Cragin is a large neighborhood on the outskirts of Chicago. Most homes in this neighborhood are charming single family homes of one or two stories. Yards are not large, but they are generally unfenced and there is a generous divider between sidewalk and street so you will find this neighborhood a good place to walk your dog on a loose leash or skateboard, bicycle, or rollerblade at his side. Be cautious about any pedestrians, however.
There are several charming regional parks within Cragin including Blackhawk Park with ball fields and pleasant walking trails between the trees. This also includes Chicago Park, that offers a smaller walking area and several recreational fields. A short distance from Cragin is Belmont Central Park which provides fields and water features to walk in and around during your visit. For more extensive wilderness exploration, you have a distance to travel to the Schiller Woods which can provide more challenging trails.
Walking through Cragin this very pleasant and easy going. There are few areas where you will struggle with the terrain. Long, straight blocks lend themselves well to being on wheels with your dog, and plenty of attractive tree-cover makes it a cooler spot on sunny days.
If you are looking for a change from neighborhood walking, there are several regional parks available to you, including Blackhawk Park and Chicago Park. Outside of Cragin, Belmont Central Park gives you more areas to explore, as well as a cute little pond with a tiny bridge that is perfect for exposing a young puppy to the sight of water and having her walk over a bridge for the first time. Be cautious when crossing any water, however.
If you are looking for more opportunities to explore with your dog, you will have to travel for a bit of a distance to the Schiller Woods which offers miles of natural woodland exploration along the Des Plaines River.
While there is not much green space within Cragin itself, a gorgeous woodland area is a little distance away and worth the travel if you want access to a more natural space. The forest ranging along the Des Plaines River includes the La Framboise Reserve and the Fullerton Woods family picnic area, among many others.
A trail runs along the river for the entire distance, so you can enjoy the gorgeous river views for your entire walk. This is a lovely place to explore with your dog and a great place to experience a natural shoreline that will reveal all sorts of wildlife.
You have a great chance of seeing water and wading birds, as well as raccoons and foxes or even larger wildlife like deer in this extensive forested area. Throughout the parks, there are grassy areas where you can get out of the tree cover for a bit and enjoy playing a game of fetch or frisbee.