Fare Guide

Estimated lowest fares found within 7 days

Cheapest Airline American Airlines

The cheapest airline(s) flying from Westchester County to Chicago is American Airlines.

  • American Airlines American Airlines
  • Delta Air Lines Delta Air Lines
  • JetBlue Airways JetBlue Airways
Cheapest Month October

Travel Period: October 2024 - September 2025

The cheapest month(s) to fly from Westchester County to Chicago is October.

  • Oct 2024
  • Nov 2024
  • Dec 2024
  • Jan 2025
  • Feb 2025
  • Mar 2025
  • Apr 2025
  • May 2025
  • Jun 2025
  • Jul 2025
  • Aug 2025
  • Sep 2025
Cheapest Day of the Week Wednesday

The cheapest day(s) of the week to fly from Westchester County to Chicago is Wednesday.

  • Sun Sunday
  • Mon Monday
  • Tue Tuesday
  • Wed Wednesday
  • Thu Thursday
  • Fri Friday
  • Sat Saturday

Flight Schedules

Last Updated: Mon, 2 Sep, 2024

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      • Availability
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      • 07:20 HPN
        08:48 ORD
        2Hrs, 28m Direct
      • HPNWestchester County Airport 07:20 - ORD 08:48 2h 28m Direct
      • HPNWestchester County Airport 07:20
      • ORDChicago O'Hare International Airport 08:48
      • 2h 28m
      • Direct
      • American Airlines (AA 3496)Embraer 170
      • American Airlines (AA 3496)
        • M
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        • F
        • S
        • S
      • Embraer 170
      • 12:02 HPN
        13:30 ORD
        2Hrs, 28m Direct
      • HPNWestchester County Airport 12:02 - ORD 13:30 2h 28m Direct
      • HPNWestchester County Airport 12:02
      • ORDChicago O'Hare International Airport 13:30
      • 2h 28m
      • Direct
      • American Airlines (AA 3812)Embraer 170
      • American Airlines (AA 3812)
        • M
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        • F
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        • S
      • Embraer 170
      • 16:32 HPN
        18:00 ORD
        2Hrs, 28m Direct
      • HPNWestchester County Airport 16:32 - ORD 18:00 2h 28m Direct
      • HPNWestchester County Airport 16:32
      • ORDChicago O'Hare International Airport 18:00
      • 2h 28m
      • Direct
      • American Airlines (AA 3808)Embraer 170
      • American Airlines (AA 3808)
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      • Embraer 170
      • 06:00 HPN
        11:57 MDW
        6Hrs, 57m 1 Stop (ATL)
      • HPNWestchester County Airport 06:00 - MDW 11:57 6h 57m 1 Stop (ATL) Atlanta
      • HPNWestchester County Airport 06:00
        ATLAtlanta Hartsfield-Jackson Intl Airport 11:05
      • ATLAtlanta Hartsfield-Jackson Intl Airport 08:21
        MDWChicago Midway Airport 11:57
      • 6h 57m (2h 44m)
      • 1 Stop ATL · Atlanta 2h 44m
      • Delta Air Lines (DL 2379)Boeing 717
        Delta Air Lines (DL 2417)Boeing 717
      • Delta Air Lines (DL 2379)
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        • F
        • -
        • S
      • 06:00 HPN
        10:53 ORD
        5Hrs, 53m 1 Stop (ATL)
      • HPNWestchester County Airport 06:00 - ORD 10:53 5h 53m 1 Stop (ATL) Atlanta
      • HPNWestchester County Airport 06:00
        ATLAtlanta Hartsfield-Jackson Intl Airport 09:50
      • ATLAtlanta Hartsfield-Jackson Intl Airport 08:21
        ORDChicago O'Hare International Airport 10:53
      • 5h 53m (1h 29m)
      • 1 Stop ATL · Atlanta 1h 29m
      • Delta Air Lines (DL 2379)Boeing 717
        Delta Air Lines (DL 1147)Boeing 737 900
      • Delta Air Lines (DL 2379)
