The Chickasaw Turnpike, also designated State Highway 301 (SH-301), is a controlled-access toll road in the rural south central region of the U.S. state of Oklahoma. A two-lane freeway, it stretches for 13.3 miles (21.4 km) from north of Sulphur to just south of Ada. The Oklahoma Turnpike Authority (OTA) owns, maintains, and collects tolls on the turnpike. The first section of the Chickasaw Turnpike opened on September 1, 1991.

The Chickasaw resulted from a compromise between urban and rural legislators. Originally, it was part of a now-canceled plan to connect southern and eastern Oklahoma with a longer turnpike. It was also intended to link Ada to the Interstate system. A four-mile (6.4 km) segment of the turnpike was transferred to the Oklahoma Department of Transportation (ODOT), making it a toll-free road, in 2011.

The Chickasaw Turnpike takes a southwest-to-northeast route, passing through only two counties, Murray and Pontotoc. The turnpike begins in Murray County at U.S. Highway 177 (US-177) north of Sulphur; west of this interchange, the road becomes SH-7 Spur. The turnpike continues northeast into Pontotoc County. Just north of the county line is a barrier toll plaza, the only plaza along the route. Beyond the tollbooth lies an interchange serving the town of Roff. This is a partial interchange, providing access to Roff for eastbound travelers and access to the westbound lanes from Roff. The Chickasaw Turnpike then ends at SH-1.

The Chickasaw Turnpike has only two lanes for the majority of its length; however, there is a short eastbound passing lane. The Chickasaw is the only two-lane turnpike in Oklahoma. Lightly traveled, the road is used by about 2,000 vehicles per day.

The Chickasaw Turnpike was originally envisioned as a corridor running from Interstate 35 (I-35) near Davis to I-40 near Henryetta. Proposed by southern Oklahoma politicians, the turnpike was intended to promote economic development by connecting Ada to the Interstate Highway System. 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. Bellmon had the turnpike built with only two lanes and shortened it to its current termini. Dewey F. Bartlett, Jr., an OTA board member (and future mayor of Tulsa), was later quoted as saying "I think it stinks. We never wanted to build it. It was not anything we thought was appropriate. But in order to build the three turnpikes that were necessary, that is the only way they would build it."

Bonds for the first section were approved in 1989. The bonds specifically permitted the turnpike to be transferred to the Oklahoma Department of Transportation and become a free road, the only turnpike in Oklahoma eligible for this type of transfer. At the time, however, ODOT director Bobby Green said that his agency could not buy the turnpike due to a lack of funds. The Chickasaw cost nearly $44 million to build (equivalent to $73.1 million in 2024). Its first section opened on September 1, 1991. Originally, the turnpike began at SH-7 west of Sulphur, proceeding northeast to the US-177 junction, then continuing northeast on its present-day alignment.

As part of his 1994 turnpike package, Governor David Walters proposed expanding the Chickasaw Turnpike to four lanes and extending it to Henryetta. The Chickasaw improvements were eventually cut from the package, which ultimately died when a commission overseeing the sale of bonds by state agencies voted against it.