Flight Schedules

Last Updated: Fri, 2 May, 2025

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  • Availability
    • M
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    • S
  • 06:30 PNS
    12:20 ORD
    5Hrs, 50m Direct
  • PNSPensacola Municipal Airport 06:30 - ORD 12:20 5h 50m Direct
  • PNSPensacola Municipal Airport 06:30
  • ORDChicago O'Hare International Airport 12:20
  • 5h 50m
  • Direct
  • United Airlines (UA 2124)Boeing 737 700
  • United Airlines (UA 2124)
    • -
    • -
    • -
    • -
    • -
    • S
    • -
  • Boeing 737 700
  • 06:30 PNS
    12:20 ORD
    5Hrs, 50m Direct
  • PNSPensacola Municipal Airport 06:30 - ORD 12:20 5h 50m Direct
  • PNSPensacola Municipal Airport 06:30
  • ORDChicago O'Hare International Airport 12:20
  • 5h 50m
  • Direct
  • United Airlines (UA 2124)Airbus
  • United Airlines (UA 2124)
    • M
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    • T
    • F
    • -
    • S
  • Airbus
  • 11:10 PNS
    13:52 ORD
    2Hrs, 42m Direct
  • PNSPensacola Municipal Airport 11:10 - ORD 13:52 2h 42m Direct
  • PNSPensacola Municipal Airport 11:10
  • ORDChicago O'Hare International Airport 13:52
  • 2h 42m
  • Direct
  • American Airlines (AA 4285)Embraer Emb 175
  • American Airlines (AA 4285)
    • -
    • -
    • -
    • -
    • -
    • S
    • S
  • Embraer Emb 175
  • 14:05 PNS
    16:46 ORD
    2Hrs, 41m Direct
  • PNSPensacola Municipal Airport 14:05 - ORD 16:46 2h 41m Direct
  • PNSPensacola Municipal Airport 14:05
  • ORDChicago O'Hare International Airport 16:46
  • 2h 41m
  • Direct
  • United Airlines (UA 2179)Airbus
  • United Airlines (UA 2179)
    • M
    • T
    • W
    • T
    • F
    • S
    • S
  • Airbus
  • 14:50 PNS
    17:05 MDW
    2Hrs, 15m Direct
  • PNSPensacola Municipal Airport 14:50 - MDW 17:05 2h 15m Direct
  • PNSPensacola Municipal Airport 14:50
  • MDWChicago Midway Airport 17:05
  • 2h 15m
  • Direct
  • Southwest Airlines (WN 2317)Boeing 737 Max 8 Passenger
  • Southwest Airlines (WN 2317)
    • -
    • -
    • -
    • -
    • -
    • -
    • S
  • Boeing 737 Max 8 Passenger
  • 16:15 PNS
    18:25 MDW
    2Hrs, 10m Direct
  • PNSPensacola Municipal Airport 16:15 - MDW 18:25 2h 10m Direct
  • PNSPensacola Municipal Airport 16:15
  • MDWChicago Midway Airport 18:25
  • 2h 10m
  • Direct
  • Southwest Airlines (WN 800)Boeing 737 700
  • Southwest Airlines (WN 800)
    • -
    • -
    • -
    • -
    • -
    • S
    • -
  • Boeing 737 700
  • 05:30 PNS
    10:41 ORD
    5Hrs, 11m 1 Stop (CLT)
  • PNSPensacola Municipal Airport 05:30 - ORD 10:41 5h 11m 1 Stop (CLT) Charlotte
  • PNSPensacola Municipal Airport 05:30
    CLTCharlotte Airport 09:20
  • CLTCharlotte Airport 08:13
    ORDChicago O'Hare International Airport 10:41
  • 5h 11m (1h 07m)
  • 1 Stop CLT · Charlotte 1h 07m
  • American Airlines (AA 2256)Airbus
    American Airlines (AA 1038)Boeing 737 Max 8 Passenger
  • American Airlines (AA 2256)
    • M
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    • T
    • F
    • -
    • S
  • 05:30 PNS
    10:41 ORD
    5Hrs, 11m 1 Stop (CLT)
  • PNSPensacola Municipal Airport 05:30 - ORD 10:41 5h 11m 1 Stop (CLT) Charlotte
  • PNSPensacola Municipal Airport 05:30
    CLTCharlotte Airport 09:20
  • CLTCharlotte Airport 08:13
    ORDChicago O'Hare International Airport 10:41
  • 5h 11m (1h 07m)
  • 1 Stop CLT · Charlotte 1h 07m
  • American Airlines (AA 2256)Airbus
    American Airlines (AA 1038)Boeing 737 Max 8 Passenger
  • American Airlines (AA 2256)
    • -
    • -
    • -
    • -
    • -
    • S
    • -
  • 10:49 CVG
    08:13 CLT
    5Hrs, 45m 1 Stop (ORD)
  • CVGCincinnati Northern Kentucky Intl Airport 10:49 - CLT 08:13 5h 45m 1 Stop (ORD) Chicago
  • CVGCincinnati Northern Kentucky Intl Airport 10:49
