14 cities
| City | Rank | 2025 Pop. ↓ | 2020 Pop. | Annual Change | Density | Area (mi²) | Type |
|---|---|---|---|---|---|---|---|
| Jackson | 1 | 24,027 | 23,209 | 1.29% | 698 | 34 | Township |
| Seymour | 2 | 22,640 | 22,058 | 0.52% | 1,866 | 12 | City |
| Brownstown | 3 | 5,864 | 5,685 | 1.3% | 93 | 63 | Township |
| Redding | 4 | 5,381 | 5,217 | 1.36% | 158 | 34 | Township |
| Brownstown | 5 | 3,090 | 3,024 | 0.42% | 1,909 | 2 | Town |
| Owen | 6 | 1,645 | 1,576 | 1.67% | 30 | 55 | Township |
| Crothersville | 7 | 1,520 | 1,504 | 0.2% | 1,310 | 1 | Town |
| Carr | 8 | 1,392 | 1,340 | 1.46% | 34 | 41 | Township |
| Driftwood | 9 | 971 | 938 | 1.57% | 35 | 28 | Township |
| Grassy Fork | 10 | 702 | 689 | 1.01% | 18 | 40 | Township |
| Medora | 11 | 649 | 638 | 0.31% | 2,135 | 0 | Town |
| Vallonia | 12 | 358 | 292 | 0.28% | 474 | 1 | CDP |
| Salt Creek | 13 | 311 | 301 | 1.63% | 7 | 43 | Township |
| Freetown | 14 | 214 | 317 | -4.89% | 309 | 1 | CDP |
Jackson is the largest city in Jackson County, with a population of 24,027.
Freetown is the smallest city in Jackson County, with a population of 214.
There are 14 cities in Jackson County, Indiana.