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        • F
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        • S
      • 06:00 HPN
        10:37 ORD
        5Hrs, 37m 1 Stop (CLT)
      • HPNWestchester County Airport 06:00 - ORD 10:37 5h 37m 1 Stop (CLT) Charlotte
      • HPNWestchester County Airport 06:00
        CLTCharlotte Airport 09:25
      • CLTCharlotte Airport 07:59
        ORDChicago O'Hare International Airport 10:37
      • 5h 37m (1h 26m)
      • 1 Stop CLT · Charlotte 1h 26m
      • American Airlines (AA 5097)Crj 700 Canadair Regional
        American Airlines (AA 545)Boeing 737 800
      • American Airlines (AA 5097)
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      • 06:30 HPN
        12:14 ORD
        6Hrs, 44m 1 Stop (DCA)
      • HPNWestchester County Airport 06:30 - ORD 12:14 6h 44m 1 Stop (DCA) Washington
      • HPNWestchester County Airport 06:30
        DCAWashington Ronald Reagan National Airport 10:59
      • DCAWashington Ronald Reagan National Airport 07:46
        ORDChicago O'Hare International Airport 12:14
      • 6h 44m (3h 13m)
      • 1 Stop DCA · Washington 3h 13m
      • American Airlines (AA 5678)Crj 700 Canadair Regional
        American Airlines (AA 1269)Boeing 737 800
      • American Airlines (AA 5678)
        • -
        • -
        • -
        • -
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        • S
        • -
      • 06:30 HPN
        12:13 ORD
        6Hrs, 43m 1 Stop (DCA)
      • HPNWestchester County Airport 06:30 - ORD 12:13 6h 43m 1 Stop (DCA) Washington
      • HPNWestchester County Airport 06:30
        DCAWashington Ronald Reagan National Airport 11:00
      • DCAWashington Ronald Reagan National Airport 07:46
        ORDChicago O'Hare International Airport 12:13
      • 6h 43m (3h 14m)
      • 1 Stop DCA · Washington 3h 14m
      • American Airlines (AA 5678)Crj 700 Canadair Regional
        American Airlines (AA 1269)Boeing 737 800
      • American Airlines (AA 5678)
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        • F
        • -
        • -
      • 06:30 HPN
        10:55 ORD
        5Hrs, 25m 1 Stop (DCA)
      • HPNWestchester County Airport 06:30 - ORD 10:55 5h 25m 1 Stop (DCA) Washington
      • HPNWestchester County Airport 06:30
        DCAWashington Ronald Reagan National Airport 09:45
      • DCAWashington Ronald Reagan National Airport 07:46
        ORDChicago O'Hare International Airport 10:55
      • 5h 25m (1h 59m)
      • 1 Stop DCA · Washington 1h 59m
      • American Airlines (AA 5678)Crj 700 Canadair Regional
        American Airlines (AA 978)Airbus
      • American Airlines (AA 5678)
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        • -
      • 07:59 HPN
        12:19 ORD
        5Hrs, 20m 1 Stop (CLT)
      • HPNWestchester County Airport 07:59 - ORD 12:19 5h 20m 1 Stop (CLT) Charlotte
      • HPNWestchester County Airport 07:59
        CLTCharlotte Airport 11:10
      • CLTCharlotte Airport 09:58
        ORDChicago O'Hare International Airport 12:19
      • 5h 20m (1h 12m)
      • 1 Stop CLT · Charlotte 1h 12m
      • American Airlines (AA 5403)Crj 700 Canadair Regional
        American Airlines (AA 2052)Boeing 737 800
      • American Airlines (AA 5403)
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        • S
      • 10:05 HPN
        16:01 ORD
        6Hrs, 56m 1 Stop (CLT)
      • HPNWestchester County Airport 10:05 - ORD 16:01 6h 56m 1 Stop (CLT) Charlotte
      • HPNWestchester County Airport 10:05