    PNSPensacola Municipal Airport 05:30
  • ORDChicago O'Hare International Airport 11:15
    CLTCharlotte Airport 08:13
  • 5h 45m (1h 15m)
  • 1 Stop ORD · Chicago 1h 15m
  • American Airlines (AA 4004)Embraer 170
    American Airlines (AA 2256)Airbus
  • American Airlines (AA 4004)
    • -
    • -
    • -
    • -
    • -
    • S
    • -
  • 10:49 CVG
    08:13 CLT
    5Hrs, 45m 1 Stop (ORD)
  • CVGCincinnati Northern Kentucky Intl Airport 10:49 - CLT 08:13 5h 45m 1 Stop (ORD) Chicago
  • CVGCincinnati Northern Kentucky Intl Airport 10:49
    PNSPensacola Municipal Airport 05:30
  • ORDChicago O'Hare International Airport 11:15
    CLTCharlotte Airport 08:13
  • 5h 45m (1h 15m)
  • 1 Stop ORD · Chicago 1h 15m
  • American Airlines (AA 4004)Embraer 170
    American Airlines (AA 2256)Airbus
  • American Airlines (AA 4004)
    • M
    • T
    • W
    • T
    • F
    • -
    • S
  • 05:30 PNS
    12:18 ORD
    6Hrs, 48m 1 Stop (CLT)
  • PNSPensacola Municipal Airport 05:30 - ORD 12:18 6h 48m 1 Stop (CLT) Charlotte
  • PNSPensacola Municipal Airport 05:30
    CLTCharlotte Airport 11:04
  • CLTCharlotte Airport 08:13
    ORDChicago O'Hare International Airport 12:18
  • 6h 48m (2h 51m)
  • 1 Stop CLT · Charlotte 2h 51m
  • American Airlines (AA 2256)Airbus
    American Airlines (AA 2279)Boeing 737 800
  • American Airlines (AA 2256)
    • M
    • T
    • W
    • T
    • F
    • -
    • S
  • 05:30 PNS
    12:18 ORD
    6Hrs, 48m 1 Stop (CLT)
  • PNSPensacola Municipal Airport 05:30 - ORD 12:18 6h 48m 1 Stop (CLT) Charlotte
  • PNSPensacola Municipal Airport 05:30
    CLTCharlotte Airport 11:04
  • CLTCharlotte Airport 08:13
    ORDChicago O'Hare International Airport 12:18
  • 6h 48m (2h 51m)
  • 1 Stop CLT · Charlotte 2h 51m
  • American Airlines (AA 2256)Airbus
    American Airlines (AA 2279)Boeing 737 800
  • American Airlines (AA 2256)
    • -
    • -
    • -
    • -
    • -
    • S
    • -
  • 06:00 PNS
    10:35 MDW
    4Hrs, 35m 1 Stop (BNA)
  • PNSPensacola Municipal Airport 06:00 - MDW 10:35 4h 35m 1 Stop (BNA) Nashville
  • PNSPensacola Municipal Airport 06:00
    BNANashville Airport 09:00
  • BNANashville Airport 07:30
    MDWChicago Midway Airport 10:35
  • 4h 35m (1h 30m)
  • 1 Stop BNA · Nashville 1h 30m
  • Southwest Airlines (WN 2563)Boeing 737 800
    Southwest Airlines (WN 3678)Boeing 737 700
  • Southwest Airlines (WN 2563)
    • M
    • -
    • -
    • T
    • F
    • -
    • -
  • 06:00 PNS
    12:30 MDW
    6Hrs, 30m 1 Stop (BNA)
  • PNSPensacola Municipal Airport 06:00 - MDW 12:30 6h 30m 1 Stop (BNA) Nashville
  • PNSPensacola Municipal Airport 06:00
    BNANashville Airport 10:50
  • BNANashville Airport 07:30
    MDWChicago Midway Airport 12:30
  • 6h 30m (3h 20m)
  • 1 Stop BNA · Nashville 3h 20m
  • Southwest Airlines (WN 2563)Boeing 737 800
    Southwest Airlines (WN 2210)Boeing 737 800
  • Southwest Airlines (WN 2563)
    • M
    • -
    • -
    • T
    • F
    • -
    • -
  • 06:00 PNS
    12:45 ORD
    6Hrs, 45m 1 Stop (BNA)
  • PNSPensacola Municipal Airport 06:00 - ORD 12:45 6h 45m 1 Stop (BNA) Nashville
  • PNSPensacola Municipal Airport 06:00
    BNANashville Airport 10:50
  • BNANashville Airport 07:30
    ORDChicago O'Hare International Airport 12:45
  • 6h 45m (3h 20m)
  • 1 Stop BNA · Nashville 3h 20m
  • Southwest Airlines (WN 2563)Boeing 737 800
    Southwest Airlines (WN 4520)Boeing 737 800
  • Southwest Airlines (WN 2563)
    • M
    • -
    • -
    • T
    • F
    • -
    • -
  • 06:15 PNS
    12:12 ORD
    5Hrs, 57m 1 Stop (PHL)
  • PNSPensacola Municipal Airport 06:15 - ORD 12:12 5h 57m 1 Stop (PHL) Philadelphia
  • PNSPensacola Municipal Airport 06:15
    PHLPhiladelphia International Airport 10:41
  • PHLPhiladelphia International Airport 09:49
