Things to do
Six honest picks. Not sixty.
From Wikipedia + OpenStreetMap. No affiliate links, no crowd bias.
Haymarket Martyrs' Monument
The Haymarket Martyrs' Monument is a funeral monument and sculpture located at Forest Home Cemetery in Forest Park, Illinois, a suburb of Chicago. Dedicated in 1893, it commemorates the defendants involved in labor unrest who were blamed, convicted, and executed for the still unsolved bombing during the Haymarket Affair (1886). The monument's bronze sculptural elements are by artist Albert Weinert. On February 18, 1997, the monument was designated a National Historic Landmark.
Wikipedia → Nuclear Energy
Nuclear Energy (1964–1966) is a bronze sculpture by Henry Moore on the campus of the University of Chicago at the site of the world's first nuclear reactor, Chicago Pile-1. The first human-made self-sustaining nuclear chain reaction was created here on December 2, 1942. The sculpture is set in a granite paved quadrangle, with the paving stones radiating outward from the sculpture, and memorial plaques mounted on an adjacent wall. The memorial site is a National Historic Landmark and Chicago Landmark.
Wikipedia → Old Chicago Post Office
The Old Chicago Main Post Office is a nine-story-tall office building in downtown Chicago, Illinois, U.S. The building was designed by Graham, Anderson, Probst & White and built in 1921. The structure of the building was expanded greatly in 1932 to serve Chicago's great volume of postal business, increased significantly by the mail-order businesses of Montgomery Ward and of Sears. The building is listed on the National Register of Historic Places.
Wikipedia → Manhattan Building
The Manhattan Building is a 16-story building at 431 South Dearborn Street in Chicago, Illinois. It was designed by architect William Le Baron Jenney and constructed from 1889 to 1891. It is the oldest surviving skyscraper in the world to use a purely skeletal supporting structure. It is the sixth oldest surviving building in the city. The building was the first home of the Paymaster Corporation, and is listed on the National Register of Historic Places on March 16, 1976, and designated a Chicago Landmark on July 7, 1978.
Wikipedia → Old Colony Building
The Arc at Old Colony is a 17-story landmark building in the Chicago Loop community area of Chicago, Illinois. Designed by the architectural firm Holabird & Roche in 1893–94, it stands at approximately 215 feet and was the tallest building in Chicago at the time it was built. The building was designated a Chicago Landmark on July 7, 1978. It was the first tall building to use a system of internal portal arches as a means of bracing the structure against high winds.
Wikipedia → Monadnock Building
The Monadnock Building is a 16-story skyscraper located at 53 West Jackson Boulevard in the south Loop area of Chicago, Illinois, United States. The north half of the building was designed by the firm of Burnham & Root and built starting in 1891. At 215 feet, it is the tallest load-bearing brick or masonry building ever constructed. It also employed the first portal system of wind bracing in the United States. Its ornamented staircases represent the first structural use of aluminum in building construction. The later south half, constructed in 1893, was designed by Holabird & Roche and is similar in color and profile to the original, but the design is more traditionally ornate. When completed, it was the largest office building in the world. The success of the building was the catalyst for an important new business center at the southern end of the Loop.
Wikipedia → 
