The earth will cast its shadow on the moon Monday night:
But on the longest night of the year, a full moon will disappear at 1:40 a.m. behind the Earth's shadow. There won't be another total lunar eclipse on the night of the winter solstice for 84 years.
Weather permitting — and the forecast isn't favorable in the Chicago area, calling for clouds building Monday and snow overnight — the eclipse will be visible everywhere in the continental United States, and at its darkest, the moon will be halfway up from the horizon in the south-southwest sky.
We'll be able to see the moon start to disappear around 12:30 am Central time, with a total eclipse from 1:40 am until 2:53 am.
Unfortunately, the weather forecast calls for snow, which in Chicago just makes everything look yellow. (Chicago uses sodium-vapor streetlights that cast banana-yellow light.) But if you're up, or you live west of here and have better weather, go out and look.