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June 1, 2022

Chicago Summer Bucket List – Top 15 Things to Do 

Read this Chicago Summer Bucket List for the Top 15 Things to Do to help you plan your Chicago visit! 

It’s probably no secret that Chicago, AKA the Windy City, is known for cold winters, making the summertime the best time to enjoy this beautiful city. Chicago is the most vibrant in the summer, with many activities and things to do! If you are in Chicago for one day or several weeks, there is plenty of things to do in the summer.

1. Learn About the Beautiful Buildings on an Architectural Boat Tour

Voted number one boat tour in North America in 2021, the Chicago Architecture Foundation Center River Cruise should be top on your Chicago Summer Bucket List. It lasts for 1.5 hours and starts at the northeast corner of Michigan Avenue. The tour guide gives you so much history about Chicago, and you get to enjoy it while cruising along the Chicago River, seeing some of the best architecture in the world.

Chicago River

2. Take a Stroll Along the Chicago Riverwalk

If taking a boat ride along the river isn’t for you, then you can take a stroll along the river. The revitalized Chicago Riverwalk has new restaurants, bars, and a fabulous walkway; the riverwalk is one of Chicago’s top places to see! It is fun to watch the boats go by and see all the stunning buildings.

3. Enjoy the Lake Front Trail

One of the truly magnificent aspects of Chicago is Lake Michigan. And enjoying its splendor during the summer months is a must! The Lakefront Trail is 18.5 miles long and winds along the lake, giving you beautiful views of the skyline, parks, museums, and beaches. One of the best beaches in the city is North Avenue Beach because it has lots of space, beach volleyball courts, and you can rent jet skis and paddleboards.

View of Lake Michigan and Lake Front Trail
View of Lake Michigan and Lake Front Trail

The Lake Front Trail is a great place to be active by walking, cycling, jogging, or rollerblading! And you can stop by the famous Navy Pier, which is known for its giant Ferris wheel, restaurants, and dock for some exciting boat tours on Lake Michigan.

North Avenue Beach
North Avenue Beach

4. Check Out a Neighborhood Festival

The summertime is a great time to explore the Chicago neighborhoods by going to a festival! There are 77 neighborhoods in Chicago, and each has its unique vibe, history, and things to do. Every summer, there are festivals to enjoy in many of these neighborhoods. Many of them have live music, arts and crafts, and foods from local restaurants to try, like the famous Chicago deep dish pizza!

There are likely 3 to 4 festivals at least going on every weekend! Here are some fun ones to check out:

  • Andersonville Midsommarfest – Early June
  • Do Division Street Fest – Early June
  • Wells Street Art Festival – Mid June
  • Northalsted Market Days – Early August
  • Printer’s Row Art Fest – Mid August
  • Chicago Jazz Festival – Early September
  • Printer’s Row Lit Fest – Mid September

5. Listen to Music in Millennium Park

In the summer, a fantastic thing about Chicago is the variety of free events to enjoy! One of these free events is the Millennium Park Summer Music Series, which takes place on Mondays and Thursdays from June to August at the Jay Pritzker Pavilion. There are a variety of music genres for everyone to enjoy. So bring your blanket to lay on the lawn, listen to the music, and take in the beautiful skyline.

Jay Pritzker Pavillion at Millennium Park
Jay Pritzker Pavillion at Millennium Park

6. Have a Picnic in a Park

There are plenty of green spaces to visit in the vast urban city of Chicago, which makes it a great place to enjoy nature. A great way to spend an afternoon is having a picnic in a park. Each park is different in size and character.

Nature Boardwalk at Lincoln Park
Nature Boardwalk at Lincoln Park

Here are the best ones to check out!

  • Lincoln Park
  • Humboldt Park
  • Millennium Park
  • Grant Park
  • Garfield Park
  • Palmer Square Park
  • Maggie Daley Park

For more information on the Chicago parks, go to the Chicago Park District.

Rose Garden in Grant Park
Rose Garden in Grant Park

7. Walk on the 606 Trail

The 606 Trail, also known as the Bloomingdale Trail, is an elevated trail created on an abandoned rail line. It is 2.7 miles long and goes from Ashland Avenue to Ridgeway Avenue.

The 606 Trail
The 606 Trail

The 606 Trail is similar to the Highline in New York City. However, the 606 goes through some of Chicago’s diverse neighborhoods, such as Bucktown and Logan Square, giving it that Chicago neighborhood feeling. There are 12 access points about every quarter mile with ramps making it accessible to all to enjoy!

Go to the 606 Trail site for more information!

8. Cheer on the North or South Side Baseball Teams

Another must-do on this Chicago Summer Bucket List is watching a baseball game! Chicago is lucky to have so many pro sports teams, and there are two MLB baseball teams, the Chicago Cubs and Chicago White Sox. Many locals have their favorite and may be partial to the side of town where they grew up. Chicago Cubs are on the city’s north side in the Wrigleyville neighborhood, and the Chicago White Sox are on the south side in Bridgeport.

