Indianola probably began in 1875, when H. M. McElhany moved to the area and opened a one-room store. The store also served as a mail drop for local residents. The mail was delivered by horseback from the nearby town of Canadian, Oklahoma. McElhany stayed in business for about three years, then sold the store to Albert S. Cornelison and James H. Bynum. An actual post office was established at Indianola, Indian Territory on January 16, 1891, with Bynum being appointed as the first postmaster.
At the time of its founding, Indianola was located in Tobucksy County, Choctaw Nation.
According to the Encyclopedia of Oklahoma History and Culture, there are two versions of how the community acquired its name. One version says the name was on a stove in the general store. The other version says that the name honored Indianola, Mississippi.
The first school in Indianola was organized in February 1895. In 1898, Lyman H. Perkins, a Choctaw farmer who had originally all the land on which Indianola was built, donated 1 acre for construction of a Methodist church. In 1902, the Fort Smith and Western Railway built a track north of town. Indianola quickly relocated to be adjacent to the track, and the residents built a new school building. Lyman Perkins and his wife donated 4 acres to the new town, which retained the name Indianola. The former site was simply called "Old Town." By 1910, the community claimed 781 residents, which was the all-time high.

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Located eighteen miles north of McAlester on State Highway 113 in northwestern Pittsburg County, Indianola lies on the south bank of the South (main) Canadian River, which now joins Lake Eufaula. Located in the Choctaw Nation, Indian Territory, the town originally stood several hundred yards south and east of the location of Indianola School.

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