The Best Places to Take a Walk in Chicago

Walking Paths and Scenic Routes in Chicago

Chicago is a beautiful city for walking and exploring. With its many parks, gardens, and outdoor spaces, there is no shortage of places to enjoy a relaxing stroll. Below are some of the scenic spots that are worth wandering around.
Millennium Park
Millennium Park
Millennium Park is a famous public space that's located in Grant Park. The 24.5 acre park is near the Lake Michigan shoreline and includes a number of famous attractions such as Cloud Gate, Crown Fountain, Lurie Garden and a number of outdoor performance areas.
Loop, Chicago, Illinois, 60601
Grant Park
Grant Park
Grant Park is a large and impressive public space in the city's central business district. This large park is where you'll find the famous Millennium Park, Buckingham Fountain, the Art Institute of Chicago, and the Museum Campus. There are a number of gardens, sport fields, and performances venues found in the park as well.
Printer's Row, Chicago, Illinois
If you're looking for more information about Chicago, read The Best Places to Run in Chicago and The Best Playgrounds in Chicago.
Ping Tom Memorial Park
Ping Tom Memorial Park
Located in Chicago's Chinatown, this park has a pagoda-style pavilion, bamboo gardens, and a playground. The waterfront park spans 17 acres and there are places nearby where you can rent kayaks. The Field House is a recreational area in the park that has a pool with slides and a fitness center. From here you can enjoy great views of the Chicago skyline. Throughout the year there are a number of events held here including Shakespeare in the Park. Runners and walkers will appreciate the trails through the park as well.
300 West 19th Street, Chinatown, Chicago, Illinois, 60616
Chicago Riverwalk
Chicago Riverwalk
The Chicago River is an iconic part of the city, and it runs parallel to the lakeshore through the heart of the city. The Riverwalk is along a popular stretch of the river, and it's lined with many great restaurants and some of Chicago's most impressive architecture. You can wander along the Riverwalk, rest at one of the many benches, take in the impressive views or simply people watch.
Loop, Chicago, IL, 60601
Lincoln Park Conservatory
Lincoln Park Conservatory
This impressive Victorian style greenhouse has four separate sections that include the Orchid House, Palm House, Fern Room, and Show House. There's also an outdoor Formal Garden and the English Grandmother's Garden. This is a beautiful conservatory and it's free to the public.
2391 N Stockton Dr, Lincoln Park, Chicago, IL, 60614
Maggie Daley Park
Maggie Daley Park
Maggie Daley Park is an impressive park with a 1/4 mile long ice skating/roller skating ribbon. There's also a 40 ft tall climbing wall and a play garden for kids. The playground includes a pirate ship play structure with slides, rope bridges, and climbing areas. There's also a 18 hole mini golf course in the park.
337 E Randolph St, Millennium Park, Chicago, IL, 60601
Chase Promenade
Chase Promenade is a tree-lined pedestrian walkway in Millennium Park. It spans 8 acres and hosts regular exhibitions and festivals.
Chase Promenade Central, Loop, Chicago, Illinois
Union Park
This 13 acre park is located in the Near West Side area. The park has large fields, playgrounds, a swimming pool, tennis courts, basketball courts, and baseball fields. The playgrounds have slides, swings, and plenty of space for kids to run around.
1566 West Washington Boulevard, Near West Side, Chicago, Illinois, 60612
Chicago has plenty more to offer, so see also our other articles: Things to do Along the Magnificent Mile (and in River North) and Quintessential Neighborhoods in Chicago.
Prairie Avenue Historic District
The Prairie Avenue Historic District is in the Near South Side community. It was the location of the Battle of Fort Dearborn and later became a luxury residential neighborhood following the Great Chicago Fire. Today there are a number of small museums housed in the former mansions.
1920 South Prairie Avenue, Near South Side, Chicago, Illinois, 60616
Lakeview
