theatre to the Allstate Arena, there are constantly big-name artists coming through Chicago.



Here are a few concerts you might want to see this month:

(3) Go to a Game

May is prime time for baseball. We have two baseball teams here, so there are plenty of options for families to go catch a game!



Here are a few of the more popular teams in this city that are playing in May:

A day at the ballpark is the perfect family outing. Check out the rest of our family-friendly activities below. 

(4) Enjoy the Theatre

Chicago has multiple theatre productions running during the month of May, from new musicals to long-running favorites. Click here for a full list of shows.


Chicago is a Tony-winning musical about a nightclub dancer who commits murder and works to clear her name of any suspicion.

Set in the 1920s, you won’t want to miss one of the longest-running Broadway musicals. Suggested for ages 13+. Dates: May 7 – 12, 2019




The story of Rent follows seven struggling artists throughout one year of their lives. Suggested for ages 13+. Dates: May 10 – 19, 2019


Falsettos is intended to be a subversive play that takes a look at the AIDS crisis through the life of one man who is trying to make his new partner fit into his and his son’s life. Suggested for ages 13+. Dates: May 28 – June 29, 2019

(5) Chicago Antiques + Arts + Design Show

May 16-19, 2019

This large and historic building will once again host the Chicago Antiques + Arts + Design Show, bringing in 75 vendors from across the country and the world.



Here you’ll find fine antiques and decorative arts from ancient treasures to modern 20th century finds.

(6) Maifest

May 30 – June 2, 2019

In Lincoln Square, you will find one of the best kick-offs to summer festivals.

For the 24th year, the Maifest festival will showcase the best of live entertainment and food throughout the city to celebrate Chicago’s German heritage.



Like Oktoberfest, but for spring – you’ll find a maypole, dancing, fun, and German food and beer! 

(7) Mole de Mayo

May 24-26, 2019

Come celebrate Cinco de Mayo a little late at this Pilsen tradition. Pilsen is a historic neighborhood southwest of downtown.

This weekend celebration features “mole” from local restaurants and other tasty food, crafts, a wrestling ring, and live entertainment.



If you’re enjoying your time in the Pilsen neighborhood, spend a little longer and take our Pilsen self guided tour! 

And for more things to do at night, check out the nighttime activities section below. 

(8) Food Truck Social at the Zoo

May 11, 2019

Come visit the Lincoln Park Zoo after hours for this Food Truck Social featuring dozens of food trucks.

Beyond some of the best food trucks in the city, there will be a DJ, fun activities, and of course, all of the animals.



Our Lincoln Park and Gangster Tour will drop you off at the zoo with plenty of time to participate in the festivities.

This is the perfect opportunity for the whole family to enjoy the zoo and the nightlife!

For more family-friendly festivals and things to do, check out our family-friendly section

(9) Belmont-Sheffield Music Fest

May 25-26, 2019

Local bands, food, and street vendors line Sheffield Avenue at this Memorial Day weekend festival. Come kick off summer at this outdoor fest!



No tickets are required to enjoy the festival, but they do ask for a $5 donation at the door. 

(10) Consider a Tourist Pass

A lot of the highlights in Chicago have admission costs and while you do have to pay for a tourist pass, it can work in your favor and get you free admission into a museum or attraction you were already planning on visiting.

Each Chicago Tourist Discount Pass includes a variety of fun family-friendly activities and attractions. 



Here are just a few examples of locations you can visit either for free or at a discount with one of these tourist passes.

Even better, admission to these attractions with a tourist pass may include Fast Track/Skip the Line entry.


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Many of our top ten activities are perfect for the evening hours, such as seeing the traveling production of Rent, but below are some other suggestions to fill in your evenings during the month of May.



Read our post about the top 10 things to do in Chicago at night for more ideas. 

Chicago Philharmonic & Cirque de la Symphonie

May 26, 2019

Performing on stage next to the classical musicians of the Chicago Philharmonic, you’ll find acrobats, clowns and strongmen acting out choreographed circus-like performances.

This family-friendly event present cinematic scores with entertaining acts at the Harris Theatre in Chicago.

Look for discounted tickets on TodayTix. And don’t forget about the regular Chicago Symphony performances throughout the month!

Navy Pier Fireworks

May 25, 2019

Summer truly takes off with the start of Navy Pier Fireworks. On the 25th, the season begins with the fireworks show beginning at 10:15 pm.



These shows will continue all summer long, lighting up the sky every Wednesday and Saturday night.

Our Riverwalk and History Tour will bring you right to the big show!

Go to a Game Bar

Explore some of Chicago’s best game bars. Whether you want to try an arcade bar with some pinball and Pacman or try a classic board game, Chicago has a bar for you. 

Batting Cages

Practice your baseball skills right outside of historic Wrigley Field at the batting cages at Sluggers.

Beyond the batting cages, you can participate in other games such as skeeball, and catch some games on the TVs at this beloved sports bar. 

