Fare Guide

Estimated lowest fares found within 7 days

Cheapest Airline Spirit Airlines

The cheapest airline(s) flying from Pensacola to Chicago is Spirit Airlines.

  • Spirit Airlines Spirit Airlines
  • American Airlines American Airlines
  • United Airlines United Airlines
  • Southwest Airlines Southwest Airlines
Cheapest Month December

Travel Period: December 2024 - November 2025

The cheapest month(s) to fly from Pensacola to Chicago is December.

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

The cheapest day(s) of the week to fly from Pensacola to Chicago is Friday.

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

Flight Schedules

Last Updated: Sat, 2 Nov, 2024

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      • Availability
        • M
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      • 14:20 PNS
        17:02 ORD
        2Hrs, 42m Direct
      • PNSPensacola Municipal Airport 14:20 - ORD 17:02 2h 42m Direct
      • PNSPensacola Municipal Airport 14:20
      • ORDChicago O'Hare International Airport 17:02
      • 2h 42m
      • Direct
      • United Airlines (UA 5264)Crj Canadair Regional
      • United Airlines (UA 5264)
        • -
        • -
        • -
        • -
        • F
        • -
        • -
      • Crj Canadair Regional
      • 14:20 PNS
        16:58 ORD
        2Hrs, 38m Direct
      • PNSPensacola Municipal Airport 14:20 - ORD 16:58 2h 38m Direct
      • PNSPensacola Municipal Airport 14:20
      • ORDChicago O'Hare International Airport 16:58
      • 2h 38m
      • Direct
      • United Airlines (UA 5264)Embraer 175
      • United Airlines (UA 5264)
        • M
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        • T
        • -
        • S
        • S
      • Embraer 175
      • 18:25 PNS
        00:25 MDW
        6Hrs, 00m 1 Stop (BNA)
      • PNSPensacola Municipal Airport 18:25 - MDW 00:25 6h 1 Stop (BNA) Nashville
      • PNSPensacola Municipal Airport 18:25
        BNANashville Airport 22:50
      • BNANashville Airport 19:50
        MDWChicago Midway Airport 00:25
      • 6h (3h)
      • 1 Stop BNA · Nashville 3h
      • Southwest Airlines (WN 3401)Boeing 737 700
        Southwest Airlines (WN 1647)Boeing 737 800
      • Southwest Airlines (WN 3401)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • 18:33 PNS
        00:16 ORD
        5Hrs, 43m 1 Stop (CLT)
      • PNSPensacola Municipal Airport 18:33 - ORD 00:16 5h 43m 1 Stop (CLT) Charlotte
      • PNSPensacola Municipal Airport 18:33
        CLTCharlotte Airport 22:56
      • CLTCharlotte Airport 21:18
        ORDChicago O'Hare International Airport 00:16
      • 5h 43m (1h 38m)
      • 1 Stop CLT · Charlotte 1h 38m
      • American Airlines (AA 5055)Canadair Regional
        American Airlines (AA 1180)Boeing 737 800
      • American Airlines (AA 5055)
        • M
        • -
        • -
        • T
        • F
        • -
        • S
      • 20:00 PNS
        01:00 MDW
        5Hrs, 00m 1 Stop (HOU)
      • PNSPensacola Municipal Airport 20:00 - MDW 01:00 5h 1 Stop (HOU) Houston
      • PNSPensacola Municipal Airport 20:00
        HOUHouston Hobby Airport 22:40
      • HOUHouston Hobby Airport 21:45
        MDWChicago Midway Airport 01:00
      • 5h (55m)
      • 1 Stop HOU · Houston 55m
      • Southwest Airlines (WN 2382)Boeing 737 700
        Southwest Airlines (WN 1732)Boeing 737 700
      • Southwest Airlines (WN 2382)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • 05:25 PNS
        10:48 ORD
        5Hrs, 23m 1 Stop (CLT)
      • PNSPensacola Municipal Airport 05:25 - ORD 10:48 5h 23m 1 Stop (CLT) Charlotte
      • PNSPensacola Municipal Airport 05:25
        CLTCharlotte Airport 09:33
      • CLTCharlotte Airport 08:10
        ORDChicago O'Hare International Airport 10:48
