Nestled up against the seven-mile strip of Lincoln Park, Oakland is one of the 77 officially recognized communities that make up Greater Chicago. Not too long ago, Oakland's skyline was defined by many housing projects. However, many of them have been torn down and are being replaced by condos and new single-family homes as this old part of the Greater Chicago area is slowly enjoying a rebirth. The district does still have a large percentage of multifamily housing, but there are plenty of sidewalks for you and your four-legged friend to make good use of. Sitting on the shore of Lake Michigan can make winters here frigid with high winds and low wind-chill factors to deal with along with a significant amount of snow. Spring, summer, and fall typically range from warm to hot and humid. During the summer months, you may want to get your walks in early in the morning or later in the evening.
The terrain here is much the same as most of Greater Chicago in that it is incredibly flat. It is so flat you can stand at one end of S. Lake Park Ave. and see all the way to the other end. Although you might think flat terrain makes for a boring walk, it does give the two of you a way to rack up the miles. Many of the sidewalks are crumbling and you really need to pay attention while you are walking. In the southern section of Oakland, many of the streets are tree lined and have grass strips for your pup to pee on. In the northern section, trees seem to have taken a back seat or been lost to the elements as they become few and far between along most of the sidewalks, leaving you exposed to the summer sun if you go walking during the day.
Oakland has a pretty large selection of green spaces in comparison to many of the surrounding communities. There are several parks in the community to take your pup for a walk in, but there are far more vacant lots that have grown over where you may also be able to take your pooch out on to do his business. Keep in mind that just because it might be an abandoned lot, you still need to clean up after he goes.
On the east side of Oakland lies Burnham Park: a six-mile stretch of trails, grass, and trees that you and your dog can spend countless hours in. The park also gives you access to the 41st Street Beach where the two of you can cool off on a hot summer day. If the beach doesn't sound right, there are several parks scattered through Oakland that are pet-friendly and great places to take your pooch out for a little exercise.