American Airlines
seems to offer al least 9 daily flights from
Chicago
(ORD) to New York LaGuardia airport (LGA) in 2010 and each of those flights seems to be with an MD-80.
American Airlines
seems to offer 4 daily flights from
Chicago
(ORD) to
New York Newark (EWR) in 2010. Most of these flights are with MD-80. Also the Boeing 737-800 is used.
American Airlines
seems to offer just one daily flight from
Chicago
(ORD) to
New York JFK in 2010. This flight seems to be with a Boeing 757-200 and leaves Chicago at 1:10 pm and arrives in New York at 4:25 pm.
above: an American Airlines Boeing 757-200