Chicago, IL

7+ Ideas to Do in Chicago This Spring and Summer

Rene Cizio

Taking a staycation in Chicago or maybe visiting for a few days? Chicago summer is an awesome time of year to explore the city because so many activities become available.

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Photo by the author

Whether you’re visiting the city for the first time or a long-term resident, chances are there’s something on this list for you. Even if you’ve done all of these things before, they’re never the same twice, so get out and try them again.

Walk the 606

The 606 is a super cool elevated walking, biking, running trail that spans three miles on the city’s northwest side.

Also called the Bloomingdale Trail after the old abandoned train line it was created from. It’s now a green space that features various trail systems and event spaces.

The 606 connects to six parks across four different neighborhoods and bringing together arts, history, and design so that any visit to the 606 is a multi-sensory experience.

I particularly love the street art and murals you’ll find along the entryways.

There are 12 access points to enter the 606 about every quarter-mile throughout Wicker Park, Bucktown, Humboldt Park and Logan Square.

The project is named for Chicago’s 606 zip code. Hands up 606ers.

Find it along Bloomingdale Ave (1800 N), from Ashland Ave (1600 W) on the east to Ridgeway Ave (3750 W) on the west.

Lincoln Park

Lincoln Park is a 1.188-acre garden jewel in the middle of the bustling city. You’re able to get to it from many access points and, with many sights to see, have many reasons for doing so.

The park is often bustling with people sunning themselves in the grass, playing sports, riding bikes, walking, jogging and partaking in various outdoor activities. You won’t be alone in Lincoln Park.

Interestingly, from 1843-1859, the park was Chicago’s City Cemetery with thousands of graves. In the 1860s they were all exhumed and moved elsewhere to build out the park for the public, but many graves were forgotten and found in later developments. This just makes it great for a late-night Halloween stroll, IMO.

The only remaining obvious evidence of the cemetery is the Couch Memorial, a big freestanding tomb near North and Clark streets.

In the Park You’ll Also Find

  • The Lincoln Park Zoo
  • Lincoln Park Conservatory
  • The Chicago History Museum
  • The Peggy Notebaert Nature Museum
  • The Alfred Caldwell Lily Pool
  • The North Pond Nature Sanctuary
  • Lincoln Park Archery Range
  • North Avenue Beach and Oak Street Beach
  • Five playgrounds
  • A bunch of statues

Find Lincoln Park between 500-5700 N. Lake Shore Drive.

Tall Ship Sailboat

Take in the world-famous Chicago skyline and enjoy Lake Michigan from a massive sailboat on The Tall Ship Windy.

The Tall Ship Windy is a 148-foot, traditional four-masted gaff topsail schooner that sets sail from Navy Pier multiple times a day.

They host a variety of different themed tours including a sunset sail with views of the skyline, an informational architecture sail and a pirate sail.

While on the boat, they’ll tell you all about its construction and even let you help raise and lower the sails. I helped raise one of the forward sails. It was a lot harder than it looks, so if you’re thinking of volunteering, be prepared. We also sang pirate songs.

Find it at Navy Pier.

Kayak the Chicago River

A summer day in Chicago is not complete unless you’ve spent some time on the river. Renting a kayak and seeing the famed Chicago architecture from the water itself is incomparable.

There are various tour companies that rent kayaks and paddleboards, or you can opt for a guide. Guides are a good choice if you’re not familiar with the river and its backward current and traffic patterns.

I kayaked with Kayak Chicago on one of their architectural tours through downtown Chicago. There were a few inexperienced kayakers, but the tour began with a lesson, and by the end, they were pros (just like me 😉

The guides had stories about the buildings that I’d never heard (and I’ve heard most of them) and even shared a wealth of information about Goose Island (ever heard of the beer?). It was a super fun day on the water.

Find them at 1220 W. Le Moyne St.

Riverboat Architecture Tour

The Chicago Architecture Center offers the city’s best boat tour. There’s also a series of more than a dozen other fabulous architecture tours – many that you can do on foot.

The river tour, held on Chicago’s First Lady riverboat, is about 90 minutes long. It packs 100 years of fascinating Chicago history as told through the architecture.

You can sit inside the boat or on the roof deck. A guide with a microphone will tell you about 50 different buildings that line the Chicago River as you tour through the city.

A Chicago summer trip is not complete until you’ve gotten on the river. Plus, if you’re interested in the buildings that make up this great city, there is no better way to see to them. The CAC is THE authority on Chicago architecture.

They offer the tour during the day or at night. I recommend the sunset tour as you can get photos in the daytime, sunset, and night.

Find the center at 111 E. Wacker Dr.

Bonus: Two Awesome Chicago-Only Museums

Ernest Hemingway Birthplace

In Oak Park, just a few miles outside of downtown is the house where celebrated American Pulitzer Prize-winning author Ernest Hemingway was born in 1899.

Hemingway lived in the house for his first six years and the museum focuses on that time period. The scheduled, docent-led tours take about 45 minutes. It’s about the family, the era, and the influence each had on shaping Ernest and the writer he would become.

Enjoy the Chicago summer and take a walk a few blocks away. There you can see his boyhood home (600 North Kenilworth Avenue), which is now a private residence.

Bonus: Right across the street is a Frank Lloyd Wright-designed house.

Visit Hemingway’s Birthplace at 339 N. Oak Park Ave, Oak Park, Illinois, 60602, and support them by buying one of papa’s books in their little gift shop.

Frank Lloyd Wright home and studio tour

Just blocks away, also in Oak Park, is the Frank Lloyd Wright Home and Studio. Isn’t it fascinating that two creative geniuses grew up in the same neighborhood? (You know Walt Disney was from here too?!?! what is in the water?!?)

The 45-minute guided tour is of Wright’s Home and studio, where he lived and worked in the early 1900s. He developed the first uniquely “American architecture” known as the “Prairie Style.”

During the tour, you’ll see many early, unique features of his style, including stained glass, built-ins, furniture designs, the architect’s studio, and original woodwork and sculpture.

While you’re there, make sure you tour the gardens and see the many sculptures he created outside of the home.

Frank Lloyd Wright neighborhood tour

Frank Lloyd Wright also designed many homes and buildings in the surrounding neighborhood, which is now a historic district. Buy a map and treat yourself to walk the picturesque Chicago summer walk along tree-lined streets filled with one-of-a-kind homes.

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Digital nomad, solo road tripping through the USA in my van. I write about travel, adventure, culture, and self-improvement. Pictures on Instagram @renecizio

Chicago, IL
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