The far Southeast Side neighborhood of Woodlawn is surrounded by lush green woodlands, sprawling golf courses, landscaped parks and college campus grounds. Its easternmost border flanks the Lake Michigan shoreline and nearly a third of its acreage is covered by the winding paths, green lawns and lagoons of Jackson Park. 

Much of Woodlawn’s charm is its namesake abundance of trees and beautiful green grass lawns. The residential streets enjoy tall, leafy canopies and numerous playlots and parks that boast verdant environs for local recreation and outdoor pastimes. Some of the smaller community hangouts include Prairie Wolf Park, Mamie Till Mobely Park, Huckleberry Playlot and Moccasin Ranch Playlot. These pocket-sized sites mostly have playground equipment, park benches, baseball fields and basketball courts. For a wider variety of activities, head over to Jackson Park which has everything from Japanese gardens and sandy beaches to putting greens and sailboat slips.

Originally designed by famed landscape architect Frederick Law Olmsted, Jackson Park is a stunning example of public parkland at its finest. It was the site of the 1893 World’s Fair Columbian Exposition’s “White City” and has since been transformed into a 540+ acre destination spot with something for every interest. One can stroll the tranquil paths of Osaka Garden on a forested, lagoon-surrounded island where exotic Asian vegetation and trickling stone-crafted waterfalls soothe the senses. There’s also a driving range and a par 5, 18-hole golf course that will challenge even the most accomplished scratch golfer. For the athletically inclined, Jackson Park has a full roster of sporting facilities: tennis and basketball courts, soccer and football fields, baseball and softball diamonds, fitness center and gym, jogging and walking trails, and plenty of open green space to just run around and stretch the legs.      

Woodlawn is also next door to Washington Park, another larger Chicago public park that offers tons to do with family and friends. Washington Park’s southern boundary is 60th Street, which is Woodlawn’s northern limit. The rest of the northern side of the neighborhood is lanked by Midway Plaisance Park, an old-timey promenade peppered with fountains, monuments and long rows of shrubbery. Among the scenic, old-fashioned milieu of Midway Plaisance is a large ice skating rink shared by the Chicago Park District and the University of Chicago. University of Chicago’s campus is just north of Woodlawn, boasting a picturesque backdrop of ivy-covered buildings and tree-shaded commons.   

With Lake Shore Drive, the expressway and the Metra rail all running through the neighborhood, Woodlawn is well connected to the city center and other parts of Chicago. Those with cars can travel north to downtown on Lake Shore Drive (which curves along the community’s eastern edge) or take the I-94 Dan Ryan Expressway up to the Loop’s west side. The Chicago Skyway (I-90) re-converges with I-94 a few blocks west of Woodlawn, giving motorists a couple of convenient options for highway travel.

Anyone interested in taking public transportation in Woodlawn can hop on the Metra train at either 67th Street or 63rd Street. There is also another stop just north of the neighborhood at 59th Street. The CTA also services the area with several bus routes and the Green Line L train, which has a terminus in Woodlawn at 63rd Street and Cottage Grove. The Green Line makes a stop at King Drive and 63rd Street (on the neighborhood’s western border) before heading north to the downtown Loop.

Woodlawn Real Estate