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Joseph Curtis settled in what became Niles in 1827, and John Dewes followed in 1831. The settlement was originally called “Dutchman’s Point”, referring to German immigrants who followed, including John Plank of Hesse-Darmstadt (who sold whiskey to passing travelers and remaining Native Americans) and the Ebinger brothers of Stuttgart, as well as John Schadiger, Julius Perren, John-Jackson Ruland (d. 1880) and Revolutionary war soldier John Ketchum.

Many people of Native American ancestry lived in the area; Chief Blackhawk reportedly often smoked a peace pipe with Christian Ebinger. Article 4 of the Second Treaty of Prairie du Chien, signed on July 29, 1829, between the United States government and several chiefs of the Chippewa, Ottawa, and Potawatamie left particular tracts of land to individuals of mixed-Native American ancestry. Among them were Billy Caldwell, Victoria Pothier, and Jane Miranda. Land titled to these individuals eventually established part of the border of Niles. During the 1832 Black Hawk War, one band of Native Americans may have reached Billy Caldwell’s property as part of an attempt to reclaim land lost to the United States. Hostilities ended in 1833, and most Native Americans immediately left, moving west of the Mississippi River

The Ebingers settled near Milwaukee and Touhy Avenues in the early 1830s. John Ebinger had been the head gardener for King William in Württemberg, Germany, but moved to the United States (initially Ann Arbor, Michigan) when he was 62. His eldest son Frederick had traveled to Chicago and worked on the pier or harbor by 1832, and was soon joined by his brother John Jr. and their wives, as well as John Plank. John Ebinger and his youngest son Christian (at 21 newly married to orphaned Barbara Reuhle of Stuttgart in 1834; both of whom walked the route to enable their elders to ride) packed and traveled to join them, but found Chicago too swampy to farm. After their horse stepped on a rattlesnake and died shortly after crossing the North Branch of the Chicago River on an Indian trail leading towards Milwaukee, the Ebingers built a cabin at Milwaukee and Harlem Avenues, and laid claim to 80 acres (0.32 km²) of land. The older Ebinger brothers (one of whom married the sister of Fort Dearborn’s commanders’ wife) soon joined them, as did the Planks. John Plank soon sold his house to Mr. Phillips, who opened a store and became the area’s first postmaster. Christian Ebinger or his son of the same name (born 1835 and the first white child born in the area, d. 1879), became the first minister to be ordained in their German Evangelical Association, and served as the Village Collector, Township Assessor and Overseer of the Poor (from 1852 to 1865) and Highway Commissioner, as well as left seven surviving children.