City Guide / Chicago

A Local’s Guide to the 15 Best Outdoor Activities in Chicago

By Kailey Hansen | Oct 11, 2022
Boat sailing the Chicago River, one of the best outdoor activities in Chicago, Illinois.

Chicago might be known for its restaurants, museums, and performing arts, but it also offers outdoor events and attractions to keep its residents enjoying the fresh air. No matter the season, there is something for everyone, such as spending your summer kayaking in Lake Michigan, your spring on your bike zooming down a lakefront trail, your fall enjoying a Bears game, and your winter perusing a cozy German market.

Whether you prefer to stay active or hunker down for a bite to eat on a patio (or both!), the Windy City does not disappoint, with its lush green spaces and gardens, diverse street festivals, beaches, outdoor events, and more.

As a local who has lived in the area my whole life, here are 15 of the best outdoor attractions and events to experience after moving to Chicago:

1. Sail the Chicago River

The Chicago River and downtown Chicago skyline USA

Downtown Chicago is home to some of the city’s best architecture (and tallest buildings!). With the Chicago River winding through this major metropolis, locals have the unique opportunity to set sail in the middle of the city. Hop aboard a Wendella Boat Cruise for a guided tour of the city’s most prominent skyscrapers and their history.

The adventurous at heart can also opt for a kayak tour with one of the many boat rentals. Paddle through the city’s center at sunset or watch a fireworks show illuminating the river!

Tips From a Landing Member

“If you have an afternoon and about $50 to spare, I highly recommend taking an urban kayak for a spin. Just make sure to bring a waterproof phone case (or buy one from the kayak rental) so you can snap pics on the boat without the risk of drowning your phone!”

— Becca, “Tales of a Digital Nomad: How I Spent the Summer Living in Chicago

2. Stroll through street festivals

When good weather hits, expect to find a plethora of festivals located outdoors throughout the city. Almost every neighborhood has them, from popular downtown festivals such as Taste of Chicago (come hungry!) and Chicago Blues Festival to local street fairs such as Burger Fest in Roscoe Village or Lakeview East Festival of the Arts in Lakeview. While each respective festival differs, you’re bound to find good eats, live music, fun activities, plenty to drink, and amazing local vendors.

3. Enjoy the Chicago Air & Water Show

One of the most beloved annual events is the Air & Water Show, which takes place each summer and draws in massive crowds. Snag your spot early and spectate breathtaking showcases by the U.S. Navy Blue Angels, U.S. Navy Parachuting Team, U.S. Coast Guard, and more. The show includes stunning performances from aircraft and boats and is an item to add to your bucket list.

4. Snap a photo at “The Bean”

Downtown skyscrapers reflected in the mirror surface of The Bean sculpture in Millennium Park in Chicago, Illinois.

Post a picture at The Bean or your visit to Chicago didn’t happen—just saying. Perhaps the most iconic landmark in the city is the massive, reflective bean-shaped sculpture that sits in the middle of Millennium Park. Formally known as “Cloud Gate,” this destination is one of the most popular and is a must when you’re exploring downtown. The Bean is also located by a number of other outdoor landmarks that are photo-worthy, such as the Art Institute lions down the street or Buckingham Fountain a few blocks over.

5. Spend a day at Millennium Park

Millenium Park in Chicago

Smack dab in the middle of the Windy City’s bustling epicenter lies Millennium Park. Spanning 25 acres, this park is home to public artwork, an ice skating rink during winter, and a gorgeous greenspace that features fun activities throughout the year. Catch an outdoor movie in the park during summer, picnic while you enjoy annual concerts from staple performing arts institutions (such as Broadway In Chicago, the Lyric Opera, or the Chicago Symphony Orchestra), or wander an art market. No matter the outdoor activity or event of your choosing, you’ll get a great view of the city’s gorgeous architecture during your time at the park.

6. Visit the Chicago Botanic Garden

View of Chicago Botanic Garden, Glencoe, Illinois, USA

Just outside the city in the suburb of Glencoe lies a property with 27 unique gardens to explore. The Chicago Botanic Garden is home to an English Welsh garden, Japanese garden, rose garden, sensory garden, and more. It’s a great way to get out of the hustle and bustle of the city and experience the serenity of nature. Plus, there are a variety of fun events hosted throughout the year such as outdoor fitness classes and a light display during winter.

7. Get active on the Lakefront Trail

Early morning view of the Michigan Lakefront Trail in Chicago city, Illinois, USA.

While cities might get a reputation for not offering good walking trails, Chicago boasts the Lakefront Trail which is, well, lakefront. You’re going to get some amazing views of Lake Michigan while walking, jogging, or biking. This pedestrian path travels 18 miles along the coastline and is a hotspot during the warmer months, particularly for residents with bikes. Once you’ve gotten your steps in, visit a neighborhood park for a bit of rest and relaxation or hang out at one of the city’s beaches.