        CLTCharlotte Airport 14:48
      • CLTCharlotte Airport 12:01
        ORDChicago O'Hare International Airport 16:01
      • 6h 56m (2h 47m)
      • 1 Stop CLT · Charlotte 2h 47m
      • American Airlines (AA 5431)Crj 700 Canadair Regional
        American Airlines (AA 2576)Airbus
      • American Airlines (AA 5431)
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        • S
      • 10:05 HPN
        14:06 ORD
        5Hrs, 01m 1 Stop (CLT)
      • HPNWestchester County Airport 10:05 - ORD 14:06 5h 01m 1 Stop (CLT) Charlotte
      • HPNWestchester County Airport 10:05
        CLTCharlotte Airport 13:00
      • CLTCharlotte Airport 12:01
        ORDChicago O'Hare International Airport 14:06
      • 5h 01m (59m)
      • 1 Stop CLT · Charlotte 59m
      • American Airlines (AA 5431)Crj 700 Canadair Regional
        American Airlines (AA 1650)Boeing 737 800
      • American Airlines (AA 5431)
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        • S
      • 10:15 HPN
        14:31 ORD
        5Hrs, 16m 1 Stop (ATL)
      • HPNWestchester County Airport 10:15 - ORD 14:31 5h 16m 1 Stop (ATL) Atlanta
      • HPNWestchester County Airport 10:15
        ATLAtlanta Hartsfield-Jackson Intl Airport 13:30
      • ATLAtlanta Hartsfield-Jackson Intl Airport 12:35
        ORDChicago O'Hare International Airport 14:31
      • 5h 16m (55m)
      • 1 Stop ATL · Atlanta 55m
      • Delta Air Lines (DL 4920)Canadair Regional
        Delta Air Lines (DL 1477)Boeing 737 900
      • Delta Air Lines (DL 4920)
        • M
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      • 10:15 HPN
        14:59 MDW
        5Hrs, 44m 1 Stop (ATL)
      • HPNWestchester County Airport 10:15 - MDW 14:59 5h 44m 1 Stop (ATL) Atlanta
      • HPNWestchester County Airport 10:15
        ATLAtlanta Hartsfield-Jackson Intl Airport 14:07
      • ATLAtlanta Hartsfield-Jackson Intl Airport 12:35
        MDWChicago Midway Airport 14:59
      • 5h 44m (1h 32m)
      • 1 Stop ATL · Atlanta 1h 32m
      • Delta Air Lines (DL 4920)Canadair Regional
        Delta Air Lines (DL 1739)Boeing 717
      • Delta Air Lines (DL 4920)
        • M
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      • 11:29 HPN
        15:46 ORD
        5Hrs, 17m 1 Stop (DCA)
      • HPNWestchester County Airport 11:29 - ORD 15:46 5h 17m 1 Stop (DCA) Washington
      • HPNWestchester County Airport 11:29
        DCAWashington Ronald Reagan National Airport 14:34
      • DCAWashington Ronald Reagan National Airport 12:42
        ORDChicago O'Hare International Airport 15:46
      • 5h 17m (1h 52m)
      • 1 Stop DCA · Washington 1h 52m
      • American Airlines (AA 5282)Crj 700 Canadair Regional
        American Airlines (AA 1187)Airbus
      • American Airlines (AA 5282)
        • M
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        • S
      • 12:30 HPN
        18:32 ORD
        7Hrs, 02m 1 Stop (DTW)
      • HPNWestchester County Airport 12:30 - ORD 18:32 7h 02m 1 Stop (DTW) Detroit
      • HPNWestchester County Airport 12:30
        DTWDetroit Wayne County 18:05
      • DTWDetroit Wayne County 14:18
        ORDChicago O'Hare International Airport 18:32
      • 7h 02m (3h 47m)
      • 1 Stop DTW · Detroit 3h 47m
      • Delta Air Lines (DL 3976)Canadair Regional
        Delta Air Lines (DL 1656)Airbus
      • Delta Air Lines (DL 3976)
        • M
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        • F
        • -
        • S
      • 12:30 HPN
        16:24 ORD
        4Hrs, 54m 1 Stop (DTW)
