Sign for Madalyn the Hot Dog Lady of Crown Point Indiana in 2010. Sadly, Madalyn hasn't been in the square for the summer of 2011 and has apprantly retired. She was a part of life in Crown Point for a long time and will be missed. Crown Point is located in Northwest Indiana with a population of over 37,000. Crown Point and Lake County are about 50 miles from Chicago and are considered part of the "Chicagoland" area. Crown Point has a traditional small town America feel with a main street consisting of the old Lake County Courthouse surrounded by numerous small businesses, known as "the square", including a theater, ice cream shop, antique stores, and restaurants.