Chicago’s 10 Best Outdoor Adventures

Here’s a list of first-rate recreational activities to tackle in the Second City.

By Kara Silva


Chicago is home to some of the nation’s best museums, finest food and most dedicated sports fans, but it’s also devoted to preserving its green spaces. It may come as a surprise, but the Second City is actually considered one of the most environmentally conscious major cities in the country, making it a perfect place for both culture-cramming and adventure-seeking.

Here are 10 family-friendly (and COVID-friendly) activities that embrace outdoor recreation in this Midwestern metropolis.

1. Paddle the Chicago River after dark

Once the sun sets, Chicago is awakened by the hum of city lights pouring from skyscrapers and scattering across the river like glitter. Kayaking the Chicago River after dark provides a stark contrast to the waterway’s otherwise busy daytime vibes. Founded in 1997, Wateriders started the first-ever Chicago River kayaking excursion, and – since then – the tour operator has led thousands of urban-adventure seekers on paddle trips of all types, from its History and Architecture tour to a Ghosts and Gangsters nighttime paddle.

Logistics: Wateriders is located at the East Bank Club Riverwalk, 500 N. Kingsbury St. The one-and-a-half-hour Moonlight Paddle tour costs $50 for adults, $35 for kids (under age 16), and no charge for children small enough to fit into a child seat (usually 2 to 4 years old).

2. Lollygag at Oak Street Beach

Surrounded by a stunning skyline dotted with the historic Drake Hotel and the “John Hancock” building, Oak Street Beach feels like it’s smackdab in the middle of all the action. Sandwiched between Lake Shore Drive and Lake Michigan, Oak Street Beach is a popular spot to spend some family time in the sun and sand without feeling like you’ve left the city. Enjoy a tropical drink while taking in the imported palm trees at the onsite café and bar before enjoying a pick-up-game of sand volleyball.

Logistics: Oak Street Beach, 1000 N. Lake Shore Drive, is located near the Streeterville/Gold Coast neighborhoods. Beach access is free.

3. Hop on (and off) The 606 Bloomingdale Trail

The 606, a 2.7-mile elevated trail set 18 feet above street level, takes its name from the common numerals in Chicago zip codes. What was once an old industrial rail line is now a year-round recreational walkway with green spaces, and bike and jogging paths that connect the city’s hip west side neighborhoods – Wicker Park/Bucktown, Logan Square and Humboldt Park. With 12 access points located roughly every quarter-mile, hop on and off to enjoy surrounding shops, restaurants, bakeries or even a dessert bar – Mindy’s HotChocolate is the home of Chicago James Beard Award-winning pastry chef Mindy Segal.

Logistics: Take the CTA Blue Line to the Western or Damen stops for the easiest access points along The 606. Mindy’s HotChocolate is located at 1747 N. Damen Ave. Exit The 606 at the Damen access point.

4. Picnic and a flick at the Jay Pritzker Pavilion

Situated in the 25-acre Millennium Park, the Frank Gehry-designed Jay Pritzker Pavilion boasts breathtaking skyline views and free entertainment. Movie-goers flock to the pavilion on Tuesday evenings for the “Summer Film Series,” which pairs picnicking with a Blockbuster hit, cult classic or family favorite. The 40-foot LED screen is fit with an aerial sound-system spanning the fixed seating area and 95,000-square-foot Great Lawn area, which accommodates nearly 15,000 people.

Logistics: Jay Pritzker Pavilion is located at 201 E. Randolph St. Films screen at 6:30 p.m. Seating is on a first come, first served basis. Bring your own food, alcoholic and non-alcoholic beverages.

Note: The “Summer Film Series” has been discontinued in 2021 due to the pandemic.

5. Stay and play at Maggie Daley Park

Let your kids’ imagination run wild at the 20-acre Maggie Daley Park. The park was completed in 2015 and is quickly becoming a must-see (and play) Chicago stop for families. Even though it’s basically a playground, the park lives up to the city’s reputation for quality architecture. Built in the “spirit of ‘Alice and Wonderland’ and ‘Charlie and the Chocolate Factory,’ according to the Chicago Park District’s website, the park features a 3-acre play garden, the city’s first rock climbing park, slides of all kinds, an enchanted forest, “Watering Hole” splash pad, custom-built metal play ship, mini-golf course, picnic groves, an ice-skating ribbon (in the winter) and more. Special events offered include a Valentine’s Day Dance, Egg Hunt and Skate with Santa.

Logistics: Maggie Daley Park is open from 6 a.m. to 11 p.m. 365 days a year. It is located at 337 E. Randolph St. and can be accessed from Randolph Street, along Lakeshore Drive, Monroe Street or the BP Bridge.

