Pill Hill is a relatively affluent middle-class neighborhood in the Calumet Heights area of South Chicago. The name comes from the number of doctors living here who worked at the South Chicago Hospital. Over time, the community has become home to a variety of residents seeking a quiet place to call home. While there are no parks within the community, there are dog parks and pet supply stores within easy driving distance. But if you are looking for anything more than fast food, you won't find it near Pill Hill. You will have to drive to find something more upscale.
Like the rest Chicago, you can expect bitter cold winters with plenty of snow coming in off the lake with weeks of sub-freezing temperatures and icy sidewalks to deal with. Summer brings plenty of hot weather and sunshine, the perfect atmosphere to spend time out in the sun in one of the parks along nearby Lake Michigan.
Pill Hill is just another flat neighborhood in a city full of level ground. You might be fooled into thinking there would be at least one hill in Pill Hill, but this is not the case. You might think this would make for some very boring and non-strenuous walks, but there are other ways to get your exercise in beside going up and down hills. Thankfully, there are plenty of wide sidewalks with grass berms for the two of you to walk on. The trick is to try walking around different blocks, try out the grassy areas behind the elementary school, and go for distance once your dog's paws have toughened up enough to handle the pavement.
Keep in mind the temperature of the concrete as you get ready to go for a walk. In the summer months it can be hot enough to burn poor Fido's pads and in the winter, it can be cold enough to cause frostbite.
You would think a community like Pill Hill would have at least one small park for you to go walking in but, unfortunately, the nearest park of any kind will take a drive in the car. The nearest park is Van Wissinger Prairie covering more than 3,900 acres and playing host to a vast range of wildlife including deer, black-crowned night herons, Blanding's turtles, bald eagles, and more. The prairie was developed with connectivity in mind as there are miles of trails and greenways for you to explore. Many of the animals here are on the list of endangered species or are considered protected.
Alternatively, the nearest off-leash dog park is Jackson Bark over on the lake shore where you can let Fido run around while you relax in the shade. Or you can take them for a nice long walk on the many trails running through Jackson Park and around the East Lagoon in the sunshine.