| | Chester, WI | Madison, WI | United States |
| Population | 760 | 265,447 | 329,725,481 |
| Female Population | 46.7% | 50.0% | 50.5% |
| Male Population | 53.3% | 50.0% | 49.5% |
| Median Age | 38.8 | 31.5 | 38.4 |
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| Population - 2010 | 688 | 233,977 | 309,327,143 |
| Population - 2000 | 960 | 208,054 | 285,036,114 |
| Population - 1990 | 1,393 | 191,262 | 251,960,433 |
| Pop. 2000 to Now | -31.5% | 26.5% | 15.6% |
| Pop. 1990 to Now | -52.8% | 37.6% | 30.8% |
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| Population Density | 23.2 | 3,368.1 | 93.4 |
| Land Area | 32.7 | 78.8 | 3,531,905.4 |
| Water Area | 1.4 | 22.0 | 264,836.8 |
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| Est. Total Population By Age | | | |
| | Chester, WI | Madison, WI | United States |
| Age 0 to 4 | 5.4% | 5.1% | 5.9% |
| Age 5 to 9 | 6.2% | 4.4% | 6.1% |
| Age 10 to 14 | 6.6% | 4.6% | 6.6% |
| Age 15 to 17 | 2.2% | 2.4% | 3.9% |
| Age 18 to 20 | 3.8% | 8.3% | 4.0% |
| Age 21 to 24 | 5.1% | 12.1% | 5.2% |
| Age 25 to 34 | 15.1% | 19.2% | 13.8% |
| Age 35 to 44 | 12.0% | 12.5% | 12.9% |
| Age 45 to 54 | 13.2% | 9.6% | 12.6% |
| Age 55 to 59 | 6.4% | 5.0% | 6.7% |
| Age 60 to 64 | 9.1% | 4.7% | 6.3% |
| Age 65 to 74 | 7.2% | 7.4% | 9.6% |
| Age 75 to 84 | 4.9% | 3.3% | 4.5% |
| Age 85 and over | 2.8% | 1.3% | 1.9% |
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| Race | | | |
| | Chester, WI | Madison, WI | United States |
| White | 98.9% | 72.0% | 59.4% |
| Black | 0.0% | 6.7% | 12.2% |
| Asian | 0.0% | 8.9% | 5.6% |
| Native American | 0.0% | 0.3% | 0.6% |
| Hawaiian, Pacific Islander | 0.0% | 0.0% | 0.2% |
| Other | 0.0% | 0.4% | 0.4% |
| Two or More Races | 0.9% | 4.0% | 3.2% |
| Hispanic | 0.1% | 7.8% | 18.4% |
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| Marriage & Family | | | |
| | Chester, WI | Madison, WI | United States |
| Married Population | 56.1% | 38.0% | 49.8% |
| Currently Married | 55.6% | 37.2% | 48.0% |
| Married but Separated | 0.5% | 0.7% | 1.8% |
| Single Population | 43.9% | 62.0% | 50.2% |
| Never Married | 28.9% | 50.3% | 33.8% |
| Divorced | 7.6% | 8.5% | 10.8% |
| Widowed | 7.4% | 3.3% | 5.6% |
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| Household Size | 2.59 | 2.16 | 2.60 |
| Households | 293 | 117,324 | 124,010,992 |
| Family Households | 193 | 52,482 | 80,755,759 |
| Married couple, w/children | 34.2% | 31.3% | 30.5% |
| Married couple, no children | 44.0% | 46.1% | 42.9% |
| Non Family Households | 100 | 64,842 | 43,255,233 |
| Single householder, w/children | 10.4% | 14.7% | 15.8% |
| Single householder, no children | 11.4% | 7.9% | 10.8% |