6. Enjoy nature’s remedy in Lincoln Park

Lincoln Park is a result of the efforts made by local leaders to protect the city’s most prized real estate – the lakefront. Bigger than both New York’s Central Park and San Francisco’s Golden Gate Park, Chicago’s lakefront-located Lincoln Park measures more than 1,200 acres and features a free zoo and conservatory. This north side spot offers beaches, boating and the Lakefront Trail. The Lincoln Park Conservatory provides an escape to paradise, with its exotic and tropical flora, and wildlife enthusiasts can enjoy the Judy Istock Butterfly Haven with more than 40 species; the North Pond Nature Sanctuary, which is home to 200 species of resident and migratory birds; and the 35-acre Lincoln Park Zoo, which was established in 1868, making it the one of the oldest zoos in North America.

Logistics: Park hours are from 6 a.m. to 11 p.m. Paid parking is available in Chicago Park District lots in the area.

7. Tinker in the treetops of Bemis Woods

For a day of soaring, swinging and climbing, head 20 miles out of the city and into the woods. The Go Ape Treetop Adventure Course in Bemis Woods boasts five zip lines totaling nearly 3,000 feet of fun, a “double Tarzan” swing, 40 obstacles 40 feet above the ground, rope ladders, trapezes, bridges and spiders’ webs. The season runs from April 1 through Nov. 30, and the “Adventure Course” takes two to three hours to complete.

Logistics: The adventure course is located at Bemis Woods-South (Ogden Ave. west of Wolf Road, near Western Springs). The cost is $58 for adults (16 and older) and $38 for children (ages 10 to 15). A one-hour “Journey Course” is offered for $28 a person. Call Go Ape at 800-971-8271 for available time slots.

8. Presidential haunts in Hyde Park

Follow in the footsteps of 44th president Barrack Obama with a visit to his neighborhood home – Hyde Park. Stroll along the tree-lined streets to some of Obama’s south side haunts, including his Kenwood red-brick mansion; the Hyde Park Hair Salon, where his barber of 20 years reins; and Valois Restaurant, the cafeteria-style diner that the former president frequented and enjoyed his usual order of egg whites, turkey sausage, hash browns, wheat toast and hot tea. In nearby Jackson Park is where the Obama Foundation plans to open the Barack Obama Presidential Center, likely in 2021, according to Choose Chicago – the official destination marketing organization for the city. Also, fans of the book “The Devil in the White City” may like to know that Hyde Park was home to the 1893 World’s Columbian Exposition. While in Jackson Park, stop by Osaka Garden, a.k.a. Garden of the Phoenix, a Japanese strolling garden and a remnant of the World’s Fair. 

Logistics: The Obama family mansion is located at 5046 S. Greenwood Ave. To tour the Hyde Park area rent a Divvy bike, Chicago’s affordable bicycle share system; it’s $15 for a day pass.

9. Peruse public art in Pilsen

Situated on the lower west side of the city, the largely Mexican-American neighborhood of Pilsen is a celebration of culture and creativity. Along 18th and 16th streets and beyond, art and activism converge in the form of dozens of outdoor murals. Award-winning public artist Hector Duarte even used his own Pilsen home (1900 W. Cullerton St.) as a canvas to spur a conversation about the struggles of Mexican immigration.

Logistics: Pilsen is 4.5 miles from the Magnificent Mile. Take the CTA Pink Line ‘L’ train to 18th Street station.

10. Hike by bike at night

There’s nothing quite like exploring the Windy City on two wheels, especially after dark. Bobby’s Bike Hike offers nighttime cycling tours to witness local landmarks come alive in the evening hours. The Night Bike Tour follows the Lakefront Trail, hitting highlights like Olive Park, Oak Street Beach, Chicago Riverwalk, Millennium Park, Buckingham Fountain, the world-renowned Museum Campus, and ends with fireworks at Navy Pier (on select dates). All cyclists must be age 13 and older. Bobby’s also offers a Tike Hike: Kid’s Edition Bike Tour for younger families, among other unique cycling and walking tours.

Logistics: Bikes and equipment are provided. The Night Bike Tour takes three hours and covers roughly eight miles. Visitors can upgrade to an electric bike for an additional fee.

This article was updated in May 2021.

Kara Silva – September 2019

ROAM Contributor   

During her decade-long career in journalism, Kara has given a voice to the voiceless, brought attention to important issues, and – most notably – mastered the art of traveling on a journalist’s salary! Writer by day, reader by night and lover of the great outdoors, Kara lives in a picturesque river town in the Chicago ’burbs with her Brazilian husband, 8-month-old daughter, obese cat and delinquent Siberian husky.  


© ROAM Family Travel 2019 – All rights reserved


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