Flight Schedules

Last Updated: Mon, 2 Dec, 2024

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      • Availability
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      • 12:26 EYW
        14:55 ORD
        3Hrs, 29m Direct
      • EYWKey West International Airport 12:26 - ORD 14:55 3h 29m Direct
      • EYWKey West International Airport 12:26
      • ORDChicago O'Hare International Airport 14:55
      • 3h 29m
      • Direct
      • United Airlines (UA 751)Boeing 737 700
      • United Airlines (UA 751)
        • -
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        • T
        • F
        • S
        • S
      • Boeing 737 700
      • 13:07 EYW
        15:38 ORD
        3Hrs, 31m Direct
      • EYWKey West International Airport 13:07 - ORD 15:38 3h 31m Direct
      • EYWKey West International Airport 13:07
      • ORDChicago O'Hare International Airport 15:38
      • 3h 31m
      • Direct
      • American Airlines (AA 3676)Embraer 170
      • American Airlines (AA 3676)
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        • T
        • F
        • S
        • S
      • Embraer 170
      • 16:19 EYW
        18:50 ORD
        3Hrs, 31m Direct
      • EYWKey West International Airport 16:19 - ORD 18:50 3h 31m Direct
      • EYWKey West International Airport 16:19
      • ORDChicago O'Hare International Airport 18:50
      • 3h 31m
      • Direct
      • United Airlines (UA 2263)Boeing 737 700
      • United Airlines (UA 2263)
        • M
        • T
        • W
        • T
        • F
        • S
        • S
      • Boeing 737 700
      • 19:59 EYW
        00:26 ORD
        5Hrs, 27m 1 Stop (MIA)
      • EYWKey West International Airport 19:59 - ORD 00:26 5h 27m 1 Stop (MIA) Miami
      • EYWKey West International Airport 19:59
        MIAMiami International Airport 21:45
      • MIAMiami International Airport 20:50
        ORDChicago O'Hare International Airport 00:26
      • 5h 27m (55m)
      • 1 Stop MIA · Miami 55m
      • American Airlines (AA 4064)Embraer Emb 175
        American Airlines (AA 376)Boeing 737 800
      • American Airlines (AA 4064)
        • M
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        • -
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        • F
        • S
        • S
      • 08:01 EYW
        12:07 ORD
        5Hrs, 06m 1 Stop (CLT)
      • EYWKey West International Airport 08:01 - ORD 12:07 5h 06m 1 Stop (CLT) Charlotte
      • EYWKey West International Airport 08:01
        CLTCharlotte Airport 10:59
      • CLTCharlotte Airport 10:20
        ORDChicago O'Hare International Airport 12:07
      • 5h 06m (39m)
      • 1 Stop CLT · Charlotte 39m
      • American Airlines (AA 680)Airbus
        American Airlines (AA 2279)Boeing 737 800
      • American Airlines (AA 680)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • 08:01 EYW
        12:12 ORD
        5Hrs, 11m 1 Stop (CLT)
      • EYWKey West International Airport 08:01 - ORD 12:12 5h 11m 1 Stop (CLT) Charlotte
      • EYWKey West International Airport 08:01
        CLTCharlotte Airport 11:01
      • CLTCharlotte Airport 10:20
        ORDChicago O'Hare International Airport 12:12
      • 5h 11m (41m)
      • 1 Stop CLT · Charlotte 41m
      • American Airlines (AA 680)Airbus
        American Airlines (AA 2279)Boeing 737 800
      • American Airlines (AA 680)
        • M
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        • -
        • T
        • F
        • -
        • S
      • 08:01 EYW
        12:12 ORD
        5Hrs, 11m 1 Stop (CLT)
      • EYWKey West International Airport 08:01 - ORD 12:12 5h 11m 1 Stop (CLT) Charlotte
      • EYWKey West International Airport 08:01
        CLTCharlotte Airport 11:01
      • CLTCharlotte Airport 10:20
        ORDChicago O'Hare International Airport 12:12
      • 5h 11m (41m)
      • 1 Stop CLT · Charlotte 41m
      • American Airlines (AA 680)Airbus
        American Airlines (AA 2279)Airbus A321 Neo
      • American Airlines (AA 680)
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        • -
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        • -
        • -
        • -
        • -
      • 08:01 EYW
        14:12 ORD
        7Hrs, 11m 1 Stop (CLT)
