I suggest that the way to get from Chicago to New York (I am planning a similar trip, but backwards, in the summer) is via Buffalo, and the Eerie Canal bikeway or roads that parallel it. (The bikeway itself runs all the way to Albany, 380-something miles, but it tends to get dull after a while.) Approach New York City not from the west, but from the north. Take the Canal Bikeway to Rochester, then head southeast on 96 to Ithaca (great college town, great food, great beer), then southerly to Owego and on to Binghamton. Due east to Deposit, New York, then the Delaware River Scenic Route to Port Jervis. Very nice riding, beautiful, cool and hilly and generally calm, with good roads (paving crew is a good job in those parts, so they pave and re-pave a lot.) Port Jervis to New Paltz through the Shawanagunk Mountains (a lovely valley road most of the way, once you get out of Port Jervis and nearby towns.) New Paltz--another nice college town--to Poughkeepsie across the Walkway Over The Hudson, a pedestrian bridge that everyone has gone wild over in those parts. Cut across Duchess and Putnam Counties to Brewster (more nice roads) and there you'll pick up the North County Trailway, 40-odd miles of rail trail that goes straight down into the close-in New York suburbs. North County Trailway becomes the South County Trailway which --with one notable nasty gap you will have to pick your way through in Yonkers--drops you in Van Cortland Park in the Bronx. From there, look for the High Bridge to cross the East River into Upper Manhattan, then the Hudson River bikepath from the top of Manhattan to the bottom. Welcome to New York. If you are looking for a suitable beachy end to the trip, put your bike and gear on a Long Island Railroad train and go to Montauk and the Hamptons. Nice riding out there, too. (The city to Montauk is a favorite 100-miler for some, but much of it is too gritty for my taste.)