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27 Fabulous Outdoor Activities in Chicago This Summer

Summer in Chicago is nothing short of spectacular. Winter has finally melted away, replacing all of its depressing gray tones with shady green trees, calm blue water, and colorful flowers. From lush parks to sweeping waterfront views and from relaxing cruises to lively rooftop bars, these are the best outdoor activities in Chicago.

Hotels.com asked me to share my favorite things to do outside in Chicago in the summertime.

While I’ve never been colder (or more miserable) than exploring Chicago in the winter, summers in the Windy City are another story! Rather than chunks of ice floating toward a grey horizon, boats of all shapes and sizes fill the blue waters. Instead of bundled-up figures racing to their destinations in the arctic cold, sunbathers relax on colorful beach blankets. Whether you’re drawn to the water, want to see the sights, or prefer to relax at a rooftop bar, these are the best outdoor activities in Chicago in the summer.

Have You Visiting Chicago in the Summertime?

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Sage Advice: Whether you stay on the Magnificent Mile, along the waterfront, or in the suburbs, find the perfect Windy City accommodation with one of these fabulous hotels in Chicago, Illinois. 

1. Take an Architectural Tour

If you’re visiting Chicago in the summer for the first time, an architectural boat tour is a can’t-miss experience. Typically about an hour long, you’ll glide past some of Chicago’s most famous landmarks, including Willis Tower (the tallest skyscraper in Chicago), the Wrigley Building, and Navy Pier.

If you want to step inside some of Chicago’s most magnificent buildings, this architectural boat tour gives you the best of both worlds. After admiring the Chicago skyline from the water, set out on foot to see the art deco interior of the Merchandise Mart, Chicago’s Union Station, and several other impressive buildings on and near the Chicago River.   

Sage Advice: If you’ve already taken an architectural boat tour, consider a different boating experience. You’ll discover a variety of options, including food cruises and sunset sails

2. Take a Water Taxi

A yellow water taxi in Chicago

Sure, you can easily and affordably explore Chicago on foot or by taking the train, but a water taxi is the perfect summer transportation. And for less than a deep-dish pizza, you can hop on and off the water taxi all day!


3. Hit the Beach

People who live on the East or West Coast often buy into the popular Midwestern stereotype that there aren’t any beaches in the middle of the country. However, Lake Michigan provides miles of shoreline and approximately 25 sandy beaches in the Windy City.

Sage Advice: If you’re visiting Chicago with your furry best friend, the northern tip of Montrose Beach is dog friendly.

Related Article:  Petiquette 101:  Dog Etiquette Rules to Follow When Traveling with Your Dog

4. Kayak Down the Chicago River

Red and yellow kayaks in the water

If you’d rather be on the water, then rent a colorful kayak and see the city from a truly unique perspective. You can also paddle with purpose by joining conservation experts from Shedd Aquarium. Through their Kayak for Conservation Program, you’ll learn about the Chicago River as you watch for wildlife and help remove litter.

Or kayak down the Chicago River on Wednesday and Saturday nights during the summer. From your unique spot on the water, you’ll get to experience the Navy fireworks display like never before!

5. Stroll Along the Riverwalk

Chicago Riverwalk sign with Wrigley Building in the background

Stretching more than a mile along the water, the Chicago Riverwalk is a pedestrian pathway on the south bank of the Chicago River that features four distinct districts. Enjoy the fresh air, sunshine, and scenery by taking a leisurely walk or simply sitting at a bar or restaurant with a view.

For insight into the art, architecture, and history of the area, take this guided walking tour that includes stops at the Wrigley Building, Tiffany Dome, and more. Or explore at your own pace with this self-guided walking tour of the Chicago Riverwalk.

Sage Advice: You can take the water taxi to the Chicago Riverwalk.

Related Article:  Best Riverwalks in the US (East of the Mississippi)

6. Walk, Hike, or Bike the Lakefront Trail

To spend more time in the sunshine along Lake Michigan, walk, hike, or bike the Lakefront Trail. Stretching from Kathy Osterman Beach to the South Shore Cultural Center, this 18-mile path provides pedestrians and cyclists with dedicated lanes. If you travel the entire length of the Lakefront Trail, your journey will take you past Lincoln Park, Navy Pier, Shedd Aquarium, the Museum of Science and Industry, and many other Chicago attractions.

Sage Advice: Here’s a fast and easy way to rent a bike in Chicago.

7. Explore The 606

The Bloomingdale Trail (also known as The 606) in Chicago

What it lacks in lakefront views, The 606 (also known as the Bloomingdale Trail) makes up for in coolness factor. Traveling due north out of Humboldt Park, what was once an abandoned rail line is now a 2.7-mile multi-use recreational trail for walkers, runners, and cyclists that is steeped in history and accented with public art.

8. Try an Interactive Scavenger Hunt

One of my favorite ways to get the lay of a new land is through an interactive scavenger hunt. They flexibly fit into any itinerary and can be completed at your pace. Check out the Chicago Loop, meander along the Magnificent Mile, or spend a day at the zoo with these popular Chicago scavenger hunts.

