11 cities
| City | Rank | 2026 Pop. ↓ | 2020 Pop. | Annual Change | Density | Area (mi²) | Type |
|---|---|---|---|---|---|---|---|
| Spirit Lake | 1 | 5,590 | 5,464 | 0.38% | 1,236 | 5 | City |
| Milford | 2 | 3,219 | 3,335 | -0.59% | 1,497 | 2 | City |
| Arnolds Park | 3 | 1,263 | 1,116 | 2.02% | 708 | 2 | City |
| Lake Park | 4 | 1,146 | 1,173 | -0.35% | 726 | 2 | City |
| Okoboji | 5 | 711 | 765 | -1.25% | 405 | 2 | City |
| Orleans | 6 | 494 | 520 | -0.8% | 438 | 1 | City |
| Wahpeton | 7 | 332 | 346 | -0.6% | 277 | 1 | City |
| West Okoboji | 8 | 312 | 308 | 0.32% | 249 | 1 | City |
| Terril | 9 | 298 | 334 | -1.97% | 549 | 1 | City |
| Superior | 10 | 124 | 133 | -0.8% | 289 | 0 | City |
| Gruver | 11 | 61 | 66 | -1.61% | 480 | 0 | City |
Spirit Lake is the largest city in Dickinson County, with a population of 5,590.
Gruver is the smallest city in Dickinson County, with a population of 61.
There are 11 cities in Dickinson County, Iowa.