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Like the Pilsen Open Studios event in neighboring Pilsen, the annual Little Village Arts Fest opens the doors of the several art studios and participating businesses in the neighborhood for a weekend of browsing and community spirit.
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.
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.
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.
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.