| Index | Winchester | Illinois | National |
| Average Test Scores | 31% | 33% | 48% |
| Student/Teacher ratio | 26:1 | 18:1 | 16:1 |
| Total public schools | 2 | 3,938 | 79,221 |
| Total private schools | n/a | 1,438 | 24,874 |
| Total post-secondary schools | n/a | 306 | 7,963 |
| Index | Winchester | Illinois | National |
| Completed 8th grade | 91.8% | 86.2% | 84.3% |
| Completed high school | 89.2% | 84.7% | 83.0% |
| Completed some college | 43.1% | 61.8% | 59.4% |
| Completed associate degree | 24.7% | 40.7% | 38.5% |
| Completed bachelors | 17.0% | 32.9% | 30.3% |
| Completed masters | 6.3% | 12.7% | 11.5% |
| Completed professional degree | 2.2% | 3.4% | 3.3% |
| Completed doctorate | 0.6% | 1.2% | 1.3% |
There are a total of 2 public schools, n/a private schools and n/a post-secondary schools in Winchester. Using the proficiency score averages, the average test scores for Winchester, IL schools is 31%. The average student to teacher ratio is 26:1. In Winchester, IL, an average of 91.8% of students have completed 8th grade and an average of 89.2% have completed high school.
| City | Population | Avg. Test Scores | National Avg. |
| Concord, IL | 170 | 41% | 15.1% |
| Murrayville, IL | 582 | 32% | 33.3% |
| Roodhouse, IL | 1,656 | 32% | 34.4% |
| Griggsville, IL | 1,454 | 25% | 47.9% |
| South Jacksonville, IL | 3,132 | 25% | 49.0% |
| Winchester, IL | 1,717 | 31% | 34.9% |
| City | Population | Avg. Test Scores | National Avg. |
| Shirley, MA | 1,716 | 49% | 1.6% |
| North Berwick, ME | 1,716 | 46% | 5.2% |
| Panguitch, UT | 1,718 | 41% | 15.6% |
| Hatch, NM | 1,718 | 24% | 50.7% |
| Lester Prairie, MN | 1,719 | 52% | 8.3% |
| Winchester, IL | 1,717 | 31% | 34.9% |
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