What to do in Chicago in June (2019)

This post covers the best things to do in Chicago this June, including a top 10 list as well as a family-friendly, nighttime activities, and free things to do, all updated for 2019.


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If you’re looking for the best things to do in June, take a look at our suggestions for the best activities here, which include sports, theatre, and festivals.

And for ideas on some of Chicago’s most popular tourist activities, check out the following post:

Some of the things we’ve listed here are included in one of the available tourist attraction discount passes.

(1) Poke’mon Go Tour 

In celebration of Poke’mon Go Fest Chicago 2019 (June 13 – 16) we present a fully interactive, AR/RL tour of ChicagoPokemon Go Chicago Walking Tour

You must have a reservation, so be sure to snag your spot!




Have you ever wanted to know a bit more about all those Poke’ Stops you’re spinning and Gyms you’re battling?

Sure, there is a picture and sometimes a blurb of info but they can only fit so much on those little discs.

A huge part of this game is exploring the world around you while playing. It’s what makes this game truly different from all the other games on your phone.

(2) Go to a Concert

There are quite a few big-name acts coming through Chicago in June. We’ve listed the highlights below, but you can find all major June concerts here.



The teens in your group will love acts like Ariana Grande! To see some more family-friendly activities, check the section below.

(3) Go to a Sporting Event

Soccer and baseball are both in full swing, and hockey is in the last few weeks of the Stanley Cup Tournament.

June is the perfect time to indulge in your competitive side with local teams.



Seeing a big game is a great way to spend your afternoon or evening! For more things to do at night, check the section down below.

(4) Attend the Theatre

From family-friendly superheroes to more adult subjects, Chicago has several opportunities to add a theatre show to an evening of your visit.

We have more nighttime activities listed below.

PJ Masks Live

PJ Masks Live is a fun, family-friendly stage show based on the cartoon show. With fun music and acrobatics, kids aged 2+  will enjoy watching Catboy, Owlette, and Gekko save the day.

Dates: June 7 – 9, 2019




Falsettos is a play that takes a look at the AIDS crisis through the eyes of a man bringing his new partner into his and his son’s life. Suggested for ages 13+.

Dates: May 28 – June 29, 2019

See what else is playing in town.

(5) Printer’s Row Lit Festival 

This is the largest outdoor Literature Festival in the Mid-West! There are loads of books, authors, signings, and events.



Much of it is free though some parts of the festival are ticketed. Plus, there is an entire Children’s Literature area that will be a blast for the kiddos.

It is located at Historic Printer’s Row downtown near Congress and Dearborn. And you can find more family-friendly activities in the section below.

It takes place from June 8 – 9, 2019.

(6) Chicago Blues Music Festival

This is a fun opportunity to really sink into the Chicago Blues scene. Enjoy artists like Buddy Guy, Zora Young, and Willie Dixon and Muddy Waters for free.



This year the Chicago Blues Festival will have delicious food trucks nearby! It takes place from June 7 – 9 from 11:00 am – 9:30 pm daily.  

For more nighttime events, check out the things to do at night section below.

(7) Eat Up at RibFest

Vegetarians might want to avoid this event since it will be filled with seasoned and barbequed ribs! There will be food, drink, and music at RibFest.



It was featured on the Food Network in 2014 with Eating America Anthony Anderson. 

The Fest dates are from June 14 – 16, 2019. 

(8) See the Old Town Art Fair

The Old Town Art Fair has been going for over 70 years.  This lovely historic neighborhood is a delightful backdrop to peruse the work of 250 chosen artists. 



Want an excellent Chicago souvenir? Buy local art! 

The fair is June 8 – 9 from 10:00 am – 6:00 pm.

(9) Celebrate Pride Fest

The Pride Festival and Parade is a huge party that celebrates the Chicago LGBTQ+ community on the weekend of June 22 – 23, since all of June is Pride Month.



There will be music, plenty of food and drink, and karaoke and contests in Boystown off of Halsted. The parade will be the following weekend on June 30, 2019. These events are free to attend.

For more free things to do, check out this section below.

(10) See More 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 family-friendly activities and attractions. 

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


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Many of our top ten activities are perfect for the evening hours, but below are some other suggestions to fill in your evenings during the month of June, including night tours, the symphony, and craft brew events. 



Read our post about the Top Ten Things to Do in Chicago at Night for more ideas. 

Take a Night Tour

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

Expect to laugh more than you scream as you learn about past hauntings and the (sometimes funny) reasons behind local ghost stories.

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

Craft Brews at the Zoo

The Lincoln Park Zoo is known for always having fun, interactive events and concerts for all ages.

Lincoln Park Zoo and Lou Dog Events are hosting their annual Craft Brews beer festival at Lincoln Park Zoo!

Savor a selection of 120+ specialty beers from local and regional breweries.

This event is on June 14 – 15 from  6:00 pm – 10:00 pm for an adults-only night out.

See the Local Music Scene

As you might guess after grooving at the Chicago Blues Festthere are plenty of local musical experiences at night. 


This photo of House of Blues Chicago is courtesy of TripAdvisor


If you’re looking for even more opportunities to check out the local music scene, take a look at some of the more popular venues: 

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 Packman or try a classic board game, Chicago has a bar for you.

Check out our favorite game bars across the city

Enjoy the Symphony

The Chicago Symphony has multiple concerts in June this year. From listening to An American in Paris to some more sophisticated composers, there will probably be something for everyone.



The most exciting for many, including families, might be the showing of Harry Potter and the Prisoner of Azkaban with the symphony playing the score live in-theatre on June 27. 

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 skee-ball, and catch some games on the TVs at this beloved sports bar.


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



Check out our post about Family Friendly Activities in Chicago for a more complete guide. 

See a Child-Friendly Show

PJ Masks Live is a fun, family-friendly stage show based on the cartoon show. With fun music and acrobatics, kids aged 2+  will enjoy watching Catboy, Owlette, and Gekko save the day.

Dates: June 7 – 9, 2019

Go to a Baseball Game

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

The Cubs play north of downtown at Wrigley Field, and the White Sox play south of the skyscrapers at the Guaranteed Rate Field. Tour both stadiums, or just enjoy the fresh air while cheering on our Chicago teams!

Find Your Tickets Here:

Visit 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.


This photo of Maggie Daley Park is courtesy of TripAdvisor


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. 

Go to a Museum

Museums are a great option for families. Chicago has a lot of museums that are very interactive and great for children, such as:

Explore the Farmers Market

Now that the weather is warming up, farmers markets will begin to pop up across the city! From produce to homemade crafts and baked goods, you will definitely find something interesting or delicious.


This photo of Near North Chicago Farmer’s Market is courtesy of TripAdvisor


Markets are open almost every day of the week on Tuesdays, Wednesdays, Thursdays, Saturdays, and Sundays. 

Find a list of the city’s markets and their schedules here


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There are many free activities to take advantage of in Chicago including walking tours, the zoo, and other attractions.



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

Go on a Summertime Walking Tour

The weather is perfect to see some of the most famous Chicago sights on a pay-what-you-wish walking tour with us!

The North Loop and Millennium Park Tour will take you to the famous bean art installation, Marshall Fields, and more. 

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. 

Stroll the Riverwalk

With the warmer weather, it is the perfect time to explore the 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

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.


This photo of Chicago Cultural Center Visitor Information Center is courtesy of TripAdvisor


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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