14 Outdoor Things to do in Chicago This Summer

– By Tom Schaffner

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Cold and icy weather generally forces residents and visitors to deal with two distinct Chicago seasons — the “indoor season” and the “outdoor season.”  Not surprisingly, the indoor season closely aligns with the fall and winter months (October through March) and the outdoor season closely matches the spring and summer months (April through September).

A list of indoor activities in Chicago usually includes museums, sporting events (such as hockey or basketball), visiting interesting taverns and restaurants, shopping excursions, bowling lanes, indoor gardens and conservatories, gyms & fitness facilities, and much more.  The outdoor season means warmer weather and endless opportunities for unique activities and outdoor things to do in Chicago. When the cold finally lets go, Chicagoans head outside in full force. Here’s how to make the most of the city’s outdoor season.

Outdoor Things to Do in Chicago

1. Lincoln Park Zoo
2. Take in a Ball Game
3. The Lakefront Trail
4. Kayak the Chicago River
5. Japanese Garden
6. Visit a Cemetery
7. The 606
8. Public Art in the Loop
9. Art on the Mart
10. Charter a Boat
11. Chess Pavilion
12. Chicago Riverwalk
13. Beaches
14. Navy Pier

1. Lincoln Park Zoo

Although the Lincoln Park Zoo is open 365 days a year, there’s always more to see and do during the warmer weather than during the harsh winter months. Founded in 1868, the Lincoln Park Zoo is the fourth oldest zoo in the nation and, like other zoos, allows visitors to view the animals in areas that replicate their natural habitats. If you’re looking for outdoor things to do in Chicago that involve roaming around beautiful landscaping with manicured lawns and scenic gardens all throughout a 35-acre site, then The Zoo should be at the top of your list. It is located in the heart of the Lincoln Park neighborhood. Admission is free.

2. Take in a Ball Game

Warmer weather means baseball in Chicago, and both Chicago baseball teams –the Cubs and the White Sox– are once again welcoming fans to the ballpark for another exciting season. While season ticket holders still get early access, plenty of seats are available to the general public and can be easily purchased online. I don’t know about you, but there’s nothing quite like the crack of the bat, a cold beer in one hand, and a hot dog in the other. It just feels like summer in Chicago.

3. The Lakefront Trail

Walk, run, bike, or rollerblade Chicago’s magnificent Lakefront Trail, which stretches for 18 wonderfully scenic miles and offers a variety of outdoor things to do in Chicago all in one place. Along the way, you’ll pass parks, the Museum Campus, Soldier Field, McCormick Place, many views and perspectives of Chicago’s skyline, the South Shore Cultural Center, and many more sites and attractions.  Because there is so much to see and do on the Lakefront Trail, many locals insist that traveling this unique path is like taking a “stay-cation” in Chicago.

4. Kayak the Chicago River

Natives and early explorers of Chicago traveled by canoe on the North and South Branches of the Chicago River to reach what would later be called Lake Michigan. You can do the same at various locations along the River with guided tours that depart during all hours of the day, for nighttime sails, and even trips that are timed to coincide with special events that take place in the city, such as the weekly fireworks show at Navy Pier.

5. Japanese Garden

Located in Jackson Park just south of the Museum of Science and Industry is a Japanese garden sometimes referred to as the “Garden of the Phoenix” or the “Osaka Garden,” (Osaka is a sister city of Chicago).  The garden was a gift to Chicago from Japan in honor of the World’s Columbian Exposition (1893) which was held in Jackson Park.  The blossoming of the cherry trees in spring is an annual highlight of the park, however, the entire garden is beautifully landscaped and located on a secluded island in the park.

