Featuring guest writer Michael Williams. Photography by Flo
From colorful blooms to blankets of snow, Chicago is lucky to experience a full spectrum of seasons. Yet, it can be hard to appreciate the shifts in nature and all their glory in a city that offers endless indoor activities.
The good news is that there is plenty to do outside in Chicago too. Outdoor Chicago activities will provide you with fresh air and a dose of vitamin D. Besides, you may find a new appreciation for Chicago’s community, history, and natural beauty. Whether you are looking for Chicago staycation ideas or are planning on popping into The Windy City for a visit, these outdoor Chicago activities won’t disappoint.
Additionally, the majority of outings on this list are either free or budget-friendly. After all, a day spent exploring Chicago shouldn’t cost you an arm and a leg!
Explore Chicago Through Historic Tours
Wooden Alley 
While popular historical architecture pieces are always a go-to, such as the Chicago Cultural Center and the Water Tower, lesser-known architectural gems are overflowing with history and potent beauty. Ideas for self-guided tours include historic apartments like the Bush Temple, shops with historic facades like those in the Old Town Triangle District, or the sculptures scattered throughout The Loop.
Looking for a bit of guidance while exploring the city? Guided tours are available as walking tours and river cruises. Or, for an extra bit of fun, you can hop in your own kayak for an architectural tour along the waterway, such as those provided by Water Riders.
Shop the Farmers Markets
Support the community and spend a relaxing Sunday at a Farmers Market. The Andersonville Farmers Market that runs from spring to fall, is the perfect place to take a stroll and get your fill of delicious food. Vendors offer local fare that includes everything from fresh produce to handmade treats. This venue also has a fantastic selection of handmade goods that are great to beautify your home—and who isn’t trying to do that these days.
Another Farmers Market worth a tour is the historic Maxwell Street Market that has been in operation for approximately a century. They offer live entertainment, vintage finds, and crafted wares on top of fresh food.
Glide Around in Maggie Daley Park
Maggie Daley Park is home to many wonderful attractions, but the Skating Ribbon tops the list. This winding path is walkable in the summer, but a layer of ice transforms it into a skate path if you fast forward to winter. You can bring your skates or rent some for a small fee. Getting a thermos with some hot chocolate isn’t necessary, but it is certainly recommended to elevate your winter skating adventure. After all, who doesn’t like a warm treat on a chilly winter day?
In the summer months, be sure to check out the Cancer Survivors’ Garden and the many picnic groves found throughout this greenspace located in The Loop.
Go for a Stroll
Take a 1.25-mile stroll along the water on the Chicago Riverwalk. Pack your lunch to enjoy a picnic on one of the many benches that provide picturesque views of the water and architecturally stunning buildings nearby. This path is remarkably breathtaking in the autumn as the leaves begin to turn, but it is a delight year-round.
Prefer rollerblading or skateboarding? The 606 may be for you created from elevated rail lines transformed into walking trails after outliving their original use. Take a roll, walk, or run down them to get a view of the surrounding neighborhoods while fitting in a bit of exercise.
Explore the City by Seeking Out Art
It is no secret that Chicago is full of great museums and art galleries, but you can find art right on the streets—especially in Pilsen. Colorful Murals artfully display Pilsen’s Mexican heritage throughout neighborhood streets. This street art is almost everywhere you look in this historic area. You’ll find the largest concentration and variety along the train tracks that run along 16th street.
If you want to make your own art, grab your sketchpad or canvas and head to Washington Square Park. There are plenty of trees to provide shade as you make your masterpiece. Plus, this greenspace is dripping in subject matter possibilities! From the expertly crafted flower gardens surrounding the Victorian fountain to the historic Newberry Library, you are sure to find something that sparks your creativity.
Escape to Nature
There is nothing like a hike to get a great view of nature and clear the mind. Great places to hike while exploring the city include The 606, Lincoln Park Trail, and Chicago Lakefront Trail. However, if you want to step outside of city limits and take to the woods, there is always the Waterfall Glen Forest Preserve. It is located about an hour away from the city.
Nature lovers will also rejoice with the exceptional views at Chicago Botanic Garden. In the warmer months, this area boasts 26 gardens on 385 acres, as well as a stunning 45-foot waterfall. Head there between November and January to be treated to an artful display of lights sprinkled throughout the park called Lightscape (tickets required for this event).
Head to Lincoln Park
There is always something happening in the largest park in Chicago. Lincoln Park spans an impressive seven miles along Lake Michigan’s shore and is a popular destination among both tourists and locals. In this nature escape, you will find bird sanctuaries, nature reserves, and beaches among the options for outdoor activities. It’s the perfect destination for any outdoor Chicago activity seekers.
You can also get your fill of art with statues modeled after Alexander Hamilton, Hans Christian Anderson, Ben Franklin, and William Shakespeare. And you can’t forget the Abraham Lincoln Monument and U.S. Grant Monument, both of which you don’t want to overlook.
There’s an abundance of outdoor Chicago activities for all ages that vary by season. For further ideas, keep an eye on local listings in the area for occasional or one-time outdoor events. Happy exploring!