      • EYWKey West International Airport 08:01 - ORD 14:12 7h 11m 1 Stop (CLT) Charlotte
      • EYWKey West International Airport 08:01
        CLTCharlotte Airport 13:04
      • CLTCharlotte Airport 10:20
        ORDChicago O'Hare International Airport 14:12
      • 7h 11m (2h 44m)
      • 1 Stop CLT · Charlotte 2h 44m
      • American Airlines (AA 680)Airbus
        American Airlines (AA 1052)Boeing 737 800
      • American Airlines (AA 680)
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        • T
        • F
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        • S
      • 10:00 EYW
        14:47 ORD
        5Hrs, 47m 1 Stop (TPA)
      • EYWKey West International Airport 10:00 - ORD 14:47 5h 47m 1 Stop (TPA) Tampa
      • EYWKey West International Airport 10:00
        TPATampa International Airport 12:45
      • TPATampa International Airport 11:15
        ORDChicago O'Hare International Airport 14:47
      • 5h 47m (1h 30m)
      • 1 Stop TPA · Tampa 1h 30m
      • Silver Airways (3M 135)Atr Turboprop
        United Airlines (UA 2187)Boeing 737 800
      • Silver Airways (3M 135)
        • -
        • T
        • -
        • -
        • -
        • -
        • -
      • 10:00 EYW
        14:47 ORD
        5Hrs, 47m 1 Stop (TPA)
      • EYWKey West International Airport 10:00 - ORD 14:47 5h 47m 1 Stop (TPA) Tampa
      • EYWKey West International Airport 10:00
        TPATampa International Airport 12:45
      • TPATampa International Airport 11:15
        ORDChicago O'Hare International Airport 14:47
      • 5h 47m (1h 30m)
      • 1 Stop TPA · Tampa 1h 30m
      • Silver Airways (3M 135)Atr Turboprop
        United Airlines (UA 2187)Boeing 737 900
      • Silver Airways (3M 135)
        • -
        • -
        • W
        • -
        • F
        • -
        • S
      • 10:00 EYW
        14:47 ORD
        5Hrs, 47m 1 Stop (TPA)
      • EYWKey West International Airport 10:00 - ORD 14:47 5h 47m 1 Stop (TPA) Tampa
      • EYWKey West International Airport 10:00
        TPATampa International Airport 12:45
      • TPATampa International Airport 11:15
        ORDChicago O'Hare International Airport 14:47
      • 5h 47m (1h 30m)
      • 1 Stop TPA · Tampa 1h 30m
      • Silver Airways (3M 135)Atr Turboprop
        United Airlines (UA 2187)Airbus A321 Neo
      • Silver Airways (3M 135)
        • M
        • -
        • -
        • T
        • -
        • S
        • -
      • 10:29 EYW
        16:42 ORD
        7Hrs, 13m 1 Stop (MIA)
      • EYWKey West International Airport 10:29 - ORD 16:42 7h 13m 1 Stop (MIA) Miami
      • EYWKey West International Airport 10:29
        MIAMiami International Airport 14:15
      • MIAMiami International Airport 11:20
        ORDChicago O'Hare International Airport 16:42
      • 7h 13m (2h 55m)
      • 1 Stop MIA · Miami 2h 55m
      • American Airlines (AA 3700)Embraer Emb 175
        American Airlines (AA 1813)Boeing 737 800
      • American Airlines (AA 3700)
        • M
        • -
        • -
        • T
        • F
        • S
        • S
      • 10:55 EYW
        16:31 ORD
        6Hrs, 36m 1 Stop (FLL)
      • EYWKey West International Airport 10:55 - ORD 16:31 6h 36m 1 Stop (FLL) Broward County
      • EYWKey West International Airport 10:55
        FLLFort Lauderdale/Hollywood Intl Airport 14:00
      • FLLFort Lauderdale/Hollywood Intl Airport 12:00
        ORDChicago O'Hare International Airport 16:31
      • 6h 36m (2h)
      • 1 Stop FLL · Broward County 2h
      • Silver Airways (3M 93)Atr Turboprop
        United Airlines (UA 1840)Airbus A321 Neo
      • Silver Airways (3M 93)
        • M
        • T
        • -
        • T
        • F
        • S
        • S
      • 10:55 EYW
        16:31 ORD
        6Hrs, 36m 1 Stop (FLL)
      • EYWKey West International Airport 10:55 - ORD 16:31 6h 36m 1 Stop (FLL) Broward County
      • EYWKey West International Airport 10:55
        FLLFort Lauderdale/Hollywood Intl Airport 14:00
      • FLLFort Lauderdale/Hollywood Intl Airport 12:00
        ORDChicago O'Hare International Airport 16:31
      • 6h 36m (2h)
      • 1 Stop FLL · Broward County 2h
      • Silver Airways (3M 93)Atr Turboprop
        United Airlines (UA 1840)Boeing 737 900