    ORDChicago O'Hare International Airport 12:12
  • 5h 57m (52m)
  • 1 Stop PHL · Philadelphia 52m
  • American Airlines (AA 5325)Canadair Regional
    American Airlines (AA 3313)Boeing 737 800
  • American Airlines (AA 5325)
    • -
    • -
    • -
    • -
    • -
    • S
    • -
  • 06:15 PNS
    12:41 ORD
    6Hrs, 26m 1 Stop (PHL)
  • PNSPensacola Municipal Airport 06:15 - ORD 12:41 6h 26m 1 Stop (PHL) Philadelphia
  • PNSPensacola Municipal Airport 06:15
    PHLPhiladelphia International Airport 11:04
  • PHLPhiladelphia International Airport 09:49
    ORDChicago O'Hare International Airport 12:41
  • 6h 26m (1h 15m)
  • 1 Stop PHL · Philadelphia 1h 15m
  • American Airlines (AA 5325)Canadair Regional
    American Airlines (AA 3313)Boeing 737 800
  • American Airlines (AA 5325)
    • M
    • T
    • W
    • T
    • F
    • -
    • S
  • 06:35 PNS
    11:25 MDW
    4Hrs, 50m 1 Stop (BNA)
  • PNSPensacola Municipal Airport 06:35 - MDW 11:25 4h 50m 1 Stop (BNA) Nashville
  • PNSPensacola Municipal Airport 06:35
    BNANashville Airport 09:50
  • BNANashville Airport 08:05
    MDWChicago Midway Airport 11:25
  • 4h 50m (1h 45m)
  • 1 Stop BNA · Nashville 1h 45m
  • Southwest Airlines (WN 2563)Boeing 737 800
    Southwest Airlines (WN 2210)Boeing 737 Max 8 Passenger
  • Southwest Airlines (WN 2563)
    • -
    • -
    • -
    • -
    • -
    • S
    • -
  • 07:00 PNS
    13:22 ORD
    6Hrs, 22m 1 Stop (DFW)
  • PNSPensacola Municipal Airport 07:00 - ORD 13:22 6h 22m 1 Stop (DFW) Dallas
  • PNSPensacola Municipal Airport 07:00
    DFWDallas/Fort Worth Intl Airport 10:55
  • DFWDallas/Fort Worth Intl Airport 09:10
    ORDChicago O'Hare International Airport 13:22
  • 6h 22m (1h 45m)
  • 1 Stop DFW · Dallas 1h 45m
  • American Airlines (AA 2052)Boeing 737 800
    American Airlines (AA 2754)Boeing 737 Max 8 Passenger
  • American Airlines (AA 2052)
    • M
    • T
    • W
    • T
    • F
    • S
    • S
  • 07:20 PNS
    14:22 ORD
    7Hrs, 02m 1 Stop (TPA)
  • PNSPensacola Municipal Airport 07:20 - ORD 14:22 7h 02m 1 Stop (TPA) Tampa
  • PNSPensacola Municipal Airport 07:20
    TPATampa International Airport 12:20
  • TPATampa International Airport 10:00
    ORDChicago O'Hare International Airport 14:22
  • 7h 02m (2h 20m)
  • 1 Stop TPA · Tampa 2h 20m
  • Silver Airways (3M 82)Aerospatiale Alenia Atr 42
    United Airlines (UA 2184)Airbus A321 Neo
  • Silver Airways (3M 82)
    • M
    • T
    • W
    • T
    • F
    • S
    • S
  • 07:25 PNS
    12:18 ORD
    4Hrs, 53m 1 Stop (CLT)
  • PNSPensacola Municipal Airport 07:25 - ORD 12:18 4h 53m 1 Stop (CLT) Charlotte
  • PNSPensacola Municipal Airport 07:25
    CLTCharlotte Airport 11:04
  • CLTCharlotte Airport 10:15
    ORDChicago O'Hare International Airport 12:18
  • 4h 53m (49m)
  • 1 Stop CLT · Charlotte 49m
  • American Airlines (AA 5353)Canadair Regional
    American Airlines (AA 2279)Boeing 737 800
  • American Airlines (AA 5353)
    • M
    • T
    • W
    • T
    • F
    • S
    • S
  • 07:25 PNS
    14:06 ORD
    6Hrs, 41m 1 Stop (CLT)
  • PNSPensacola Municipal Airport 07:25 - ORD 14:06 6h 41m 1 Stop (CLT) Charlotte
  • PNSPensacola Municipal Airport 07:25
    CLTCharlotte Airport 13:00
  • CLTCharlotte Airport 10:15
    ORDChicago O'Hare International Airport 14:06
  • 6h 41m (2h 45m)
  • 1 Stop CLT · Charlotte 2h 45m
  • American Airlines (AA 5353)Canadair Regional
    American Airlines (AA 1052)Airbus
  • American Airlines (AA 5353)
    • M
    • T
    • W
    • T
    • F
    • S
    • S
  • 07:30 PNS
    13:30 MDW
    6Hrs, 00m 1 Stop (DAL)
  • PNSPensacola Municipal Airport 07:30 - MDW 13:30 6h 1 Stop (DAL) Dallas
  • PNSPensacola Municipal Airport 07:30
    DALDallas/Fort Worth Love Field Airport 11:15
  • DALDallas/Fort Worth Love Field Airport 09:25
