I figured AA would switch to RJs on this route after the F100s are withdrawn. While I think MD-80 service could be profitable as HPN-ORD is a high yield route, AA may not be allowed to operate that size aircraft on the route.
HPN's traffic is very heavily regulated and the airport has been one of the hottest political issues in Westchester County for well over a decade. I know that there are restrictions on the amount of traffic and the times at which flights can operate, so there might be restrictions as to the size of the a/c that can operate.
I agree that dropping this to RJ service would be a mistake as UA directly competes on the route with 737s (and, if making a connection, one can take Northwest's DC-9s to Detriot and connect there). Unfortunately, if AA is not allowed to operate an MD-80 on the route, it might not have a choice.
FYI, last fall UA was operating at least one RJ service on the ORD-HPN route, in addition to the mainline service.