BEST Things to Do in Chicago in August, 2023 (From a Local!)

Searching for what to do in Chicago this August? Here are the best things to do in Chicago in August (from a local) – from fun outdoor activities and events to the top attractions.

I suggest bookmarking this blog post as I plan to update it regularly with new events and activities.

Chicago in August

August is a popular month to visit Chicago. The weather is hot and sunny and locals and visitors are happy to be outside enjoying summer fun.

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What to Pack for Chicago in August

For out of town visitors, please note that the weather in Chicago in August can get very hot and humid. Here are some things to pack if you are visiting Chicago in August for the first time:
• Comfortable walking shoes – Chicago is a very walkable city so you will do a lot of walking
• Reusable water bottle – It can get very hot so it is important to stay hydrated
• Sunglasses
• A hat
• A travel umbrella – It does occasionally rain in August
• Light sweater (and scarf) – For cooler nights and cold air conditioned places
• Waterproof case for your phone – if you plan to go kayaking
• External battery for your phone – it will be hard to find someplace to recharge your phone’s battery when you are outdoors
• Mosquito repellant- Mosquitos can be an issue if you are planning to be outside around dusk or in the evening especially at Navy Pier
• Sunscreen -Especially if you are planning to spend a lot of time outdoors
• Bathing suit and other beach essentials (if you are planning to spend time at the beach)

If you forget to bring something essential, don’t worry. There are many drugstores all over the city if you need to pick something up.

Things to Do in Chicago in August

Below are the best things to do in Chicago in August including all of the best August events and festivals.

Take an Architecture River Cruise

weekend in chicago bucket list

Chicago has amazing architecture and the best way enjoy it is by going on an architecture river cruise.

Take a Lake Cruise

skyline from lake cruise in Chicago in the summer
If you enjoy being on the water, a lake cruise is also a fun activity. While you don’t get to see the buildings up close like on a architecture river cruise, you do get to enjoy skyline views. August is one of the best months for a lake cruise as the cool breeze on the water is refreshing on a hot day. If your time is short, you can do a combination river and lake cruise. Lake cruises depart from Navy Pier or the Michigan Avenue bridge.

Watch Fireworks

Navy Pier puts on free fireworks shows every Wednesday (at 9 pm) and Saturday night (at 10 pm) the entire month.

You don’t have to visit Navy Pier to enjoy the fireworks, you can see them from the lakefront and various restaurants.

You can also see fireworks from the water on a fireworks lake or river cruise or a fireworks kayak tour.

You can also join a fireworks segway tour.

Hang out on the Riverwalk

best things to do chicago travel blog

The Chicago Riverwalk is one of the best spots in Chicago for boat and people watching. There are also restaurants, bars, shops and spots to sit and relax along the way.

August is one of the best times of the year to visit Chicago

Where: Along the south bank of the Chicago River in downtown Chicago from Lake Michigan to west of Franklin Street. You can see a map of attractions on the Riverwalk here.

Hours: Open daily from 6 a.m. to 11 p.m.

Watch Digital Art at Art on theMart

Art on the Mart
Looking for a unique thing to do at night? Check out Art on theMART, the largest permanent digital art projection in the world, projecting contemporary artwork across the 2.5-acre river-façade of theMART. Free 30-minute program of projections are shown twice nightly. Spectators can watch the show from the jetty section of the Chicago Riverwalk on Wacker Drive between Wells Street and Franklin Street.

Take a Kayak Tour

A fun way to explore the city is to go kayaking in the Chicago River. There are several companies that offer kayaking tours in Chicago including Urban Kayaks, Kayak Chicago and Wateriders.

Please note that you will get a little wet so bring a waterproof case for your phone and water-resistant or quick-drying clothing.

You can also rent kayaks at Ohio Street Beach.

See the Chicago Air & Water Show

The Chicago Air & Water Show takes place in Chicago every August and is the largest FREE show of its kind in the United States and one of Chicago’s most popular events. The show can be viewed for free along the lakefront from Fullerton to Oak Street, with North Avenue Beach as the focal point.

If you want to avoid the crowds on the beach, you can see the show from a tall ship windy VIP cruise.

