Even as summer comes to a close, there’s no shortage of epic activities to enjoy outside in the Windy City. Plus, you’ll want to take advantage of the outdoors while you can, as winter will be here before you know it.
Whether you just moved to Chicago, are renting an apartment in Lincoln Park, or are just passing through – there’s plenty of outdoor adventure waiting for you to take advantage of. To help you get started, we teamed up with Chicago locals and experts and asked for their best recommendations on the top outdoor activities in Chicago – see what they had to say.
1. Visit Jack’s Pumpkin Pop-Up for some fall-themed fun
Nothing says fall quite like pumpkins and corn mazes, and you can find both at Jack’s Pumpkin Pop-Up. Located on Goose Island, the event starts on September 22 and is a great outdoor activity in Chicago for those looking to have a true fall experience.
“Hit the bullseye at Ax throwing, try mining for Gems, search the corn maze for the one-of-a-kind hidden “boo-zy” bar, or simply spend time sorting through over 10,000 pumpkins for your favorite to take home for Spooky Season,” says Chicago resident Elizabeth Bortz. “After showing off your skills at Jack’s infamous carnival games, snack on festive autumn treats and sip seasonal brews & specialty cocktails at full-service bars from pop-up sponsor Samuel Adams while you embrace the true Chicago sweater weather. Whether you’re seeking a striking nighttime Halloween lights display, the ultimate outdoor pumpkin-themed party with dozens of fall-themed Instagrammable memories, or a one-of-a-kind hidden bar in the corn maze, Jack’s Pumpkin Pop Up is always for all ages, and there’s something for everyone.”
2. Spend a day by the Chicago River
If you’re looking for a great place to enjoy the scenery and get some fresh air, look no further than the Chicago River. Its central location in the city makes it a convenient local outdoor getaway.
“I love being outdoors and always make it a point when visiting a new city to explore fun activities I can do outside,” says Cheryl McColgan, founder of Heal Nourish Grow. “Chicago is well known for its shops and restaurants, but the city also has plenty to do outdoors. While visiting family a few weeks ago, we took a cruise on the Chicago River. It was a great way to see the city’s unique architecture and learn some history. Although it seems like a very “touristy” thing, many locals also enjoy it. You can purchase drinks on board, and there is ample seating. We chose the sunset cruise, which still offered plenty of history and facts, but they also have cruises focused on architecture. If you’re looking for fun things to do outdoors in Chicago, I absolutely recommend a river cruise.”
Rachael Martinson of the Midwest Dimples blog agrees.“To see a unique view of our city, get on the Chicago River,” she says. “There are many fun ways to do this, whether through Chicago’s architectural tours, renting an electric boat to self-navigate, or hopping on a water taxi. You’ll get a great taste of how beautiful this city is.”
3. Take in Chicago’s history with a walking tour of the Pilsen Historic District
Chicago was incorporated as a city in 1837. With such an extensive history, the Windy City is home to plenty of culture and historic architecture, and a great way to see this is by walking through the Pilsen Historic District.
“In Chicago, a great outdoor activity that is a must-do is to take a walking tour of Pilsen,” says Chicago local Iesha Vincent of the LivingLesh blog. “You can take the tour yourself, but one of the best ways to tour is with a Chicago Greeter – a tour guide that can lead you to stunning art and historical places free of charge. During a walking tour in Pilsen, you can learn about the thriving culture, marvel at the many murals, and locate hidden gems such as unique boutiques, hidden speakeasies, and more.”
4. Kayak tour on the Chicago River
If you’re looking for outdoor activities that get you on the water, you can sign up for a kayak tour on the Chicago River. It’s a unique way to learn more about the city while also having an epic experience.
“I have a ton of favorite outdoor activities in Chicago, but one of my very favorites is to do a kayak tour along the Chicago River,” says Chicago local Dana Ivy of the I Adore What I Love blog. “I’ve done it during the day, but they have night tours that look awesome too! There’s nothing more incredible than kayaking amongst the city’s skyscraper buildings and lights! It’s a memory-making experience that you will never forget.”
5. Learn about the city’s haunted past with a segway tour
Segways and ghosts are an odd pairing on paper, but in Chicago, they make for a truly unique outdoor activity as you can go on a haunted segway tour of the city.
“The first of its kind in Chicago, this tour showcases the sites of haunted Fort Dearborn, the Iroquois Theater disaster, the Morgue on State, the Dead Alley, and the past home of Al Capone’s haunted yacht,” says Jim Grillo of Here’s Chicago. “Some say that you can still hear the sounds of screaming. We have more haunted places and stories to share, so come along and glide with us if you dare.”
6. Bike along Lake Michigan
One of the benefits of living in Chicago is the ability to enjoy its proximity to the Great Lakes. Biking along the shores of Lake Michigan can be a great outdoor activity that offers picturesque views of the city.