      • HPNWestchester County Airport 12:30 - ORD 16:24 4h 54m 1 Stop (DTW) Detroit
      • HPNWestchester County Airport 12:30
        DTWDetroit Wayne County 16:00
      • DTWDetroit Wayne County 14:18
        ORDChicago O'Hare International Airport 16:24
      • 4h 54m (1h 42m)
      • 1 Stop DTW · Detroit 1h 42m
      • Delta Air Lines (DL 3976)Canadair Regional
        Delta Air Lines (DL 2358)Boeing 717
      • Delta Air Lines (DL 3976)
        • M
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        • F
        • -
        • S
      • 12:30 HPN
        17:04 MDW
        5Hrs, 34m 1 Stop (DTW)
      • HPNWestchester County Airport 12:30 - MDW 17:04 5h 34m 1 Stop (DTW) Detroit
      • HPNWestchester County Airport 12:30
        DTWDetroit Wayne County 16:53
      • DTWDetroit Wayne County 14:18
        MDWChicago Midway Airport 17:04
      • 5h 34m (2h 35m)
      • 1 Stop DTW · Detroit 2h 35m
      • Delta Air Lines (DL 3976)Canadair Regional
        Delta Air Lines (DL 3869)Embraer 175
      • Delta Air Lines (DL 3976)
        • M
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        • F
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      • 12:30 HPN
        16:34 ORD
        5Hrs, 04m 1 Stop (DTW)
      • HPNWestchester County Airport 12:30 - ORD 16:34 5h 04m 1 Stop (DTW) Detroit
      • HPNWestchester County Airport 12:30
        DTWDetroit Wayne County 16:10
      • DTWDetroit Wayne County 14:18
        ORDChicago O'Hare International Airport 16:34
      • 5h 04m (1h 52m)
      • 1 Stop DTW · Detroit 1h 52m
      • Delta Air Lines (DL 3976)Canadair Regional
        Delta Air Lines (DL 2358)Boeing 717
      • Delta Air Lines (DL 3976)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • 12:30 HPN
        16:15 MDW
        4Hrs, 45m 1 Stop (DTW)
      • HPNWestchester County Airport 12:30 - MDW 16:15 4h 45m 1 Stop (DTW) Detroit
      • HPNWestchester County Airport 12:30
        DTWDetroit Wayne County 16:00
      • DTWDetroit Wayne County 14:18
        MDWChicago Midway Airport 16:15
      • 4h 45m (1h 42m)
      • 1 Stop DTW · Detroit 1h 42m
      • Delta Air Lines (DL 3976)Canadair Regional
        Delta Air Lines (DL 3869)Embraer 175
      • Delta Air Lines (DL 3976)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • 12:52 HPN
        17:30 MDW
        5Hrs, 38m 1 Stop (ATL)
      • HPNWestchester County Airport 12:52 - MDW 17:30 5h 38m 1 Stop (ATL) Atlanta
      • HPNWestchester County Airport 12:52
        ATLAtlanta Hartsfield-Jackson Intl Airport 16:36
      • ATLAtlanta Hartsfield-Jackson Intl Airport 15:14
        MDWChicago Midway Airport 17:30
      • 5h 38m (1h 22m)
      • 1 Stop ATL · Atlanta 1h 22m
      • Delta Air Lines (DL 2973)Boeing 717
        Delta Air Lines (DL 1739)Airbus
      • Delta Air Lines (DL 2973)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • 12:52 HPN
        17:53 MDW
        6Hrs, 01m 1 Stop (ATL)
      • HPNWestchester County Airport 12:52 - MDW 17:53 6h 01m 1 Stop (ATL) Atlanta
      • HPNWestchester County Airport 12:52
        ATLAtlanta Hartsfield-Jackson Intl Airport 17:00
      • ATLAtlanta Hartsfield-Jackson Intl Airport 15:14
        MDWChicago Midway Airport 17:53
      • 6h 01m (1h 46m)
      • 1 Stop ATL · Atlanta 1h 46m
      • Delta Air Lines (DL 2973)Boeing 717
        Delta Air Lines (DL 2241)Airbus
      • Delta Air Lines (DL 2973)
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        • F
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        • S
      • 12:52 HPN
        17:54 MDW
        6Hrs, 02m 1 Stop (ATL)
