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Cook County

Chicago

The best family-friendly hikes and walks around Chicago

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3,331

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Family friendly hiking trails around Chicago offer a diverse range of outdoor experiences, from urban greenways with city views to extensive forest preserves and river trails. The region's landscape includes lakefront paths along Lake Michigan, reclaimed prairies, and woodlands, providing varied terrain for all ages. These areas feature mostly flat or gently rolling terrain, making them accessible for family outings.

Best family friendly hiking trails around Chicago

  • The most popular family friendly hiking route is Northwestern Medicine Wellness Way Fitness…

Last updated: April 26, 2026

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#1.

Northwestern Medicine Wellness Way Fitness Trail

2.95km

00:45

10m

10m

Lace up your shoes for an easy 1.8-mile (2.9 km) hike along the Northwestern Medicine Wellness Way Fitness Trail. This paved route offers continuous, sweeping views of Lake Michigan and…

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3.0

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16

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4.54km

01:08

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Embark on an easy urban hike along the Bloomingdale Trail, a flat, paved path offering a unique elevated perspective of Chicago. This accessible route spans 2.8 miles (4.5 km) with…

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13

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Step onto the Chicago Lakefront Trail for an easy urban hike that blends cityscapes with refreshing lake views. This 2.5 miles (4.0 km) route offers continuous vistas of Lake Michigan…

Easy

Embark on the Magnificent Mile and Navy Pier Walk, an easy urban hike that guides you through the heart of Chicago. This route covers 3.3 miles (5.3 km) with a…

Easy

The Catherine Chevalier Woods River Loop offers an easy hiking experience, winding through lush oak and hickory woodlands. You will enjoy picturesque views of the Des Plaines River as the…

Easy
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Hiking Collection by

VisitTheUSA

Tips from the Community

UrbanExolorer_Mando
September 29, 2025, Captain on the Helm

Beautiful sunrise views

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Navy Pier is a popular tourist attraction in Chicago, located on the shore of Lake Michigan

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The view is truly spectacular. You'll see iconic skyscrapers like the Willis Tower, 875 N. Michigan Ave (formerly the John Hancock Center), and the elegant St. Regis Chicago, all forming an impressive panorama over Lake Michigan.

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In the movie The Blues Brothers, Chez Paul is a high-end restaurant where Jake and Elwood Blues go to find their former bandmate, Alan "Mr. Fabulous" Rubin. Rubin, a trumpet player for the band, has left the music world and is now the maitre d' at the snooty establishment. The exterior shots of Chez Paul in The Blues Brothers were filmed at the actual location of the restaurant, which was at 660 North Rush Street in Chicago's River North neighborhood. While the exterior was the real deal, the interior scenes of the restaurant were actually shot on a soundstage on the West Coast. This was a common practice for film productions, as the owner of Chez Paul reportedly said it was easier than "shipping the McCormick mansion to the West Coast." The restaurant, which was a well-known institution in Chicago, has since closed.

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This is one of the many forest preserves along the Des Plaines River Trail. There are picnic tables, bathrooms and parking for trail access here. You can enjoy some great views of the river from here as well.

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Lisa
September 27, 2024, Navy Pier

"The People's Pier" is home to some of Chicago's most iconic attractions, including the Centennial Wheel, day cruises on the Chicago River and Lake Michigan, the Chicago Shakespeare Theater and Virtual Rush, a 4D virtual reality adventure through a futuristic vision of Chicago.

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Kokou
September 16, 2024, Ohio Street Beach

Very nice beach with cool view on Lake shore drive…

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Frequently Asked Questions

How many family-friendly hiking trails are available around Chicago?

There are over 200 family-friendly hiking routes around Chicago, with more than 150 of them rated as easy, making them perfect for outings with children. You'll find a diverse range of options, from urban paths with city views to tranquil forest preserve trails.

What kind of terrain can we expect on family hikes in the Chicago area?

The Chicago area offers a variety of terrain suitable for families. You'll find many paved trails, like the Bloomingdale Trail or sections of the Chicago Lakefront Trail, which are great for strollers. Other trails wind through forest preserves, offering wood-chipped paths, gravel, or natural surfaces through woodlands, prairies, and savannas. Even some state parks a short drive away feature more rugged trails through canyons and along rivers.

Are there any easy, short loop trails suitable for young children?

Yes, many trails are designed with families in mind. For a pleasant loop, consider the Catherine Chevalier Woods River Loop, which offers a gentle path through nature. The region's forest preserves often feature shorter, well-maintained loops perfect for little legs.

What are some scenic landmarks or natural features we can see on these family-friendly hikes?

Chicago's family-friendly hikes offer a mix of urban and natural beauty. Along the Chicago Lakefront Trail, you'll enjoy stunning views of the city skyline and Lake Michigan, passing by iconic spots like Buckingham Fountain. Inland, forest preserves like Waterfall Glen feature unique geological formations and even a small waterfall. You can also explore highlights like Cloud Gate (The Bean) or the Magnificent Mile on urban walks.

Are there dog-friendly options for family hikes in the Chicago area?

Many forest preserves and parks in the Chicago area welcome dogs on their trails, provided they are leashed. It's always a good idea to check specific park regulations before you go, but generally, you'll find plenty of opportunities to bring your furry family members along for the adventure.

What is the best time of year for family hiking around Chicago?

Spring, summer, and fall all offer wonderful conditions for family hiking in Chicago. Spring brings blooming wildflowers and comfortable temperatures, while summer is perfect for lakefront walks and enjoying lush greenery. Autumn showcases spectacular fall foliage in the forest preserves. Even mild winter days can be enjoyable for a crisp walk, though some trails may be icy or muddy.

Is parking generally available at trailheads for family hikes?

Yes, most forest preserves and larger parks in the Chicago area that host hiking trails provide dedicated parking lots. For urban trails like the Bloomingdale Trail or the Chicago Lakefront Trail, street parking or nearby garages are often available, though they might require payment, especially in busier areas.

Can we access family-friendly trails using public transport in Chicago?

Absolutely. Many urban trails, such as the Chicago Lakefront Trail and the Bloomingdale Trail, are easily accessible via Chicago's extensive CTA bus and 'L' train system. Some forest preserves on the outskirts of the city might require a combination of public transport and a short walk or ride-share, but many are quite reachable.

What do other hikers enjoy most about family-friendly trails in Chicago?

The family-friendly trails around Chicago are highly rated by the komoot community, with an average score of 4.57 stars. Reviewers often praise the accessibility of nature within and near the city, the well-maintained paths, and the variety of experiences, from urban sightseeing to peaceful forest walks. The ease of finding suitable routes for all ages and skill levels is also frequently highlighted.

Are there any specific permits or fees required for hiking on these trails?

Generally, no specific permits or fees are required for hiking on most public trails within Chicago's parks and forest preserves. However, some specialized areas or events might have different rules, and parking fees can apply in certain urban or popular locations. State parks like Starved Rock, while a bit further out, typically have free entry but may charge for parking.

Are there any trails that offer a mix of urban exploration and natural beauty?

Yes, Chicago excels at blending urban and natural experiences. The Magnificent Mile and Navy Pier Walk combines city landmarks with lakefront views. The Chicago Lakefront Trail offers continuous views of both the skyline and Lake Michigan, providing a unique urban-nature blend.

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