      • Silver Airways (3M 93)
        • -
        • -
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        • -
        • -
        • -
        • -
      • 11:14 EYW
        16:16 ORD
        6Hrs, 02m 1 Stop (DCA)
      • EYWKey West International Airport 11:14 - ORD 16:16 6h 02m 1 Stop (DCA) Washington
      • EYWKey West International Airport 11:14
        DCAWashington Ronald Reagan National Airport 14:54
      • DCAWashington Ronald Reagan National Airport 13:59
        ORDChicago O'Hare International Airport 16:16
      • 6h 02m (55m)
      • 1 Stop DCA · Washington 55m
      • American Airlines (AA 4640)Embraer Emb 175
        American Airlines (AA 1762)Boeing 737 800
      • American Airlines (AA 4640)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • 11:14 EYW
        18:21 ORD
        8Hrs, 07m 1 Stop (DCA)
      • EYWKey West International Airport 11:14 - ORD 18:21 8h 07m 1 Stop (DCA) Washington
      • EYWKey West International Airport 11:14
        DCAWashington Ronald Reagan National Airport 16:59
      • DCAWashington Ronald Reagan National Airport 13:59
        ORDChicago O'Hare International Airport 18:21
      • 8h 07m (3h)
      • 1 Stop DCA · Washington 3h
      • American Airlines (AA 4640)Embraer Emb 175
        American Airlines (AA 2959)Airbus
      • American Airlines (AA 4640)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • 11:24 EYW
        16:16 ORD
        5Hrs, 52m 1 Stop (DCA)
      • EYWKey West International Airport 11:24 - ORD 16:16 5h 52m 1 Stop (DCA) Washington
      • EYWKey West International Airport 11:24
        DCAWashington Ronald Reagan National Airport 14:54
      • DCAWashington Ronald Reagan National Airport 14:09
        ORDChicago O'Hare International Airport 16:16
      • 5h 52m (45m)
      • 1 Stop DCA · Washington 45m
      • American Airlines (AA 4640)Embraer Emb 175
        American Airlines (AA 1762)Boeing 737 800
      • American Airlines (AA 4640)
        • M
        • T
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        • T
        • F
        • -
        • S
      • 11:24 EYW
        18:36 ORD
        8Hrs, 12m 1 Stop (DCA)
      • EYWKey West International Airport 11:24 - ORD 18:36 8h 12m 1 Stop (DCA) Washington
      • EYWKey West International Airport 11:24
        DCAWashington Ronald Reagan National Airport 17:13
      • DCAWashington Ronald Reagan National Airport 14:09
        ORDChicago O'Hare International Airport 18:36
      • 8h 12m (3h 04m)
      • 1 Stop DCA · Washington 3h 04m
      • American Airlines (AA 4640)Embraer Emb 175
        American Airlines (AA 2959)Airbus
      • American Airlines (AA 4640)
        • M
        • -
        • -
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        • F
        • -
        • S
      • 12:37 EYW
        20:01 ORD
        8Hrs, 24m 1 Stop (BOS)
      • EYWKey West International Airport 12:37 - ORD 20:01 8h 24m 1 Stop (BOS) Boston
      • EYWKey West International Airport 12:37
        BOSBoston Logan International Airport 17:53
      • BOSBoston Logan International Airport 16:08
        ORDChicago O'Hare International Airport 20:01
      • 8h 24m (1h 45m)
      • 1 Stop BOS · Boston 1h 45m
      • JetBlue Airways (B6 2064)Airbus A220 300
        JetBlue Airways (B6 2311)Airbus A220 300
      • JetBlue Airways (B6 2064)
        • -
        • -
        • -
        • -
        • F
        • -
        • -
      • 12:55 EYW
        18:09 ORD
        6Hrs, 14m 1 Stop (CLT)
      • EYWKey West International Airport 12:55 - ORD 18:09 6h 14m 1 Stop (CLT) Charlotte
      • EYWKey West International Airport 12:55
        CLTCharlotte Airport 16:58
      • CLTCharlotte Airport 15:15
        ORDChicago O'Hare International Airport 18:09
      • 6h 14m (1h 43m)
      • 1 Stop CLT · Charlotte 1h 43m
      • American Airlines (AA 1816)Airbus
        American Airlines (AA 2569)Boeing 737 800
      • American Airlines (AA 1816)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • 18:15 CMH
        15:15 CLT
        6Hrs, 51m 1 Stop (ORD)
      • CMHColumbus Port Columbus Intl Airport 18:15 - CLT 15:15 6h 51m 1 Stop (ORD) Chicago
      • CMHColumbus Port Columbus Intl Airport 18:15
        EYWKey West International Airport 12:55
