Direct flights from Westchester County to Chicago
All flights from HPN to ORD non-stop. There are direct flights from Westchester Co (HPN), New York, USA to Chicago O Hare International (ORD), Illinois, USA with American Airlines. 35 weekly departures are currently scheduled on this route. Departure times range from 06:00 to 18:30 depending on the schedule period. The flight distance is 740 miles (1191 km). Flight time ranges from 2 hours and 35 minutes to 3 hours.
Westchester County
, USA
Flight schedule from Westchester County to Chicago with American Airlines
This is a weekly direct flight schedule for American Airlines. Use the arrows or click on the date to change week. Click on any flight departure time to show more information and check availability.
Flight
The timetable & schedule information was updated at 2026-09-21
Westchester County to Chicago scheduled departures
Select a date to see every published non-stop departure between HPN and ORD.
HPN - ORD route facts
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Distance740 miles (1191 km)
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Flight time2 hours and 35 minutes to 3 hours
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Airline American Airlines
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Airline alliancesoneworld
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CabinsEconomy First
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Hub airportsORD
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Arrival terminalsTerminal 3
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AircraftEmbraer 175, Embraer 170 and Canadair (Bombardier) Regional Jet 700 and Challenger 870
