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 the summer.

Summertime 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
Reusable water bottle – It can get hot and humid so it is important to stay hydrated
• Sunglasses
• A hat
• A travel umbrella – It does occasionally rain in the summer
• Light sweater (and scarf) – For cooler days, lake cruises, indoor places with frigid AC
Waterproof case – For your phone if you plan to go kayaking
External battery for your phone – to recharge your phone’s battery when you are outdoors
• Mosquito repellent – If you plant to be outside around dusk and in the evening.
• Sunscreen – a must if spending a lot of time outdoors in the summer
• 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

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

If you enjoy being on the water, a lake cruise is a great outdoor thing to do in Chicago. While you don’t get to see the buildings up close like on a architecture river cruise, you do get to enjoy skyline views. Summer is the best season 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.


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.

Watch the Water Displays at Buckingham Fountain

Buckingham Fountain in Chicago in summertime

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.

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. 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 — in 10 genre-defying concerts.

Take Photos at the Bean

The Bean at Millenium Park is a must on any Chicago bucket list

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.

Although the Bean is very very touristy, don’t skip it.  It is a great photo spot and a must on any Chicago bucket list.

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 large Ferris wheel (click here to purchase a fast pass ticket and skip the long line), rides and games, restaurants, shops, the Chicago Children’s Museum and the Chicago Shakespeare Theater.  

Navy Pier puts on a free fireworks show on Wednesday and Saturday nights in the summer.

Navy Pier is also the starting point for various sightseeing tours, boat rides and cruises.


Watch Free Fireworks

As mentioned above, Navy Pier puts on a fireworks show every Wednesday night (9:30-9:40pm) and Saturday night (10:15-10:25pm) from Memorial Day weekend through Labor Day weekend. While you can watch the fireworks show from Navy Pier, you can also watch it from various spots along the lakefront and some restaurants and bars. Another great option for watching the fireworks is a lake or river cruise which will stop on the water for passengers to enjoy the show.


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 the 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.  Oak Street Beach and Ohio Street Beach are conveniently located close to the major tourist attractions. North Avenue Beach is more of a party beach and is located close to Lincoln Park.

If you are thinking getting in the water to cool down, you can check the swimming conditions 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. Congress.  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 other street art in Logan Square and Wicker Park on this street art tour.

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

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

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.

Visit 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 also home to Lincoln Park Zoo (which offers free admission), the Lincoln Park Conservatory 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.

Free Millennium Park Summer Workouts

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.

When: Saturdays, July 3–August 28 from 8:30am–12:15pm. Detailed schedule is as follows:

Tai Chi 8:30-9:15am
Yoga 9:30-10:15am
Pilates 10:30-11:15am
Zumba 11:30-12:15pm

Watch Free Movies in the Park

Every summer you can watch free movies in the evenings 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.

When: July 6, 2021 through September 14, 2021 at dusk. Click here to see the schedule.

Attend an Outdoor Festival

Summer is busy season for outdoor festivals and events  – with at least one or 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), Taste of Chicago To-Go (July 7–11, 2021), Windy City Smokeout (July 8-11, 2021), Southport Art Fair (July 10-11, 2021), Chicago Auto Show (July 15-19, 2021), Belmont-Sheffield Music Festival (July 17-18, 2021), Wicker Park Fest (July 23-25, 2021), Lollapalooza Festival (July 29-August 1, 2021), Chinatown Summer Fair (July 31-August 1, 2021), Windy City Rubber Ducky Derby (August 5, 2021), Northalsted Market Days (August 6-8, 2021), Printer’s Row Art Fest (August 7-8, 2021),  Wells Street Art Festival (August 14-15, 2021), Chicago Air and Water Show (August 21-22, 2021), Gold Coast Art Fair (August 21-22, 2021), Taste of Greektown (August 27-29, 2021), Sundays on State, SummerDance, ARC Music Festival (September 4-5, 2021), Pitchfork Music Festival (September 10-12, 2021), Printers Row Lit Fest (September 11-12, 2021), Hyde Park Summer Fest (September 11-12, 2021), Riot Fest (September 17–19, 2021) and Chicago In Tune (until September 19, 2021).

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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