Best Things to Do in Chicago in the Summer

Wondering what there is to do in Chicago this summer? Below are the best things to do in Chicago in June, July and August.

Summer is one of the best times of the year to visit Chicago – and the most popular! Both locals and visitors are happy to be outdoors enjoying the warm weather.  In addition to the top tourist attractions that you can see year round, there are more fun events, activities and things to do in Chicago during the summer.

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What to Pack for Chicago in the Summer

Summers in Chicago are usually hot although you might need a light sweater on a cooler day or at night. Here are some things to pack if you are visiting Chicago in the summer for the first time:

• Comfortable walking shoes – Chicago is a very walkable city so you will do a lot of walking
• Face masks – Chicago requires face masks for entry to all indoor attractions and some outdoor attractions
Reusable water bottle – It can get hot and humid so it is important to stay hydrated
• Sunglasses
• A hat
Travel umbrella – It does occasionally rain in the summer
• Light sweater (and scarf) – For cooler days and frigid AC
Waterproof case – For your phone if you plan to go kayaking
• 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 located close to the popular tourist attractions if you need to pick something up.

Things to Do in Chicago in the Summer

Below are the best things to do in Chicago in the summer.

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.

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.

Summer 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.

Go Kayaking in the River

A fun way to explore the city in the summer 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.

See the Water Displays at Buckingham Fountain

Buckingham Fountain, a well known Chicago Landmark in the center of Grant Park, is one of the largest fountains in the world. Buckingham Fountain will be turned sometime before Memorial Day.

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 whch begins at 10:35 p.m.

Listen to Free Music at the Jay Pritzker Pavilion in Millennium Park

A great Chicago activity in the summer is listening to free concerts at the Jay Pritzker Pavilion in Millennium Park. Advance reservations are required this year.

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 take place 6:30pm on Wednesdays, Fridays and Saturdays from July 2 – August 21, 2021. You can see the full schedule here.

The Millennium Park Summer Music Series (August 2–September 16, 2021) will feature a wide variety of genre-defying music from established and emerging artists. The lineup will be announced soon and reservation information will be announced closer to the concert dates.

See the Bean at Millennium Park

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

If you have seen photos of Chicago on social media, chances are you have seen photos of Cloud Gate (also called The Bean), the famous mirrored sculpture in Millennium Park. Millennium Park is a free attraction and is a portion of the Grant Park.  In addition to Cloud Gate, Millennium Park also includes the Jay Pritzker Pavilion, the Crown Fountain sculpture (more below) and Lurie Garden.

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

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).

Play at Maggie Daley Park

If you are visiting Chicago with kids, head to Maggie Daley Park, a large public park connected to Millennium Park. The park has play areas for kids of various ages as well as a climbing wall,  tennis courts and pickleball courts and a 18-hole miniature golf course.

Have Fun at Navy Pier

Navy Pier can be somewhat of a tourist trap but it is a must do if you are visiting Chicago with toddlers or kids. There are fun attractions at Navy Pier including a Ferris wheel, restaurants, shops, the Chicago Children’s Museum, and the Chicago Shakespeare Theater.  Navy Pier is also the starting point for various sightseeing tours and cruises.

Shop (or Window Shop) on the Magnificent Mile

Join the throngs of visitors and locals shopping (or window shopping) on The Magnificent Mile. The Magnificent Mile (or The Mag Mile), is an upscale section of Michigan Avenue, running from Oak Street to the Chicago River. Although some of the stores on Michigan Avenue are pricey, it is totally free to window shop. Landmarks on the Mag Mile include the 360 Observation Deck, the historic Chicago Water Tower and the Tribune Tower.

Explore the Lakefront

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.

Spend Time at the Beach

Most people don’t think of Chicago as a beach destination but Chicago has many beaches on Lake Michigan.  The most popular beaches are located downtown (Oak Street and North Avenue) but they are also the busiest.  Two of the best beaches for more of a local feel include Kathy Osterman Beach and Foster Avenue Beach which are both located north of downtown.

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. Congress.  It is part of the Wabash Arts Corridor which is walking distance to Millennium Park, The Art Institute of Chicago and other tourist attractions.

Another famous mural is The Greetings From Chicago Mural at 2226 N Milwaukee Ave, in Chicago’s Logan Square neighborhood.  Pilsen is another neighborhood where you can find tons of street art (and great Mexican food).

Watch a Baseball Game

what to see in Chicago

Chicago is known for their love of their sports teams, so if you are visiting during the summer 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.

Visit Local Farmers Markets in Chicago

From May through October, you can find many farmers markets around Chicago. These markets are a great place to buy healthy, local, farm-fresh foods from local farms.

Two of the best farmers markets in Chicago are the Green City Market in Lincoln Park and the Logan Square Farmers Market.

You can see the list and schedule of all Chicago farmers markets here.

Lincoln Park

Lincoln Park, a large park along the lakefront, is a must see summer attraction.

Lincoln Park has a few great instagram spots including the bridge over the South Pond which has a great Chicago skyline view. Another nearby photo spot is the Peoples Gas Education Pavilion (aka the Honeycomb) in the Nature Boardwalk.

The park is home to Lincoln Park Zoo (which offers free admission), the Alfred Caldwell Lily Pool, the North Pond Nature Sanctuary, the Lincoln Park Conservatory, Theatre on the Lake, the Chicago History Museum and the Peggy Notebaert Nature Museum.

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.

Watch Free Movies in the Park

Ever 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. The schedule has yet to be released so check back for more information.

Attend an Outdoor Festival

Many outdoor festivals or events take place in Chicago in the summer – with at least one of more festivals taking place every weekend.  Some Chicago festivals are very well known and attract thousands of visitors, but there are many festivals and events in Chicago where you will mostly find locals. If you enjoy food, music and people watching, check to see if there are any festivals or events going on while you are in town.

Some festivals and events happening this summer in Chicago include: Old Town Art Fair (June 12-13, 2021), Pride in the Park (June 26-27, 2021), Windy City Smokeout (July 8-11, 2021), Southport Art Fair (July 10-11, 2021), Chicago Auto Show (July 15-19, 2021), Chinatown Summer Fair (July 17-18, 2021), Belmont-Sheffield Music Festival (July 17-18, 2021), Northalsted Market Days (August 6-8, 2021), Sundays on State, Taste of Chicago To-Go, and SummerDance.

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.

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

If you have extra time in Chicago and want to explore more of the Midwest, here are the best day trips from Chicago.

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



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