The enigmatic octagon atop the George Cleveland Hall Branch of the Chicago Public Library caps one of the most important libraries in the city.

A terrific bit of Orthodox vernacular architecture stashed on a Chicago side street, Holy Trinity was designed by Louis Sullivan of all people.

It looks almost depilated after losing all its ornamentation - like a face with no eyebrows - but after more than 125 years as a school, the present-day Near North Montessori school must have great bones.

Small but attractive indeed–Norwegian-American architects Michaelsen & Rognstad designed this Italian Baroque-inspired terracotta jewel for olive oil importer William Bertini in 1922. A renovation of an Italianate originally built in 1877, the building is a neat microcosm of the path of River North.

Lot going on here: begun as the Cooper-Monatah Hotel, but requisitioned by the federal government for use as a military hospital before it ever opened. Operated for years as a segregationist white-only apartment hotel. Home to a legendary jazz venue that served integrated audiences.