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Things to Do in Chicago in May (2020)

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This post covers the best things to do in Chicago this May, including, free, family-friendly, as well as nighttime activities, all updated for 2020. 

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Disclosure: While our recommendations are always unbiased, we may receive a small share of sales through some of the links below at no cost to you. See the full text.


Chicago is in full bloom in May!  It is a great time to visit as summer is just around the corner.  

Check out the suggestions below for a variety of activities, including sports, theatre, music, and lots of indoor activities to stay warm !

For some of the more popular things to do in Chicago, read the following posts:

(1) Go to a Game

Chicago is a big sports town no matter what season!  If you are visiting and want to feel like a local- be sure to catch a game. 

In May, be sure to catch a ball game at Wrigley Field or U.S. Cellular Field (Comiskey Park if any locals are reading this).

Click here for a list of all sporting events happening this month.



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

(2) Catch a Concert

If you love music, then Chicago is a great town for you.  There are many intimate music venues in Chicago to explore throughout the city or giant concert venues!

Here are just a few of the larger-scale concerts happening in May of 2020.



Here are just a few of the larger-scale concerts happening in May of 2020:

(3) Take a Sightseeing Tour

Take advantage of the lovely weather on a pay-what-you-like walking tour in the Windy City.  We have a variety of tour options for all types of travelers!


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If you’d prefer a bus tour, we have a great comparison of Chicago’s best. From hop-on-hop-off buses to dedicated tours, you’ll find one to suit you here.

(4) Enjoy the Theatre

Chicago is home to many many regional theatres, small black box spaces, and Broadway Tour houses. There is something for everyone!  

To see a full calendar of all shows or to buy tickets for shows, see Stubhub's listings here

Here are just a few of the many shows happening in May 2020.



To see a full calendar of all shows and get a real taste of Chicago theatre, check out the not-for-profit League of Chicago Theatres.

Check out our self-guided theatre tour to admire the exterior of some of the oldest movie palaces in the downtown Loop.

(5) See the Gospel Music Festival

On May 26-30, 2020, come to the largest free and outdoor gospel music festival right here in the Windy City! 



This event is located in Chicago’s beloved Millennium Park surrounded by sculptures, architecture, and the Lurie Gardens.  

This annual music festival will have a variety of artists performing. For more information or to check out the musicians, click here.

(6) See More for Less with a Chicago City Pass

Many of Chicago’s biggest attractions have entry fees. While you do pay for a tourist discount pass, it can give you a bulk discount and free admission into some interesting tours and museums, saving you up to 55%.

They can also save you time with skip-the-ticket-line privileges. Each Chicago tourist discount pass includes a variety of fun activities and attractions.


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Here are a few examples of what you can visit with a tourist pass, for a discount or for free.

For more details, make sure to read our full post covering Chicago tourist passes.

(7) Watch the Polish Constitution Day Parade

May 2, 2020, is the Polish Constitution Day Parade! Since Chicago has the largest population of Polish outside of Poland- it makes perfect sense.

This parade celebrates the ratification of the Polish Constitution in 1791, the first democratic constitution in Europe.



For well over a century, this parade is a Chicago staple. This is a free event that is family-friendly.

Plus, for the movie-lovers, this is meant to be the parade that Ferris Bueller famously sings Danke Schoen on a float. 

(8) Go to a Neighborhood Festival

Once the weather starts to warm up, Chicagoans love to celebrate!  There are many festivals in May.  Here are two we think are among the best.

The annual Mole de Mayo is on May 22-24, 2020. Head to historic Pilsen to see live Lucha Libre wrestling! 

There will also be music, dancing, and plenty of tasty food vendors!



MayFest is on May 29-31, 2020. This annual festival offers music, entertainment, and lots of food to chomp on.

Bark in the Park is on May 9, 2020 (CANCELLED), near Soldier Field. Bring your dog to this one for dog massages, pawdicure spas, caricature drawings, live music and more.  All proceeds go to The Anti-Cruelty Society.

(9) Celebrate Cinco de Mayo

There are many ways to celebrate May 5 in Chicago!  Head to Little Village for the Cinco De Mayo Parade at 12 pm on May 5 with the family!

If you are looking to really let loose, join a Cinco de Mayo themed Cantina Crawl.



