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The 16 Best Walks in Chicago

For those seeking to explore the vibrant city of Chicago on foot, there is no shortage of options to choose from. From picturesque lakefront paths to historic neighborhoods, the Windy City offers a wide variety of walks for all preferences.

Whether you are a nature lover looking for scenic views or a history buff interested in exploring the city's past, Chicago has something for everyone. With so many options available, it can be tough to decide which walk to embark on. To help you make your decision, here is a list of factors to consider:

Now, without further ado, here are The 16 Best Walks in Chicago for you to explore and enjoy.

How this ranking works

This guide does not try to list everyone. It is our pick of walks in Chicago, built on each business's public reputation and on how central this service is to what it does.

Some businesses pay for a fuller profile or a featured position. It is only open to those that have already passed our selection, and it is always marked.

Top 3Full rankingMapTips for choosing

Our 16 local picks compared

Chicago Riverwalk - West End#1
What sets it apart
  • Beautiful city and park with lots to explore.

  • Great dining and drinking options for a peaceful experience amidst the crowds.

  • Perfect place for a leisurely stroll alongside skyscrapers and delicious food.

Chicago Riverwalk - West End

4.9419 reviews
306-370 W Wacker Dr, Chicago, IL 60654, United States

Chicago Riverwalk - West End is a mesmerizing Park located in Chicago that offers a stunning view of the downtown buildings and river. It is conveniently close to Union Station, making it a perfect spot for a quick walk while waiting for a train to explore the city. Visitors can enjoy the lush green space and observe the bustling activity of tourists on boats cruising down the river.

The Riverwalk provides a unique vantage point to experience the city from the water, passing by historic city bridges and soaring skyscrapers. For an extra thrill, guests can opt for evening kayak trips to witness the captivating fireworks display lighting up the lake on Wednesdays and Saturdays during summer. Urban Kayaks offers guided tours and kayak rentals for those craving adventure.

Customer reviews highlight the following key points:

Riverwalk, Chicago#2
What sets it apart
  • This place is simply wonderful for a leisurely stroll. A versatile and picturesque route for any walker.

  • Beautiful view. Recommended for a memorable experience. Elevators may be available.

  • Absolutely beautiful. Breathtaking views and cleanliness. Appreciation for updates and renovations.

Riverwalk

4.816,663 reviews
22 E Wacker Dr, Chicago, IL 60601, United States

Riverwalk offers an unforgettable experience for visitors seeking a leisurely stroll along the scenic Chicago River. Whether you want to walk alongside the water's edge or explore the downtown area crossing bridges, Riverwalk provides a versatile and picturesque route for any walker. The attraction is also wheelchair-accessible, ensuring everyone can enjoy its beauty.

Lakefront Trail - Fullerton - 2400 N, Chicago#3
What sets it apart
  • A beautiful and well-kept trail with stunning views of the lake and skyline

  • Great for outdoor activities like walking, biking, and jogging

  • Relaxing and well-maintained environment

Lakefront Trail - Fullerton - 2400 N

4.9260 reviews
Lakefront Trl, Chicago, IL 60614, United States

Lakefront Trail - Fullerton - 2400 N offers a variety of activities such as birdwatching, cycling, hiking, and more. With accessibility features like a wheelchair-accessible car park and entrance, it caters to all visitors. Customers have left glowing reviews, mentioning key points like:

Experience the beauty of Chicago at Lakefront Trail!

The 606, Chicago#4
What sets it apart
  • Easy and chill trail with plenty of bench spots to relax and enjoy the sun

  • Perfect for walks and bike rides, regardless of the season

  • Great place for various activities like running, biking, and walking dogs

  • Well-landscaped and easy access points with public water fountains available

The 606

4.81,762 reviews
1805 N Ridgeway Ave, Chicago, IL 60647, United States

The 606 is a popular Hiking area in Chicago, IL, offering a range of Activities such as cycling, hiking, jogging, and walking. The trail is perfect for families with Children, as it is kid-friendly with designated hikes. Dog owners can also enjoy this spot with a dedicated Dog park and areas where Dogs are allowed. The trail is well-maintained, with amenities like a skateboarding area available.

