Best Things to Do in Chicago in August

Wondering what to do in Chicago this August? Here are the best things to do in Chicago in August (from a local).

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

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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.

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

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.


Take a kayak tour in the river

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. They even offer evening tours for those that want to avoid the summer heat and sun.

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

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. You can also hop on a water taxi here on the weekends.

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

If you are looking for a unique thing to do in Chicago 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 nightly at 9:00 & 9:30 p.m. Spectators can watch the show from the jetty section of the Chicago Riverwalk on Wacker Drive between Wells Street and Franklin Street.

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.

Hang out at Navy Pier

rides at Navy Pier Chicago
Navy Pier can be somewhat of a tourist trap but it 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.

Navy Pier has a free fireworks show every Wednesday from 9:30-9:40 pm and Saturday from 10:15-10:25 pm.

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


Watch Fireworks

You can see fireworks in Chicago all summer. As mentioned above, Navy Pier puts on free fireworks shows every Wednesday and Saturday night in the summer. 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 fireworks lake cruises.


See the U.S. Navy Blue Angels Show (reimagined Chicago Air & Water Show)

The Chicago Air & Water Show is a free annual air show held every August on the lakefront and one of Chicago’s most popular festivals. In place of the usual Chicago Air and Water Show, this year’s show will be scaled down and only consist of a special solo flight demonstration by the U.S. Navy Blue Angels. The best viewing locations along the lakefront are between Oak Street and Fullerton Avenue.

When: August 21 & 22, 2021 from 12–1pm. (On August 20, practice runs from 10am–2pm.)

Listen to free music at 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. Performances are Wednesdays, Fridays and Saturdays through August 21. You can see the full schedule here.

The Millennium Park Summer Music Series (Mondays from 6:30–8:30pm) will feature a wide variety of genre-defying music from established and emerging artists.

See the Bean at Millennium Park

The Bean at Millenium Park is a must on any one day in Chicago itinerary

Right next to the Jay Pritzker Pavilion in Millennium Park, don’t miss Cloud Gate (also called The Bean), the famous mirrored sculpture.

Although the Bean is very very touristy, don’t skip it.  It is one of the most instagrammable places in Chicago and it is a great photo spot.

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 the Crown Fountain (which is also located in Millennium Park).

See the water displays at Buckingham Fountain

Buckingham Fountain in Chicago

Buckingham Fountain, a well known Chicago landmark in the center of Grant Park, is one of the largest fountains in the world.

When the water is turned on, it produces a major water display for 20 minutes every hour with a center jet shoots water to a height of 150 feet into the air. Beginning at dusk, a spectacular light and music display accompanies the major water display. Major displays begin daily at 9:00 a.m. and continue thereafter, every hour on the hour, except for the final major display in the evening which begins at 10:35 p.m.

Sundays on State

Chicago Theatre instagram photo spot

In an effort to bring people safely back to the Loop, Chicago Loop Alliance will transform State Street from Madison to Lake into an open street on select Sundays in the summer. This portion of the street will be closed to vehicle traffic to give pedestrians a chance to experience arts and culture, active recreation, retail, restaurants, and bars against the backdrop of State Street’s iconic architecture like the Chicago Theatre (one of the best Chicago photo spots).

Where: State Street from Madison to Lake

When: August 8, 22 and 29 from 11 a.m.-8 p.m. Click here for more information.

Watch free movies in the park

Every summer you can watch free movies in Chicago’s public parks with the annual Movies in the Parks series. Movies in the Parks is part of Night Out in the Parks, which will feature more than 350 outdoor cultural & arts events in parks throughout the city this summer.  Movies start at dusk.

Join free exercise classes at Millennium Park

Want to join free yoga (and other exercise classes) while also spending time outside? The Millennium Park Summer Workouts program offers free Tai Chi, Yoga, Pilates and Zumba classes on Saturday mornings at Millennium Park Great Lawn.

Hang out at 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 is more of a party beach.

If you are thinking of swimming or dipping in the water to cool down, you can 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.

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 their schedule here.

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.

Other neighborhoods that have a high concentration of street art include Pilsen as well as West Town.

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 great place to walk, run or bike. There are several access points so you can get off the trail to explore the various neighborhoods.

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 and events scheduled for August include: Windy City Smokeout (August 4-7, 2022), Windy City Rubber Ducky Derby (August 5, 2021), Northalsted Market Days (August 6-8, 2021), LatiNxt Music Festival, (August 6-7, 2021), Printer’s Row Art Fest (August 7-8, 2021), World Naked Bike Ride (August 14, 2021), Wells Street Art Festival (August 14-15, 2021), Gold Coast Art Fair (August 21-22, 2021), and Taste of Greektown (August 27-29, 2021).

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

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



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