Company Logo - Home Link

What to do in Chicago in August (2021)

Book A Guided Walking Tour

This post covers the best things to do in Chicago this August, including free events, family-friendly activities and things to do at night, updated for 2021.




Chicago is a wonderful city to visit during the summer months - especially 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.

Tourist Passes Reviewed


1. Go to a Sporting Event

August is filled with several options if you are a sports lover.  You can choose baseball, Women’s basketball, and soccer.

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.



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. Click here for a fuller list.



Click here for a larger list.

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.



To see a full calendar of all shows, click here.  

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

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. Chicago Hot Dog Fest 

From August 6th-8th, the Chicago History Museum hosts the city's largest picnic as they honor the "hot dog" - a favorite food of Chicagoans for 100 years! 



Entrance is by suggested donation ($5 per person and $20 per family). The dogs aren't for free sadly!

There will be lots of live music, family activities and plenty of hot dogs served in many different styles.

For more information, click here.

NOTE: Dates for this event have not yet been confirmed, but all indications are that it will be taking place.

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 their website, Art at the Mart.

7. Go to Lollapalooza 

This world-famous music festival returns for another year from July 29th - August 1st in Grant Park.

This year's headliners are Ariana Grande, Childish Gambino, The Strokes, Tame Impala, The Chainsmokers and more. There will over 100 bands performing. 



If you have never been to Lollapalooza, now's your chance. Get tickets here.

8. Chicago Air and Water Show 

On August 21st-22nd, head over to North Avenue Beach to see daredevil pilots, jets, and flying teams performing for the crowds below.

Admission is free and the stunts and activities go on from 10 am - 3 pm both days. Get all the details here.



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

This is a great activity for the whole family! 

NOTE: The dates for this event have not yet been confirmed, but it is looking likely that they will still hold the show this year.

9. Attend an August Festival

Chicago loves to celebrate and hold festivals during the summer months. Check out Choose Chicago for a full event calendar.

Below we list just a few of the many August festivals.



  • Millennium Park Music Series
  • Jefferson Park Arts & Music Festival
  • Wells Street Art Festival
  • Grant Park Music Festival
  • Sangria Festival
  • Edison Park Fest

TIP: 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.

CANCELLED: Chicago Jazz Festival 

Say goodbye to summer with some free, fantastic jazz. From August 23-Sept. 1 the annual Chicago Jazz Festival takes place in Millennium Park.  

Since 1979, this festival has celebrated the talent of local, national, and international jazz musicians. More details are here.



Learn more about Millennium Park where this festival is held on our Pay-What-You-Like walking tour of the Loop & Millennium Park.

Or if you prefer to move at your own pace, use our self-guided Millennium Park Tour.

NOTE: This event was sadly canceled for 2021.


Back to Top



There are many free activities to take advantage of in Chicago including some we have mentioned some 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 

On August 14th, 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. 

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

NOTE: This event might be postponed due to the pandemic.

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

For the entire month of August, the city offers free exercise classes at Pritzker Pavilion.


  • Tai Chi at 7 am
  • Yoga at 8 am
  • Pilates at 9 am
  • Zumba® at 10 am

Tuesdays and Thursdays

  • Yoga at 7:30 am

Check out the exercise class schedule here.

NOTE: This event may not be available in 2021 due to the pandemic.

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!

The Loop & Millennium Park Tour goes through Daley Plaza!

Chicago Summer Dance

All summer long you can enjoy live music or DJ’s spinning at public parks in Chicago. Some of the events even include a dance lesson before folks start to boogie!

Here are a few examples of just the first week of August:

  • Friday, August 9, 6–9:30 pm: Ballroom, Waltz, Tango
  • Saturday, August 10, 6–9:30 pm: Chicago Blues, West Coast Swing, Hustle
  • Sunday, August 11, 4–7 pm: Salsa and Cha-Cha
  • Wednesday, August 14, 6–9 pm: 1920s, ‘30s & ‘40s classic swing
  • Friday, August 16, 6–9:30 pm: Chicago Blues, Swing, & Rock-n-Roll) 

Here's the full calendar.

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


Back to Top


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.

Head to Adult Night at Lincoln Park Zoo 

On August 8, the Lincoln Park Zoo hosts a kid-free event where the grown-ups can enjoy the cash bar while checking out the animals and listening to educational talks.

Check out their site for more details and ticket information.

NOTE: This event was pushed forward to June 26th, 2021.

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 at to watch a movie in the lawn with the skyline as a backdrop!  

  • August 2nd: Creed
  • August 5th: TBD

Bring your own picnic blankets for this superhero-filled summer.

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.

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 skee-ball, and catch some games on the TVs at this beloved sports bar.

Go Out for a Cocktail

Chicago has speakeasies – fitting for the mobster history of the Windy City, 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.


Back to Top



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.

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 was canceled due to the pandemic.

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.  

Attend Stories, Songs and Circle Games

Lurie Garden presents an interactive and free event for your little ones on August 11th at 11:00 am.  Kiddos between 4-6 will sing like sparrows and play pretend!

For more details or to register, click here.

NOTE: This event has not been confirmed for August of 2021.

Go to a Baseball Game

We have two baseball teams here, so there are plenty of options for families to go catch a game!

The Cubs play north of downtown at Wrigley Field, and the White Sox play south of the skyscrapers at the Guaranteed Rate Field.

Tour both stadiums, or just enjoy the fresh air while cheering on our Chicago teams!

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, 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.


Back to Top



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: September 26th, 2021
Back to Top