- Chicago, Illinois to Montauk Point, Long Island: Approximately 850 miles (1,368 km)
- Chicago, Illinois to Hempstead, Long Island: Approximately 830 miles (1,336 km)
- Chicago, Illinois to New York City (on the western end of Long Island): Approximately 750 miles (1,207 km)
Please note that these are approximate distances as measured in a straight line. The actual driving or travel distance between these two locations may be different due to the geographical features and road networks.