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What to Do in Chicago in June (2021)

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This post covers the best things to do in Chicago this June, including a top 10 list as well as family-friendly, nighttime activities, and free things to do, all updated for 2021.

Let's dive in!


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.

Keep in mind that these concerts can still be postponed or canceled because of the pandemic, but they are still currently scheduled to take place in June of 2021.

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.

NOTE: The MLB currently has plans to allow a limited amount of fans back into the parks in 2021, but this could change depending on Covid-19 numbers.

The Chicago Fire and the Chicago Sky may take a different approach based on the pandemic, so we recommend checking before you buy any tickets.

3. Go to the Theatre

Chicago is home to many regional theatres, small black box spaces, and Broadway Tour houses. 

With that being said, there aren't as many shows happening this June because of the pandemic.

The main event this month will be a stage adaptation of Steel Magnolias, which will be playing at Drury Lane Theatre from June 18th - August 8th.

Chicago Travel Tips and Hacks

You may also have a chance to catch Singin' in the Rain at Lyric Opera of Chicago from June 4th - 27th.

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!  

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. Experience the Chicago Symphony Orchestra

There are a lot of concerts taking place in Chicago this month, but most of the performers are either pop, rock & roll, or country musicians.

If you prefer classical music, the Chicago Symphony Orchestra will have a few performances to enjoy from June 10th - 13th.

Although these shows are still scheduled to take place, it's worth noting that any change in government policy could result in the cancellation or postponing of all these concerts.

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.

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. Go to the Supernatural Convention

Fans of the hit television show Supernatural might be disappointed that it has finally come to an end, but at least they're still doing conventions!

The official Supernatural Convention is planned for June 4th - 6th at the Donald E. Stephens Convention Center.

Fans will be able to meet and get autographs from their favorite actors and artists during this convention.

There will be a lot of actors and other people attached to the show coming to this event, including none other than Jensen Ackles and Jared Padalecki.

8. Attend a Neighborhood Festival

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

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

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

Andersonville Midsommarfest in Andersonville.  There will be vendors, food, and music!

Craft Beer Fest at Morton Arboretum on June 21st.  Enjoy a craft beer surrounded by nature!

NOTE: While some of these events are scheduled to take place in 2021, the majority of the festivals listed have yet to announce their plans for this year.

Before you head out to any of these festivals, make sure to check and see if they are still taking place.

9. Celebrate Pride Fest

The Pride Festival and Parade is a huge party that celebrates the Chicago LGBTQ+ community this month, 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.

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

NOTE: Dates have not been announced for 2021 yet, but both events are still scheduled to take place.

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 11th-13th, 2021.

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

NOTE: This is still scheduled to take place in 2021.


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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.

Cinepocalypse Film Festival

Head to the Music Box for Cinepocalypse  to enjoy dynamic features, guests, and shorts! 

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

NOTE: This event was postponed in 2020 due to the pandemic, and they have yet to announce its return in 2021.

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.

NOTE: There is no information yet about whether or not this will return in 2021, but if the pandemic is under control by then, it might make a comeback.

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.

NOTE: This attraction may or may not be open to the public in June. Check their website to determine whether or not they are open and at what capacity.

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.

NOTE: This activity may not be available due to the pandemic, but as of yet, there have been no cancellations announced for June.


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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. 

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.

NOTE: This company has switched over to doing live streams of their performances to prevent the spread of Covid-19.

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.

NOTE: This event has been canceled due to Covid-19, and it probably won't return until things are looking better.

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. 

NOTE: The Lincoln Park Zoo is once again open as of March 5th, 2021.

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.

NOTE: This activity could be canceled or postponed depending on the pandemic numbers.


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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 12th-13th, 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.

NOTE: Some museums might be closed or only offering limited access to prevent the spread of Covid-19.

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

NOTE: This event will be streamed and broadcast on television to help prevent the spread of Covid-19.

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!

NOTE: There have been no plans to cancel this event in 2021.

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

NOTE: Depending on what phase of recovery the city is undergoing in June, these markets may or may not be open.

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. 

NOTE: This attraction might be closed or offer limited capacity due to the pandemic, but we're all hoping this won't be a problem in June.


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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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