“When I was growing up in Chicago, biking the long stretch of the lakefront was the most fun for me, ” says local blogger Stephanie Pyrzynski of Tinley Park Mom. “There’s an old saying that “driving is the only way to see a country,” and in Chicago, biking is the true way of knowing and falling in love with Chicago. There are so many combinations and stretches of the Chicago lakefront to choose to explore. Plus, you can start and stop at any point in the city where you want to settle for the day too.”
7. Rent boats, jet skis, and more for fun on the water
Lake Michigan offers more than just a pretty view, though. There are several outdoor activities that you can do on the water as well.
“With Lake Michigan calling adventure seekers out to the water, those looking for thrills can just head down to one of Chicago’s water sports rentals and enjoy a day of paddleboarding, boating, kayaking, or canoeing on the lake,” says Marianne Moraru of PropertyShark, a real estate company that operates in Chicago. “For extra thrills, you can rent a high-powered jet ski for those extra wavy days, go wakeboarding and give flyboarding a go. For those interested in challenging activities but not looking for motor-powered activities, you can try a yoga class out on the water on a paddleboard.”
8. Spend a day at one of Chicago’s beaches
Chicago may not necessarily be known for its beaches, but that doesn’t mean they don’t have any to offer.
According to Nausheen Farishta of Globe Gazers, beach lovers will feel at home in this midwestern metropolis. “Spend time at the beach,” she says. “Picnic on the beach with a view of the Chicago skyline, or visit a beach restaurant like Whispers at Oak Street Beach.”
You can also enjoy outdoor activities at North Avenue Beach.
“Whether you love outdoor sports, chilling with friends, or just want to escape from city life, North Avenue Beach is always the right place,” says Chicago local Alina Schweiger from the World of Lina blog. “In summer, you can take a dip in the lake or sunbathe, whereas, in other seasons, the lakeshore path is perfect for rollerblading, biking, or a casual stroll. A plus point is the stunning skyline view you can enjoy while enjoying a picnic or having a conversation with friends.”
9. Take in the scenery on the Chicago Riverwalk
For a relaxing outdoor activity in the city, take a stroll down the Chicago Riverwalk. It’s located on the south bank of the Chicago River and stretches from Lake Michigan to Lake Street. Take a leisurely stroll while soaking in the sights and sounds of the Windy City.
Chicago local Tanya Taylor of the Travels & Treasures blog is a huge fan of the Chicago Riverwalk. “Along the path are outdoor restaurants and some of the most interesting architecture and art sculptures. You’ll find family-friendly activities like a museum, kayaking, and boat tours. In the evening, couples can enjoy a romantic sunset cruise. There is something for everyone. Also, don’t miss Art on the Mart.”
10. Hang out at Harvester Park
Chicago has no shortage of outdoor spaces that locals can enjoy. Harvester Park covers 37 acres and includes a playground, tennis courts, sand volleyball, and more, making it the perfect place for outdoor activities in Chicago.
“You don’t have to travel across the country to get a taste of the landmarks along Route 66,” says Chicago resident Annie Tandy of the Kidlist blog. “Harvester Park in Burr Ridge has a playground dedicated to turning the journey into an enjoyable experience where you can whoosh down a tube slide from the top of the Willis Tower, balance on surf boards like you’re in Santa Monica, bounce on in-ground trampolines that imitate the sinkholes in Santa Rosa, play in a replica of the Blue Whale of Catoosa, and more. It’s a space filled with color and things to explore that you and the kids in your life will love. Harvester Park has the Route 66 playground and a music barn, sand play area, fossil dig, treehouse, and water play area in this sprawling park filled with recreation opportunities.”
11. Find peace and tranquility at the Garden of the Phoenix
It can be hard to find peace and quiet in a large city like Chicago, but the Garden of the Phoenix, also known as the Osaka Garden, is the perfect outdoor space for rest and relaxation.
“Tucked behind the Museum of Science in Industry, Garden of the Phoenix offers a peaceful oasis in the heart of the city,” according to the Chicago on the Cheap blog. “An authentic Japanese garden, this green space boasts a waterfall, stone pathways, and a moon bridge that stretches over a lagoon. Fragrant cherry blossom trees are a popular attraction during the spring, but Sky Landing, Yoko Ono’s gleaming first public artwork, draws visitors all year round.”
12. Take advantage of restaurant patios and enjoy a meal outdoors
Even as we transition from summer to fall, Chicago is still a perfect place to enjoy a nice meal outside. Enjoy fresh, delicious food while you get some fresh air.
“With Fall looming, our time for al fresco dining is coming to a close,” says Jessie Eisner-Kleyle from Becovic, a Chicago real estate firm. “Get all of the patio time you can at your favorite restaurants and their patios -there are plenty of Chicago restaurants with outdoor seating to choose from. Little Bad Wolf is one of our favorites.”
