What to Do in Chicago in June (2020)

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 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.


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. 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 the major June concerts here.


2. Go to a Sporting Event

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



For a list of all sporting events happening this month, check StubHub.

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

3. Go to 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 June calendar.



Here are just a few of the many shows happening this month.

To see a full calendar of all shows and get a real taste of Chicago theatre, check out Chicago’s 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.

4. Go on a Sightseeing Tour

Grab your sunscreen and water bottle and join a sightseeing tour!  We offer pay-what-you-like walking tours 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.

5. 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.

6. 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.


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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.

7. 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.

It takes place from June 6 – 7, 2020. It is located at Historic Printer’s Row downtown near Congress and Dearborn.



Plus, there is an entire Children’s Literature area that will be a blast for the kiddos. You can find more family-friendly activities in the section below.

Much of it is free though some parts of the festival are ticketed. Find other free events below.

8. Attend a Neighborhood Festival

Once the weather starts to warm up, Chicagoans love to celebrate!  There are many festivals in June. Below we list the best ones. 



Greek Fest in Lincoln Park is June 5-7. There will be lots of food vendors to enjoy!

West Loop Fizz Fest in the West Loop on June 6-7. Expect hard seltzer tastings and family-friendly activities.

Andersonville Midsommarfest in Andersonville June 12 -14.  There will be vendors, food, and music!

Craft Beer Fest at Morton Arboretum on June 20.  Enjoy a craft beer surrounded by nature!

9. Celebrate Pride Fest

The Pride Festival and Parade is a huge party that celebrates the Chicago LGBTQ+ community on the weekend of June 20 – 21, 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 Pride Parade will be the following weekend on June 28, 2020.

These events are free to attend. For more free things to do, check out the section below.

10. Eat Up at RibFest

Ribs and rock’n’roll?  Yes, please!  There will be food, drink, and music at RibFest



The Fest dates are from June 12-14, 2020.

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


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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!


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

Take a Night Tour

For a lovely view, stroll along our  Twilight Chicago Riverwalk & History Tour which ends a 10-minute walk from Navy Pier. 

Looking to see a different side of Chicago? Take a walk with some spooky history on our evening Ghost TourYou can expect to laugh more than you scream as you learn about past hauntings. 

You will also learn some of the dark histories of The White City.

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

Star Wars at 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 Star Wars: Return of the Jedi with the symphony playing the score live in-theatre on June 24-June 27, 2020. 

Cinepocalypse Film Festival

Head to the Music Box for Cinepocalypse on June 4-7, 2020 to enjoy dynamic features, guests, and shorts! 

The Music Box is an excellent backdrop for this well-known horror film fest.

Craft Brews at the Zoo

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 19-20, 2020, from  6:00 pm – 10:00 pm for an adults-only night out.

Art on the Mart

Head the Riverwalk at sunset to see an amazing art projection called Art on the Mart on the Merchandise Mart Building (a building so large, it has its own zip code!)

Fireworks at Navy Pier

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.

See an Improv Or Comedy Show

Chicago is well known for comedy and improv. Just ask Tina Fey, Amy Poehler, or Steve Carell. Here are some performers in town this month:

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.

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:

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, 2020.

Check their website for more information.

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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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. 

Poke’mon Go Tour 

In celebration of Poke’mon Go Fest Chicago 2020, (dates TBA), we present a fully interactive, AR/RL tour of Chicago – Pokemon Go Chicago Walking Tour.

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.

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

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.

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!  

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 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 in our blog post.

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. 

Maxwell Street Market

A fun street fair to enjoy is the Maxwell Street Market on Sunday mornings between 7:00 am – 3:00 pm which has been a Chicago tradition for over 100 years. 

Take in the bargains and culture at this year-round market. The market has free admission. For more details, see 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.

Attend the Old Town Art Fair

Voted America’s #1 Art Fair for the fourth year in a row!  You’ll walk along tree-lined streets of Chicago’s historic Old Town Triangle District.

Experience 250 nationally acclaimed artists, a Garden Walk, Music, activities for children, food and drinks.  

The fair is June 8 – 9, 2020, from 10:00 am – 6:00 pm. Click here for more information about the event.

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

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.

Visit a Free Museum

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.

Chicago Summerdance

Head downtown to the Spirit of Music Garden in Grant Park, starting on June 25, 2020. 

There are 48 different live bands + DJs will perform throughout the summer Wednesdays – Sundays until August 22.  Feeling a little insecure about your dancing skills? Brush up with dance lessons beforehand!  

Events located at Grant Park Spirit of Music Garden. Click here for more information

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!

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.

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

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 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. 


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