The best dog-friendly hikes and walks around Chicago

The Bloomingdale Trail, also known as The 606, offers a truly unique urban hiking experience in Chicago. This elevated greenway provides city views as you pass through neighborhoods like Wicker Park and Bucktown, observing an eclectic mix of architecture and public art, including the murals at Park No. 567. The smooth, paved surface, with its central concrete path and softer rubberized running tracks, makes this 2.8-mile (4.5 km) route accessible for all, with a minimal 8 feet (2 metres) of elevation gain.

Planning your visit is easy, with 12 ADA-compliant ramps providing access along the route. While there isn't dedicated parking, street parking is available in the surrounding areas, and public transport is a good option. The trail is rated easy and takes about 1 hour and 8 minutes, but it can get very busy on nice weekend mornings or summer evenings, so consider an early start or a weekday visit for a calmer experience.

This trail is the heart of "The 606" park system, transforming an abandoned elevated railway line into a car-free urban escape. It's notable as the longest elevated greenway of its kind in the Western Hemisphere, connecting communities and offering amenities like bike repair stations and water fountains. The Exelon Observatory at Ridgeway also provides a unique spot for stargazing and sunset views.

The Chicago Riverwalk offers a truly unique urban hiking experience, transforming a former industrial area into a vibrant public space. This easy 2.0-mile (3.2 km) route, with its minimal 20 feet (6 metres) of elevation gain, takes around 48 minutes to complete, guiding you past towering skyscrapers and offering close-up views of the Chicago River. You'll encounter public art installations, including the impressive "Art on theMART" digital projection, and even floating wetland gardens, blending nature with the bustling city.

Planning your visit is straightforward, as the paved path is suitable for all, including those with strollers or wheelchairs. While accessible year-round, the Riverwalk can get busy, especially during warmer summer months. To enjoy a more serene experience and avoid the crowds, consider starting your walk early in the morning. You'll find plenty of benches for relaxation and numerous waterfront dining options along the way.

This award-winning pedestrian-friendly destination is considered a premier experience in downtown Chicago, celebrated for its harmonious blend of urban development and natural elements. Beyond walking, you can rent kayaks or take boat tours directly from the Riverwalk, offering a different perspective of the city's architecture and the revitalized river. It's an excellent choice for a leisurely stroll, providing a refreshing escape within the urban core.

Discover the Montrose Harbor Trail, an easy hike that offers a refreshing escape along Chicago's Lake Michigan shoreline. This 3.0-mile (4.8 km) route features a gentle elevation gain of only 26 feet (8 metres), making it perfect for a relaxed outing. You can expect to complete the trail in about 1 hour and 12 minutes, enjoying picturesque lakefront and harbor views, especially from the Montrose Harbor Cityview.

Planning your visit is straightforward, as the trail is easily accessible within Lincoln Park. Its urban location means you can reach it by various means, though specific parking details are best checked locally. The path itself offers a comfortable experience for most visitors, with flat and varied surfaces that include both paved and mulch sections.

Beyond the scenic waterfront, the trail provides a unique opportunity to explore the Bill Jarvis Migratory Bird Sanctuary. This haven for birdwatching features diverse natural elements and wooded areas, all set against the iconic backdrop of the Chicago skyline. It is a great spot to observe local wildlife and enjoy a moment of tranquility.

Embark on the North Branch Red Trail for a challenging hike that stretches 19.5 miles (31.4 km) through the scenic Forest Preserves of Cook County. You will gain 215 feet (65 metres) in elevation over an estimated 7 hours and 56 minutes, making this a difficult route best suited for experienced hikers. As you follow the path, you will meander along the tranquil North Branch of the Chicago River, enjoying lush, wooded landscapes and the vibrant native plants that line its banks. Keep an eye out for local wildlife, including deer and various waterfowl, as you immerse yourself in this refreshing natural setting. The trail offers a peaceful escape with diverse scenery, passing through notable areas like Indian Road Woods and Caldwell Woods. This long-distance route provides a substantial challenge and a rewarding outdoor experience.

Planning your visit to the North Branch Red Trail is straightforward, as the route is well-maintained and clearly marked, making it easy to navigate. You will find convenient access points with parking available along its extensive length, ensuring a smooth start to your adventure. Restrooms and picnic areas are also situated at various points, providing comfortable stops during your long hike. Consider starting early in the day to allow ample time to complete the nearly eight-hour journey, especially if you plan to explore the full distance.

This trail stands out as a significant pathway within the Forest Preserves of Cook County, offering a unique opportunity to experience the natural beauty of the Chicago River's North Branch. It provides a continuous, immersive experience through a series of interconnected preserves, creating a vital green corridor. The largely wooded environment offers a consistent sense of being away from urban bustle, even though you are close to the city. It's an excellent choice if you are looking for an extended, challenging hike that showcases the region's natural environment and offers a refreshing escape into nature.