My own travel style used to be to drive hard and alternate nights between in-the-car and cheap motels. Now it's rent a house and settle in for several days to a week. High-end hotels were never my style, but I grew up near one and attended functions there so I see their allure. A quick search for 'historic hotels' yielded a couple of possibilities that seem to meet your criteria:
Two to three hours from Chicago (Michael is right about what's within an hour of the city.):
The Cornerstone Inn in Washington IL
The Mark Twain Hotel in Peoria IL
and
The Brown Hotel in Louisville KY
AZBuck