Hiking Around Chicago: 8 Places to Hike in the City, North Shore or a Short Drive Away

When warmer temps hit Chicago, it’s impossible to stay inside. The blue skies and sunshine past 7 p.m. allow us ample time to take in the natural beauty of the Midwest. There’s so much to explore, from lakeside walks and dog-friendly beaches to waterfalls and state parks. So, why not plan an afternoon or weekend getaway at some of the best hiking spots around Chicago? Here are eight of our favorites.

In the City & Suburbs

If you’re new to hiking or looking for a relaxing walk with beautiful city views, check out these hikes in the heart of Chicago. 

Lincoln Park Trail

Length: 5 miles
Dogs: Yes, leashed
Difficulty: Easy
Location: Lincoln Park

This lakeside hike is part of the Lakeshore Trail and provides gorgeous waterfront views of the city. The trail is flat and evenly paved, with separate lanes for bicyclists and walkers. It’s also a great hike for kids, with plenty of grassy areas along the trail to run and play safely. Don’t forget to bring sunglasses, a water bottle, and a light jacket, as the lake breeze can get a bit chilly, even on the warmest of days. 

Montrose Harbor Trail

montrose harbor
Courtesy of Chicago Park District

Length: 5.4 miles
Dogs: Yes, leashed
Difficulty: Easy
Location: Uptown 

If you’re looking for a dog-friendly hike near the city, visit Montrose Harbor Trail. The walk is part of the Lake Shore Trail, with paved trails for bikers and walkers. You’ll start at Belmont Harbor and hike north along the lake until you reach Montrose Harbor, steps from Chicago’s popular Montrose Dog Beach. Make sure to wear comfortable walking shoes and bring an extra towel if you plan on letting your pup swim in Lake Michigan. 

The 606 Trail

Photo by Alyssa Schukar, Courtesy of Illinois Office of Tourism

Length: 5.5 miles
Dogs: Yes, leashed
Difficulty: Easy
Location: Logan Square

The 606 Trail runs alongside the Bloomingdale Trail with 12 access points every quarter mile. While most people visit this trail for a quick run, walk, or bike ride, it’s also a wonderful place to spend a weekend afternoon with the family. The 606 hosts cultural events and art shows throughout the summer, all designed to showcase the trail and the community. 

North Branch Trail System

chicago botanic gardens trail
Photo courtesy of Arun Antony

Length: 36.7 miles
Dogs: Yes, leashed
Difficulty: Easy
Location: Chicago, Glenview, Morton Grove, Niles, Northbrook, Northfield, Skokie & Winnetka

The North Branch Trail System connects Chicago to the Chicago Botanic Garden in Glencoe, with trail loops through ecological restoration sites throughout. The system is paved, making it easy for walking, running and even biking. With multiple access points, the trail is an easy way to explore year-round.

Day Trip Hikes

Consider these Midwest hiking staples if you’re a more seasoned hiker and have time to explore outside of the city.

Waterfall Glen Forest Preserve

Length: 11 miles
Dogs: Yes, leashed
Difficulty: Easy
Location: Darien

Who knew the Midwest had waterfalls? Waterfall Glen Forest is home to the Rocky Glen waterfall, plus a range of prairies, savannas, and oak-maple woodlands. It’s home to nearly 740 plant species and 300 types of mammals, birds, amphibians, and reptiles. Not to mention several quarries throughout the preserve that you can visit to go fishing. Trails are open to hikers, bicyclists, horseback riders, and cross-country skiers. Your four-legged friend can join but must remain leashed at all times. 

Devils Lake

Length: Varied
Dogs: Yes, leashed
Difficulty: All levels
Location: Baraboo, Wisconsin

Devils Lake is one of Wisconsin’s most beloved state parks, with more than 27,000 acres of land to explore. One of the most popular hikes for first-timers is East Buff Trail. It’s a 1.6-mile hike with breath-taking rock formation views, including a picturesque Devils Doorway. Aside from walks, Devils Lake also offers swimming, fishing, hunting, rock climbing, kayaking, skiing, and sledding. 

Starved Rock

Photo courtesy of ©Adam Alexander Photography, Courtesy of Illinois Office of Tourism

Length: 5.1 miles
Dogs: Yes, leashed
Difficulty: Moderate 
Location: Deer Park

Starved Rock is one of the most well-known hikes among Chicagoans, and for a good reason! There are 13 miles of trails to explore, with buffs, canyons, and seasonal waterfalls most active in the spring after heavy rainfall. The Illinois River runs through the park providing a great place to fish and canoe. Remember some snacks or even a packed lunch, as you’ll likely spend the whole day enjoying the wilderness. 

Kettle Moraine State Forest 

Length: Varied
Dogs: Some trails, leashed
Difficulty: Moderate/Hard
Location: Kewaskum, Wisconsin

Located about two hours north of Chicago is the Kettle Moraine State Forest. There are nearly 30,000 acres of rolling hills, lakes, and grasslands, but that’s not what sets this destination apart. Kettle Moraine attracts visitors because of its glacial features, which you can see on the Ice Age Trail. Beware, the Ice Age Trail is 31 miles and is a challenging course for more experienced hikers. However, you get a view of the glacial landscape on the Parnell Loop leading to the forest’s highest point.

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Jessica Braun Gervais is a Chicago-based freelance writer specializing in health, wellness, and fitness. She earned a B.A. in Journalism from Columbia College and has written content for various health and wellness institutions. Jessica Braun’s passion for wellness comes from her life as an elite athlete competing in Muay Thai kickboxing competitions across the country. In addition to sharing her expertise through writing, Jessica Braun also works as a group fitness instructor and personal trainer. When she’s not writing or training, Jessica Braun enjoys reading historical fiction novels, discovering new coffee shops, and cuddling with her cattle dog, Brady.