      • HPNWestchester County Airport 12:52 - MDW 17:54 6h 02m 1 Stop (ATL) Atlanta
      • HPNWestchester County Airport 12:52
        ATLAtlanta Hartsfield-Jackson Intl Airport 17:00
      • ATLAtlanta Hartsfield-Jackson Intl Airport 15:14
        MDWChicago Midway Airport 17:54
      • 6h 02m (1h 46m)
      • 1 Stop ATL · Atlanta 1h 46m
      • Delta Air Lines (DL 2973)Boeing 717
        Delta Air Lines (DL 2241)Boeing 717
      • Delta Air Lines (DL 2973)
        • -
        • -
        • -
        • T
        • -
        • -
        • -
      • 12:52 HPN
        18:33 ORD
        6Hrs, 41m 1 Stop (ATL)
      • HPNWestchester County Airport 12:52 - ORD 18:33 6h 41m 1 Stop (ATL) Atlanta
      • HPNWestchester County Airport 12:52
        ATLAtlanta Hartsfield-Jackson Intl Airport 17:25
      • ATLAtlanta Hartsfield-Jackson Intl Airport 15:14
        ORDChicago O'Hare International Airport 18:33
      • 6h 41m (2h 11m)
      • 1 Stop ATL · Atlanta 2h 11m
      • Delta Air Lines (DL 2973)Boeing 717
        Delta Air Lines (DL 2879)Boeing 737 900
      • Delta Air Lines (DL 2973)
        • M
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        • F
        • -
        • S
      • 13:36 HPN
        17:49 ORD
        5Hrs, 13m 1 Stop (CLT)
      • HPNWestchester County Airport 13:36 - ORD 17:49 5h 13m 1 Stop (CLT) Charlotte
      • HPNWestchester County Airport 13:36
        CLTCharlotte Airport 16:35
      • CLTCharlotte Airport 15:33
        ORDChicago O'Hare International Airport 17:49
      • 5h 13m (1h 02m)
      • 1 Stop CLT · Charlotte 1h 02m
      • American Airlines (AA 5180)Crj 700 Canadair Regional
        American Airlines (AA 536)Airbus
      • American Airlines (AA 5180)
        • M
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        • T
        • F
        • S
        • S
      • 15:00 HPN
        20:59 ORD
        6Hrs, 59m 1 Stop (ATL)
      • HPNWestchester County Airport 15:00 - ORD 20:59 6h 59m 1 Stop (ATL) Atlanta
      • HPNWestchester County Airport 15:00
        ATLAtlanta Hartsfield-Jackson Intl Airport 19:55
      • ATLAtlanta Hartsfield-Jackson Intl Airport 17:22
        ORDChicago O'Hare International Airport 20:59
      • 6h 59m (2h 33m)
      • 1 Stop ATL · Atlanta 2h 33m
      • Delta Air Lines (DL 4931)Canadair Regional
        Delta Air Lines (DL 1577)Boeing 737 900
      • Delta Air Lines (DL 4931)
        • -
        • -
        • W
        • -
        • -
        • -
        • -
      • 15:00 HPN
        20:59 ORD
        6Hrs, 59m 1 Stop (ATL)
      • HPNWestchester County Airport 15:00 - ORD 20:59 6h 59m 1 Stop (ATL) Atlanta
      • HPNWestchester County Airport 15:00
        ATLAtlanta Hartsfield-Jackson Intl Airport 19:55
      • ATLAtlanta Hartsfield-Jackson Intl Airport 17:22
        ORDChicago O'Hare International Airport 20:59
      • 6h 59m (2h 33m)
      • 1 Stop ATL · Atlanta 2h 33m
      • Delta Air Lines (DL 4931)Canadair Regional
        Delta Air Lines (DL 1139)Boeing 737 900
      • Delta Air Lines (DL 4931)
        • M
        • -
        • -
        • T
        • F
        • -
        • S
      • 15:00 HPN
        19:30 ORD
        5Hrs, 30m 1 Stop (ATL)
      • HPNWestchester County Airport 15:00 - ORD 19:30 5h 30m 1 Stop (ATL) Atlanta
      • HPNWestchester County Airport 15:00
        ATLAtlanta Hartsfield-Jackson Intl Airport 18:20
      • ATLAtlanta Hartsfield-Jackson Intl Airport 17:22
        ORDChicago O'Hare International Airport 19:30
      • 5h 30m (58m)
      • 1 Stop ATL · Atlanta 58m
