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What to do in Chicago in August

Updated: March 8, 2024
 By Mel

This post covers the best things to do in Chicago this August.

We include free events, family-friendly activities, and things to do at night, updated for 2023.


Chicago is a wonderful city to visit during the summer months - especially in August!

Check out the suggestions below for a variety of activities, including sports, theatre, music, and of course, summer festivals.

For some of the more popular things to do in Chicago, read the following posts:

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

1. Go to a Sporting Event

August is filled with several options if you are a sports lover.  

Seeing a big game is a great way to spend an evening. For more things to do at night, check the section on nighttime activities below.




For other games, check out the full list of sports taking place in August in Chicago.

Fun fact: Chicago’s soccer team is named after the Great Chicago Fire of 1871.  You can learn about the great fire on our Birth of the Skyscraper-Architecture Tour!

2. Go to a Concert

Chicago is a great city to enjoy music and see a concert. There are many venues from giant spaces to intimate bars.

Below are some of the big names in town in August.

Concerts in Chicago

Concerts Further Afield

Music Festivals

  • Lollapalooza | August 3rd-6th | Grant Park | Featuring: Kendrick Lamar, Billie Elish, Red Hot Chili Peppers, and more

Click here for additional performances in the Chicago area in August.

3. Go on a Sightseeing Tour

Fill up your water bottle, get your sunscreen, and explore the city on a guided walking tour!

We offer pay-what-you-like walking tours multiple times each week.

If you’d prefer to enjoy 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.  

Some buses will be open-air and some may be air-conditioned to beat the heat!

To go for something more adventurous in the August heat, try a kayaking tour that goes on the famed Chicago River or an architecture-focused river cruise.

4. Go to a Comedy Show

Although the theatrical season won't be starting in cities like Chicago until October/November, there are still plenty of great comedians planning performances in the area this August.

Each of these performances is scheduled to take place either in Chicago or within 30 minutes of the downtown area.

Comedy Shows

Comedy Clubs

Check here to see a full calendar of comedy shows in the Chicago area in August.

If your heart is set on Chicago's theatre scene, check out our self-guided theatre tour to admire the exterior of some of the oldest movie palaces in the Loop.

5. Attend the Grant Park Music Festival

From June 14 - August 19th, 2023, the Grant Park Orchestra and Chorus bring concerts to the park.

You'll find classical music and family-friendly events. Many of the seats are completely free!

Choose from A Salute to Rhapsody in Blue, Broadway hits, pieces by top composers like Beethoven and Dvorak, and more.

For more information and a schedule of events, visit the festival's Grant Park Music Festival website.

6. Admire Art on the Mart

While strolling along the Riverwalk in the evening, be sure to walk along the south side of the Chicago River so that you can see a newer art installation called “Art on the Mart”.

It is a series of non-sponsored projections on the side of a historic Chicago building called the Merchandise Mart. 

Find out more from the Art at the Mart website.

7. Spend Sundays on State Street

On specific summer days, State Street is open only to pedestrian traffic. This allows the award-winning and widely-attended "Sunday's On State" block party to take place.

Here you'll find some of the best Chicago vendors on offer. Food and drinks, art and shopping, recreation, and culture. 

This year's events take place on August 13th from 11 am - 6 pm.

Attendance is free. For more information, visit the Sundays on State Street website.

8. Chicago Air and Water Show

Head over to North Avenue Beach and the lakefront to see daredevil pilots, jets, and flying teams performing for the crowds below.

This Chicago tradition since 1959 features civilian and military pilots doing amazing stunts. 

Events take place over August 19th & 20th (with a practice on August 18th.

Admission is free and the stunts and activities go on from 10:00 AM - 2:00 PM on both days.

This is a great activity for the whole family! 

Get all the details on the Chicago Air & Water website.

9. Attend a Festival

Chicago loves to celebrate and hold festivals during the summer months. 

Whether you're interested in food, shopping, or music, you'll find a festival or event celebrating it in August in Chicago.

Music Festivals

Food and Drink Festivals

Neighborhood Festivals

Arts Festival

Note that many of these festivals are free to attend! 

10. Save Money with a Chicago Tourist 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 at select attractions.

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.

For more details, make sure to read our full post covering Chicago tourist passes.


There are many free activities to take advantage of in Chicago including some we have mentioned above like taking a pay-what-you-like walking tour, seeing the Air and Water Show, or hearing Jazz.

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

Watch the Bud Billiken Parade 

In August you can see the Bud Billiken Parade, the largest and oldest African-American parade in the world. 

Since 1929, it's been marching through the streets of the Bronzeville neighborhood in celebration.

The parade concludes in Washington Park with a large picnic with local vendors and performers.

For more information and the date of the parade, check out the Bud Billiken Parade website.

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 open for the public to explore for free.

