Flight Schedules

Last Updated: Fri, 2 May, 2025

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      • Availability
        • M
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      • 20:10 ORD
        23:29 HPN
        2Hrs, 19m Direct
      • ORDChicago O'Hare International Airport 20:10 - HPN 23:29 2h 19m Direct
      • ORDChicago O'Hare International Airport 20:10
      • HPNWestchester County Airport 23:29
      • 2h 19m
      • Direct
      • American Airlines (AA 3752)Embraer 170
      • American Airlines (AA 3752)
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        • S
      • Embraer 170
      • 08:22 ORD
        11:29 HPN
        2Hrs, 07m Direct
      • ORDChicago O'Hare International Airport 08:22 - HPN 11:29 2h 07m Direct
      • ORDChicago O'Hare International Airport 08:22
      • HPNWestchester County Airport 11:29
      • 2h 07m
      • Direct
      • American Airlines (AA 3812)Embraer 170
      • American Airlines (AA 3812)
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        • T
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        • S
        • S
      • Embraer 170
      • 12:49 ORD
        15:59 HPN
        2Hrs, 10m Direct
      • ORDChicago O'Hare International Airport 12:49 - HPN 15:59 2h 10m Direct
      • ORDChicago O'Hare International Airport 12:49
      • HPNWestchester County Airport 15:59
      • 2h 10m
      • Direct
      • American Airlines (AA 4200)Embraer 170
      • American Airlines (AA 4200)
        • M
        • T
        • W
        • T
        • F
        • S
        • S
      • Embraer 170
      • 18:39 ORD
        21:59 HPN
        2Hrs, 20m Direct
      • ORDChicago O'Hare International Airport 18:39 - HPN 21:59 2h 20m Direct
      • ORDChicago O'Hare International Airport 18:39
      • HPNWestchester County Airport 21:59
      • 2h 20m
      • Direct
      • American Airlines (AA 3499)Embraer 170
      • American Airlines (AA 3499)
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        • S
      • Embraer 170
      • 06:00 ORD
        10:50 HPN
        3Hrs, 50m 1 Stop (DCA)
      • ORDChicago O'Hare International Airport 06:00 - HPN 10:50 3h 50m 1 Stop (DCA) Washington
      • ORDChicago O'Hare International Airport 06:00
        DCAWashington Ronald Reagan National Airport 09:30
      • DCAWashington Ronald Reagan National Airport 08:54
        HPNWestchester County Airport 10:50
      • 3h 50m (36m)
      • 1 Stop DCA · Washington 36m
      • American Airlines (AA 523)Boeing 737 800
        American Airlines (AA 5282)Crj 700 Canadair Regional
      • American Airlines (AA 523)
        • -
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        • -
      • 06:00 ORD
        10:59 HPN
        3Hrs, 59m 1 Stop (DCA)
      • ORDChicago O'Hare International Airport 06:00 - HPN 10:59 3h 59m 1 Stop (DCA) Washington
      • ORDChicago O'Hare International Airport 06:00
        DCAWashington Ronald Reagan National Airport 09:39
      • DCAWashington Ronald Reagan National Airport 08:54
        HPNWestchester County Airport 10:59
      • 3h 59m (45m)
      • 1 Stop DCA · Washington 45m
      • American Airlines (AA 523)Boeing 737 800
        American Airlines (AA 5282)Crj 700 Canadair Regional
      • American Airlines (AA 523)
        • -
        • -
        • -
        • -
        • -
        • -
        • S
      • 07:00 ORD
        13:15 HPN
        5Hrs, 15m 1 Stop (CLT)
      • ORDChicago O'Hare International Airport 07:00 - HPN 13:15 5h 15m 1 Stop (CLT) Charlotte
      • ORDChicago O'Hare International Airport 07:00
        CLTCharlotte Airport 11:10
      • CLTCharlotte Airport 10:05
        HPNWestchester County Airport 13:15
      • 5h 15m (1h 05m)
      • 1 Stop CLT · Charlotte 1h 05m
      • American Airlines (AA 1784)Boeing 737 800
        American Airlines (AA 5180)Crj 700 Canadair Regional
      • American Airlines (AA 1784)
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        • S
      • 07:50 ORD
        14:33 HPN
        5Hrs, 43m 1 Stop (DCA)
      • ORDChicago O'Hare International Airport 07:50 - HPN 14:33 5h 43m 1 Stop (DCA) Washington
      • ORDChicago O'Hare International Airport 07:50
        DCAWashington Ronald Reagan National Airport 13:15
      • DCAWashington Ronald Reagan National Airport 10:44
        HPNWestchester County Airport 14:33
      • 5h 43m (2h 31m)
      • 1 Stop DCA · Washington 2h 31m