      • Delta Air Lines (DL 4931)Canadair Regional
        Delta Air Lines (DL 2879)Boeing 737 900
      • Delta Air Lines (DL 4931)
        • -
        • T
        • -
        • -
        • -
        • S
        • -
      • 15:15 HPN
        19:37 ORD
        5Hrs, 22m 1 Stop (DCA)
      • HPNWestchester County Airport 15:15 - ORD 19:37 5h 22m 1 Stop (DCA) Washington
      • HPNWestchester County Airport 15:15
        DCAWashington Ronald Reagan National Airport 18:25
      • DCAWashington Ronald Reagan National Airport 16:29
        ORDChicago O'Hare International Airport 19:37
      • 5h 22m (1h 56m)
      • 1 Stop DCA · Washington 1h 56m
      • American Airlines (AA 5254)Crj 700 Canadair Regional
        American Airlines (AA 1188)Boeing 737 800
      • American Airlines (AA 5254)
        • M
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        • W
        • T
        • F
        • -
        • S
      • 16:25 HPN
        21:38 MDW
        6Hrs, 13m 1 Stop (ATL)
      • HPNWestchester County Airport 16:25 - MDW 21:38 6h 13m 1 Stop (ATL) Atlanta
      • HPNWestchester County Airport 16:25
        ATLAtlanta Hartsfield-Jackson Intl Airport 20:45
      • ATLAtlanta Hartsfield-Jackson Intl Airport 18:53
        MDWChicago Midway Airport 21:38
      • 6h 13m (1h 52m)
      • 1 Stop ATL · Atlanta 1h 52m
      • Delta Air Lines (DL 4946)Canadair Regional
        Delta Air Lines (DL 1076)Boeing 717
      • Delta Air Lines (DL 4946)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • 16:25 HPN
        21:38 MDW
        6Hrs, 13m 1 Stop (ATL)
      • HPNWestchester County Airport 16:25 - MDW 21:38 6h 13m 1 Stop (ATL) Atlanta
      • HPNWestchester County Airport 16:25
        ATLAtlanta Hartsfield-Jackson Intl Airport 20:45
      • ATLAtlanta Hartsfield-Jackson Intl Airport 18:53
        MDWChicago Midway Airport 21:38
      • 6h 13m (1h 52m)
      • 1 Stop ATL · Atlanta 1h 52m
      • Delta Air Lines (DL 3686)Canadair Regional
        Delta Air Lines (DL 1076)Boeing 717
      • Delta Air Lines (DL 3686)
        • M
        • T
        • W
        • T
        • F
        • -
        • S
      • 16:25 HPN
        20:59 ORD
        5Hrs, 34m 1 Stop (ATL)
      • HPNWestchester County Airport 16:25 - ORD 20:59 5h 34m 1 Stop (ATL) Atlanta
      • HPNWestchester County Airport 16:25
        ATLAtlanta Hartsfield-Jackson Intl Airport 19:55
      • ATLAtlanta Hartsfield-Jackson Intl Airport 18:53
        ORDChicago O'Hare International Airport 20:59
      • 5h 34m (1h 02m)
      • 1 Stop ATL · Atlanta 1h 02m
      • Delta Air Lines (DL 3686)Canadair Regional
        Delta Air Lines (DL 1577)Boeing 737 900
      • Delta Air Lines (DL 3686)
        • -
        • -
        • W
        • -
        • -
        • -
        • -
      • 16:25 HPN
        20:59 ORD
        5Hrs, 34m 1 Stop (ATL)
      • HPNWestchester County Airport 16:25 - ORD 20:59 5h 34m 1 Stop (ATL) Atlanta
      • HPNWestchester County Airport 16:25
        ATLAtlanta Hartsfield-Jackson Intl Airport 19:55
      • ATLAtlanta Hartsfield-Jackson Intl Airport 18:53
        ORDChicago O'Hare International Airport 20:59
      • 5h 34m (1h 02m)
      • 1 Stop ATL · Atlanta 1h 02m
      • Delta Air Lines (DL 3686)Canadair Regional
        Delta Air Lines (DL 1139)Boeing 737 900
      • Delta Air Lines (DL 3686)
        • M
        • -
        • -
        • T
        • F
        • -
        • S
      • 17:24 HPN
        21:01 ORD
        4Hrs, 37m 1 Stop (DTW)
      • HPNWestchester County Airport 17:24 - ORD 21:01 4h 37m 1 Stop (DTW) Detroit