Beyond the art that lines the walls, you will find free traveling films, lectures, and performances here.

Check out their calendar of events to see what is going on during your visit.

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!

Check out our Gold Coast Tour to see the historic old homes of Chicago’s elite.

Explore the Farmers Market

Enjoy local produce before the summer ends! From tasty veggies to locally made jams to homemade crafts and baked goods, you will definitely find something interesting or delicious.

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.

Exercise in the Park

On Saturdays, from May through August, Chicago puts on the Millennium Park Summer Workouts series.

The classes take place on the Great Lawn and are completely free to attend.

You'll find Pilates, Zumba, Yoga, and Tai Chi.

Check out the exercise class schedule here.

Under the Picasso

There are free events all summer long at Daley Plaza by the Picasso Statue.

Often during the lunch hours which means you can bring a picnic and enjoy the entertainment!

If you'd like to join us, our Loop & Millennium Park Tour goes right through Daley Plaza.

Chicago SummerDance in the Parks

All summer long you can enjoy live music or DJs spinning at public parks around Chicago. 

Some of the events even include a dance lesson before folks start to boogie!

Here's the full calendar of concerts and dance classes.

For even more free activities, see our post on the top free things to do in Chicago.


Many of our top ten activities are perfect for the evening hours, such as seeing a sporting event, going to the theater or attending a concert.

Below are some more ideas. Be sure to read our post about the top things to do in Chicago at night for even more suggestions.

Take a Night Tour

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 history of The White City.

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

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

Attend a Candlelight Concert

This concert series, taking place at various locations throughout Chicago, is truly magical.

Classical music is played by candlelight, creating an atmosphere that is both relaxing and enjoyable.

Concerts in January include The Best of Hans Zimmer, a Tribute to ABBA, and a Tribute to Taylor Swift.

Tickets can be purchased here.

See an Improv Show

Chicago is well known for comedy and improv. Just ask Tina Fey, Amy Poehler, or Steve Carell. Below are just a few places to catch an evening show.  

You may be seeing seasoned Chicago improvisers or you might catch a group of students, but who knows? One of them could be the next Chris Farley.

See the Local Music Scene

There are plenty of local musical experiences at night.  

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:

Water Flicks at Navy Pier

This summer head to Navy Pier's Pols Bros Park Lake Stage to watch a movie on the lawn with the skyline as a backdrop!  

Bring your own picnic blankets.

Check out the Water Flicks website for more details.

Go to a Game Bar

Whether you want to try an arcade bar with some pinball and Pac-man or try a classic board game, Chicago has a game bar for you.

Check out our favorite game bars across the city.

Go Hit at the 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 skeeball, and catch some games on the TVs at this beloved sports bar.

Go Out for Drinks

Chicago has speakeasies – fitting for the mobster history of the Windy City - and also some of the Best Rooftop Bars.

In our Guide to Chicago Bars, you can find out about historic bars, game bars, and where to have a pint while playing some trivia.

If you’re looking for more than just atmosphere and want to find one of the best Craft Beers, we can make sure you find a local pint.

Be sure to check out our post on top things to do in Chicago at night for even more suggestions.


Throughout this post, we have listed several activities that are suitable for kids, such as seeing an outdoor movie, going to a sports game, or seeing a musical. 

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

Be sure to check out our post about family-friendly activities in Chicago for a more complete guide.

Go to a Museum

In August, when the days are a bit too hot, an air-conditioned museum is a good place to be!

Chicago has a lot of museums that are very interactive and ideal for kids such as:

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.

Have Fun at the Chicago Library

The Chicago Public Library, Jefferson Park Branch has Preschool Story Time. Kiddos between 3-5 will get to enjoy songs, rhymes, and books.

Other branches offer Family Story Time for kids of all ages, Baby Story Time for kids up to age 3, and other activities around art, science, and crafts.

For a look at their August schedule, check their website.

Peggy Notebaert Nature Museum

Visit this lovely nature museum and attend one of the many kid-friendly events.  

From storytelling to animal encounters to even helping to feed the animals, there is something for every little visitor.  

Visit the Shedd Aquarium

Head to the Shedd Aquarium with your little ones

You can wander around and view the aquatic wildlife that lives at the zoo.

There's also a 4-D Experience covering sharks, one covering the Octopus, and a third covering Splash and Bubbles, some very colorful fish.

You can also book a guided tour or book a private meeting with a Beluga Whale or some penguins!

Visit the Shedd's website for more information.

Play in a Park

Chicago is full of green grass and playgrounds for kids to get out their energy.

One of the best parks, Maggie Daley Park, is nestled between downtown and Lake Michigan.

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, a mini-golf, and tennis courts.

Find out about the many great parks in Chicago by reading our post, Chicago's Beautiful Parks.

See our post about family-friendly activities in Chicago for even more great things to do.

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: March 8th, 2024
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