    MDWChicago Midway Airport 13:30
  • 6h (1h 50m)
  • 1 Stop DAL · Dallas 1h 50m
  • Southwest Airlines (WN 2318)Boeing 737 800
    Southwest Airlines (WN 1194)Boeing 737 Max 8 Passenger
  • Southwest Airlines (WN 2318)
    • M
    • -
    • -
    • T
    • F
    • -
    • -
  • 07:45 PNS
    12:45 ORD
    5Hrs, 00m 1 Stop (BNA)
  • PNSPensacola Municipal Airport 07:45 - ORD 12:45 5h 1 Stop (BNA) Nashville
  • PNSPensacola Municipal Airport 07:45
    BNANashville Airport 10:50
  • BNANashville Airport 09:15
    ORDChicago O'Hare International Airport 12:45
  • 5h (1h 35m)
  • 1 Stop BNA · Nashville 1h 35m
  • Southwest Airlines (WN 2563)Boeing 737 800
    Southwest Airlines (WN 4520)Boeing 737 800
  • Southwest Airlines (WN 2563)
    • -
    • -
    • -
    • -
    • -
    • -
    • S
  • 07:45 PNS
    14:45 MDW
    7Hrs, 00m 1 Stop (BNA)
  • PNSPensacola Municipal Airport 07:45 - MDW 14:45 7h 1 Stop (BNA) Nashville
  • PNSPensacola Municipal Airport 07:45
    BNANashville Airport 13:10
  • BNANashville Airport 09:15
    MDWChicago Midway Airport 14:45
  • 7h (3h 55m)
  • 1 Stop BNA · Nashville 3h 55m
  • Southwest Airlines (WN 2563)Boeing 737 800
    Southwest Airlines (WN 1989)Boeing 737 700
  • Southwest Airlines (WN 2563)
    • -
    • -
    • -
    • -
    • -
    • -
    • S
  • 08:00 PNS
    12:45 ORD
    4Hrs, 45m 1 Stop (BNA)
  • PNSPensacola Municipal Airport 08:00 - ORD 12:45 4h 45m 1 Stop (BNA) Nashville
  • PNSPensacola Municipal Airport 08:00
    BNANashville Airport 10:50
  • BNANashville Airport 09:30
    ORDChicago O'Hare International Airport 12:45
  • 4h 45m (1h 20m)
  • 1 Stop BNA · Nashville 1h 20m
  • Southwest Airlines (WN 2189)Boeing 737 800
    Southwest Airlines (WN 4212)Boeing 737 700
  • Southwest Airlines (WN 2189)
    • -
    • T
    • W
    • -
    • -
    • -
    • -
  • 08:05 PNS
    13:55 MDW
    5Hrs, 50m 1 Stop (DAL)
  • PNSPensacola Municipal Airport 08:05 - MDW 13:55 5h 50m 1 Stop (DAL) Dallas
  • PNSPensacola Municipal Airport 08:05
    DALDallas/Fort Worth Love Field Airport 11:40
  • DALDallas/Fort Worth Love Field Airport 10:00
    MDWChicago Midway Airport 13:55
  • 5h 50m (1h 40m)
  • 1 Stop DAL · Dallas 1h 40m
  • Southwest Airlines (WN 2318)Boeing 737 800
    Southwest Airlines (WN 1194)Boeing 737 800
  • Southwest Airlines (WN 2318)
    • -
    • -
    • -
    • -
    • -
    • S
    • -
  • 09:05 PNS
    14:55 ORD
    5Hrs, 50m 1 Stop (IAH)
  • PNSPensacola Municipal Airport 09:05 - ORD 14:55 5h 50m 1 Stop (IAH) Houston
  • PNSPensacola Municipal Airport 09:05
    IAHHouston George Bush Intercontinental Airport 12:00
  • IAHHouston George Bush Intercontinental Airport 10:56
    ORDChicago O'Hare International Airport 14:55
  • 5h 50m (1h 04m)
  • 1 Stop IAH · Houston 1h 04m
  • United Airlines (UA 2049)Boeing 737 900
    United Airlines (UA 2417)Airbus A321 Neo
  • United Airlines (UA 2049)
    • -
    • -
    • -
    • -
    • -
    • S
    • -
  • 09:05 PNS
    14:55 ORD
    5Hrs, 50m 1 Stop (IAH)
  • PNSPensacola Municipal Airport 09:05 - ORD 14:55 5h 50m 1 Stop (IAH) Houston
  • PNSPensacola Municipal Airport 09:05
    IAHHouston George Bush Intercontinental Airport 12:00
  • IAHHouston George Bush Intercontinental Airport 10:56
    ORDChicago O'Hare International Airport 14:55
  • 5h 50m (1h 04m)
  • 1 Stop IAH · Houston 1h 04m
  • United Airlines (UA 2049)Boeing 737 900
    United Airlines (UA 2417)Boeing 737 900
  • United Airlines (UA 2049)
    • M
    • T
    • W
    • T
    • F
    • -
    • S
  • 09:07 PNS
    16:05 ORD
    6Hrs, 58m 1 Stop (MIA)
  • PNSPensacola Municipal Airport 09:07 - ORD 16:05 6h 58m 1 Stop (MIA) Miami
  • PNSPensacola Municipal Airport 09:07
    MIAMiami International Airport 13:40
  • MIAMiami International Airport 11:49
