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Photo: John Delano, Attribution via Wikimedia Commons
Chicagoans can't get enough Towers of Sears. This is the original, which at a height of 250 feet served as Sears' headquarters until the move into the slightly taller building downtown. Once the largest commercial building in the world, the tower must now content itself with being the tallest in the Far West Side. A short jaunt in either direction on Arthington St will reveal more grandiose old Sears buildings, from the power plant and warehouses to the west to the headquarters building just across the street to the east.
The Sears, Roebuck and Company Complex is a building complex in the community area of North Lawndale in Chicago, Illinois. The complex hosted most of department-store chain Sears' mail order operations between 1906 and 1993, and it also served as Sears' corporate headquarters until 1973, when the Sears Tower was completed. Of its original 40-acre (16 ha) complex, only three buildings survive and have been adaptively rehabilitated to other uses. The complex was designated a National Historic Landmark in 1978, at which time it still included the 3,000,000-square-foot mail order plant, the world's largest commercial building when it was completed. That building has been demolished, its site taken up by the Homan Square redevelopment project.
© OpenStreetMap contributors
History-filled Chicago park 15 minutes west of downtown, with some fun outdoor sculptures, plenty of green space, and a fabulous fieldhouse. It's in a rough neighborhood, though you can take the L right to the park, which is safe.
Amazing botanical conservatory, one of the largest indoor gardens in the world, which is often blessed with large-scale contemporary art installations as well as frequent family-oriented events. Definitely bring the kids, who will not lack for things to climb on and strange environments to run around in. Perhaps in an effort to assuage especially fearful Chicagoans, the L stop actually hovers directly above the conservatory entrance, so definitely don't pass this place over for fear of the surrounding neighborhood. There is also ample free lot and on-street parking right around the main building.
Home of two lagoons, Jens Jensen formal garden, statues of bison and Alexander von Humboldt, a Queen Anne style stable and refectory, and, for a while in 2019, even a baby gator (escaped). The park features food trucks with Puerto Rican cuisine and views of downtown Chicago.
For sake of comprehensiveness, you might want to drive by this Frank Lloyd Wright house in Austin after a tour of his numerous buildings in neighboring Oak Park. The house is a textbook example of success in applying the Prairie School design principles of strong horizontals and open interiors. Look especially for the attractive windows (not originals, unfortunately), whose patterns have inspired a line of Frank Lloyd Wright jewelry.
Chicago's most far flung city landmark is covered with wonderfully elaborate carvings in its art deco, terra cotta exterior. The bank's construction was finished in the malapropos year of 1929.
The beautifully preserved historic house where Walt Disney was born.