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

Looking to try something new? Attend a beginner salsa dance class for singles or couples over 21 years old at Duet Dance Studios.

(10) Belmont-Sheffield Music Fest

Local bands, food, and street vendors line Sheffield Avenue at this Memorial Day weekend festival. In 2020, the dates are May 22-24.



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

For more suggestions of activities and events in Chicago all year, see our post on things to do in Chicago.


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Many of our top ten activities are perfect for the evening hours, such as seeing a sporting event, going to the theater, or attending a concert.

Below are some more ideas. 



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

Joffery Ballet’s Don Quixote 

Take the family to see their first ballet in Chicago! Joffery Ballet will be performing the classic Don Quixote from April 22-May 3, 2020.

It is a story of passion, bravery, and windmills.  There will definitely be windmills. Get tickets here from StubHub.

Navy Pier Fireworks

Navy Pier is the place to be in Chicago if you love fireworks!  The summer firework season kicks off in Chicago on May 23 and runs to September 5.

The shows happen twice a week on Wednesdays at 9:30 pm and Saturdays at 10:15 pm.

If you really want to make a night of it, book tickets for one of the many boats that offer fireworks cruises.  Click here for more details.

Take a Night Tour

Looking to see a different side of Chicago? Take a walk with some spooky history on our evening Ghost Tour.  

You can expect to laugh more than you scream as you learn about past hauntings.  You will also learn some of the dark history of the White City.

For a lovely view, stroll along our  Twilight Chicago Riverwalk & History Tour which ends a 10-minute walk from Navy Pier.  The Pier has fireworks every Wednesday and Saturday night in July.

Also, several bus tours operate night versions of their day tours.

See a Comedy or Improv Show

Chicago is well known for comedy and improv. Just ask Tina Fey, Amy Poehler, or Steve Carell.

For stand-up comedy, here are a few options in May 2020:

Here are some venues to catch an evening show.  

You may be seeing seasoned Chicago improvisers or you might catch a group of students, but who knows? One of them could be the next Chris Farley.

Have a Magical Night!

Chicago offers a couple of different places for people who want to partake in some prestidigitation.  If you are looking to be amazed by some of the greatest magicians make sure to check out these places:

Go Out for a Cocktail

Chicago is known for locally brewed craft beers and a unique liquor called Malort.  

Another fun option is to check out one of our famous speakeasies – fitting for the mobster history of the Windy City. The Office is a unique cocktail experience that is indulgent with completely personalized beverages.

Mixing music with cocktails is always fun!  Check out Kingston Mines to enjoy the blues or Davenport’s Piano bar for a unique experience.

Improvised Shakespeare

Looking for a hilarious night with the words of the bard?  Check out Chicago’s very own Improvised Shakespeare group. 

They play most Thursdays at 8 pm, Fridays at 8 pm & 10:30 pm and  Saturdays at 8 pm & 10:30 pm.  

Be sure to check out our post on top things to do in Chicago at night for even more suggestions.


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Chicago offers many free activities throughout the year.  Some of the events mentioned above are free too! Here are a few suggestions during May 2020.



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

Check Out the Chicago Cultural Center

This beautiful and historic building is free and open for the public to explore.  (See the video above).

Beyond the art that lines the walls, you will find free traveling films, lectures, and performances here. This is also a great place for children’s programming. They offer their own free tours every Wednesday – Saturday at 1:15 pm

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

Bach Week 2020

Attend Bach concerts throughout Chicago and Evanston in May. Some have paid tickets but others are free! 

On May 30, to catch “Steeped in Bach”- music from the Zimmerman Coffeehouse at the All Saints Episcopal Church in Ravenswood.

German Maifest

The German American Cultural Center is hosting a Maifest celebration with Dank Haus on May 17, 2020!  

It will be on the 6th floor of the Skyline Lounge.  Willkommen spring with a beverage and a view!

It is free admission and will have food and beverages for purchase. For more event details, click here.

Chicago House Music Conference and Festival

House music was born in Chicago! What better way to celebrate this revolutionary genre of music than to check out the annual Chicago House Music Conference and Festival on May 21- 23, 2020.

It will feature DJs and live performances showcasing the various sounds and styles of house music.

Admission is free and it will take place at the Chicago Cultural Center, Millennium Park and other venues around Chicago.