9. Get into Chicago's Gangster Past

Chicago was once the stomping grounds of notorious gangster Al Capone. Dive into the Windy City’s dark (and spooky) past with a gangsters and ghosts tour. Hear what Chicago was like when speakeasies dotted the city and bootleggers used secret underground tunnels to keep the bar stocked. And visit several downtown destinations that are rumoured to be haunted.

10. Wander through Grant Park

Buckingham Fountain in Grant Park with the Chicago skyline in the background

Providing more than 300 acres of lush greenspace along Lake Michigan less than a mile from the heart of Downtown Chicago, it’s easy to see how Grant Park earned the nickname “Chicago’s Front Yard.” Named after President Ulysses S. Grant, you’ll find some of Chicago’s most Instagrammable spots here, from the massive, iconic, 1.5-million gallon Buckingham Fountain to the quirky Crown Fountain that features everyday Chicagoans streaming water from their mouths. And in the northwest corner of Grant Park (known as Millennium Park), you’ll find the famous shiny silver bean whose official name is Cloud Gate.

Sage Advice: If you’re exploring the Windy City on an indoor activity kind of day, a CityPASS will save you money on Chicago’s top attractions. Enjoy the phenomenal exhibits at the Field Museum, study the skies at the Adler Planetarium, admire the masterpieces on display at the Art Institute of Chicago, dive into the Shedd Aquarium and more for less with the Chicago CityPASS.

Related Article: See How Much You’ll Save with a Chicago CityPASS

11. Visit a College Campus

Cadahy Science Hall at Loyola in Chicago

Chicago is home to several colleges and universities, including The University of Chicago, DePaul University, and Loyola University. No matter what your alma mater, reminisce about your college days by strolling the tree-lined paths and admiring the stately buildings.

12. Admire Frank Lloyd Wright’s Work

Robie House in Chicago

Just east of The University of Chicago campus, you’ll find one of the best examples of Frank Lloyd Wright’s Prairie-style homes when you visit the Frederick C. Robie House.

You can admire the three-story home’s long brick walls and floor-to-ceiling stained glass windows on a self-guided tour of the exterior. Or step inside for a guided tour that shows off the architect’s love of long, angular lines carried through to the rooms and high-backed furniture. 

13. Watch a Movie in the Moonlight

Sprawl out on a blanket or sit up straight in a camp chair while taking in a family-friendly movie in a participating Chicago Park. Or enjoy the retro renaissance surrounding drive-in movie theaters by cruising into a ChiTown Movie.

14. Float Like a Butterfly

Chicago’s Peggy Notebaert Nature Museum includes a 2,700-square foot greenhouse filled with tropical plants, soothing water features, and more than 1,000 butterflies.

15. Admire the Animals

Located just south of the Peggy Notebaert Nature Museum, the Lincoln Park Zoo is one of the oldest zoos in the US. Even more exciting, there is no admission fee to admire the animals or explore the surrounding gardens. 

16. Go Bird Watching

A plover with chick

The wooded strip of land that curves out into Lake Michigan just south of Montrose Beach is a bird sanctuary that provides refuge for waterfowl, shorebirds, migrating flocks, and other feathered friends. While you’re sure to see hawks, herons, and ducks year-round, spring and fall (rather than summer) are the best time to view migrating birds.

Related Article: 100+ Duck Quotes That Will Quack You Up

17. Soak in Serenity at the Graceland Cemetery

Tall white columns of a monument at Graceland Cemetery in Chicago

At first glance, a cemetery may not seem like a fabulous outdoor activity. But the Graceland Cemetery in Chicago’s north side is unlike any other. It’s the final resting place of many Chicagoans, from the city’s early settlers to political leaders and from sports heroes to prominent business leaders. Winding paths lead to beautifully architected memorials engraved with names you’ll see on Chicago hotels and street signs and convention centers — Palmer, Wacker, McCormick — and thousands of trees planted across the 120-acre site helped it become a certified arboretum.  

18. Window Shop on the Magnificent Mile

The Magnificent Mile street sign with the American flag and a building in the background

Beginning near The Wrigley Building and stretching to Lake Shore Drive, this stretch of Michigan Avenue filled with hotels, restaurants, and shops is known as The Magnificent Mile.

19. See the Start of the Mother Road

Sign in downtown Chicago markting the start of Route 66

On the other side of the Chicago River, less than a mile south of The Wrigley Building, you’ll find the start of Route 66 marked by a sign near the intersection of Michigan Avenue and Adams Street. Starting in the late 1920s, Americans embarked from this point on a 2,450-mile journey through eight states on the Mother Road to reach the Pacific Coast.

