Pilsen is located on the banks of the South Branch of the Chicago River and is bordered by the Heart of Chicago and East Pilsen. Homes in Pilsen tend to be smaller apartment buildings of three to four stories with straightforward faces that open out directly onto the sidewalk. Throughout most of Pilsen, there is no divider between sidewalk and street, so you will find yourself walking your dog very closely at your side throughout most of the neighborhood.
There are several regional parks in Pilsen where you can find some pleasant walking trails underneath mature tree cover and benches on which to rest in the midst of your walk with your dog. Sidewalks bordering the parks are also likely to be uninterrupted by intersecting traffic all the way around the proximity, so you can practice things like biking or skating with your dog on the sidewalks more easily than in the rest of the neighborhood.
Walking through most of Pilsen feels quite tight, with the buildings opening right onto the sidewalks and no dividers between sidewalk and road. There are several regional parks where you can get away from the neighborhood walking and let your dog play on a looser leash or enjoy a game of fetch or frisbee.
Dvorak Park offers a lovely shady area around the ballfield in the center. Just across the border of Pilsen, Adam Medill Park provides lots of areas and paths for you to enjoy. A little further past this park, Via Rego Park and Vernon Park provide a rest from neighborhood walking as well as several fields where you can play a good game of fetch. While most of the part of Pilsen that borders the South Branch Chicago River is devoted to industrial and private buildings, there are some areas where you can access the shoreline to enjoy walking along a natural riverbank.
There are several regional parks for you to enjoy with your dog in Pilsen, but there is not much in the way of natural space available to you in this area. The closest natural trail is across the river and some distance from Pilsen.
Ping Tom Memorial Park provides miles of space along the river. Your dog will love sniffing around in the natural shrubbery for all kinds of wildlife while you enjoy the views of the river and the breezes that it produces. You have a great chance of seeing water and wading birds like egrets and herons along the river. This large area is also a great habitat for nocturnal creatures, so you have a good chance of seeing them as well, especially if you are walking at dawn or dusk. For a closer walk, cross the river to the Palmisano Park with its wide, grassy trails and small pond area.