13. Experience outdoor activities for all ages at Maggie Daley Park
No matter how old you are, there’s something fun to do at Maggie Daley Park. From a mini-golf course to a playground and climbing wall, there’s truly something for everyone here.
“For the ultimate outdoor activity in Chicago, look no further than Maggie Daley Park,” says local blogger Cheryl Eugenio of O the Places We Go. “The park provides an urban oasis right in the heart of the city with a climbing wall, Chicago-themed mini golf, and the amazing Play Garden. The sprawling 3-acre playground is undoubtedly a kid favorite with various equipment, from slides and swings to different themed areas, including an Enchanted Forest and a splash area. Visiting Maggie Daley Park is a family favorite outdoor activity In Chicago.”
14. Keller’s Farmstand
If you’re looking to get outside and escape the big city, visit Keller’s Farmstand in nearby Oswego, IL. Take in the beautiful scenery or enjoy some fresh farm-to-table produce like sweet corn and apples.
“Keller’s Farmstand is a local day trip that everyone will enjoy,” according to the Chicago Suburban Family blog. Come any day for apple picking at one of Chicago’s largest orchards, or pick a pumpkin in our huge pumpkin patch. On weekends, explore our eight-acre corn maze, bring the kids to our Farmland playground, enjoy storytelling with a mime artist, and see the horses and animals. Our Farmstand is open daily with unique foods and homemade donuts on weekends. It’s safe outdoor fun for the whole family.”
15. Take in the local music scene at Unsigned: Chicago’s Indie Showcase
Music lovers won’t regret moving to Chicago after attending one of many live music events hosted in outdoor venues throughout the city. Unsigned is a great opportunity to familiarize yourself with homegrown artists in Chicago.
“Unsigned: Chicago’s Indie Showcase, is an outdoor, acoustic, open-mic style showcase,” says Chicago local Analisa Terenzio. “This month’s featured artist is ‘Blue Ribbon Glee Club’ and is hosted by ‘Superfrye.’”
16. Check out various house music performances throughout the city
If you’re a fan of house music, then Chicago’s the place for you. As the birthplace of house music, the city does not lack opportunities to catch performances from local artists.
“Did you know that the electronic music genre called “House” originated in Chicago in the ’80s?” says Vojtech Schlesinger of Ride in Bliss, a limousine company that operates in Chicago. “Every year, usually a weekend in September, there is a festival in Millenium Park that focuses on the past, present, and future of house music with live & DJ performances, panel talks, workshops, and lectures held at various locations around the city. And if that isn’t enough, or you are not in town during that weekend, you can visit Honorary Franklin Knuckles Way, which remembers the legend of this music. It is also near the original site of the “Warehouse,” the club where house music originated.”
You can also check out Queen, a weekly house music showcase in Chicago.
“Join smartbar sweethearts and musical contortionists Derrick Carter, Michael Serafini, and Garrett David for an evening of only the rawest Chicago house music served up by the pros,” says Genna Saccomonto of MetroChicago, a local live music venue. “This year celebrates 40 years of Metro/smartbar and ten years of Queen. Come bask in the atmospheric vibrations, dance until you drop, and celebrate one of the best parties out of Chicago.”
17. Have an epic experience at The Forge: Lemont Quarries
The Forge: Lemont Quarries is a 300-acre adventure park in nearby Lemont, IL, about a half-hour drive from Chicago. With activities ranging from ziplining and laser tag to kayaking and mountain biking, The Forge provides plenty of heart-pumping outdoor activities in the Chicago area.
“Get outdoors for the ultimate climbing and ziplining experience in the Chicagoland area,” says Brad Donati, the marketing & community director at the park. “Located in Lemont, The Forge: Lemont Quarries is just 22 miles southwest of Chicago. In 2022, the park was recognized by USA Today’s 10Best as one of the top aerial adventure parks in the county. Experience over 200 ropes course elements, rock climbing, bouldering, rappelling, and ziplining as part of the Climb & Zipline Adventure.”
18. Check out the Windy City Smokeout for beer, barbeque, and country tunes
Good food and good music aren’t hard to find in major cities, but you don’t often find them in the same place. The Windy City Smokeout easily checks both boxes. The event is hosted just outside the United Center and is a perfect outdoor activity in Chicago if you’re a fan of country music, food, or both.
“The ACM award-winning Windy City Smokeout is returning to Chicago Thursday, July 13 through Sunday, July 16 for its tenth year,” says Izzy Shaindlin, who helps to organize the event. “Hosted by Chicago’s BBQ destination, Bub City, and ACM award-winning Joe’s on Weed St., The Windy City Smokeout will bring an impressive lineup of country music stars and up-and-coming talent to the stage, including Zac Brown Band and more.”
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