11 cities
| City | Rank | 2025 Pop. ↓ | 2020 Pop. | Annual Change | Density | Area (mi²) | Type |
|---|---|---|---|---|---|---|---|
| Spirit Lake | 1 | 5,569 | 5,464 | 0.38% | 1,232 | 5 | City |
| Milford | 2 | 3,238 | 3,335 | -0.61% | 1,505 | 2 | City |
| Arnolds Park | 3 | 1,238 | 1,116 | 1.98% | 776 | 2 | City |
| Lake Park | 4 | 1,150 | 1,173 | -0.43% | 729 | 2 | City |
| Okoboji | 5 | 720 | 765 | -1.23% | 410 | 2 | City |
| Orleans | 6 | 498 | 520 | -0.99% | 442 | 1 | City |
| Wahpeton | 7 | 334 | 346 | -0.89% | 279 | 1 | City |
| West Okoboji | 8 | 311 | 308 | 0% | 248 | 1 | City |
| Terril | 9 | 304 | 334 | -1.94% | 560 | 1 | City |
| Superior | 10 | 125 | 133 | -1.57% | 291 | 0 | City |
| Gruver | 11 | 62 | 66 | -1.59% | 488 | 0 | City |
Spirit Lake is the largest city in Dickinson County, with a population of 5,569.
Gruver is the smallest city in Dickinson County, with a population of 62.
There are 11 cities in Dickinson County, Iowa.