    ORDChicago O'Hare International Airport 16:05
  • 6h 58m (1h 51m)
  • 1 Stop MIA · Miami 1h 51m
  • American Airlines (AA 3906)Embraer Emb 175
    American Airlines (AA 3067)Boeing 737 Max 8 Passenger
  • American Airlines (AA 3906)
    • M
    • T
    • W
    • T
    • F
    • S
    • S
  • 09:55 PNS
    15:20 MDW
    5Hrs, 25m 1 Stop (HOU)
  • PNSPensacola Municipal Airport 09:55 - MDW 15:20 5h 25m 1 Stop (HOU) Houston
  • PNSPensacola Municipal Airport 09:55
    HOUHouston Hobby Airport 12:55
  • HOUHouston Hobby Airport 11:40
    MDWChicago Midway Airport 15:20
  • 5h 25m (1h 15m)
  • 1 Stop HOU · Houston 1h 15m
  • Southwest Airlines (WN 1243)Boeing 737 700
    Southwest Airlines (WN 6553)Boeing 737 Max 8 Passenger
  • Southwest Airlines (WN 1243)
    • M
    • -
    • -
    • T
    • F
    • -
    • -
  • 10:23 PNS
    16:13 ORD
    5Hrs, 50m 1 Stop (DCA)
  • PNSPensacola Municipal Airport 10:23 - ORD 16:13 5h 50m 1 Stop (DCA) Washington
  • PNSPensacola Municipal Airport 10:23
    DCAWashington Ronald Reagan National Airport 14:54
  • DCAWashington Ronald Reagan National Airport 13:42
    ORDChicago O'Hare International Airport 16:13
  • 5h 50m (1h 12m)
  • 1 Stop DCA · Washington 1h 12m
  • American Airlines (AA 5216)Canadair Regional
    American Airlines (AA 1187)Boeing 737 800
  • American Airlines (AA 5216)
    • -
    • -
    • -
    • -
    • -
    • -
    • S
  • 10:32 PNS
    16:13 ORD
    5Hrs, 41m 1 Stop (DCA)
  • PNSPensacola Municipal Airport 10:32 - ORD 16:13 5h 41m 1 Stop (DCA) Washington
  • PNSPensacola Municipal Airport 10:32
    DCAWashington Ronald Reagan National Airport 14:54
  • DCAWashington Ronald Reagan National Airport 13:51
    ORDChicago O'Hare International Airport 16:13
  • 5h 41m (1h 03m)
  • 1 Stop DCA · Washington 1h 03m
  • American Airlines (AA 5216)Canadair Regional
    American Airlines (AA 1187)Boeing 737 800
  • American Airlines (AA 5216)
    • M
    • T
    • W
    • T
    • F
    • S
    • -
  • 10:35 PNS
    17:26 ORD
    6Hrs, 51m 1 Stop (CLT)
  • PNSPensacola Municipal Airport 10:35 - ORD 17:26 6h 51m 1 Stop (CLT) Charlotte
  • PNSPensacola Municipal Airport 10:35
    CLTCharlotte Airport 16:15
  • CLTCharlotte Airport 13:25
    ORDChicago O'Hare International Airport 17:26
  • 6h 51m (2h 50m)
  • 1 Stop CLT · Charlotte 2h 50m
  • American Airlines (AA 5143)Canadair Regional
    American Airlines (AA 536)Boeing 737 800
  • American Airlines (AA 5143)
    • -
    • -
    • -
    • -
    • -
    • S
    • -
  • 10:35 PNS
    17:29 ORD
    6Hrs, 54m 1 Stop (PHL)
  • PNSPensacola Municipal Airport 10:35 - ORD 17:29 6h 54m 1 Stop (PHL) Philadelphia
  • PNSPensacola Municipal Airport 10:35
    PHLPhiladelphia International Airport 16:00
  • PHLPhiladelphia International Airport 14:09
    ORDChicago O'Hare International Airport 17:29
  • 6h 54m (1h 51m)
  • 1 Stop PHL · Philadelphia 1h 51m
  • American Airlines (AA 5370)Canadair Regional
    American Airlines (AA 3063)Airbus
  • American Airlines (AA 5370)
    • -
    • -
    • -
    • -
    • -
    • -
    • S
  • 10:40 PNS
    17:29 ORD
    6Hrs, 49m 1 Stop (PHL)
  • PNSPensacola Municipal Airport 10:40 - ORD 17:29 6h 49m 1 Stop (PHL) Philadelphia
  • PNSPensacola Municipal Airport 10:40
    PHLPhiladelphia International Airport 16:00
  • PHLPhiladelphia International Airport 14:14
    ORDChicago O'Hare International Airport 17:29
  • 6h 49m (1h 46m)
  • 1 Stop PHL · Philadelphia 1h 46m
  • American Airlines (AA 5370)Canadair Regional
    American Airlines (AA 3063)Airbus
  • American Airlines (AA 5370)
    • M
    • T
    • W
    • T
    • F
    • -
    • -
  • 11:15 PNS
    17:20 MDW
    6Hrs, 05m 1 Stop (HOU)
  • PNSPensacola Municipal Airport 11:15 - MDW 17:20 6h 05m 1 Stop (HOU) Houston
