On volmer road out by the Olympia Fields Country Club there is an old
rail road viaduct, the old concrete kind with a low clearance of as I
recall 11 feet and change. There are warning signs starting a couple
miles in advance and still truckers get themselves stuck. Some of the
truckers notice at the last moment they can't fit... problem is, it's a
two lane road... on the approach from the west there are ditches on both
sides. No way to turn around. I've seen many a rig in the ditch on the
west side of the viaduct on the east bound side of the road. On the other
side there is a small driveway where a trucker can do a ten-thousand
point turn and maybe turn around. I've seen them attempting that while
jamming up traffic.

And for what? The trucks trying to avoid traffic on Lincoln Highway
(route 30)? It's not that big of a detour, go under the tracks with the
high clearance on the proper truck route.

The runner up I know for catching truckers was the 31st street viaduct
east of the Dan-Ryan. When still in it's 19th century glory it could do
some serious damage to a truck. Of course the best one I ever saw was on
35th just west of Sox Park, the trailer hit so hard it V'd it in the
middle.

Of course then there is spite... talking to this one guy he told me a
story about how he had a job driving a truck. He thought his boss was an
a.shole. His boss gave him A to B directions and insisted he take that
route. He knew the underpass didn't have enough clearance but drove into
it anyway for spite. Of course that isn't verifiable to me, but I
wouldn't put it past some people to do something like that.

I say it is.

Even here, not all unsuitable routes are signed, and you certainly
can't expect a long-hauler who probably lives hundreds of miles away
to be familiar with the routes.  That's what his maps and GPS are for.
If they or his company don't direct him to a good route, it's their
fault, not his, because they have the information and he can't get it.