6. Visit a Cemetery

This might not be on everyone’s list of outdoor things to do in Chicago, however, cemeteries are quiet, peaceful, landscaped, and are the final resting spot for notable Chicagoans, many of who have beautiful gravestones and mausoleums that adorn their tombs. On the North Side, visit Graceland Cemetery where Daniel Burnham, Ernie Banks, Roger Ebert, Marshall Field, William Le Baron Jenney, Joseph Medill, Ludwig Mies Van der Rohe, Ruth Page, George Pullman, and many other famous people are buried.  On the South Side, visit Oak Woods Cemetery, the final resting spot for Cap Anson, Enrico Fermi, John H. Johnson, Jesse Owens, William Hale Thompson, Harold Washington, Ida B. Wells, and Bill Veeck.

7. The 606

The 606 is an abandoned 2.5-mile railroad line that has been converted into an elevated trail/park that runs parallel to North Ave. on the north side of the city from Ashland Ave. on the east to Ridgeway Ave. on the west.  Perfect for joggers, walkers and bikers, the trail is clean, well-maintained and also has a number of interesting bars, restaurants and shops that can be visited along the way.  The trail takes its numeric name from the first three digits of all Chicago zip codes.

8. Public Art in the Loop

Chicago’s Loop is a veritable gallery of public art featuring works from some of the most famous artists in the world, including Picasso, Calder, Miro, Dubuffet, Chagall, and many more.  The most notable (and famous) works are all within a short walk of one another and can easily be found online.

9. Art on the Mart

This innovative digital presentation uses the broad front face of the Merchandise Mart (the side of the building that faces the Chicago River) as a screen to display projected art in nightly “programs” that begin at 8:30 p.m. and 9 p.m.  Best spot to view the presentation is from the south bank of the Chicago Riverwalk between Wells and Lake Streets. For those looking for outdoor things to do in Chicago that are truly unique to our city, then this should be on your list!

10. Charter a Boat

There’s an awfully big body of water located on Chicago’s eastern border — why not charter a boat and do some sightseeing, fishing, sun-worshipping or celebrate a special occasion (and let the crew do all of the work)?  There are plenty of charter boats in the Chicago area, your next trip is only a few clicks away.

11. Chess Pavilion

If you enjoy playing chess — or enjoy watching others play it — the place to add to your list of outdoor things to do in Chicago is the beautifully designed outdoor chess pavilion located just south of North Avenue Beach in the Lincoln Park neighborhood (just off the Lakefront Trail).  The Chess Pavilion structure has chessboards carved into it and they are sheltered from the elements by a wing-like overhang.  The structure, built in 1957, also features carvings of chess pieces as well as sculptures of free-standing pieces.

12. Chicago Riverwalk

Located on the south bank of the Chicago River between the lakefront and Lake Street, the Riverwalk is Chicago’s version of the Boardwalk in Atlantic City, it has something for everyone.  In addition to enjoying a leisurely stroll along a picturesque river, you can visit outdoor restaurants and taverns, museums, do a little fishing, take boat trips, try your hand at kayaking, view public art, and even do a little bird watching.

13. Beaches

Chicago’s 26-mile lakefront is one of the city’s greatest treasures and it’s as lively as ever. From biking and strolling the Lakefront Trail to swimming, sunbathing, or picnicking along the shore, there’s no shortage of ways to enjoy the water. With more than two dozen beaches open to the public, you’ll find everything from peaceful stretches of sand to bustling scenes near volleyball courts and beachside cafes. Whether you’re catching sunrise at Montrose or people-watching at North Avenue, Chicago’s beaches are the perfect place to soak up summer.

14. Navy Pier

Buzzing with activity, Navy Pier continues to be one of Chicago’s top lakefront destinations. With year-round attractions, you can enjoy everything from boat rides and waterfront dining to shopping, museums, and live performances. Weekly fireworks light up the skyline every Saturday night at 9 p.m., offering the perfect end to a summer evening. Whether you’re visiting with family or soaking in the views with friends, Navy Pier remains a must-see stop on the city’s lakefront.

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Holder of two journalism degrees, including a masters from Northwestern University, Tom Schaffner is a native of the Chicago area and has spent nearly 50 years as a writer, editor, publisher and professional communications consultant. He was also the founder, editor, and publisher of the Chicago File, as well as the co-owner of L Stop Tours.

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