Click here for more details about the event.

Attend the Memorial Day Parade

The Chicago Memorial Day Parade on May 23, 2020, is a great free thing to do in May with the family.  

Head downtown to State Street near Wacker to catch the parade that starts at 12pm. The parade features veterans, active military duty, and marching bands.

There will also be a wreath-laying ceremony in Daley Plaza at 11 am to honor U.S. veterans.

Check out our post on things to do on Memorial Day Weekend.

Music on the Lake

Starting in May, Navy Pier hosts free Music on the Lake.  There will be a variety of artists that you can enjoy with an incredible view of the skyline.

Be sure to explore Navy Pier while visiting!

Visit a Free or Donation Museum

There are many wonderful museums in the Windy City that are actually free!  

The Jane Addams Hull House is an incredible museum that is located in one of the original Hull House homes. 

The National Museum of Mexican Art is a donation-based museum for art lovers.

Another option is to go into the bottom of the Watertower for a small but mighty free art museum! 

If you are joining us on our Pay-What-You-Like Magnificent Mile walking tour, you will enter this museum with your tour guide.

Under the Picasso

Daley Plaza offers free programming throughout the year Under the Picasso!  There is music, festivals, markets, and interactive events.  Check their calendar for updates.  

Daley Plaza and the Picasso are also sites to see on our Loop & Millennium Park Tour.

Maxwell Street Market

Enjoy the international flare at the Maxwell Street Market on Sunday mornings between 7:00 am – 3:00 pm. Admission is always free.

The market has been a Chicago tradition for over 100 years.  Take in the bargains and culture at this year-round market.

Art on the Mart

Head the Riverwalk at sunset to see an amazing art projection called Art on the Mart.

It is projected onto the side of the Merchandise Mart Building (a building so large, it has its own zip code!) 

The Bridgeport Art Center

Located in the Bridgeport building which is a creative home for local artists and designers, there is an outdoor sculpture garden and three curated art galleries.  

On the 3rd Friday of each month between 7-10 pm, people are invited to see the painters, sculptors, photographers work.

Go to the Lincoln Park Zoo and Conservatory

The Lincoln Park Zoo and Conservatory are both free and open 365 days out of the year!

Head up to this beautiful park to visit some of the animals, especially the polar bears!

If it starts to get a little chilly you can stop into the Conservatory to warm up and see the beautiful plant life there.

For even more free activities, see our post on the top free things to do in Chicago or check out the city's free event page. 


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Throughout this post, we have listed several activities that are great options for the whole family.  

Below you will find several great options to keep your children entertained this month, including parks, museums, and theater!



Be sure to check out our post about family-friendly activities in Chicago for a more complete guide.

Chicago Kids and Kites Festival

The Kids and Kite Festival is a favorite family tradition in the Windy City on May 2, 2020. (see the video above).

Kids can build and decorate free paper kites. There are other activities for the family to enjoy, such as face painting, balloon artists, arts and crafts, all in the beautiful Lincoln Park.

Bike the Drive

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

For Bike the Drive, 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 non-profit Active Transportation Alliance.

See 42nd Street The Musical

Head to the Lyric Opera to see the fun-filled old classic 42nd Street. This play is filled with song and dance that will have the whole family tapping their feet. 

The show runs from May 29-June 21. Check their site for more information.

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 in May.

Juice Box Concerts at the Cultural Center

Head to the Cultural Center with your family of little ones every first and third Friday and Saturdays at 11:00 am-11:45 am for an engaging musical event. Concerts are free!

While this will be enjoyable for the whole family, it is geared to kids between the ages of 1-6. See their website for more.

Go to a Family-Friendly Improv Show

ComedySportz is known for being family-friendly!  It is a game inspired improv show similar to Who’s Line is it Anyway? 

If anyone on the team uses a curse word- they actually lose points! This means that this show is really made for all ages.

See our post on family-friendly activities in Chicago for more ideas.


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About The Author


Mel loves to be a tourist in her own city. With a background in performing arts, tourism, and photography, giving tours and being a story-teller comes naturally to her. She loves traveling, food, and theatre. Mel splits her time between Chicago and Los Angeles (#theatrelife) and leads tours and manages both cities!
Updated: October 12th, 2021
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