  • PNSPensacola Municipal Airport 11:15
    HOUHouston Hobby Airport 14:50
  • HOUHouston Hobby Airport 13:00
    MDWChicago Midway Airport 17:20
  • 6h 05m (1h 50m)
  • 1 Stop HOU · Houston 1h 50m
  • Southwest Airlines (WN 2736)Boeing 737 700
    Southwest Airlines (WN 1592)Boeing 737 Max 8 Passenger
  • Southwest Airlines (WN 2736)
    • -
    • -
    • -
    • -
    • -
    • -
    • S
  • 11:15 PNS
    17:29 ORD
    6Hrs, 14m 1 Stop (PHL)
  • PNSPensacola Municipal Airport 11:15 - ORD 17:29 6h 14m 1 Stop (PHL) Philadelphia
  • PNSPensacola Municipal Airport 11:15
    PHLPhiladelphia International Airport 16:00
  • PHLPhiladelphia International Airport 14:49
    ORDChicago O'Hare International Airport 17:29
  • 6h 14m (1h 11m)
  • 1 Stop PHL · Philadelphia 1h 11m
  • American Airlines (AA 5370)Canadair Regional
    American Airlines (AA 3063)Airbus
  • American Airlines (AA 5370)
    • -
    • -
    • -
    • -
    • -
    • S
    • -
  • 11:18 PNS
    17:59 ORD
    6Hrs, 41m 1 Stop (CLT)
  • PNSPensacola Municipal Airport 11:18 - ORD 17:59 6h 41m 1 Stop (CLT) Charlotte
  • PNSPensacola Municipal Airport 11:18
    CLTCharlotte Airport 16:43
  • CLTCharlotte Airport 14:00
    ORDChicago O'Hare International Airport 17:59
  • 6h 41m (2h 43m)
  • 1 Stop CLT · Charlotte 2h 43m
  • American Airlines (AA 1932)Airbus
    American Airlines (AA 536)Boeing 737 800
  • American Airlines (AA 1932)
    • M
    • T
    • W
    • T
    • F
    • -
    • S
  • 11:30 PNS
    17:05 MDW
    5Hrs, 35m 1 Stop (MCI)
  • PNSPensacola Municipal Airport 11:30 - MDW 17:05 5h 35m 1 Stop (MCI) Kansas City
  • PNSPensacola Municipal Airport 11:30
    MCIKansas City International Airport 15:40
  • MCIKansas City International Airport 13:40
    MDWChicago Midway Airport 17:05
  • 5h 35m (2h)
  • 1 Stop MCI · Kansas City 2h
  • Southwest Airlines (WN 3451)Boeing 737 800
    Southwest Airlines (WN 3672)Boeing 737 800
  • Southwest Airlines (WN 3451)
    • -
    • T
    • W
    • -
    • -
    • -
    • -
  • 11:32 PNS
    17:12 ORD
    5Hrs, 40m 1 Stop (DFW)
  • PNSPensacola Municipal Airport 11:32 - ORD 17:12 5h 40m 1 Stop (DFW) Dallas
  • PNSPensacola Municipal Airport 11:32
    DFWDallas/Fort Worth Intl Airport 14:47
  • DFWDallas/Fort Worth Intl Airport 13:39
    ORDChicago O'Hare International Airport 17:12
  • 5h 40m (1h 08m)
  • 1 Stop DFW · Dallas 1h 08m
  • American Airlines (AA 1997)Airbus
    American Airlines (AA 1559)Airbus
  • American Airlines (AA 1997)
    • M
    • T
    • W
    • T
    • F
    • S
    • S
  • 11:32 PNS
    18:24 ORD
    6Hrs, 52m 1 Stop (DFW)
  • PNSPensacola Municipal Airport 11:32 - ORD 18:24 6h 52m 1 Stop (DFW) Dallas
  • PNSPensacola Municipal Airport 11:32
    DFWDallas/Fort Worth Intl Airport 15:55
  • DFWDallas/Fort Worth Intl Airport 13:39
    ORDChicago O'Hare International Airport 18:24
  • 6h 52m (2h 16m)
  • 1 Stop DFW · Dallas 2h 16m
  • American Airlines (AA 1997)Airbus
    American Airlines (AA 2559)Boeing 787 8
  • American Airlines (AA 1997)
    • M
    • T
    • W
    • T
    • F
    • S
    • S
  • 12:32 PNS
    17:26 ORD
    4Hrs, 54m 1 Stop (CLT)
  • PNSPensacola Municipal Airport 12:32 - ORD 17:26 4h 54m 1 Stop (CLT) Charlotte
  • PNSPensacola Municipal Airport 12:32
    CLTCharlotte Airport 16:15
  • CLTCharlotte Airport 15:14
    ORDChicago O'Hare International Airport 17:26
  • 4h 54m (1h 01m)
  • 1 Stop CLT · Charlotte 1h 01m
  • American Airlines (AA 2325)Airbus
    American Airlines (AA 536)Boeing 737 800
  • American Airlines (AA 2325)
    • -
    • -
    • -
    • -
    • -
    • S
    • -
  • 12:32 PNS
    19:35 ORD
    7Hrs, 03m 1 Stop (CLT)
  • PNSPensacola Municipal Airport 12:32 - ORD 19:35 7h 03m 1 Stop (CLT) Charlotte
  • PNSPensacola Municipal Airport 12:32
