Those in Illinois that I'm familiar with:
The old Chain of Rocks Bridge can be a fine way of crossing into Illinois from St. Louis if open.
Otherwise slightly to the north, Highway 67 into Alton, IL is not too awful.
And more southerly, is the Trans America route through Chester, IL (home of Popeye).
Quincy, IL crossing is no fun,
but the worst crossing by far goes to.....drum roll please........ Cairo, IL Highway 51 or 62, either way you lose.