      • ORDChicago O'Hare International Airport 18:46
        CLTCharlotte Airport 15:15
      • 6h 51m (1h 31m)
      • 1 Stop ORD · Chicago 1h 31m
      • American Airlines (AA 6068)Crj Canadair Regional
        American Airlines (AA 1816)Airbus
      • American Airlines (AA 6068)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • 12:55 EYW
        19:24 ORD
        7Hrs, 29m 1 Stop (CLT)
      • EYWKey West International Airport 12:55 - ORD 19:24 7h 29m 1 Stop (CLT) Charlotte
      • EYWKey West International Airport 12:55
        CLTCharlotte Airport 18:16
      • CLTCharlotte Airport 15:15
        ORDChicago O'Hare International Airport 19:24
      • 7h 29m (3h 01m)
      • 1 Stop CLT · Charlotte 3h 01m
      • American Airlines (AA 1816)Airbus
        American Airlines (AA 2488)Airbus
      • American Airlines (AA 1816)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • 12:58 EYW
        17:43 ORD
        5Hrs, 45m 1 Stop (CLT)
      • EYWKey West International Airport 12:58 - ORD 17:43 5h 45m 1 Stop (CLT) Charlotte
      • EYWKey West International Airport 12:58
        CLTCharlotte Airport 16:38
      • CLTCharlotte Airport 15:18
        ORDChicago O'Hare International Airport 17:43
      • 5h 45m (1h 20m)
      • 1 Stop CLT · Charlotte 1h 20m
      • American Airlines (AA 1816)Airbus
        American Airlines (AA 2569)Airbus
      • American Airlines (AA 1816)
        • M
        • -
        • -
        • T
        • F
        • -
        • S
      • 18:15 CMH
        15:18 CLT
        6Hrs, 48m 1 Stop (ORD)
      • CMHColumbus Port Columbus Intl Airport 18:15 - CLT 15:18 6h 48m 1 Stop (ORD) Chicago
      • CMHColumbus Port Columbus Intl Airport 18:15
        EYWKey West International Airport 12:58
      • ORDChicago O'Hare International Airport 18:46
        CLTCharlotte Airport 15:18
      • 6h 48m (1h 28m)
      • 1 Stop ORD · Chicago 1h 28m
      • American Airlines (AA 6068)Crj Canadair Regional
        American Airlines (AA 1816)Airbus
      • American Airlines (AA 6068)
        • M
        • -
        • -
        • T
        • F
        • -
        • S
      • 12:58 EYW
        19:24 ORD
        7Hrs, 26m 1 Stop (CLT)
      • EYWKey West International Airport 12:58 - ORD 19:24 7h 26m 1 Stop (CLT) Charlotte
      • EYWKey West International Airport 12:58
        CLTCharlotte Airport 18:16
      • CLTCharlotte Airport 15:18
        ORDChicago O'Hare International Airport 19:24
      • 7h 26m (2h 58m)
      • 1 Stop CLT · Charlotte 2h 58m
      • American Airlines (AA 1816)Airbus
        American Airlines (AA 2488)Airbus
      • American Airlines (AA 1816)
        • M
        • -
        • -
        • T
        • F
        • -
        • S
      • 13:00 EYW
        18:42 ORD
        6Hrs, 42m 1 Stop (IAD)
      • EYWKey West International Airport 13:00 - ORD 18:42 6h 42m 1 Stop (IAD) Washington
      • EYWKey West International Airport 13:00
        IADWashington Dulles International Airport 17:22
      • IADWashington Dulles International Airport 15:43
        ORDChicago O'Hare International Airport 18:42
      • 6h 42m (1h 39m)
      • 1 Stop IAD · Washington 1h 39m
      • United Airlines (UA 6217)Embraer 175
        United Airlines (UA 2497)Boeing 737 900
      • United Airlines (UA 6217)
        • M
        • -
        • -
        • -
        • -
        • -
        • -
      • 13:00 EYW
        18:42 ORD
        6Hrs, 42m 1 Stop (IAD)
      • EYWKey West International Airport 13:00 - ORD 18:42 6h 42m 1 Stop (IAD) Washington
      • EYWKey West International Airport 13:00
        IADWashington Dulles International Airport 17:22
      • IADWashington Dulles International Airport 15:43
        ORDChicago O'Hare International Airport 18:42
      • 6h 42m (1h 39m)
      • 1 Stop IAD · Washington 1h 39m
      • United Airlines (UA 6217)Embraer 175
        United Airlines (UA 2497)Airbus
      • United Airlines (UA 6217)
        • -
        • T
        • -
        • -
        • F
        • -
        • -
      • 13:00 EYW
        18:42 ORD
        6Hrs, 42m 1 Stop (IAD)
      • EYWKey West International Airport 13:00 - ORD 18:42 6h 42m 1 Stop (IAD) Washington
      • EYWKey West International Airport 13:00
        IADWashington Dulles International Airport 17:22