    CLTCharlotte Airport 18:22
  • CLTCharlotte Airport 15:14
    ORDChicago O'Hare International Airport 19:35
  • 7h 03m (3h 08m)
  • 1 Stop CLT · Charlotte 3h 08m
  • American Airlines (AA 2325)Airbus
    American Airlines (AA 2488)Airbus
  • American Airlines (AA 2325)
    • -
    • -
    • -
    • -
    • -
    • S
    • -
  • 12:40 PNS
    17:59 ORD
    5Hrs, 19m 1 Stop (CLT)
  • PNSPensacola Municipal Airport 12:40 - ORD 17:59 5h 19m 1 Stop (CLT) Charlotte
  • PNSPensacola Municipal Airport 12:40
    CLTCharlotte Airport 16:43
  • CLTCharlotte Airport 15:24
    ORDChicago O'Hare International Airport 17:59
  • 5h 19m (1h 19m)
  • 1 Stop CLT · Charlotte 1h 19m
  • American Airlines (AA 2325)Airbus
    American Airlines (AA 536)Boeing 737 800
  • American Airlines (AA 2325)
    • M
    • T
    • W
    • T
    • F
    • -
    • S
  • 12:40 PNS
    19:35 ORD
    6Hrs, 55m 1 Stop (CLT)
  • PNSPensacola Municipal Airport 12:40 - ORD 19:35 6h 55m 1 Stop (CLT) Charlotte
  • PNSPensacola Municipal Airport 12:40
    CLTCharlotte Airport 18:22
  • CLTCharlotte Airport 15:24
    ORDChicago O'Hare International Airport 19:35
  • 6h 55m (2h 58m)
  • 1 Stop CLT · Charlotte 2h 58m
  • American Airlines (AA 2325)Airbus
    American Airlines (AA 2488)Airbus
  • American Airlines (AA 2325)
    • M
    • T
    • W
    • T
    • F
    • -
    • S
  • 12:50 PNS
    18:55 MDW
    6Hrs, 05m 1 Stop (BNA)
  • PNSPensacola Municipal Airport 12:50 - MDW 18:55 6h 05m 1 Stop (BNA) Nashville
  • PNSPensacola Municipal Airport 12:50
    BNANashville Airport 17:15
  • BNANashville Airport 14:20
    MDWChicago Midway Airport 18:55
  • 6h 05m (2h 55m)
  • 1 Stop BNA · Nashville 2h 55m
  • Southwest Airlines (WN 2563)Boeing 737 Max 8 Passenger
    Southwest Airlines (WN 3286)Boeing 737 800
  • Southwest Airlines (WN 2563)
    • -
    • T
    • W
    • -
    • -
    • -
    • -
  • 13:15 PNS
    18:05 MDW
    4Hrs, 50m 1 Stop (BNA)
  • PNSPensacola Municipal Airport 13:15 - MDW 18:05 4h 50m 1 Stop (BNA) Nashville
  • PNSPensacola Municipal Airport 13:15
    BNANashville Airport 16:30
  • BNANashville Airport 14:45
    MDWChicago Midway Airport 18:05
  • 4h 50m (1h 45m)
  • 1 Stop BNA · Nashville 1h 45m
  • Southwest Airlines (WN 2189)Boeing 737 700
    Southwest Airlines (WN 3286)Boeing 737 800
  • Southwest Airlines (WN 2189)
    • M
    • -
    • -
    • T
    • F
    • -
    • -
  • 13:35 PNS
    20:35 MDW
    7Hrs, 00m 1 Stop (STL)
  • PNSPensacola Municipal Airport 13:35 - MDW 20:35 7h 1 Stop (STL) Saint Louis
  • PNSPensacola Municipal Airport 13:35
    STLSt Louis Lambert Intl Airport 19:30
  • STLSt Louis Lambert Intl Airport 15:25
    MDWChicago Midway Airport 20:35
  • 7h (4h 05m)
  • 1 Stop STL · Saint Louis 4h 05m
  • Southwest Airlines (WN 4015)Boeing 737 700
    Southwest Airlines (WN 4422)Boeing 737 800
  • Southwest Airlines (WN 4015)
    • -
    • -
    • -
    • -
    • -
    • -
    • S
  • 14:15 PNS
    19:40 MDW
    5Hrs, 25m 1 Stop (MCI)
  • PNSPensacola Municipal Airport 14:15 - MDW 19:40 5h 25m 1 Stop (MCI) Kansas City
  • PNSPensacola Municipal Airport 14:15
    MCIKansas City International Airport 18:15
  • MCIKansas City International Airport 16:25
    MDWChicago Midway Airport 19:40
  • 5h 25m (1h 50m)
  • 1 Stop MCI · Kansas City 1h 50m
  • Southwest Airlines (WN 4022)Boeing 737 700
    Southwest Airlines (WN 4635)Boeing 737 Max 8 Passenger
  • Southwest Airlines (WN 4022)
    • -
    • -
    • -
    • -
    • -
    • S
    • -
  • 14:35 PNS
    19:35 ORD
    5Hrs, 00m 1 Stop (CLT)
  • PNSPensacola Municipal Airport 14:35 - ORD 19:35 5h 1 Stop (CLT) Charlotte
  • PNSPensacola Municipal Airport 14:35
    CLTCharlotte Airport 18:22
  • CLTCharlotte Airport 17:25
    ORDChicago O'Hare International Airport 19:35