Solider Field

May 4, 2019

If you are disappointed about missing football season, we have another excuse for you to explore the historic Solider Field, home to the Chicago Bears.



At the Chicago Beer Classic, hundreds of beer and food vendors flood the grass of Soldier Field. Taste samples of beer while learning from the brewers, then stay for the games and festivities throughout the stadium.


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There are many free activities to take advantage of in Chicago, during every season of the year. Many of our Top Ten are also free to explore, but below you will find a couple of other free options this month.



Check out our comprehensive post about the Top Free Things to Do in Chicago.

Polish Constitution Day Parade

May 4, 2019

Participate in the large Polish Parade outside of Poland. This parade celebrates the ratification of the Polish Constitution in 1791, the first democratic constitution in Europe.

This has been a Chicago tradition for over 120 years, and it draws in thousands of spectators.

Find out more about the Parade on their website.

Go to the Zoo

The Lincoln Park Zoo is one of the oldest zoos in the country, and one of the last few free zoos. Home to over 1,000 animals, this is a great stop during your time in the city.

While you are in the area, you can also explore the Lincoln Park Conservatory and the park itself.

Welcome Summer at the Outdoor Parks and Gardens

With the warmer weather, it is the perfect time to explore the Chicago Riverwalk.

This beautiful stretch will bring you below the busy streets and right along the river’s edge, lined with restaurants, art, and fountains.

Learn more about the river and the riverwalk itself on our Riverwalk and History Tour.

You can also stroll through Millennium Park. Starting in early May, the Crown Fountain is turned off for the warmer season and season tours start at Lurie Gardens. Tours highlight elements of the garden’s design and its plant life.

Memorial Day Parade

May 27, 2019

The Memorial Day festivities include a wreath-laying ceremony at the Eternal Flame found in Daley Plaza, followed by the parade that stretches along State Street, just a block over.

The parade features veterans, active military duty, and marching bands.

Learn more about Daley Plaza and the Eternal Flame on our Loop and Millennium Park Tour

Be sure to read about all the things to do in Chicago over Memorial Day Weekend.

Check out the Chicago Cultural Center

This beautiful and historic building is free and open for the public to explore. Beyond the art that lines the walls, you will find free traveling films, lectures, and performances here.

Check out their calendar of events to see what is going on during your visit.

Go to the Game Room at the Chicago Athletic Association

Inside the historic Chicago Athletic Association building you will find much more than a luxury hotel.

On the second floor, there is a Game Room with shuffleboard, pool tables, foosball, and bocce. All free to use, find the game master to make a reservation while you enjoy something to sip on.


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Some of the items mentioned in other sections are great activities for children but you might want to check out our post on family-friendly activities in Chicago for a more complete guide.



Below you will find a couple of other options to keep your children entertained this month! 

American Girl Live

The popular American Girl Dolls have their own musical in this touring production.

The musical celebrates girl power and friendship while the girls work together to get through an overnight camping trip. 

Dates: April 30 – May 12, 2019

Go to a Park

Chicago is full of green grass and playgrounds for kids to get out their energy.

One of the best parks is nestled in-between downtown and Lake Michigan, Maggie Daley Park. As one of our newest parks, it is also one of the best, with lots of different playgrounds for kids of all ages, a rock climbing wall, mini-golf, and tennis courts.

Read all about exploring the outdoors of Chicago on our blog post.

Go to a Museum

Museums are great options for families. Chicago has a lot of museums that are very interactive and great for children, such as The Field Museum, Museum of Science and Industry, and the Children’s Museum, just to name a few.

With Memorial Day at the end of the month, this is the perfect time to learn about American military history at the Pritzker Military Museum.

Though the Museum is only $5 admission, it is free on Memorial Day and the Saturday before Memorial Day.

Explore the Farmers Market

Now that the weather is warming up, farmers markets will begin to pop up across the city!

Check out the City Market in Daley Plaza which is open on Thursdays starting May 10, 2019.

Bike the Drive

May 26, 2019

Did you know that Chicago was recently voted the #1 bicycling city in America?

On May 26, 2019, you’ll find one of the best drives in the city – Lakeshore Drive – closed to traffic for over 30 miles of car-free riding.

This is a unique chance to welcome summer and bike with the lanes to yourself (and many other cyclists)

There is a fee to register (from $40-90) but the proceeds go to a great cause.

The event benefits Active Transportation Alliance which is a non-profit, member-based advocacy organization that works to make bicycling, walking and public transit safe, convenient and fun.

Chicago Kids and Kites Festival

May 4, 2019

The Kids and Kite Festival is a favorite family tradition in the Windy City, as we welcome spring weather and allow kids to run around outside with free paper kites that they can build and decorate.



There are other activities for the family to enjoy, such as face painting, balloon artists, arts and crafts, all in the beautiful Lincoln Park.