A lot of those lower than actual clearance signs are due to them be measured from the roadside curb to the bridge rather than in the travel lane. Travel lane may be 13'6"+ But it's 12'6" all the way on the right over the curb.
I've been driving in Chicago almost on a daily basis now for about 6 weeks. Before that I was always in the suburbs. Anyways there hasn't been a bridge yet that hasn't given me a heart attack haha. Put the hazards on, put it in first gear and crawl through it. Make a note on the route sheet that it's safe. At that time at least. Any bridge not marked I don't even mess with it. I often think about how much more stressful it had to be for a rookie driver in Chicago or cities alike when there was no gps and alot more low bridges like Brett mentioned. Bridges have always been there. I do agree it's a 100 percent on the driver. Should it be a fireable offense? That's on the company, but I do think a rookie driver should deserve another chance at it.
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Sad. All these towns/cities that act like truckers are undesirables should be boycotted by ALL truckers for a couple of weeks. I bet their stance would change quickly