My FI and I have decided we would like to travel Rt 66 for our honeymoon from Chicago all the way to the Pier in CA. The one snag we've been trying to iron out is how does renting a car for this work, because we are from the East Coast and will fly in to Chicago to pick up the car we will drive out. We are looking for a nicer vehicle, something that is fun to drive on winding roads with t-tops or convertible, but that we are able to leave in CA and fly home without being penalized by the rental company. Anyone have suggestions/has done something similar?