 Sheridan Road was created in the early 20th century connecting Chicago with Fort Sheridan north of the city . Both the road and the fort were named in honor of Philip Sheridan , Union general during the Civil War . Sheridan , who served as colonel of the 2nd Michigan Cavalry in 1862 , was later promoted to the rank of major general during the war . The Greater Sheridan Road Association started to promote an extension of the road south to St. Louis and north through Wisconsin and Michigan to end at Fort Wilkins in Copper Harbor by 1922 . The roadway followed US 41 's predecessor , M @-@ 15 , and included numerous road signs bearing Sheridan 's silhouette mounted on his horse Rienzi . Towns along the way were encouraged to rename city streets as Sheridan Road on Labor Day 1923 . The road was promoted until the Great Depression in the 1930s . All that remains are signs in Menominee noting that First Street was once Sheridan Road . 