      • American Airlines (AA 2345)Airbus
        American Airlines (AA 5254)Crj 700 Canadair Regional
      • American Airlines (AA 2345)
        • -
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      • 08:05 ORD
        14:30 HPN
        5Hrs, 25m 1 Stop (DCA)
      • ORDChicago O'Hare International Airport 08:05 - HPN 14:30 5h 25m 1 Stop (DCA) Washington
      • ORDChicago O'Hare International Airport 08:05
        DCAWashington Ronald Reagan National Airport 13:12
      • DCAWashington Ronald Reagan National Airport 11:00
        HPNWestchester County Airport 14:30
      • 5h 25m (2h 12m)
      • 1 Stop DCA · Washington 2h 12m
      • American Airlines (AA 2345)Airbus
        American Airlines (AA 5254)Crj 700 Canadair Regional
      • American Airlines (AA 2345)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • 10:34 ORD
        16:49 HPN
        5Hrs, 15m 1 Stop (CLT)
      • ORDChicago O'Hare International Airport 10:34 - HPN 16:49 5h 15m 1 Stop (CLT) Charlotte
      • ORDChicago O'Hare International Airport 10:34
        CLTCharlotte Airport 14:45
      • CLTCharlotte Airport 13:41
        HPNWestchester County Airport 16:49
      • 5h 15m (1h 04m)
      • 1 Stop CLT · Charlotte 1h 04m
      • American Airlines (AA 2080)Boeing 737 800
        American Airlines (AA 5606)Crj 700 Canadair Regional
      • American Airlines (AA 2080)
        • -
        • -
        • -
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        • -
      • 10:34 ORD
        16:37 HPN
        5Hrs, 03m 1 Stop (CLT)
      • ORDChicago O'Hare International Airport 10:34 - HPN 16:37 5h 03m 1 Stop (CLT) Charlotte
      • ORDChicago O'Hare International Airport 10:34
        CLTCharlotte Airport 14:36
      • CLTCharlotte Airport 13:41
        HPNWestchester County Airport 16:37
      • 5h 03m (55m)
      • 1 Stop CLT · Charlotte 55m
      • American Airlines (AA 2080)Boeing 737 800
        American Airlines (AA 5606)Crj 700 Canadair Regional
      • American Airlines (AA 2080)
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        • T
        • F
        • -
        • S
      • 11:37 ORD
        18:02 HPN
        5Hrs, 25m 1 Stop (DCA)
      • ORDChicago O'Hare International Airport 11:37 - HPN 18:02 5h 25m 1 Stop (DCA) Washington
      • ORDChicago O'Hare International Airport 11:37
        DCAWashington Ronald Reagan National Airport 16:40
      • DCAWashington Ronald Reagan National Airport 14:24
        HPNWestchester County Airport 18:02
      • 5h 25m (2h 16m)
      • 1 Stop DCA · Washington 2h 16m
      • American Airlines (AA 1485)Airbus
        American Airlines (AA 5236)Crj 700 Canadair Regional
      • American Airlines (AA 1485)
        • M
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        • T
        • F
        • S
        • S
      • 13:29 ORD
        20:16 HPN
        5Hrs, 47m 1 Stop (DCA)
      • ORDChicago O'Hare International Airport 13:29 - HPN 20:16 5h 47m 1 Stop (DCA) Washington
      • ORDChicago O'Hare International Airport 13:29
        DCAWashington Ronald Reagan National Airport 18:59
      • DCAWashington Ronald Reagan National Airport 16:29
        HPNWestchester County Airport 20:16
      • 5h 47m (2h 30m)
      • 1 Stop DCA · Washington 2h 30m
      • American Airlines (AA 311)Boeing 737 800
        American Airlines (AA 5289)Crj 700 Canadair Regional
      • American Airlines (AA 311)
        • -
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      No Schedules Sorry, there are no schedules matching your filters. Try removing one. reset
      What’s the fastest flight time from Chicago to Westchester County?

      The fastest flight time for direct flights from Chicago to Westchester County is 2 hours 7 minutes. Check latest flight schedules & prices on Wego.

      How far is Westchester County from Chicago?

      The flight distance between Chicago and Westchester County is 1154km. Check all available flights on Wego.

      When is the earliest and latest flight of the day?

      The earliest flight of the day departs at 06:00. The last flight of the day departs at 20:10. See the full list of flight times on Wego.

      How many airlines offer direct flights from Chicago to Westchester County?

      There are 1 airlines that offer direct flights from Chicago to Westchester County. Find out the list of airlines on Wego.

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