Bordering the shore of Lake Michigan to the east, Lakeview is a relaxed neighborhood with a laidback vibe. The area combines East Lakeview, Central Lakeview, Boystown, and Wrigleyville and it offers a number of entertainment options, shopping districts, as well as bars and restaurants that are popular with locals and tourists alike. There are live music venues, theaters, and dance clubs. There are also outdoor activities like the Lakefront Trail, picnic areas, a golf course, and summer street festivals. Boystown is also notable as the first gay neighborhood in the United States to gain official recognition by a city government. You can visit during June to celebrate the annual Pride Parade.
Chicago, IL
Lincoln Park
This neighborhood and park area offers a beautiful setting with nicely landscaped gardens, a quaint lily pond, and lakefront green space that has nice views of the city. The Lakefront Trail, the Lincoln Park Trail, Lincoln Park Zoo, North Avenue Beach, and Peggy Notebaert Nature Museum are all in the area. There is also plenty of shopping in Lincoln Park with many boutique shops spread among the row houses.
Chicago, IL
Loyola–Leone Beaches
These beaches stretch out for eight blocks, making them the longest stretch of beach in Chicago. Located near Loyola University in the East Rogers Park neighborhood, this area has a playground and areas that are perfect for strollers. There are also a number of sports fields nearby including baseball fields, basketball courts, and a kayak launching spot.
1222 W Touhy Ave, East Rogers Park, Chicago, IL, 60626
Washington Park
Washington Park has a number of attractions including the DuSable Museum, a bird and butterfly sanctuary, The Fountain of Time, and several lagoons.
5531 S. Martin Luther King Dr., Hyde Park, Chicago, IL, 60637
Wrigley Square
Wrigley Square, in Millennium Park, is where you'll find the Millennium Monument, which is a circular fountain with large columns. Throughout the park are temporary art installations that change regularly. There are also several places to buy snacks and drinks. Head to one of the picnic tables to enjoy your food while you soak in the setting.
Millennium Park, Chicago, IL
Planning a trip to Chicago? You might also be interested in A Nature Lover's Guide to Chicago and Best Places To Enjoy A Picnic In Chicago.
Burnham Park
Burnham Park follows the banks of Lake Michigan for six miles from 14th Street to 56th Street. It spans 600 acres and includes the Burnham Harbor, Soldier Field, and McCormick Place. The Lakefront Trail passes through the park as well. Skateboarders will appreciate Burnham Skate Park, but there are also tennis courts, a fishing pier, and several beaches. For kids, there is a playground.
South Loop, Chicago, IL
South Shore Cultural Center Park
This park was originally built as a country club but today it is a historic landmark that offers a number of classes and programs throughout the year. The park covers 65 acres and includes a golf course, grass fields, a beach, and the South Shore Nature Sanctuary.
7059 S South Shore Dr, South Shore, Chicago, IL, 60649
Belmont Harbor Dog Beach
Belmont Harbor Beach is a popular spot for running, walking, or biking. It's near Chicago's Yacht Club and, with a great fenced in area near the water, this is a popular spot for dog owners. When the weathers nice, head here for a day of relaxing, exercising, of simply enjoying the great outdoors with your dog companion.
Belmont & Lake Shore Drive, Lincoln Park, Chicago, IL, 60614
Prairie District Park
This little park has slides, climbing areas, play houses, and water misters. There's also a nice dog park where pets can run free, a running path, and a pool.
2051 S Prairie Ave, Burnham Park, Chicago, IL, 60616
Humboldt Park
Dating back to the mid 1800s, this park was at one time considered to be one of the greatest public parks in the country. Today it has rose gardens, tennis courts, an inland beach, and bike paths.
Humboldt Park, Chicago, IL
Hyde Park
Located on the South Side of Chicago, this neighborhood is rich in history. It was the location of the 1893 World's Fair and it has a number of notable residences including a home designed by Frank Lloyd Wright as well as the former home of President Barack Obama. Hyde Park sits on the edge of Lake Michigan and offers beautiful water views. It's also easily accessible to the 18 mile lakefront running and biking path. Within Hyde Park you'll find the University of Chicago, the Museum of Science and Industry, and part of Jackson Park.
Chicago, IL
Chicago has plenty more to offer, so see also our other articles: Places to Bike in Chicago and The Best Gardens in Chicago.
The 606
