Once upon a time, before Potter Palmer relocated to the swampy North Side around Schiller Street, this was the premier residental street in Chicago for the social and economic elite. George Pullman, Philip Armour and Marshall Field are but a few of the luminaries who once dwelled on what was considered Chicago's Fifth Avenue. Stately houses with gilded lobbies and huge mansions were the norm before the turn of the century. Today, this part of the city is tired, ravaged by years of economic blight and poverty. Still, parts of this once fabled stretch of road are intact and worth a look. Tours are run by the Chicago Architecture Foundation and the Glessner House museum.

Phone: (312) 744-3200

Cross Streets: Near the intersection of S Prairie Ave and E 18th St