My experience is with an item much smaller than a desk, but perhaps similar in concept.
I wanted a bigger aquarium, so searched ebay. All of any size at all were pickup only, no shipping. I found one in San Pedro, about 1 1/2 hours from me - gorgeous 55 gallon tank, great price, complete with everything, even fish. I exchanged more email about transporting that item than about any other transaction I've made. But we went to pick it up the next weekend when we already had business in LA, and I absolutely love it!
Put Chicago Area somewhere prominent in your listing, if you do decide to try - that's your best best, geographically, it seems. Also, consider non-ebay venues (gasp!) like local sale papers or antique/estate shops. No chance of being on the good end of a bidding war then, though.
Just a thought.