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Photo: MrHarman, CC BY-SA 3.0 via Wikimedia Commons
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.
Garfield Park is a 184-acre (0.74 km2) urban park located in the East Garfield Park neighborhood on Chicago's West Side. It was designed as a pleasure ground by William LeBaron Jenney in the 1870s and is the oldest of the three original parks developed by the West Side parks commission on the Chicago park and boulevard plan. It is home to the Garfield Park Conservatory, one of the largest plant conservatories in the United States. It is also the park furthest west in the Chicago park and boulevard system.
© OpenStreetMap contributors
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.
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.
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.
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.
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.
The beautifully preserved historic house where Walt Disney was born.