      • IADWashington Dulles International Airport 15:43
        ORDChicago O'Hare International Airport 18:42
      • 6h 42m (1h 39m)
      • 1 Stop IAD · Washington 1h 39m
      • United Airlines (UA 6217)Embraer 175
        United Airlines (UA 2497)Airbus
      • United Airlines (UA 6217)
        • -
        • -
        • -
        • T
        • -
        • -
        • -
      • 13:00 EYW
        18:49 ORD
        6Hrs, 49m 1 Stop (IAD)
      • EYWKey West International Airport 13:00 - ORD 18:49 6h 49m 1 Stop (IAD) Washington
      • EYWKey West International Airport 13:00
        IADWashington Dulles International Airport 17:29
      • IADWashington Dulles International Airport 15:43
        ORDChicago O'Hare International Airport 18:49
      • 6h 49m (1h 46m)
      • 1 Stop IAD · Washington 1h 46m
      • United Airlines (UA 6217)Embraer 175
        United Airlines (UA 2497)Boeing 737 900
      • United Airlines (UA 6217)
        • -
        • -
        • W
        • -
        • -
        • -
        • -
      • 13:00 EYW
        18:55 ORD
        6Hrs, 55m 1 Stop (IAD)
      • EYWKey West International Airport 13:00 - ORD 18:55 6h 55m 1 Stop (IAD) Washington
      • EYWKey West International Airport 13:00
        IADWashington Dulles International Airport 17:35
      • IADWashington Dulles International Airport 15:43
        ORDChicago O'Hare International Airport 18:55
      • 6h 55m (1h 52m)
      • 1 Stop IAD · Washington 1h 52m
      • United Airlines (UA 6217)Embraer 175
        United Airlines (UA 2497)Boeing 737 900
      • United Airlines (UA 6217)
        • -
        • -
        • -
        • -
        • -
        • -
        • S
      • 13:00 EYW
        18:55 ORD
        6Hrs, 55m 1 Stop (IAD)
      • EYWKey West International Airport 13:00 - ORD 18:55 6h 55m 1 Stop (IAD) Washington
      • EYWKey West International Airport 13:00
        IADWashington Dulles International Airport 17:35
      • IADWashington Dulles International Airport 15:43
        ORDChicago O'Hare International Airport 18:55
      • 6h 55m (1h 52m)
      • 1 Stop IAD · Washington 1h 52m
      • United Airlines (UA 6217)Embraer 175
        United Airlines (UA 2497)Airbus
      • United Airlines (UA 6217)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • 13:00 EYW
        19:45 ORD
        7Hrs, 45m 1 Stop (BOS)
      • EYWKey West International Airport 13:00 - ORD 19:45 7h 45m 1 Stop (BOS) Boston
      • EYWKey West International Airport 13:00
        BOSBoston Logan International Airport 17:42
      • BOSBoston Logan International Airport 16:34
        ORDChicago O'Hare International Airport 19:45
      • 7h 45m (1h 08m)
      • 1 Stop BOS · Boston 1h 08m
      • American Airlines (AA 4540)Embraer Emb 175
        American Airlines (AA 2877)Boeing 737 800
      • American Airlines (AA 4540)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • 13:36 EYW
        18:25 ORD
        5Hrs, 49m 1 Stop (MIA)
      • EYWKey West International Airport 13:36 - ORD 18:25 5h 49m 1 Stop (MIA) Miami
      • EYWKey West International Airport 13:36
        MIAMiami International Airport 16:00
      • MIAMiami International Airport 14:33
        ORDChicago O'Hare International Airport 18:25
      • 5h 49m (1h 27m)
      • 1 Stop MIA · Miami 1h 27m
      • American Airlines (AA 4679)Embraer Emb 175
        American Airlines (AA 3126)Boeing 737 800
      • American Airlines (AA 4679)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • 18:16 CLT
        14:33 MIA
        6Hrs, 48m 1 Stop (ORD)
      • CLTCharlotte Airport 18:16 - MIA 14:33 6h 48m 1 Stop (ORD) Chicago
      • CLTCharlotte Airport 18:16
        EYWKey West International Airport 13:36
      • ORDChicago O'Hare International Airport 19:24
        MIAMiami International Airport 14:33
      • 6h 48m (1h 32m)
      • 1 Stop ORD · Chicago 1h 32m
      • American Airlines (AA 2488)Airbus
        American Airlines (AA 4679)Embraer Emb 175
      • American Airlines (AA 2488)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • 13:36 EYW
        19:34 ORD
        6Hrs, 58m 1 Stop (MIA)
      • EYWKey West International Airport 13:36 - ORD 19:34 6h 58m 1 Stop (MIA) Miami
      • EYWKey West International Airport 13:36
