11 cities
| City | Rank | 2025 Pop. ↓ | 2020 Pop. | Annual Change | Density | Area (mi²) | Type |
|---|---|---|---|---|---|---|---|
| Spirit Lake | 1 | 5,580 | 5,462 | 0.43% | 1,234 | 4.52 | City |
| Milford | 2 | 3,291 | 3,335 | -0.27% | 1,530 | 2.15 | City |
| Arnolds Park | 3 | 1,231 | 1,115 | 1.9% | 772 | 1.59 | City |
| Lake Park | 4 | 1,148 | 1,172 | -0.43% | 728 | 1.58 | City |
| Okoboji | 5 | 717 | 766 | -1.38% | 408 | 1.76 | City |
| Orleans | 6 | 500 | 520 | -0.79% | 444 | 1.13 | City |
| Wahpeton | 7 | 337 | 347 | -0.59% | 281 | 1.20 | City |
| West Okoboji | 8 | 308 | 307 | 0% | 246 | 1.25 | City |
| Terril | 9 | 304 | 334 | -1.94% | 560 | 0.54 | City |
| Superior | 10 | 123 | 133 | -1.6% | 287 | 0.43 | City |
| Gruver | 11 | 60 | 64 | -1.64% | 472 | 0.13 | City |
Spirit Lake is the largest city in Dickinson County, with a population of 5,580.
Gruver is the smallest city in Dickinson County, with a population of 60.
There are 11 cities in Dickinson County, Iowa.