The luggage cart thing amuses me. It's rare that I'm hauling so much luggage with me that I need a cart.
However, I believe at the ORD domestic terminals, you'd have to pay for a luggage cart. So it's not like they ever run out of them. If you really needed to do this, then the upthread advice is helpful in that it's apparently a route to this hotel that doesn't run into whatever you call the cattle guard equivalent for luggage carts.