Customer reviews praise The 606 for its beautiful and safe environment, with many mentioning the trail's versatility for different activities. Some key points highlighted by visitors include:

Riverwalk - 100 W, Chicago#5
What sets it apart
  • Visitors rave about the beautiful views and tranquil atmosphere of the riverwalk.

  • The cleanliness and maintenance of the area are highly praised, ensuring a pleasant experience for all.

  • Many appreciate the variety of restaurants and leisure activities available along the riverwalk.

  • The incorporation of nature and community spaces has received accolades from visitors, making it a perfect spot for relaxation and enjoyment.

Riverwalk - 100 W

4.81,328 reviews

Open 24 hours

100 W Wacker Dr, Chicago, IL 60601, United States

Riverwalk - 100 W is a spectacular scenic spot located in the heart of Chicago. Offering breathtaking views and a serene environment, it is a must-visit destination for both locals and tourists alike.

Experience the magic of Riverwalk - 100 W and see why it remains a top attraction in Chicago.

LaBagh Woods, Chicago#6
What sets it apart
  • A great place to go hiking and enjoy a relaxing picnic surrounded by nature.

  • Accessible areas for those with mobility devices.

  • A peaceful spot to get away from the city noise and see some wildlife like deer and cool-looking birds.

LaBagh Woods

4.71,671 reviews
West Foster Avenue, N Cicero Ave, Chicago, IL 60630, United States

LaBagh Woods is a stunning nature preserve located in Chicago, IL. With a high rating of 4.7, this preserve offers an array of amenities and activities for visitors to enjoy. Hiking trails wind through the lush greenery, and there are picnic tables and a barbecue grill for those looking to enjoy a meal in nature.

Customers love the peaceful atmosphere and well-maintained spaces at LaBagh Woods. Here are a few key points from customer reviews:

Whether you're looking for a serene spot to unwind or an adventure in the great outdoors, LaBagh Woods has something for everyone. Visit their website for more information and plan your next nature escape!

Lakefront Trail - Grant Park, Chicago#7
What sets it apart
  • Excellent place to see the Chicago Skyline and enjoy a great walk.

  • Mind-blowing trail with stunning views, especially around sunset.

  • A peaceful escape from the city, perfect for walking, running, or biking.

  • Beautiful path that takes you past landmarks like the Field Museum and Shedd Aquarium.

Lakefront Trail - Grant Park

4.8145 reviews

Open 24 hours

Lakefront Trl, Chicago, IL 60605, United States

Lakefront Trail - Grant Park is an incredible hiking area located in Chicago, IL. Visitors can enjoy a range of activities such as cycling, hiking, jogging, and walking, while taking advantage of amenities like picnic tables and a skateboarding area. This beautiful trail is also dog-friendly, making it a perfect outing for the whole family.

The Lakefront Trail offers breathtaking views of the iconic Chicago skyline and Lake Michigan, making it a favorite spot for nature lovers and photographers. Customers have left glowing reviews, summarizing their experience in a few key points:

Experience the beauty and tranquility of Lakefront Trail - Grant Park today!

Bloomingdale Trail Park, Chicago#8
What sets it apart
  • Beautiful landscaping with native Illinois vegetation

  • Well-maintained cycling and jogging paths

  • Family-friendly environment with picnic areas and dog park

  • Stunning sunset views from the park

Bloomingdale Trail Park

4.71,137 reviews
1600 - 3700 W Bloomingdale Ave, Chicago, IL 60622, Chicago, IL 60647, United States

Bloomingdale Trail Park offers a fantastic outdoor experience in Chicago. With a rating of 4.7, the park boasts a variety of amenities and activities for visitors to enjoy.

Customers have left glowing reviews about their experiences at Bloomingdale Trail Park. One visitor highlighted the park's excellent amenities such as drinking fountains, security cameras, and well-labeled paths. Another mentioned the beautiful landscaping and ever-changing flora that make each visit unique. A third customer praised the park for its restrooms, family-friendly facilities, and various activities available.

Don't miss the opportunity to explore Bloomingdale Trail Park and all it has to offer for a refreshing outdoor adventure.

The Boardwalk, Chicago#9
What sets it apart
  • A photographer enjoys capturing special moments at the park and feels safe while doing so.

  • Visitors find the park clean, safe, and beautiful, making it a must-visit destination in Chicago.

  • A local appreciates the stunning views, perfect for photography, drawing, or simply enjoying the scenery.

