The best walks and hikes around Chicago

Lace up your shoes for an easy 1.8-mile (2.9 km) hike along the Northwestern Medicine Wellness Way Fitness Trail. This paved route offers continuous, sweeping views of Lake Michigan and the impressive Chicago skyline, making it perfect for a leisurely walk or a quick jog. You'll gain a minimal 30 feet (9 metres) in elevation over approximately 45 minutes, enjoying the flat, even terrain. As you go, keep an eye out for iconic sights like the Centennial Wheel and the Polk Bros Fountain, which add to the vibrant urban atmosphere. It's a refreshing way to experience the city's waterfront without a strenuous climb.

The Northwestern Medicine Wellness Way Fitness Trail is conveniently located at Chicago's Navy Pier, making it highly accessible for visitors. You can easily reach the trailhead by public transport or find ample parking options directly at Navy Pier. The route is open to the public around the clock, seven days a week, though it's always wise to check weather conditions before heading out. There are no permits or fees required to enjoy this trail, offering a hassle-free experience for everyone. Its gentle nature means it's suitable for all ages and fitness levels, so you can bring the whole family along.

This trail stands out as an urban oasis, providing a unique opportunity to connect with nature amidst the bustling city. While you won't find traditional rugged hiking terrain, the continuous waterfront views and proximity to major Chicago landmarks create a distinct experience. It's an excellent choice if you're looking for a quick, accessible outdoor activity that combines fitness with sightseeing. The trail's design caters to walking, jogging, or running, offering a different kind of outdoor adventure than a typical wilderness path.

Embark on an easy urban hike along the Bloomingdale Trail, a flat, paved path offering a unique elevated perspective of Chicago. This accessible route spans 2.8 miles (4.5 km) with a minimal elevation gain of just 8 feet (2 metres), making it perfect for a leisurely outing. You can expect to complete the journey in about 1 hour and 8 minutes, enjoying diverse urban landscapes as you go. Keep an eye out for the MINOX Sculpture and Mural near the entrance, along with various art installations and green spaces that dot the path.

Accessing the Bloomingdale Trail is straightforward, with 12 ADA-compliant ramps strategically placed about every quarter mile along its length. These numerous entry and exit points make it easy to join or leave the route at your convenience, whether you are coming from a nearby neighborhood or public transport. The trail's elevated design ensures an uninterrupted experience, as you will not encounter any street crossings during your hike. This makes it a safe and pleasant option for families and individuals looking for a seamless urban escape.

The Bloomingdale Trail is a significant part of The 606 network, transforming a former railway line into a vibrant community asset. Its elevated position provides glimpses into the neighborhoods below, showcasing a blend of modern buildings and historic architecture. This unique urban greenway stands out as a notable example of repurposing infrastructure for public enjoyment, offering both recreation and a connection to Chicago's urban fabric.

Step onto the Chicago Lakefront Trail for an easy urban hike that blends cityscapes with refreshing lake views. This 2.5 miles (4.0 km) route offers continuous vistas of Lake Michigan on one side and the impressive Chicago skyline on the other, passing by landmarks like Navy Pier. With a minimal elevation gain of just 30 feet (9 metres), you can expect to complete this scenic journey in about 1 hour and 1 minute, making it perfect for a quick escape.

When planning your visit, be aware that the paved, multi-use path can become quite busy, especially in downtown sections and during warmer months or on weekends. To enjoy a more relaxed experience, consider starting your hike during off-peak hours. The trail is easily accessible, and its flat terrain makes it suitable for hikers of all skill levels looking for a pleasant stroll along the waterfront.

This section of the Chicago Lakefront Trail provides a unique opportunity to experience the city's vibrant energy alongside its natural beauty. It's a popular artery for both recreation and commuting, showcasing Chicago's commitment to public green spaces. The route offers a dynamic backdrop, from sandy stretches like Ohio Street Beach to the bustling activity around cultural attractions, providing a distinct perspective on the Windy City.

Embark on the Magnificent Mile and Navy Pier Walk, an easy urban hike that guides you through the heart of Chicago. This route covers 3.3 miles (5.3 km) with a minimal elevation gain of just 40 feet (12 metres), making it accessible for nearly everyone. You can expect to complete this vibrant journey in about 1 hour and 21 minutes, enjoying the dynamic cityscapes and impressive architecture as you go.

When planning your visit, remember that this entire route is paved and generally flat, making it suitable for all ages, including those with strollers or wheelchairs. While the trail itself is easy, you should be prepared for crowds, especially during peak tourist seasons or events. Wearing comfortable shoes is highly recommended to fully enjoy the distance and the many sights along the way.

This unique route combines two of Chicago's most iconic destinations, offering a distinct city experience. As you hike, you will pass luxury boutiques and historic buildings like the Tribune Tower before reaching Navy Pier. Extending into Lake Michigan, the pier provides panoramic views of the city skyline and the vast lake, where you might even spot the famous Centennial Wheel.