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 2022.
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 this month. We’ve listed the highlights below, but you can find all the major June concerts here.
- New Kids On The Block
- Rick Astley
- En Vogue
- Nothing More
- Erica Banks
- Young Ca$h
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.
- Baseball | White Sox and Cubs (March - September)
- Soccer | Fire (March – October)
- Women’s Basketball| The Chicago Sky (May - October)
If the Chicago Bulls make it to the finals, they will have a few important home games to play in June. 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.
- Six: The Musical | Jun 1st - 30th
- The Sound of Music | Jun 1st - 5th
- Ain't Too Proud | Jun 1st - 5th
- Don Quixote (Joffrey Ballet) | Jun 2nd - 12th
- Disney's Winnie the Pooh | Jun 2nd - 11th
- Riverdance | Jun 3rd, 4th
- Steel Magnolias | Jun 10th - 23rd
- Blippi: The Musical | Jun 11th
- Life After | Jun 11th - 30th
- My Fair Lady | Jun 28th - 30th
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 several performances to enjoy from June 2nd - 30th.
There will be quite a few opportunities to hear some of the best classical music in history, including the works of Tchaikovsky and Beethoven.
One of the more interesting events will be Star Wars: Return of the Jedi in Concert on June 30th. Fans of the franchise shouldn't miss this chance to see one of the best sci-fi films of all time with a live musical performance from the CSO!
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.
- Shedd Aquarium
- Skydeck Chicago
- Adler Planetarium
- Art Institute of Chicago
- The Field Museum
- Museum of Science and Industry
- 360 Chicago Observation Deck
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 3rd - 5th 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 from June 3rd - 5th, 2022. There will be lots of food vendors to enjoy!
Midsommarfest takes place in Andersonville from June 10th - 12th, 2022. There will be vendors, food, and music!
Maifest will be happening at Lincoln Square from June 2nd - 5th, 2022. You can expect a lot of great live music, entertainment, and more.
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. This event takes place on June 18th - 19th, 2022.
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 26th.
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. Thankfully, 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:
- Dan Cummins | Jun 11th
- Paula Poundstone | Jun 11th
- Wanda Sykes | Jun 17th
- Mark Normand | Jun 17th
- Ari Shaffir | Jun 18th
For even more opportunities to giggle, check this list of stand-up comedy in Chicago during the month of June.
RESCHEDULED: Eat Up at RibFest
Ribs and rock’n’roll? Yes, please! There will be food, drink, and music at RibFest.
The Fest dates have been rescheduled this year and are now taking place from August 19th - 21st, 2022.
It was featured on the Food Network in 2014 with Eating America Anthony Anderson.
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.
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 2022.
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!)
The spring program will run twice nightly at 8:30 pm and 9 pm until June 29th, 2022.
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 2022, but there are indications that they still have plans to bring it back this year.
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.
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.
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 11th - 12th, 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.