Where: North Ave. Beach and along the Lakefront

Have Fun at Navy Pier

rides at Navy Pier Chicago
Navy Pier is a must do if you are visiting Chicago with toddlers or kids. Fun attractions include a large Ferris wheel (click here to purchase a fast pass ticket and skip the long line), rides and games, restaurants, shops and the Chicago Children’s Museum.

During the entire month of August, Navy Pier will be home to Pixar Putt, a pop-up, open-air 18-hole mini-golf course featuring characters from some of Pixar’s most beloved films including Toy Story, The Incredibles, Monsters, Inc., Finding Nemo, Coco, A Bug’s Life, Wall-E, and Inside Out.

If you are visiting Navy Pier on a Wednesday and Saturday, stay for the free fireworks show at night.

Navy Pier is also the starting point for many boat rides and lake cruises.

Attend a Candlelight Concert

Chicago’s Candlelight Concerts is a series of special classical music concerts that take place in beautiful venues bathed in candlelight. Some of the concerts taking place this August include:

Candlelight: A Tribute to Taylor Swift
Candlelight: A Tribute to Beyoncé
Candlelight: A Tribute to Juan Gabriel
Candlelight: A Tribute to The Bee Gees
Candlelight: Vivaldi & More at The Museum of Science and Industry

You can find the full list of candlelight concerts in Chicago here.

Listen to Concerts Under The Stars

Enjoy classical music concerts on a rooftop. Upcoming Concerts Under The Stars this August include:

Sinatra Under the Stars at AIRE
ABBA Under the Stars at AIRE

You can find the full list of Concerts Under The Stars here.

Listen to Free Music in Millennium Park

A great Chicago activity in the summer is listening to free concerts at the Jay Pritzker Pavilion in Millennium Park.

The annual Grant Park Music Festival is the only free outdoor classical-music concert series in the US. It features the Grant Park Symphony Orchestra and Grant Park Chorus along with guest performers and conductors.

The Millennium Park Summer Music Series features a wide variety of music from established and emerging artists at the iconic Jay Pritzker Pavilion.

Watch Free Movies in Millennium Park

Watch free movies outside in Millennium Park presented on the state-of- the-art, 40-foot LED screen as part of the Millennium Park Summer Film Series. Guests may take a seat at the Jay Pritzker Pavilion or lounge on the Great Lawn.

Where: Millennium Park, located at 201 E. Randolph Street.

See Famous Works of Art at the Art Institute of Chicago

Want to escape the heat and head indoors to cool off? The Art Institute of Chicago (111 S Michigan Ave) is one of best indoor attractions in Chicago.  It is one of the largest art museums in the United States and is frequently found on lists of the top museums in the world. You must purchase your ticket online in advance.

Click here to buy a fast pass ticket if you want to avoid long lines.

Splash in Crown Fountain

millenium park which includes Crown fountain is a Chicago must do in August

On hot summer days, kids (and some adults) love to splash in the water from Crown Fountain (which is also located in Millennium Park).

Enjoy the Beach

Most people don’t think of Chicago as a beach destination but Chicago has many beaches on Lake Michigan.  Oak Street Beach and Ohio Street Beach are conveniently located close to the major tourist attractions. North Avenue Beach is located close to Lincoln Park and has great skyline views of Chicago and but is also the most crowded.

You can rent SUP paddle boards at North Avenue Beach here and kayaks at Ohio Street Beach here.

If you are thinking of getting in the water, make sure to check swimming conditions here.

Walk or Bike the Lakefront Trail

Chicago lakefront

Chicago’s Lakefront Trail is a paved path on a 18-mile-long stretch along Lake Michigan. In the summer and especially on weekends, the lakefront is packed with locals and visitors walking, running and riding bikes.  Walking or biking all or part of the trail is a great way to see Chicago skyline, people watch and get some exercise. Here is a map of the trail as well as its access points.

Look for Street Art

Moose Bubblegum Bubble by Jacob Watts one of the most famous street art murals in Chicago

Chicago is full of street art and there are always new murals popping up.  One of the most famous Chicago murals is “Moose Bubblegum Bubble” (pictured above) by Jacob Watts which located at 33 E. Ida B. Wells Drive (formerly 33 E. Congress Parkway). It is part of the Wabash Arts Corridor which is walking distance to Millennium Park, The Art Institute of Chicago and other well known tourist attractions. You can find more detailed mural walks in the Loop here.

