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According to some sources, the name "Kickapoo" (Giiwigaabaw in the Anishinaabe language and its Kickapoo cognate Kiwikapawa) means "stands here and there," which may have referred to the tribe's migratory patterns. The name can also mean "wanderer". This interpretation is contested and generally believed to be a folk etymology.
The Kickapoo are an Algonquian-language people who likely migrated to or developed as a people in a large territory along the southern Wabash River in the area of modern Terre Haute, Indiana, where they were located at the time of first contact with Europeans in the 1600s. They were confederated with the larger Wabash Confederacy, which included the Piankeshaw and the Wea to their north, and the powerful Miami Tribe, to their east. A subgroup occupied the Upper Iowa River region in what was later known as northeast Iowa and the Root River region in southeast Minnesota in the late 1600s and early 1700s. This group was probably known by the clan name "Mahouea", derived from the Illinoian word for wolf, m'hwea.
The earliest European contact with the Kickapoo tribe occurred during the La Salle Expeditions into Illinois Country in the late 17th century. The French colonists set up remote fur trading posts throughout the region, including on the Wabash River. They typically set up posts at or near Native American villages. Terre Haute was founded as an associated French village. The Kickapoo had to contend with a changing cast of Europeans; the British defeated the French in the Seven Years' War and took over nominal rule of former French territory east of the Mississippi River after 1763. They increased their own trading with the Kickapoo.
The United States acquired the territory east of the Mississippi River and north of the Ohio River after it gained independence from the United Kingdom. As white settlers moved into the region from the United States' eastern areas, beginning in the early 19th century, the Kickapoo were under pressure. They negotiated with the United States over their territory in several treaties, including the Treaty of Vincennes, the Treaty of Grouseland, and the Treaty of Fort Wayne. They sold most of their lands to the United States and moved north to settle among the Wea.
Rising tensions between the regional tribes and the United States led to Tecumseh's War in 1811. The Kickapoo were among the closest allies of Shawnee leader Tecumseh. Many Kickapoo warriors participated in the Battle of Tippecanoe and the subsequent War of 1812 on the side of the British, hoping to expel the white American settlers from the region.
The 1819 treaty of Edwardsville saw the Kickapoo cede the entirety of their holdings in Illinois comprising nearly one-half area of the state, in exchange for a smaller tract on the Osage river in Missouri and $3,000 worth of goods. The Kickapoo were not eager to move, partly as their assigned tract in Missouri was made of rugged hills and already occupied by the Osage, who were their hereditary enemies. Instead, half of the population traveled south and crossed onto the Spanish side of the Red river in modern day Texas. The US government quickly mobilized to prevent this emigration and force their removal to Missouri. This remnant of Kickapoo remained in Illinois under the guidance of Kennekuk, a prominent, nonviolent spiritual leader among the Kickapoo. He led his followers during the Indian Removal in the 1830s to their current tribal lands in Kansas. He died there of smallpox in 1852.
The close of the war led to a change of federal Indian policy in the Indiana Territory, and later the state of Indiana. White American leaders began to advocate the removal of tribes to lands west of the Mississippi River, to extinguish their claims to lands wanted by white American settlers. The Kickapoo were among the first tribes to leave Indiana under this program. They accepted land in Kansas and an annual subsidy in exchange for leaving the state.