        MIAMiami International Airport 17:09
      • MIAMiami International Airport 14:33
        ORDChicago O'Hare International Airport 19:34
      • 6h 58m (2h 36m)
      • 1 Stop MIA · Miami 2h 36m
      • American Airlines (AA 4679)Embraer Emb 175
        American Airlines (AA 3062)Boeing 737 800
      • American Airlines (AA 4679)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • 13:40 EYW
        19:30 ORD
        6Hrs, 50m 1 Stop (CLT)
      • EYWKey West International Airport 13:40 - ORD 19:30 6h 50m 1 Stop (CLT) Charlotte
      • EYWKey West International Airport 13:40
        CLTCharlotte Airport 18:16
      • CLTCharlotte Airport 16:00
        ORDChicago O'Hare International Airport 19:30
      • 6h 50m (2h 16m)
      • 1 Stop CLT · Charlotte 2h 16m
      • American Airlines (AA 382)Airbus
        American Airlines (AA 2488)Boeing 737 800
      • American Airlines (AA 382)
        • -
        • T
        • W
        • -
        • -
        • -
        • -
      • 13:52 EYW
        18:25 ORD
        5Hrs, 33m 1 Stop (MIA)
      • EYWKey West International Airport 13:52 - ORD 18:25 5h 33m 1 Stop (MIA) Miami
      • EYWKey West International Airport 13:52
        MIAMiami International Airport 16:00
      • MIAMiami International Airport 14:45
        ORDChicago O'Hare International Airport 18:25
      • 5h 33m (1h 15m)
      • 1 Stop MIA · Miami 1h 15m
      • American Airlines (AA 3345)Embraer Emb 175
        American Airlines (AA 3126)Boeing 737 800
      • American Airlines (AA 3345)
        • M
        • -
        • -
        • T
        • F
        • -
        • S
      • 13:52 EYW
        19:34 ORD
        6Hrs, 42m 1 Stop (MIA)
      • EYWKey West International Airport 13:52 - ORD 19:34 6h 42m 1 Stop (MIA) Miami
      • EYWKey West International Airport 13:52
        MIAMiami International Airport 17:09
      • MIAMiami International Airport 14:45
        ORDChicago O'Hare International Airport 19:34
      • 6h 42m (2h 24m)
      • 1 Stop MIA · Miami 2h 24m
      • American Airlines (AA 3345)Embraer Emb 175
        American Airlines (AA 3062)Boeing 737 800
      • American Airlines (AA 3345)
        • M
        • -
        • -
        • T
        • F
        • -
        • S
      • 14:00 EYW
        18:28 ORD
        5Hrs, 28m 1 Stop (TPA)
      • EYWKey West International Airport 14:00 - ORD 18:28 5h 28m 1 Stop (TPA) Tampa
      • EYWKey West International Airport 14:00
        TPATampa International Airport 16:26
      • TPATampa International Airport 15:15
        ORDChicago O'Hare International Airport 18:28
      • 5h 28m (1h 11m)
      • 1 Stop TPA · Tampa 1h 11m
      • Silver Airways (3M 136)Atr Turboprop
        United Airlines (UA 2627)Boeing 737 900
      • Silver Airways (3M 136)
        • -
        • -
        • -
        • -
        • F
        • -
        • -
      • 14:00 EYW
        18:28 ORD
        5Hrs, 28m 1 Stop (TPA)
      • EYWKey West International Airport 14:00 - ORD 18:28 5h 28m 1 Stop (TPA) Tampa
      • EYWKey West International Airport 14:00
        TPATampa International Airport 16:26
      • TPATampa International Airport 15:15
        ORDChicago O'Hare International Airport 18:28
      • 5h 28m (1h 11m)
      • 1 Stop TPA · Tampa 1h 11m
      • Silver Airways (3M 136)Atr Turboprop
        United Airlines (UA 2627)Airbus A321 Neo
      • Silver Airways (3M 136)
        • M
        • T
        • W
        • T
        • -
        • S
        • S
      • 14:00 EYW
        20:02 ORD
        7Hrs, 02m 1 Stop (TPA)
      • EYWKey West International Airport 14:00 - ORD 20:02 7h 02m 1 Stop (TPA) Tampa
      • EYWKey West International Airport 14:00
        TPATampa International Airport 18:01
      • TPATampa International Airport 15:15
        ORDChicago O'Hare International Airport 20:02
      • 7h 02m (2h 46m)
      • 1 Stop TPA · Tampa 2h 46m
      • Silver Airways (3M 136)Atr Turboprop
        United Airlines (UA 2335)Boeing 737 Max 8 Passenger
      • Silver Airways (3M 136)
        • M
        • -
        • W
        • T
        • F
        • S
        • S
      • 14:10 EYW
        20:13 ORD
        7Hrs, 03m 1 Stop (EWR)
      • EYWKey West International Airport 14:10 - ORD 20:13 7h 03m 1 Stop (EWR) New York City
