The best family-friendly hikes and walks around Chicago

The Northwestern Medicine Wellness Way Fitness Trail offers a unique urban walking experience, tracing the edge of Chicago's famous Navy Pier. This easy 1.8-mile (2.9 km) loop is entirely paved and flat, with a negligible 30 feet (9 metres) of elevation gain, making it incredibly accessible for all. As you walk, you'll be treated to continuous, expansive views of Lake Michigan and the dramatic Chicago skyline, passing landmarks like the Centennial Wheel and the Polk Bros Fountain.

Planning your visit is straightforward, as the trail is open 24/7 and requires no permits or fees. It's a fantastic option for a quick 45-minute outing, whether you're looking for a leisurely stroll or a light jog. Public transport provides easy access to Navy Pier, and while parking is available, arriving earlier in the day can help you avoid peak crowds, especially if you're seeking a peaceful moment.

This trail stands out as an urban oasis, blending fitness with sightseeing in a bustling environment. It's equipped with distance checkpoints and fitness tips via QR codes, plus dedicated fitness stations at the end of the Pier for stretching or working out with a view. It's a perfect choice for beginners or anyone wanting to enjoy the city's iconic waterfront in a relaxed, family-friendly setting.

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 Lakefront Trail offers a quintessential urban escape, letting you stroll along the edge of Lake Michigan with continuous views of the water and the city's impressive skyline. This easy 2.5-mile (4.0 km) hike, with just 30 feet (9 metres) of elevation gain, is a paved, flat path that takes about 1 hour and 1 minute. You'll experience the vibrant atmosphere of Chicago's waterfront, passing by spots like Lake Shore Park and the lively Ohio Street Beach, making it a perfect quick outing for anyone looking for accessible scenery.

Planning your visit to this section of the Lakefront Trail is straightforward. While specific parking can be tricky in downtown Chicago, the area is well-served by public transport, making it easy to reach. The trail is open year-round, but it's worth noting that it can become quite busy, especially on sunny weekends and during peak tourist season. For a more relaxed experience, aim for a weekday morning or an off-peak time to enjoy the views without the crowds.

What makes the Chicago Lakefront Trail truly special is its seamless integration of natural beauty with urban attractions. It's not just a path; it's a gateway to many of Chicago's cultural institutions and parks, offering a unique perspective on the city. The trail is equipped with amenities like restrooms and concessions, and while this segment is short, it's part of a much larger 18-mile network, providing endless opportunities for exploration if you choose to extend your walk.

The Catherine Chevalier Woods River Loop offers a refreshing escape into nature, winding through diverse oak and hickory woodlands and alongside the Des Plaines River. You'll find yourself on predominantly unpaved paths, with some sections featuring a crushed limestone surface, and might even spot white-tailed deer. The trail's gentle terrain and lush scenery make it a peaceful spot for a walk.

Planning your visit is straightforward for this easy 3.1-mile (4.9 km) loop, which takes about 1 hour and 14 minutes to complete with only 32 feet (10 metres) of elevation gain. While specific parking information isn't detailed, it's a well-loved local spot, so consider an earlier start to beat any crowds. The trail is suitable for year-round enjoyment, including winter activities like skiing.

This urban oasis is a significant link in the larger Des Plaines River greenway system, offering a unique opportunity to connect with nature close to Chicago. Beyond the natural beauty, you'll encounter interesting features like urban art under bridges and the historic Indian cemetery of Alexander Robinson and his family just north of Lawrence Avenue.