      • HPNWestchester County Airport 17:24
        DTWDetroit Wayne County 20:40
      • DTWDetroit Wayne County 19:15
        ORDChicago O'Hare International Airport 21:01
      • 4h 37m (1h 25m)
      • 1 Stop DTW · Detroit 1h 25m
      • Delta Air Lines (DL 3734)Canadair Regional
        Delta Air Lines (DL 1665)Boeing 717
      • Delta Air Lines (DL 3734)
        • M
        • T
        • W
        • T
        • F
        • S
        • S
      • 18:49 HPN
        23:59 ORD
        6Hrs, 10m 1 Stop (ATL)
      • HPNWestchester County Airport 18:49 - ORD 23:59 6h 10m 1 Stop (ATL) Atlanta
      • HPNWestchester County Airport 18:49
        ATLAtlanta Hartsfield-Jackson Intl Airport 22:55
      • ATLAtlanta Hartsfield-Jackson Intl Airport 21:13
        ORDChicago O'Hare International Airport 23:59
      • 6h 10m (1h 42m)
      • 1 Stop ATL · Atlanta 1h 42m
      • Delta Air Lines (DL 4952)Canadair Regional
        Delta Air Lines (DL 1199)Boeing 737 800
      • Delta Air Lines (DL 4952)
        • M
        • T
        • W
        • T
        • F
        • -
        • S
      • 18:49 HPN
        23:59 ORD
        6Hrs, 10m 1 Stop (ATL)
      • HPNWestchester County Airport 18:49 - ORD 23:59 6h 10m 1 Stop (ATL) Atlanta
      • HPNWestchester County Airport 18:49
        ATLAtlanta Hartsfield-Jackson Intl Airport 22:55
      • ATLAtlanta Hartsfield-Jackson Intl Airport 21:13
        ORDChicago O'Hare International Airport 23:59
      • 6h 10m (1h 42m)
      • 1 Stop ATL · Atlanta 1h 42m
      • Delta Air Lines (DL 3695)Canadair Regional
        Delta Air Lines (DL 1199)Boeing 737 800
      • Delta Air Lines (DL 3695)
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      • 18:54 HPN
        23:59 ORD
        6Hrs, 05m 1 Stop (CLT)
      • HPNWestchester County Airport 18:54 - ORD 23:59 6h 05m 1 Stop (CLT) Charlotte
      • HPNWestchester County Airport 18:54
        CLTCharlotte Airport 22:45
      • CLTCharlotte Airport 20:55
        ORDChicago O'Hare International Airport 23:59
      • 6h 05m (1h 50m)
      • 1 Stop CLT · Charlotte 1h 50m
      • American Airlines (AA 5070)Crj 700 Canadair Regional
        American Airlines (AA 1628)Airbus
      • American Airlines (AA 5070)
        • M
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      • 18:55 HPN
        23:59 ORD
        6Hrs, 04m 1 Stop (CLT)
      • HPNWestchester County Airport 18:55 - ORD 23:59 6h 04m 1 Stop (CLT) Charlotte
      • HPNWestchester County Airport 18:55
        CLTCharlotte Airport 22:45
      • CLTCharlotte Airport 20:56
        ORDChicago O'Hare International Airport 23:59
      • 6h 04m (1h 49m)
      • 1 Stop CLT · Charlotte 1h 49m
      • American Airlines (AA 5070)Crj 700 Canadair Regional
        American Airlines (AA 1628)Airbus
      • American Airlines (AA 5070)
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      What’s the fastest flight time from Westchester County to Chicago?

      The fastest flight time for direct flights from Westchester County to Chicago is 2 hours 28 minutes. Check latest flight schedules & prices on Wego.

      How far is Chicago from Westchester County?

      The flight distance between Westchester County and Chicago 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 06:00. See the full list of flight times on Wego.

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

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

      All Airports in Westchester County

      Westchester County Airport HPN

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