New East Side was once the home of massive railyards and one of the biggest tangles of track you are likely to ever see. Today, the community is home to some 15,000 residents, its own park, numerous eateries, a coffee shop, and a wealth of high-rise apartments and hotels. While not a large area, it does sit right on Lake Michigan at DuSable Harbor and the entrance to the Chicago River. In the center of New East Side sits Lake Shore East Park which has a dog park for your furry, four-legged friend to meet up with his buddies in. Along with this, there are plenty of pet stores and dog-friendly parks in nearby communities for the two of you to check out. All along the Chicago River and the shore of Lake Michigan, there are trails to hike along. With these comes the Chicago Riverwalk with fantastic city views, restaurants, and more to enjoy.
The terrain here is very flat and, as you might expect, in this part of town it's been given over to large high-rise buildings and plenty of streets and sidewalks. Despite this, there still seems to be plenty of green space for you and your pup to play in as long as you clean up any messes your pooch leaves behind. While you can walk your pup along the sidewalks that line the streets here, many of the residential buildings have their own green areas complete with sidewalks and paths for your use. There are a few empty lots, but you may want to avoid them as they are still private property.
If you're going to get in a good challenging stroll, you and your pup need to take long hikes along the Chicago Riverwalk and Lakefront Trail, both of which cut through plenty of grass and trees that are sure to make your walks more enjoyable.
It might be hard to think of an area in the heart of Chicago as having any green spaces at all but New East Side has plenty of parks to choose from along with the Riverwalk and miles of trails.
Right in the heart of this small section of the city sits six acres of green space dedicated by Chicago Mayor Richard Daly in 2005. The park includes a dog park that is fenced-in and makes the perfect place to relax under the shady trees while your pooch runs off to hang out with their friends. Some areas are still under development, leaving open grassy areas to let your pup explore and, of course, just to the south across E. Randolph St. is Millennium Park which offers trails, trees, and grass to investigate just in case the River Walk and Lakeshore Trail prove to be boring. This'll also give you more opportunities to stretch your legs.