| | Wailea, HI | Chicago, IL | United States |
| Population | 6,546 | 2,742,119 | 329,725,481 |
| Female Population | 48.0% | 51.2% | 50.5% |
| Male Population | 52.0% | 48.8% | 49.5% |
| Median Age | 55.4 | 35.1 | 38.4 |
| space3 | | | |
| Population - 2010 | 6,483 | 2,697,480 | 309,327,143 |
| Population - 2000 | 5,098 | 2,896,016 | 285,036,114 |
| Population - 1990 | 3,405 | 2,783,726 | 251,960,433 |
| Pop. 2000 to Now | 12.5% | -7.5% | 15.6% |
| Pop. 1990 to Now | 68.5% | -3.8% | 30.8% |
| space4 | | | |
| Population Density | 879.4 | 12,060.3 | 93.4 |
| Land Area | 7.4 | 227.4 | 3,531,905.4 |
| Water Area | 3.3 | 6.8 | 264,836.8 |
| space | | | |
| Est. Total Population By Age | | | |
| | Wailea, HI | Chicago, IL | United States |
| Age 0 to 4 | 3.1% | 5.9% | 5.9% |
| Age 5 to 9 | 2.5% | 5.4% | 6.1% |
| Age 10 to 14 | 2.5% | 5.8% | 6.6% |
| Age 15 to 17 | 2.6% | 3.3% | 3.9% |
| Age 18 to 20 | 2.7% | 3.6% | 4.0% |
| Age 21 to 24 | 2.9% | 6.0% | 5.2% |
| Age 25 to 34 | 9.8% | 19.8% | 13.8% |
| Age 35 to 44 | 10.9% | 14.3% | 12.9% |
| Age 45 to 54 | 11.7% | 11.9% | 12.6% |
| Age 55 to 59 | 10.4% | 5.8% | 6.7% |
| Age 60 to 64 | 9.3% | 5.4% | 6.3% |
| Age 65 to 74 | 19.5% | 7.6% | 9.6% |
| Age 75 to 84 | 8.6% | 3.6% | 4.5% |
| Age 85 and over | 3.6% | 1.6% | 1.9% |
| space1 | | | |
| Race | | | |
| | Wailea, HI | Chicago, IL | United States |
| White | 70.9% | 33.1% | 59.4% |
| Black | 0.5% | 28.8% | 12.2% |
| Asian | 9.7% | 6.8% | 5.6% |
| Native American | 0.1% | 0.1% | 0.6% |
| Hawaiian, Pacific Islander | 1.5% | 0.0% | 0.2% |
| Other | 0.2% | 0.3% | 0.4% |
| Two or More Races | 6.6% | 2.2% | 3.2% |
| Hispanic | 10.4% | 28.7% | 18.4% |
| space2 | | | |
| Marriage & Family | | | |
| | Wailea, HI | Chicago, IL | United States |
| Married Population | 55.6% | 37.8% | 49.8% |
| Currently Married | 53.7% | 35.5% | 48.0% |
| Married but Separated | 1.9% | 2.3% | 1.8% |
| Single Population | 44.4% | 62.2% | 50.2% |
| Never Married | 25.5% | 48.9% | 33.8% |
| Divorced | 13.0% | 8.3% | 10.8% |
| Widowed | 5.8% | 5.0% | 5.6% |
| space5 | | | |
| Household Size | 2.31 | 2.41 | 2.60 |
| Households | 2,816 | 1,112,581 | 124,010,992 |
| Family Households | 1,920 | 574,825 | 80,755,759 |
| Married couple, w/children | 13.0% | 27.1% | 30.5% |
| Married couple, no children | 66.1% | 34.8% | 42.9% |
| Non Family Households | 896 | 537,756 | 43,255,233 |
| Single householder, w/children | 12.3% | 21.0% | 15.8% |
| Single householder, no children | 8.6% | 17.1% | 10.8% |