Best Places to Walk in Chicago

In this article, we’ve rounded up the best walking trails in Chicago and hidden gems in the city, complete with all the info you need before heading out. So, grab your sneakers (and maybe your pup’s leash), and let’s explore the Windy City’s wild side.

Most Scenic Places to Walk in Chicago

The 606 - Bloomingdale Trail

Located at 1801 N. Ridgeway Ave. in Chicago, The 606 is an easy 2.7-mile trail that’s perfect for a leisurely walk. Built on an old railroad track, this elevated trail offers awesome views of the city and is lined with lush greenery and public art. It’s super safe for women and families, and it’s pet-friendly as long as your pup is leashed. The trail connects neighborhoods like Wicker Park, Bucktown, and Logan Square, making it a convenient and scenic spot for walkers and bikers alike.

North Branch Trail

Starting at Gompers Park on Chicago’s North Side, the North Branch Trail is a moderate 22-mile trail that follows the Chicago River and Skokie Lagoons. It’s a great option for those who want a longer adventure, with plenty of nature and even some art at the Skokie Northshore Sculpture Park. The trail is pet-friendly (leashed dogs only) and safe for women and families. Whether you walk a portion or tackle the whole thing, you’ll love the peaceful vibe and beautiful views.

Millennium Park Trail

Humboldt Park

Found at 1400 N. Humboldt Dr., Humboldt Park offers an easy 2.1-mile loop around a scenic lagoon. It’s pet-friendly, with both leashed and off-leash areas for your furry friend, and it’s safe for women and families. The park is especially beautiful in the fall when the leaves change colors, and it’s a peaceful spot for birdwatching or just enjoying nature.

River Park

Located at 5100 N. Francisco Ave., River Park is an easy walk along the North Branch of the Chicago River. It’s pet-friendly, with leashed and off-leash areas, and it’s safe for women and families. The park features a beautiful waterfall, scenic paths, and plenty of green space for your pup to explore. It’s a quiet, relaxing spot for a quick walk or a picnic.

Chicago Lakefront Trail

Stretching 18.5 miles along Lake Michigan, from Edgewater to 71st Street, the Lakefront Trail is an easy to moderate walk with stunning views of the water and skyline. It’s pet-friendly (leashed dogs only) and safe for women and families. You can walk as much or as little as you want, with attractions like Navy Pier and the Museum Campus along the way. It’s one of the most scenic walks in the city.

Lincoln Park

Located at 2045 N. Lincoln Park W., Lincoln Park is an easy walk with over 1,200 acres of green space to explore. It’s pet-friendly, with leashed and off-leash areas, and it’s safe for women and families. The park features walking trails, open fields, and even a zoo. Don’t miss the Alfred Caldwell Lily Pool, a serene spot for a peaceful walk.

Grant Park

Northerly Island Park

Located at 1521 S. Linn White Dr., Northerly Island Park is an easy 1.5-mile nature trail on a picturesque peninsula along Lake Michigan. It’s pet-friendly (leashed dogs only) and safe for women and families. The trail offers stunning skyline views and a chance to spot native birds and wildlife. It’s a quiet, serene spot for a walk.

Big Marsh Walking Trail

Situated in the South Deering neighborhood, the Big Marsh Walking Trail is an easy 0.8-mile woodchip trail. It’s pet-friendly (leashed dogs welcome) and safe for women and families. The trail is part of the 300-acre Big Marsh Park, making it a great spot for birdwatching and enjoying nature.

Frequently Asked Questions

Is Chicago a Good Walking City?

Absolutely! Chicago is a fantastic city for walking. With its mix of parks, trails, and pedestrian-friendly neighborhoods, there’s always somewhere to explore on foot. The city has over 600 parks and 26 miles of lakefront trails, so you’re never far from a scenic walk. Plus, many neighborhoods like Wicker Park, Lincoln Park, and the Loop are super walkable, with wide sidewalks and plenty of things to see.

Can You Walk Downtown Chicago?

Yes, you can definitely walk downtown Chicago. The Loop, which is the heart of downtown, is super pedestrian-friendly. You can walk to iconic spots like Millennium Park, Cloud Gate, and the Art Institute of Chicago. The Chicago Riverwalk is another great option, offering a scenic path along the river with restaurants, bars, and public art. Walking downtown is a great way to soak in the city’s energy and see its famous architecture up close.

Is Chicago as Walkable as NYC?

Chicago is pretty walkable, but it’s not quite as walkable as New York City. NYC is known for its dense neighborhoods and subway system that makes it easy to get around without a car. Chicago is more spread out, so while some areas like the Loop, Lincoln Park, and Wicker Park are super walkable, others might require public transit or a bike. That said, Chicago has its own charm when it comes to walking. The lakefront trails, parks, and riverwalk offer unique experiences you won’t find in NYC. So while it’s not exactly the same, Chicago still holds its own as a walkable city.

What Is the Most Popular Street in Downtown Chicago?

The most popular street in downtown Chicago is probably Michigan Avenue, especially the section known as the Magnificent Mile. This stretch is packed with luxury shops, restaurants, hotels, and iconic landmarks like the John Hancock Center and the Wrigley Building. It’s a great place to walk, shop, and take in the city’s architecture. The Magnificent Mile is also super pedestrian-friendly, with wide sidewalks and plenty of crosswalks. Whether you’re window shopping, grabbing a bite to eat, or just people-watching, Michigan Avenue is the place to be. It’s a must-visit for anyone exploring downtown Chicago!

Final Thoughts

Chicago is full of amazing walking trails, whether you’re looking for a quick stroll or a full-day adventure. From the scenic Lakefront Trail to the peaceful Humboldt Park, there’s something for everyone. So grab your walking shoes, leash up your pup, and explore the Windy City’s wild side!