There were numerousNative American trails leading to Chicago. The most important means of transportation was canoes in the Great Lakes and on the rivers.
Trails interconnected areas not on the waterways. Sauk Trail was a Native American trail running through Illinois, Indiana and Michigan. The trail ran from Rock Island on the Mississippi River to the Illinois River near modern Peru, Illinois, then along the north bank of that river to Joliet, and on to Valparaiso, Indiana. Then it ran northeasterly to LaPorte and into southern Michigan running through Niles,Three Rivers, Ypsilanti and ending at the Detroit River near Detroit.The trail followed a winding path around natural topography including following the ridges of dune and moraines that mark the earlier glacial period Lake Michigan shorelines. European settlers improved the trail into a wagon road and later into modern highways, although these often have been straightened and rerouted.