  • Many guests highlight the park as a great place for a leisurely walk, with plenty of sitting areas and dining spots to enjoy.

The Boardwalk

4.948 reviews

Open 24 hours

300 - 390 W Wacker Dr, Chicago, IL 60654, United States

The Boardwalk is a picturesque park located in Chicago, offering a stunning view of the city's skyline and the river. This park is a favorite spot for locals and tourists alike, providing various amenities and services. Visitors can enjoy a leisurely walk, have a picnic on the grass, or simply sit and admire the view from one of the colorful chairs. The park is wheelchair-accessible, making it inclusive for all visitors. It is also dog-friendly, so you can bring your furry friends along for a stroll.

Customers have left glowing reviews about their experiences at The Boardwalk. Here are some key points from their feedback:

Catherine Chevalier Woods, Chicago#10
What sets it apart
  • Beautiful place for a walk, bike, or simple enjoyment with family and friends.

  • Great hiking and bike gravel paths throughout the area.

  • It's a nice wooded area with paths throughout and lots of animals.

  • Awesome views and perfect for experiencing all seasons, including snow!

Catherine Chevalier Woods

4.6970 reviews
N East River Rd, Chicago, IL 60634, United States

Catherine Chevalier Woods is a stunning nature preserve located in Chicago, IL. This beautiful sanctuary offers a wide range of amenities and activities for visitors to enjoy. From hiking trails to picnic tables and public toilets, this preserve has everything you need for a day immersed in nature.

Customer reviews rave about the experience at Catherine Chevalier Woods. Here are some key points from their feedback:

Visitors also appreciate the accessibility of the preserve, with options like a wheelchair-accessible car park and entrance. Additionally, dogs are allowed, making it a pet-friendly destination for all nature enthusiasts. Whether you're looking to unwind with a peaceful stroll or explore the diverse wildlife, Catherine Chevalier Woods is a must-visit location for nature lovers.

Chicago Riverview#11
What sets it apart
  • Fantastic place for a picnic, kayaking, or enjoying nature in the city

  • Offers a variety of activities like biking, walking, jogging, and boating

  • Beautiful views of the North Branch River and a peaceful escape from city noise

  • Clean and well-maintained trails suitable for cyclists and pedestrians

Chicago Riverview

4.930 reviews
N Branch Riverwalk, Chicago, IL 60618, United States

Chicago Riverview offers a variety of outdoor activities for visitors to enjoy. From birdwatching to hiking, this scenic location is perfect for those looking to explore nature in the heart of Chicago. With kid-friendly hikes and dog-friendly areas, families can also enjoy a fun day out. Customers rave about the beautiful views of the North Branch River and the peaceful escape from city noise. Visitors also appreciate the clean and well-maintained trails, making it ideal for both cyclists and pedestrians. Whether you're looking for a relaxing stroll or an energetic bike ride, Chicago Riverview has something for everyone.

Chicago River Walk at State St#12
What sets it apart
  • Offers stunning views of the Chicago River and iconic architecture

  • Abundance of activities and dining options along the waterfront

  • Ideal for families with children due to its child-friendly environment

  • A perfect place to take a stroll, relax, and enjoy the vibrant urban landscape

Chicago River Walk at State St

4.723 reviews
Wacker &, N State St, Chicago, IL 60601, United States

Chicago River Walk at State St is a captivating tourist attraction nestled in the heart of Chicago, offering visitors and locals alike a chance to marvel at the stunning views of the Chicago River, iconic architecture, and a plethora of activities and dining options along the waterfront. The accessibility of wheelchair-accessible entrances and its child-friendly environment make it an ideal spot for families and individuals of all abilities to enjoy.

Customer reviews rave about the scenic beauty and charming atmosphere of the River Walk, with fans admiring the vibrant urban landscape, peaceful water views, and diverse entertainment options. Here are some key points from customer reviews:

Walking Stick Woods Natural Area, Chicago#13
What sets it apart
  • Great natural area for kids to explore

  • Tricky entrance but worth finding

  • Quiet and peaceful walking trail

  • Overall, a really nice place

Walking Stick Woods Natural Area

4.720 reviews
5801 N Central Park Ave, Chicago, IL 60659, United States

Walking Stick Woods Natural Area is a stunning hiking area located in Chicago, IL, that offers a variety of activities for nature enthusiasts. With options for hiking, jogging, loop trails, and walking, visitors can immerse themselves in the beauty of the outdoors. The natural area is dog-friendly, allowing pet owners to explore with their furry friends.