8. Catch a game

If you’re living in the Windy City, it’s a crime not to experience game day at least once. Grab your beer and your Chicago-style hot dog and settle in at one of the iconic stadiums. Catch a baseball game at the historic Wrigley Field, home to the Cubs, or a White Sox game at Guaranteed Rate Field. During football season, you can bundle up and head to a Bears game at Soldier Field, located downtown with a gorgeous view of the skyline.

Pro tip: There is a giant parking lot at Guaranteed Rate Field that is the perfect spot for tailgating!

9. Have a picnic at Oz Park

Colorful Plants and Trees at Oz Park in Chicago

Amid happy hours and boutique shopping in the charming northside neighborhood of Lincoln Park you will find Oz Park, a 14-acre property with a community garden, tennis courts, basketball courts, a playground, and plenty of space to relax. It’s the perfect place to bring a book and read or settle in for a picnic. The park is known for its “Wizard of Oz” theme, as guests can enter the “Emerald Garden” to find statues of Scarecrow, Tin Man, Lion, and, of course, Dorothy and Toto. There is also an easy bike loop in the park if you’re looking to get an outdoor activity in.

10. Dine outside on the Chicago Riverwalk

Chicago Riverwalk sign at twilight

While the downtown sidewalks can get busy, especially during the work week, there is a path specifically created for strolling at your leisure. Take a walk along the iconic Chicago Riverwalk, where you’ll find stunning architecture along the gorgeous Chicago River and plenty of places to grab a bite to eat. It’s of the coolest areas to snag a seat at an outdoor patio—from City Winery to Chicago Brewhouse to Island Party Hut Tiki Bar and Grill.

11. Spend an afternoon at Navy Pier

Chicago city downtown urban skyline with skyscrapers over Lake Michigan with cloudy blue sky.

Known as Chicago’s “lakefront treasure,” a visit to Navy Pier truly does have something for everyone. The pier itself spans an impressive 3,300 feet and is a great place to stroll outside on a sunny day. See the city from a bird’s-eye view with a towering Ferris wheel, dine on a patio or rooftop, or catch live music—all with plenty of waterside views.

12. Spend an afternoon on a Lake Michigan Beach

You don’t need an ocean to experience a beautiful day on the coast. This city is home to a number of fun beaches along its shoreline, making a day at the beach the perfect way to soak up some sun. Set up shop on the sand and just hang out, rent a kayak and set sail, or visit a dog-friendly area for a date with your furry friend. There are a ton of ways to experience Chicago’s beaches: for example, North Avenue Beach offers lakeside yoga sessions, while Montrose Beach permits kiteboarding for thrill-seekers.

13. Shop along the Magnificent Mile

Chicago Magnificent Mile sign

A stay in Chicago is not complete without a walk along Michigan Avenue, one of the most notable streets in the city. This stretch is where you’ll find the Magnificent Mile, a truly magnificent shopping and dining district with plenty of activities and fun things to do. On a warm weather day, pop into shops, grab a bite to eat, or visit landmark buildings such as the 1,128-foot-tall John Hancock Center.

14. Admire the animals at the Lincoln Park Zoo

Male Lion. Lincoln Park Zoo. Chicago, IL.

Lions, penguins, and pythons in the middle of the city? That’s what you’ll find at the Lincoln Park Zoo. Located in Lincoln Park, this family-friendly facility offers hundreds of animals and plant species, a calendar of epic special events (such as a craft beer festival for adults), and educational conservation programs. Plus, admission to the Lincoln Park Zoo is free!

15. Experience the holidays outdoors

Long exposure photograph of the Chicago Christkindl Holiday Market. Vendors from around the world sell holiday themed products.

There is something magical about winter in the city. Sure, midwest winters are cold (and I mean cold), but the yuletide festivities are not to be missed. Enjoy a date night ice skating at Millenium Park right under The Bean, or braving the one-of-a-kind rink in Maggie Daley Park where guests can skate through a winding “ribbon” path.

Next, you’ll want to venture down State Street, where you will encounter the cheery holiday displays lining Macy’s department store windows, and then visit the city’s Christmas Tree just a few blocks over. Perhaps the most popular outdoor activity during the holidays is the German Christkindlmarket in Daley Plaza, where you can explore booths selling handcrafted ornaments, woodwork, and apparel before ordering yourself a much-needed cup of mulled wine.

Thinking about moving to Chicago?

If you’re looking to experience the great outdoor activities and attractions of Chicago, make the Windy City your temporary home with a Landing membership. Members enjoy flexible leases and fully furnished apartments in some of the most vibrant and exciting cities across the country. Browse Landing’s available apartments in Chicago, IL, today!

Kailey Hansen

Kailey Hansen is a freelance writer and communications professional based in the land of deep-dish pizza. She has lived in both the city and the suburbs of Chicago and enjoys writing about the amazing things the Windy City has to offer. When she's not dishing about the best places to grab a slice of deep-dish, you can find her writing (and obsessing) about binge-worthy TV shows for BuzzFeed and why cats are the best (and absolutely outlandish creatures) for Rover's blog, The Dog People.