The Chickasaw Turnpike was originally envisioned as a corridor running from
Interstate 35 (I-35) near
Davis to
I-40 near
Henryetta. It was proposed at the same time as three other turnpikes, which would become the
Kilpatrick Turnpike in
Oklahoma City, the
Creek Turnpike in
Tulsa, and the
Cherokee Turnpike, which bypassed a mountainous section of
US-412 in eastern Oklahoma. Rural legislators objected to the Kilpatrick and Creek Turnpikes, and moved to block them unless the Chickasaw Turnpike was built. Urban legislators relented and allowed the Chickasaw to be built as part of a compromise, with legislation requiring that the Chickasaw be built before work on the other two turnpikes could begin. The turnpike was authorized in 1987. Governor
Henry Bellmon opposed the Chickasaw Turnpike, arguing it would be a money loser. The Chickasaw cost nearly $44 million to build (equivalent to $ in ). The OTA voted on November 11, 2002, to open discussions about transferring the Chickasaw to ODOT. The transfer would also include a one-time payment of $14 million (equivalent to $ in ) for maintenance. The turnpike had deteriorated since its original construction; ODOT director
Gary Ridley said that recurrent pavement problems necessitated constant repairs. He also mentioned that there were other issues, such as right-of-way problems, that could endanger ODOT's ability to draw from the federal highway trust fund. House Speaker Pro Tempore-designate
Danny Hilliard opposed the transfer on the grounds of the road's poor condition, as well as objecting to the partial interchanges. The lawmaker called the Chickasaw Turnpike "an albatross" and said "I told them that unless the Turnpike Authority brought that turnpike up to ODOT specifications, and completed the interchanges at Roff and US-177 north at Sulphur, we're not interested in having that thing dumped on the taxpayers." Construction constraints required the entire turnpike to be closed in March, The turnpike reopened on September 29, 2006. The Chickasaw Turnpike originally bore no numbered designation. On August 2, 2021, the Oklahoma Transportation Commission unanimously approved a motion to apply the SH-301 designation to the turnpike. ODOT Director
Tim Gatz stated in the Transportation Commission meeting that the numbering addition was primarily to aid in navigation using digital mapping and routing applications. ==Tolls==