Another famous mural is The Greetings From Chicago Mural at 2226 N Milwaukee Ave, in Chicago’s Logan Square neighborhood. You can see this mural and more on this street art tour.

Walk the 606

The 606 is Chicago’s version of The Highline in NYC, an elevated trail goes through 2.7 miles of the city’s northwest side neighborhoods: Wicker Park, Bucktown, Humboldt Park, and Logan Square.  It is a bit off the beaten tourist path but it is a great place to walk or ride a bike. There are several access points so you can get off the trail to explore the various neighborhoods.

Museum of Contemporary Art Tuesdays on the Terrace

The Museum of Contemporary Art hosts the popular Tuesdays on the Terrace this summer. Enjoy free music highlighting artists from Chicago’s internationally renowned jazz community at at MCA’s Anne and John Kern Terrace Garden. Light refreshments and a full bar with cold beverages, wine, and cocktails are available for purchase on the upper terrace.

Where: Museum of Contemporary Art, 220 E Chicago Ave, Chicago, IL 60611

Cost: Free tickets must be reserved in advance.

Jazzin’ at the Shedd

Listen to live jazz music at the Shedd Aquarium this summer. The popular midweek Jazzin’ at the Shedd series combines great Jazz music, the city skyline, fireworks and animals. Relax with a drink on the breezy terrace and take in their unbeatable city view or stroll the aquarium.

Where: Shedd Aquarium, 1200 S DuSable Lake Shore Dr, Chicago, IL 60605

Cost: Adult $39.95 ($19.95 for Chicago residents), Children (3-11) $29.95 ($14.95 for Chicago residents), Members $14.95

Watch a Baseball Game

what to see in Chicago

Chicago is known for their love of their sports teams, so if you are visiting in August you might want to attend a baseball game. To those unfamiliar, historic Wrigley Field is home to one of the city’s baseball teams – the Cubs. Whether a fan of the Cubs, baseball in general or just a fun atmosphere, a day at the 100 year old ballpark is a must for locals and tourists alike. You don’t need to enjoy baseball to enjoy a Cubs game – it is fun to just soak in the atmosphere.

You can find the Cubs schedule here and the Chicago White Sox schedule here.

Eat or Drink on a Rooftop

Chicago has several rooftop bars and restaurants with amazing views of Chicago.  Here are some of the best rooftops in Chicago:

Cindy’s (12 S Michigan Ave) – Restaurant and bar on the rooftop of the Chicago Athletic Association Hotel located across Millennium Park which offers panoramic instagram worthy views of Millennium Park and Lake Michigan. This is a popular spot and the wait for the elevator can be long but if you visit around the time it opens you can enjoy the great views without the crowds.

LH ON 22 (85 East Wacker Drive) – Enjoy classic cocktails and small bites from the outdoor LH terrace of LondonHouse Chicago which offers great views of the Chicago River, Lake Michigan and the Magnificent Mile.

The J. Parker (1816 N Clark St) on the rooftop of the Hotel Lincoln with great views of Lincoln Park.

Kennedy Rooftop (1551 W North Ave) on top of the Hyatt Place Wicker Park, has amazing skyline views.

Attend an Outdoor Festival

Want to enjoy live music, food, drink and people watch? August is a popular month for outdoor festivals and events in Chicago. Outdoor festivals taking place in August include: Lollapalooza Festival, Dancing In The Streets, Retro on Roscoe, Edison Park Fest, Northalsted Market Days (August 10-11, 2024), Clark After Dark, Ribfest Chicago and Bucktown Arts Fest.

More Chicago August Events

In addition to the activities mentioned above, other August events include: Chicago Ducky Derby, Bud Billiken® Parade and Life Time Chicago Triathlon (August 24 – 25, 2024).

As you can see there are many things to do in Chicago in August.

If you are looking for more things to do in Chicago in August or the rest of the summer, see my list of the Best Things to do in Chicago in the Summer.

Planning a trip to Chicago? Check out my Chicago guides and itineraries:



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