      • EYWKey West International Airport 14:10
        EWRNewark Liberty International Airport 18:29
      • EWRNewark Liberty International Airport 17:13
        ORDChicago O'Hare International Airport 20:13
      • 7h 03m (1h 16m)
      • 1 Stop EWR · New York City 1h 16m
      • United Airlines (UA 1513)Boeing 737 700
        United Airlines (UA 254)Boeing 737 900
      • United Airlines (UA 1513)
        • M
        • -
        • -
        • -
        • -
        • -
        • -
      • 14:22 EYW
        20:13 ORD
        6Hrs, 51m 1 Stop (EWR)
      • EYWKey West International Airport 14:22 - ORD 20:13 6h 51m 1 Stop (EWR) New York City
      • EYWKey West International Airport 14:22
        EWRNewark Liberty International Airport 18:29
      • EWRNewark Liberty International Airport 17:25
        ORDChicago O'Hare International Airport 20:13
      • 6h 51m (1h 04m)
      • 1 Stop EWR · New York City 1h 04m
      • United Airlines (UA 1513)Boeing 737 700
        United Airlines (UA 254)Boeing 737 900
      • United Airlines (UA 1513)
        • -
        • -
        • -
        • T
        • F
        • -
        • -
      • 14:22 EYW
        21:52 ORD
        8Hrs, 30m 1 Stop (EWR)
      • EYWKey West International Airport 14:22 - ORD 21:52 8h 30m 1 Stop (EWR) New York City
      • EYWKey West International Airport 14:22
        EWRNewark Liberty International Airport 20:10
      • EWRNewark Liberty International Airport 17:25
        ORDChicago O'Hare International Airport 21:52
      • 8h 30m (2h 45m)
      • 1 Stop EWR · New York City 2h 45m
      • United Airlines (UA 1513)Boeing 737 700
        United Airlines (UA 546)Boeing 737 900
      • United Airlines (UA 1513)
        • -
        • -
        • -
        • T
        • F
        • -
        • -
      • 14:23 EYW
        20:45 ORD
        7Hrs, 22m 1 Stop (LGA)
      • EYWKey West International Airport 14:23 - ORD 20:45 7h 22m 1 Stop (LGA) New York City
      • EYWKey West International Airport 14:23
        LGANew York La Guardia Airport 19:00
      • LGANew York La Guardia Airport 17:29
        ORDChicago O'Hare International Airport 20:45
      • 7h 22m (1h 31m)
      • 1 Stop LGA · New York City 1h 31m
      • American Airlines (AA 4600)Embraer Emb 175
        American Airlines (AA 1263)Boeing 737 Max 8 Passenger
      • American Airlines (AA 4600)
        • M
        • -
        • -
        • -
        • -
        • -
        • -
      • 14:23 EYW
        21:37 ORD
        8Hrs, 14m 1 Stop (LGA)
      • EYWKey West International Airport 14:23 - ORD 21:37 8h 14m 1 Stop (LGA) New York City
      • EYWKey West International Airport 14:23
        LGANew York La Guardia Airport 19:57
      • LGANew York La Guardia Airport 17:29
        ORDChicago O'Hare International Airport 21:37
      • 8h 14m (2h 28m)
      • 1 Stop LGA · New York City 2h 28m
      • American Airlines (AA 4600)Embraer Emb 175
        American Airlines (AA 417)Airbus
      • American Airlines (AA 4600)
        • M
        • -
        • -
        • -
        • -
        • -
        • -
      • 14:23 EYW
        21:37 ORD
        8Hrs, 14m 1 Stop (LGA)
      • EYWKey West International Airport 14:23 - ORD 21:37 8h 14m 1 Stop (LGA) New York City
      • EYWKey West International Airport 14:23
        LGANew York La Guardia Airport 19:57
      • LGANew York La Guardia Airport 17:34
        ORDChicago O'Hare International Airport 21:37
      • 8h 14m (2h 23m)
      • 1 Stop LGA · New York City 2h 23m
      • American Airlines (AA 4555)Embraer Emb 175
        American Airlines (AA 417)Airbus
      • American Airlines (AA 4555)
        • -
        • -
        • -
        • T
        • F
        • -
        • S
      • 14:24 EYW
        21:52 ORD
        8Hrs, 28m 1 Stop (EWR)
      • EYWKey West International Airport 14:24 - ORD 21:52 8h 28m 1 Stop (EWR) New York City
      • EYWKey West International Airport 14:24
        EWRNewark Liberty International Airport 20:10
      • EWRNewark Liberty International Airport 17:27
        ORDChicago O'Hare International Airport 21:52
      • 8h 28m (2h 43m)
      • 1 Stop EWR · New York City 2h 43m
      • United Airlines (UA 1513)Boeing 737 700