Guaranteed Rate Field, home of the Chicago White Sox
Guaranteed Rate Field, home of the Chicago White Sox

If you are looking to check out one of the oldest ballparks in the major league, then go to Wrigley Field. Historic Wrigley Field is known for the ivy-covered walls, the iconic red marquee, and hand-turned scoreboard. And it’s also great because it is located right in the heart of the Wrigleyville neighborhood. So you can check out the local bars and restaurants before or after the game! Either way, you can’t go wrong whichever field you decide to visit!

9. Enjoy the Wonders of “The Bean”

One of the most impressive attractions in Chicago is a massive piece of art called Cloud Gate or known as The Bean. Anish Kapoor, the artist, appropriately named it Cloud Gate as it reflects the beautiful city skyline and the clouds and sky above. This bean-shaped sculpture is one of the largest outdoor permanent art installations at 33 feet high, 42 feet wide, and 66 feet long. Adults and kids love it because the shape of the mirrored Bean creates fun reflections for selfies!

The Bean in Millennium Park
The Bean in Millennium Park

10. Go to a Concert at Ravinia

While not located right in the city, Ravinia is a beautiful outdoor music festival venue located north of Chicago. Locals and visitors alike love to visit Ravinia because of the beautiful grounds and accessibility on the Metra train from downtown Chicago. There is no need to worry about driving or parking; you can take the train right up to the entrance!

Pavillion at Ravinia
Pavillion at Ravinia

Another reason Chicagoans love Ravinia is for the picnicking! It’s a great place to enjoy the music under the stars on your blanket with your friends or significant other, sipping on your favorite beverage, and eating delicious snacks! If sitting on the lawn isn’t for you, they do have seats you can purchase in the pavilion.

People enjoying music at Ravinia on the lawn
People enjoying music at Ravinia on the lawn

Check out the latest schedule for Ravinia and book your tickets!

11. Kayak Down the Chicago River

The Chicago Riverwalk is one of the top things to do in Chicago, and kayaking down the Chicago River is another one of the best things to do in the summer. It’s just another way to enjoy the architecture surrounding the Chicago River, but you’ll get some upper body exercise while doing it! Kayak Chicago is open from the end of April to October. Go to Kayak Chicago for more information.

Kayakers on the Chicago River
Kayakers on the Chicago River

12. See the Animals at Lincoln Park Zoo

A great family fun activity is going to the Lincoln Park Zoo! Located in Lincoln Park in Chicago, just north of downtown, it’s a great place to hang out for the day. Lincoln Park Zoo has nearly 200 unique species from around the world.

Check out the newly renovated home for the lions and big cats at the Pepper Family Wildlife Center. Or go to the Regenstein Center for African Apes. Another favorite is the Kovler Seal Pool, where you can see the seals swim underwater.

13. Get Local at a Farmer’s Market

Chicago has access to some delicious produce and beautiful flowers from the local farms in Illinois and neighboring states, Wisconsin, Michigan, and Indiana. In addition, every day of the week, there are farmers’ markets in neighborhoods all around Chicago.

Beautiful sunflowers at a farmer’s market in Chicago
Beautiful sunflowers at a farmer’s market in Chicago

A couple of the local’s favorites are Green City Market in Lincoln Park, which is on Saturdays from April to November. And the Logan Square Farmers Market is on Logan Square Boulevard on Sundays from May to October.

Get the latest information and schedule for the Chicago City Markets.

14. Lollapalooza

One of the most anticipated outdoor concerts in the summer is Lollapalooza. This giant live music festival is in downtown Chicago in Grant Park and has nine stages and 170 plus bands. Typically taking place at the end of July, it is over four days from Thursday to Sunday. You can buy tickets for 1-day, 2-days, 3-days, or all four days.

15. Rooftops

This Chicago Summer Bucket List wouldn’t be complete without visiting a rooftop. On a beautiful summer night in Chicago, a wonderful place to be is on a rooftop. Seeing the city of Chicago from a rooftop gives you a whole new perspective of the city. So have a cocktail while looking out at the city and the lights below.

Some popular Chicago rooftop bars include:

  • Joy District – River North
  • Cindy’s Rooftop – Millennium Park
  • Upstairs at the Gwen – River North
  • Utopian Tailgate – Old Town
  • Kennedy Rooftop – Wicker Park
Rooftop in the West Loop neighborhood
Rooftop in the West Loop neighborhood


This Chicago Summer Bucket List provides the top things to do in Chicago in the summer. With so many things to do and see in Chicago, these travel tips will help you enjoy your visit to this beautiful city. From taking a highly rated architectural boat tour to enjoying the city views from a city rooftop, there is something for everyone to enjoy.

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