Visitors have also praised the awesome camp available and the enjoyable space for kids to play. One reviewer commented on the longevity of living in the city with kids and noted that places like this enhance their experience. With a high rating of 4.7, this natural area is a must-visit for anyone looking to connect with nature in the heart of Chicago.

Lakefront Trail - Ohio Street Beach, Chicago#14
What sets it apart
  • Combination of long-distance exercise and picturesque views

  • Well-maintained safety measures and separate lanes for different activities

  • Convenient parking and accessibility for bikes and scooters

  • Beautiful scenery for walking, running, biking, and more

Lakefront Trail - Ohio Street Beach

4.711 reviews

Open 24 hours

600 N Lake Shore Dr, Chicago, IL 60611, United States

Lakefront Trail - Ohio Street Beach is a popular hiking area located in Chicago, Illinois, offering a serene escape along Lake Michigan. With separate lanes for walkers/runners and cyclists/skateboarders/rollerbladers, visitors can enjoy their preferred form of exercise safely. The well-traveled paths provide a sense of security, even for lone users during the day. The stunning views of the downtown skyline make for dynamic photo opportunities, creating a memorable experience for all.

Customer reviews highlight the following key points:

Nature Boardwalk at Lincoln Park Zoo, Chicago#15
What sets it apart
  • "A great place to walk around with stunning views of the skyline."

  • "Amazingly awesome experience for the whole family. Great food, helpful staff, and friendly volunteers."

  • "Delightful and well-maintained wooden structure that offers a peaceful nature walk close to the city."

  • "Beautiful day out with the family. A must-visit for families with kids in town."

Nature Boardwalk at Lincoln Park Zoo

4.8774 reviews
2121 N Stockton Dr, Chicago, IL 60614, United States

Nature Boardwalk at Lincoln Park Zoo is a popular destination in Chicago for nature lovers and families alike. This wooden structure surrounding the South Pond in Lincoln Park offers visitors a chance to immerse themselves in nature with minimal disturbance. The boardwalk provides a serene escape in the bustling city, allowing guests to enjoy native plants, vibrant wildlife, and a variety of aquatic animals like fish, turtles, frogs, ducks, and swans. With well-maintained paths and plenty of seating areas, it's a perfect spot to unwind and connect with the natural world.

Customer reviews rave about the experience at Nature Boardwalk at Lincoln Park Zoo:

Visit Nature Boardwalk at Lincoln Park Zoo for a relaxing and educational experience surrounded by nature's beauty.

Canalport Riverwalk Park, Chicago#16
What sets it apart
  • A cool, unique walking park with lovely water views and plenty of geese to see.

  • An odd yet charming break from the typical picturesque parks in the city.

  • A great spot for a bike ride or a leisurely walk to appreciate the industrial backdrop.

  • Some visitors mentioned the lack of fish while enjoying the beautiful scenery.

Canalport Riverwalk Park

4.570 reviews
2900 S Ashland Ave, Chicago, IL 60608, United States

Canalport Riverwalk Park offers a unique experience for visitors to enjoy a peaceful natural setting right in the city. Surrounded by serene waterways, this park is a hidden gem that provides a much-needed respite from the hustle and bustle of urban life. With its wheelchair-accessible entrance and dog-friendly policy, it's a welcoming space for all.

Whether you're looking for a simple stroll along the river, a spot to sit and relax, or a place to observe the industrial activity across the water, Canalport Riverwalk Park has something for everyone. Don't miss out on this delightful oasis in the heart of Chicago.

The comparison in brief

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Map of Walks in Chicago

Explore Chicago like never before with our comprehensive map of all the top walking trails in the city. From the iconic Magnificent Mile to the serene paths along Lake Michigan, there is something for everyone to enjoy. Lace up your walking shoes and discover the beauty and history of the Windy City on foot.

Tips for choosing Walks in Chicago

  1. Duration of the walk.
  2. Difficulty level.
  3. Points of interest along the route.
  4. Accessibility.
  5. Seasonal variations.

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