Company Logo - Home Link

What to Do in Chicago in June

Updated: May 17, 2023
 By Mel

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 2023.

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.

And be sure to check out our post on the weather in June in Chicago.

1. Attend a Concert

There are quite a few big-name acts coming through Chicago this month.

We’ve listed the highlights below, but you can find all the major June concerts here.



re:SET | June 23rd-25th

  • LDC Soundsystem
  • Boygenius
  • Steve Lacy
  • James Blake
  • Toto y Moi
  • and more!

Heatwave Music Festival | June 10th-11th

  • Griz
  • Gryffin
  • Kx5
  • Slander
  • Loud Luxury
  • and more!

For even more opportunities to enjoy live music this month, check this list of concerts in Chicago during June.

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.




  • Sky
  • Bulls | if they make it to the NBA Finals

Make sure to order your tickets ahead of time if you don't want to miss out!

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 regional theatres, small black box spaces, and Broadway Tour houses. 

As such, there will be plenty of great theatrical performances to see throughout the month of June.

Plays and Musicals

Performance Art

Kids Shows

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 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 several performances to enjoy from June 1st - 29th.

There will be quite a few opportunities to hear some of the best classical music by some of the best-known composers.

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. Attend the Chicago Blues Festival

The annual Chicago Blues Festival is one of the largest blues festivals in the world and attracts huge crowds.

It takes place in Grant Park, across multiple stages, and is *free* to attend!

Some of the most famous names in blues music have performed here, including BB King, Howlin' Wokd, and Muddy Waters.

The date for 2023 hasn't been announced yet, but it normally takes place in the month of June. They should be updating their website with dates before the festival.

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 from June 9th-11th, 2023.

Midsommarfest takes place in Andersonville from June 9th-11th, 2023.

Maifest will be happening at Lincoln Square. The 2023 dates haven't been released yet.

At each, you can expect food, some traditional, drinks, live music, entertainment, and more.

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.

Events take place on June 17th-18th, 2023.

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 June 25th.

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

10. See a Stand-up Comedy Performance

If you're in need of a good laugh, you might want to consider going to see some stand-up comedy.

There will be several great comics performing in and around Chicago in June.

Here are a few of the best comedy shows to see this month:

For even more opportunities to giggle, check this list of a stand-up comedy shows in Chicago during the month of June.

Eat Up at RibFest Chicago

Ribs and rock’n’roll?  Yes, please! 

Each year in June there's a 3-day festival with food, drink, and music, all of it found at RibFest Chicago. 

Think 50,000 lbs of pork and 60,000 attendees, and you'll understand how much this festival is loved.

The Fest dates haven't been listed yet in 2023, but they are expected to be announced soon.

Check out the RibFest Chicago website for information.

Fill up at the Chicago Food Truck Festival

What happens when you gather dozens of food trucks from around Chicago together in one place?

You get the chance to try some amazing culinary creations from some very talented chefs.

General admission is free, but there is a cost for VIP tickets. Tickets can be purchased online.

Head to the South Loop June 24th-25th, 2023. Visit the website for more information.


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!

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 Tour

You 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.

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: The official schedule for this event has yet to be provided for 2023 but they say they are posting the schedule soon.

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.


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.

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. 

Visit Maxwell Street Market

A fun street fair to enjoy is the Maxwell Street Market on Sunday mornings between 7:00 am – 3:00 pm

This 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.


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 the 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 10th-11th, 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.

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. 


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: May 17th, 2023
Back to Top