I’ve heard this story since coming to Chicago. Problem is, I can’t find a single reference to it anywhere else other than word-of-mouth.
What’s the deal? Is it true? What is the penalty?
No cite, but it can’t possibly be true. When us bunkins from downstate Illinois go up to the Big City, we like to take our pickups. Gotta put the goat somewhere, you know 
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Seriously, tho, I’m sure the CPD has bigger fish to fry than pulling over pickups on Lakeshore Drive. Than, and how long would such an ordinance hold up in court, anyway?
:smack:
That
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Maybe it is a different kind of pick-ups they’re referring to?
Did you check anti-prostitution laws? 
I’m not from Chicago, but I can relate a similar situation in Boston, on Storrow Drive.
Storrow Drive runs along the Charles River, it’s run by the Metropolitan District Commission (which oversees parks and stuff like that), and a sign reads that it’s “For Pleasure Vehicles Only.” I spent almost five years as a tow truck driver, and some of my colleagues had been pulled over for towing cars down the road. (Of course, we were allowed to go on Storrow Drive to pick up a car that was disabled there—we’d call the police for permission first.)
Anyway, a long time ago, even if you bought a pickup truck for private use, you had to register it with commercial license plates. And commercial vehicles aren’t allowed on Storrow Drive. So sometimes you’d hear of them pulling over some guy in his F150, even though he was just going to dinner or something.
Oddly, the car-based Chevrolet El Camino was still considered a pickup truck, and therefore had commercial plates. And the truck-based Chevrolet Suburban was considered a station wagon, and it got passenger plates.
Nowadays, regardless of size, any vehicle bought for personal use gets a regular, passenger license plate, so the pickups-on-Storrow-Drive situation no longer exists here.
How are trucks registered in your state? Also, I’d consider making a phone call to whichever police agency patrols Lakeshore Drive.
I have lived in Chicago my whole life and I can tell you without a doubt that this is in fact true. There are signs posted along LSD stating that pickups are not allowed. I don’t know how strictly it’s enforced but I do know people who have been ticketed.
I believe it’s no trucks at all allowed on LSD.
“how long would such an ordinance hold up in court, anyway?”
It’s held up so far. As Chris Luongo suggests, it’s not a ban on pickup trucks alone, it’s a ban on commercial vehicles on a boulevard or parkway. Even though Lake Shore Drive is hardly used for pleasure nowadays, the idea behind the boulevards and parkways originally was that they were supposed to be tree-lined pleasure drives in, and connecting, the parks. Years ago, the Chicago Park District had its own police force that patrolled the boulevards and parkways as well as the parks themselves.