20. Discover a Moment of Zen

An arched Japanese footbridge stretching across blue water in Jackson Park in Chicago

On a wooded island in the lagoon south of the Museum of Science and Industry, you’ll discover a peaceful Japanese garden with elements dating back to the World’s Columbian Exposition in the late 1800s. Named the Garden of the Phoenix after the temple constructed by the Japanese government for the expo, it now includes “Skylanding,” 12 steel lotus petals designed by Yoko Ono, John Lennon’s widow

Sage Advice: Despite its name, the Chicago Botanic Garden is about 40 minutes north of the city in Glencoe. Although it is a big of a trek from downtown Chicago, the 385-acre park is absolutely magnificent in the summer (and well worth the trip).

21. Root for the Home Team

Sign outside Wrigley Field in Chicago

Although Chicago is home to two major league baseball teams, I have yet to meet a White Sox fan. Even before they ended a 108-year drought by winning the World Series in a nail-biter of a seventh game in 2016, the locals always seemed to be Cubs fans. So one of the best summertime activities in Chicago is to explore the Wrigleyville area and then sit back with peanuts, Cracker Jack, and a cold beer to cheer on the home team at a Cubs game.

22. Follow the Yellow Brick Road

Although L. Frank Baum’s most famous book takes place in Kansas, he penned the tale near Chicago’s Lincoln Park neighborhood. That’s why you’ll discover a collection of statues featuring a scarecrow, tin man, cowardly lion, and pigtailed farm girl in ruby slippers at Oz Park.

23. Scout for Street Art

Photo by Carol Guttery

In addition to gleaming lotus petals and whimsical statues, keep an eye out for magnificent murals and other public art displays throughout Chicago. One of the most popular murals in Chicago is the “Greetings from Chicago” postcard mural on the northwest side of 2226 N. Milwaukee Ave. Along the Magnificent Mile, keep an eye out for a Warhol-like mural of Marilyn Monroe at the intersection of Michigan Ave and Erie St. Another famous mural features a moose blowing a giant pink bubble of gum at 33 E. Congress.

Use this fantastic article by Wayfaring Views to explore the street art in three Chicago neighborhoods, including some of the city’s most popular pieces.

Sage Advice:  If you take the “L” from Chicago Midway to downtown, watch for the moose mural on the left (west) side of the train.

24. Buy Fresh Fruits, Veggies, and More at a Farmers Market

Boxes of peaches for sale at a farmers market in Chicago

Summertime in Chicago brings several farmer’s markets with locally grown produce, freshly baked goods, cut flowers, live music, and more. The longest-running farmers market is the City Market at Daley Plaza, a short walk from the Bean in Millennium Park. The Maxwell Street Market is a Sunday-only affair, with Mexican food vendors who draw a crowd with handmade tortillas and tamales. And the Green City Market in Lincoln Park is Chicago’s largest farmers market that boasts its own cookbook.

25. Sip a Beer in the Garden

A flight of beer samples in an iron rack

Spend a sunny afternoon in Chicago at one of its beer gardens, sipping some suds, catching up with friends, and watching the world go by. The Northman Beer & Cider Garden on the Chicago Riverwalk combines great beer with spectacular water views. Just south of the Rosehill Cemetery, Half Acre Beer Co also offers excellent beer and a lovely outdoor space.

26. Hit a Hot Dog Stand

A Chicago-style hot dog with French fries and a beer

If you’re visiting a city known for its own special breed of (hot) dog, be sure to give it a try! What makes a Chicago-style hot dog so special? It’s so much more than a regular frankfurter in a long bun! For starters, the hot dog is placed in a steamed bun dusted with poppy seeds. Then toppings are added in this order:  yellow mustard, sweet pickle relish, diced onion, sliced tomatoes, thin pickle spears, spicy sport peppers, and a sprinkle of celery salt.

27. Cap Off the Night with a View

Enjoy the sights and sounds of Chicago at night from the vantage point of a rooftop bar. Located on the third floor of the Festival Hall at the Navy Pier, pair the adult beverage of your choice with breathtaking views of Lake Michigan and the Chicago skyline at Offshore Rooftop & Bar. With 36,000 square feet of indoor and outdoor space, Offshore is the nation’s largest rooftop bar, and there’s hardly a bad seat in the house!

What are Your Favorite Outdoor Activities in Chicago in the Summertime?

What do you enjoy most about the Windy City in the summer? Any additional tips and tricks to pass along? Share your experiences in the comments section below.

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4 thoughts on “27 Fabulous Outdoor Activities in Chicago This Summer”

  1. Jenn | By Land and Sea

    Chicago is one of those cities we have talked about visiting, but have never gone. Part of that is because I’ve always wondered what there is to do here. I appreciate this list of ideas! It appears there are a lot of great things in the summer months!

  2. My daughter was an exchange student in Chicago and, of course, I visited her. It was in September and still very summery and nice so that we got to explore the city and I have really fond memories. Sadly, by then, it was too cold to enjoy lake Michigan. I particularly loved the artsy side of the city 😉

    1. Oh, how fun! Chicago is such a great town, but I agree that Lake Michigan would be too cold in September.

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