The best dog-friendly hikes and walks around Chicago

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.

Explore the heart of Chicago on the Riverwalk, an easy 2.0 miles (3.2 km) hiking route that offers a unique perspective of the city's iconic architecture. You will experience minimal elevation gain, just 20 feet (6 metres), making it a comfortable stroll for about 48 minutes. As you walk, you'll find yourself immersed in an urban canyon, with towering skyscrapers reflecting in the water and landmarks like the LaSalle Street Bridge overhead, creating a dynamic and engaging atmosphere.

Planning your visit to the Riverwalk is straightforward, as it is easily accessible within downtown Chicago. You can reach various entry points using public transportation, and parking options are also available nearby. The path is paved and largely flat, making it suitable for most visitors. Along the way, you will discover numerous restaurants, bars, and cafes, perfect for a break or a meal while enjoying the riverside views.

The Chicago Riverwalk is more than just a path; it is designed with distinct "coves" or "rooms," each offering a different experience. From relaxing at The River Theater to observing floating wetland gardens at The Jetty, these unique sections provide varied landscapes and activities. This multi-use pathway allows you to connect with the city's vibrant energy and its natural elements, showcasing a blend of urban development and thoughtful design.

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.