        United Airlines (UA 546)Boeing 737 900
      • United Airlines (UA 1513)
        • -
        • -
        • -
        • -
        • -
        • -
        • S
      • 14:26 EYW
        21:52 ORD
        8Hrs, 26m 1 Stop (EWR)
      • EYWKey West International Airport 14:26 - ORD 21:52 8h 26m 1 Stop (EWR) New York City
      • EYWKey West International Airport 14:26
        EWRNewark Liberty International Airport 20:10
      • EWRNewark Liberty International Airport 17:29
        ORDChicago O'Hare International Airport 21:52
      • 8h 26m (2h 41m)
      • 1 Stop EWR · New York City 2h 41m
      • United Airlines (UA 1513)Boeing 737 700
        United Airlines (UA 546)Boeing 737 900
      • United Airlines (UA 1513)
        • -
        • -
        • W
        • -
        • -
        • -
        • -
      • 14:27 EYW
        20:13 ORD
        6Hrs, 46m 1 Stop (EWR)
      • EYWKey West International Airport 14:27 - ORD 20:13 6h 46m 1 Stop (EWR) New York City
      • EYWKey West International Airport 14:27
        EWRNewark Liberty International Airport 18:29
      • EWRNewark Liberty International Airport 17:30
        ORDChicago O'Hare International Airport 20:13
      • 6h 46m (59m)
      • 1 Stop EWR · New York City 59m
      • United Airlines (UA 1513)Boeing 737 700
        United Airlines (UA 254)Boeing 737 900
      • United Airlines (UA 1513)
        • -
        • T
        • -
        • -
        • -
        • -
        • -
      • 14:27 EYW
        21:52 ORD
        8Hrs, 25m 1 Stop (EWR)
      • EYWKey West International Airport 14:27 - ORD 21:52 8h 25m 1 Stop (EWR) New York City
      • EYWKey West International Airport 14:27
        EWRNewark Liberty International Airport 20:10
      • EWRNewark Liberty International Airport 17:30
        ORDChicago O'Hare International Airport 21:52
      • 8h 25m (2h 40m)
      • 1 Stop EWR · New York City 2h 40m
      • United Airlines (UA 1513)Boeing 737 700
        United Airlines (UA 546)Boeing 737 900
      • United Airlines (UA 1513)
        • -
        • T
        • -
        • -
        • -
        • -
        • -
      • 14:36 EYW
        21:19 ORD
        7Hrs, 43m 1 Stop (DFW)
      • EYWKey West International Airport 14:36 - ORD 21:19 7h 43m 1 Stop (DFW) Dallas
      • EYWKey West International Airport 14:36
        DFWDallas/Fort Worth Intl Airport 18:55
      • DFWDallas/Fort Worth Intl Airport 16:57
        ORDChicago O'Hare International Airport 21:19
      • 7h 43m (1h 58m)
      • 1 Stop DFW · Dallas 1h 58m
      • American Airlines (AA 1827)Airbus
        American Airlines (AA 566)Boeing 737 800
      • American Airlines (AA 1827)
        • M
        • -
        • -
        • T
        • F
        • S
        • S
      • 14:54 EYW
        19:24 ORD
        5Hrs, 30m 1 Stop (CLT)
      • EYWKey West International Airport 14:54 - ORD 19:24 5h 30m 1 Stop (CLT) Charlotte
      • EYWKey West International Airport 14:54
        CLTCharlotte Airport 18:16
      • CLTCharlotte Airport 17:14
        ORDChicago O'Hare International Airport 19:24
      • 5h 30m (1h 02m)
      • 1 Stop CLT · Charlotte 1h 02m
      • American Airlines (AA 1222)Airbus
        American Airlines (AA 2488)Airbus
      • American Airlines (AA 1222)
        • M
        • -
        • -
        • T
        • F
        • S
        • S
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      What’s the fastest flight time from Key West to Chicago?

      The fastest flight time for direct flights from Key West to Chicago is 3 hours 29 minutes. Check latest flight schedules & prices on Wego.

      How far is Chicago from Key West?

      The flight distance between Key West and Chicago is 2000km. Check all available flights on Wego.

      When is the earliest and latest flight of the day?

      The earliest flight of the day departs at 08:01. The last flight of the day departs at 19:59. See the full list of flight times on Wego.

      How many airlines offer direct flights from Key West to Chicago?

      There are 2 airlines that offer direct flights from Key West to Chicago. Find out the list of airlines on Wego.

      All Airports in Key West

      Key West International Airport EYW

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