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Between the Midway and Jackson Park, a neighborhood built for a world’s fair audience: greystone rows and courtyard buildings, a lakefront park with a gilded statue and a Japanese garden, and the biggest construction project on the South Side rising on its eastern edge.
Woodlawn boomed when the 1893 World’s Columbian Exposition landed in Jackson Park on its doorstep, and the housing shows that origin: greystones, brick two-flats, and courtyard buildings put up for a neighborhood that expected crowds. The University of Chicago’s campus has grown steadily along the Midway Plaisance on its northern edge, and 63rd Street, once one of the South Side’s great commercial and jazz strips, carries the neighborhood’s main business life.
On the east edge, the Obama Presidential Center campus has been taking shape along Stony Island Avenue at Jackson Park, the largest investment the neighborhood has seen in generations.
The park Frederick Law Olmsted shaped for the fair is Woodlawn’s front yard: the Garden of the Phoenix on its wooded island, the 1918 gilded Statue of the Republic at 63rd and Hayes remembering the fair, harbors, a golf course, and the lakefront trail running north to the Loop. The Midway Plaisance adds a mile-long green between Woodlawn and Hyde Park with a winter ice rink.
The Green Line ends at Cottage Grove and 63rd, the Red Line stops at 63rd on the Dan Ryan side, and the Metra Electric’s 63rd Street station covers the middle, so three rail options split the neighborhood between them. Lake Shore Drive begins its run downtown at the park’s edge.
Greystone rows and brick two-flats dominate, with courtyard condo buildings near the parks, frame cottages on the western blocks, and new construction filling lots at a pace the South Side has not seen in decades. Two-flats here can be exceptional buys for owner-occupants who want rent helping the mortgage; read our investment guide and building-reading guide first, and the foundations guide explains what a century-old greystone’s basement should look like.
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