  • 5h (57m)
  • 1 Stop CLT · Charlotte 57m
  • American Airlines (AA 5380)Canadair Regional
    American Airlines (AA 2488)Airbus
  • American Airlines (AA 5380)
    • M
    • T
    • W
    • T
    • F
    • S
    • S
  • 15:05 PNS
    19:50 MDW
    4Hrs, 45m 1 Stop (DAL)
  • PNSPensacola Municipal Airport 15:05 - MDW 19:50 4h 45m 1 Stop (DAL) Dallas
  • PNSPensacola Municipal Airport 15:05
    DALDallas/Fort Worth Love Field Airport 17:40
  • DALDallas/Fort Worth Love Field Airport 17:00
    MDWChicago Midway Airport 19:50
  • 4h 45m (40m)
  • 1 Stop DAL · Dallas 40m
  • Southwest Airlines (WN 2318)Boeing 737 700
    Southwest Airlines (WN 2307)Boeing 737 700
  • Southwest Airlines (WN 2318)
    • -
    • T
    • W
    • -
    • -
    • -
    • -
  • 15:05 PNS
    21:30 ORD
    6Hrs, 25m 1 Stop (DAL)
  • PNSPensacola Municipal Airport 15:05 - ORD 21:30 6h 25m 1 Stop (DAL) Dallas
  • PNSPensacola Municipal Airport 15:05
    DALDallas/Fort Worth Love Field Airport 19:10
  • DALDallas/Fort Worth Love Field Airport 17:00
    ORDChicago O'Hare International Airport 21:30
  • 6h 25m (2h 10m)
  • 1 Stop DAL · Dallas 2h 10m
  • Southwest Airlines (WN 2318)Boeing 737 700
    Southwest Airlines (WN 3677)Boeing 737 700
  • Southwest Airlines (WN 2318)
    • -
    • T
    • W
    • -
    • -
    • -
    • -
  • 15:05 PNS
    21:55 MDW
    6Hrs, 50m 1 Stop (DAL)
  • PNSPensacola Municipal Airport 15:05 - MDW 21:55 6h 50m 1 Stop (DAL) Dallas
  • PNSPensacola Municipal Airport 15:05
    DALDallas/Fort Worth Love Field Airport 19:45
  • DALDallas/Fort Worth Love Field Airport 17:00
    MDWChicago Midway Airport 21:55
  • 6h 50m (2h 45m)
  • 1 Stop DAL · Dallas 2h 45m
  • Southwest Airlines (WN 2318)Boeing 737 700
    Southwest Airlines (WN 4232)Boeing 737 800
  • Southwest Airlines (WN 2318)
    • -
    • T
    • W
    • -
    • -
    • -
    • -
  • 15:11 PNS
    21:30 ORD
    6Hrs, 19m 1 Stop (IAH)
  • PNSPensacola Municipal Airport 15:11 - ORD 21:30 6h 19m 1 Stop (IAH) Houston
  • PNSPensacola Municipal Airport 15:11
    IAHHouston George Bush Intercontinental Airport 18:42
  • IAHHouston George Bush Intercontinental Airport 17:10
    ORDChicago O'Hare International Airport 21:30
  • 6h 19m (1h 32m)
  • 1 Stop IAH · Houston 1h 32m
  • United Airlines (UA 4956)Embraer
    United Airlines (UA 520)Boeing 757 300 Series
  • United Airlines (UA 4956)
    • M
    • -
    • W
    • T
    • F
    • -
    • -
  • 15:11 PNS
    21:32 ORD
    6Hrs, 21m 1 Stop (IAH)
  • PNSPensacola Municipal Airport 15:11 - ORD 21:32 6h 21m 1 Stop (IAH) Houston
  • PNSPensacola Municipal Airport 15:11
    IAHHouston George Bush Intercontinental Airport 18:42
  • IAHHouston George Bush Intercontinental Airport 17:10
    ORDChicago O'Hare International Airport 21:32
  • 6h 21m (1h 32m)
  • 1 Stop IAH · Houston 1h 32m
  • United Airlines (UA 4956)Embraer
    United Airlines (UA 520)Boeing 737 900
  • United Airlines (UA 4956)
    • -
    • -
    • -
    • -
    • -
    • -
    • S
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What’s the fastest flight time from Pensacola to Chicago?

The fastest flight time for direct flights from Pensacola to Chicago is 2 hours 10 minutes. Check latest flight schedules & prices on Wego.

How far is Chicago from Pensacola?

The flight distance between Pensacola and Chicago is 1274km. Check all available flights on Wego.

When is the earliest and latest flight of the day?

The earliest flight of the day departs at 05:30. The last flight of the day departs at 05:30. See the full list of flight times on Wego.

How many airlines offer direct flights from Pensacola to Chicago?

There are 3 airlines that offer direct flights from Pensacola to Chicago. Find out the list of airlines on Wego.