Because this neighborhood sits along Lake Michigan, the weather in Woodlawn is more temperate for walking than in some inland neighborhoods. Winter in Chicago is cold and summers are hot and humid. Fortunately, the lake moderates temperatures and provides cool breezes off the water on hot summer days, making walking more pleasant for those enjoying their daily outing.
Much of Woodlawn consists of residential buildings, most of which are multi-story walk-up townhouses and apartments, but some single-family residences also exist in the neighborhood. Many buildings are historic, constructed of brick, and have architectural features reflecting the time periods in which they were developed in this long-established neighborhood. The neighborhood is bounded on the north by the Midway Plaisance and the University of Chicago.
The neighborhood is flat, and streets are comfortable to walk on foot with no inclines or steep stretches. There are many undeveloped tracts of land and some vacant properties that provide good places to walk and play with your dog. Rail tracks that run through the east side of the area form a barrier for pedestrians and their pets, so exercise caution when exploring these areas in order to avoid running afoul of any train traffic. Woodlawn is adjacent to Lake Michigan and Jackson Park is located along the shoreline of this community.
The 500-acre Jackson Park located on the east side of the community on the shores of Lake Michigan provides a flagship greenway for Woodlawn residents. This park has many trails winding through natural open areas and access to the 18-mile Chicago Lakefront Trail. Jackson Park is also connected to the Midway Plaisance with bike trails and pedestrian ways along a large, green space that stretches to Washington Park.
Washington Park provides 366 acres of recreational and natural space. Both Washington Park and Jackson Park have lagoons and fishing and Jackson Park features a marina and beaches on the lake. These areas provide miles of walking trails and interesting natural greenways along with water for canine residents to take in on long walks near Woodlawn. There are also some smaller parks and playgrounds in the area including Anita Young Boswell Park, Flying Squirrel Pak, and numerous playlots and botanical gardens. There is no shortage of greenways in Woodlawn.