Chicago is an urban area filled with packed residential areas and bustling roads that make it pretty hard to get a decent walk in with your pup. The city does offer lots of parks just for that problem, and even offer trails in the area of Bessemer Park, where Fido can enjoy a leisurely walk through the shaded space while remaining on a leash.
This quiet area exists in the neighborhood of South Chicago, right towards the southern tip of the city near Calumet River. With plenty of parking off the road, one of the best places to starts on the Bessemer Park trails is in the southern part of the park. The trail starts off surrounded by thick trees, and this shaded area passes people playing tennis and basketball. The trail begins to curve northward, where it has a number of sights of baseball fields, a playground, and kids playing at the community center.
Along the trail are water fountains and benches, although you and Fido will have to venture onto a smaller trail to reach picnic benches, trash bins, and restrooms near the community center. Although a good portion of the main trail is covered in trees, the middle section is open to the sun. Then, you and Fido can walk into a shaded area before you reach the end, where you'll be able to enjoy the Bessemer Park Nature and Wildlife Garden, which offers small trails that loop around nature shrubs, wildflowers, and trees. Once on the main trail again, it ends after only a short walk at the northeast corner of the park, this is where you and Fido will have to turn back to get back to the start.
Whether you're here to view the scenic wildlife garden, watch kids play, or relax in one of the shaded fields next to the trail, you and Fido will find plenty to do in this cozy park.