This renovation project has turned an elevated railway track into a 2.7 mile path that weaves through the North Side of the city, passing through Logan Square, Humboldt Park, Wicker Park, and Bucktown. It connects a handful of parks and is the perfect place to enjoy a walk, bike ride, or short run.
Humboldt Park, Chicago, IL
Garfield Park
Garfield Park is a popular city park on the West Side of the city in the Garfield Park neighborhood. It has a number of recreational facilities including baseball, boxing, basketball, tennis, and swimming. There's also a playground and trails for running, walking and bike riding. When the weather isn't cooperating, you can head inside to the Garfield Park Conservatory, which has about 120,000 plants from 600 different species in a 1.6 acre indoor space.
300 N. Central Park Ave., Garfield Park, Chicago, IL, 60624
Lakefront Trail
The Chicago Lakefront Trail is a 18.5-mile long trail that is great for running, walking, biking, and even skateboarding. It runs alone the western shore of Lake Michigan and it's popular with locals, tourists, athletes, and commuters. From the trail you can access the lake at different points and the trail passes by a number of different recreational areas including Lincoln Park, Grant Park, Burnham Park, and Jackson Park.
Chicago, IL
North Avenue Beach
North Avenue Beach is a popular summer destination when it fills with locals playing volleyball and families playing in the sand. Swimming is popular when the water gets warm and there is plenty of water sports equipment available for rent including kayaks, stand-up paddleboards, and jet skis. Bands frequently play at the beach house and there's also ice cream and margaritas available.
1601 N. Jean-Baptiste Pointe DuSable Lake Shore Drive, Lincoln Park, Chicago, IL, 60611
Winnemac Park
This 22 acre park offers a number of sports and activities as well as a playground and an impressive Fourth of July fireworks display.
5100 N Leavitt St, Lincoln Square, Chicago, IL, 60625
Walden Pond & Thoreau's Cabin
Henry David Thoreau, the famous American author, wrote some of his most famous works at this cabin which is now a museum and park. Visitors can walk around the famous Walden Pond which has a small beach area and walking trails. It's a nice spot for a swim in the summer. The area is now a state park and open to the public.
915 Walden St, Concord, Massachusetts
If you're looking for more information about Chicago, read The Best Outdoor Activities in Chicago and The Best Parks in Chicago.
Jackson Park
This is a 600 acre park that sits on the edge of Lake Michigan on the South Side of Chicago. It has a variety of facilities including basketball, tennis courts, and playgrounds. The Osaka Garden is also on the grounds, which is a Japanese style garden that's on an island in the park's east lagoon. There are also several beaches and a running track that visitors can take advantage of.
6401 S Stony Island Ave, South Shore, Chicago, IL, 60637
Indiana Dunes National Park
This is a relatively new national park, and it's a popular day trip for Chicago locals who want to escape the city. It has three miles of pristine lake shore that is lined with dunes, marshes, grassland, and forest. There are plenty of places to hike and explore, as well as nine beaches that are great for relaxing in the sun on a warm day.
1050 N Mineral Springs Rd, Chesterton, IN, 46304
How much does it cost?

Prices for activities, things to do, and tours range from $5 to $498. The average cost for a tour or tickets is $94. A few of the best options are below.

Where to Stay in Chicago


Vacation Rental Prices in Chicago

How much do vacation rentals cost in Chicago? Prices vary by location, date, size of the place, and the level of luxury. See below for options.

Find the best vacation rental for your travel style.

We love VRBO because of their commitment to small businesses. VRBO is part of the Expedia family, one of the biggest names in travel.

Budget Your Trip

Budget Your Trip has average travel costs for thousands of cities around the world, all provided by other travelers. You can also register to organize your spending by category and location with graphs, maps, charts, and tables.

Search for Travel Costs

Share This Page

Some of the links on this website are sponsored or affiliate links which help to financially support this site. By clicking the link and making a purchase, we may receive a small commission, but this does not affect the price of your purchase.