      • 5h 23m (1h 23m)
      • 1 Stop CLT · Charlotte 1h 23m
      • American Airlines (AA 5510)Canadair Regional
        American Airlines (AA 1668)Boeing 737 Max 8 Passenger
      • American Airlines (AA 5510)
        • M
        • -
        • -
        • T
        • F
        • S
        • S
      • 05:25 PNS
        10:50 ORD
        5Hrs, 25m 1 Stop (CLT)
      • PNSPensacola Municipal Airport 05:25 - ORD 10:50 5h 25m 1 Stop (CLT) Charlotte
      • PNSPensacola Municipal Airport 05:25
        CLTCharlotte Airport 09:33
      • CLTCharlotte Airport 08:10
        ORDChicago O'Hare International Airport 10:50
      • 5h 25m (1h 23m)
      • 1 Stop CLT · Charlotte 1h 23m
      • American Airlines (AA 5510)Canadair Regional
        American Airlines (AA 1668)Boeing 737 Max 8 Passenger
      • American Airlines (AA 5510)
        • -
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        • -
        • -
        • -
        • -
      • 05:25 PNS
        12:11 ORD
        6Hrs, 46m 1 Stop (CLT)
      • PNSPensacola Municipal Airport 05:25 - ORD 12:11 6h 46m 1 Stop (CLT) Charlotte
      • PNSPensacola Municipal Airport 05:25
        CLTCharlotte Airport 10:59
      • CLTCharlotte Airport 08:10
        ORDChicago O'Hare International Airport 12:11
      • 6h 46m (2h 49m)
      • 1 Stop CLT · Charlotte 2h 49m
      • American Airlines (AA 5510)Canadair Regional
        American Airlines (AA 2279)Boeing 737 800
      • American Airlines (AA 5510)
        • -
        • -
        • -
        • T
        • F
        • -
        • S
      • 05:25 PNS
        12:15 ORD
        6Hrs, 50m 1 Stop (CLT)
      • PNSPensacola Municipal Airport 05:25 - ORD 12:15 6h 50m 1 Stop (CLT) Charlotte
      • PNSPensacola Municipal Airport 05:25
        CLTCharlotte Airport 11:10
      • CLTCharlotte Airport 08:10
        ORDChicago O'Hare International Airport 12:15
      • 6h 50m (3h)
      • 1 Stop CLT · Charlotte 3h
      • American Airlines (AA 5510)Canadair Regional
        American Airlines (AA 2279)Boeing 737 800
      • American Airlines (AA 5510)
        • M
        • -
        • -
        • -
        • -
        • -
        • -
      • 05:25 PNS
        12:24 ORD
        6Hrs, 59m 1 Stop (CLT)
      • PNSPensacola Municipal Airport 05:25 - ORD 12:24 6h 59m 1 Stop (CLT) Charlotte
      • PNSPensacola Municipal Airport 05:25
        CLTCharlotte Airport 11:13
      • CLTCharlotte Airport 08:10
        ORDChicago O'Hare International Airport 12:24
      • 6h 59m (3h 03m)
      • 1 Stop CLT · Charlotte 3h 03m
      • American Airlines (AA 5510)Canadair Regional
        American Airlines (AA 2279)Boeing 737 800
      • American Airlines (AA 5510)
        • -
        • T
        • W
        • -
        • -
        • -
        • -
      • 05:40 PNS
        12:50 MDW
        7Hrs, 10m 1 Stop (HOU)
      • PNSPensacola Municipal Airport 05:40 - MDW 12:50 7h 10m 1 Stop (HOU) Houston
      • PNSPensacola Municipal Airport 05:40
        HOUHouston Hobby Airport 10:25
      • HOUHouston Hobby Airport 07:25
        MDWChicago Midway Airport 12:50
      • 7h 10m (3h)
      • 1 Stop HOU · Houston 3h
      • Southwest Airlines (WN 2382)Boeing 737 800
        Southwest Airlines (WN 6525)Boeing 737 800
      • Southwest Airlines (WN 2382)
        • -
        • -
        • -
        • -
        • F
        • -
        • -
      • 06:08 PNS
        13:12 ORD
        7Hrs, 04m 1 Stop (DCA)
      • PNSPensacola Municipal Airport 06:08 - ORD 13:12 7h 04m 1 Stop (DCA) Washington
      • PNSPensacola Municipal Airport 06:08
        DCAWashington Ronald Reagan National Airport 11:59
      • DCAWashington Ronald Reagan National Airport 09:20
        ORDChicago O'Hare International Airport 13:12
      • 7h 04m (2h 39m)
      • 1 Stop DCA · Washington 2h 39m
      • American Airlines (AA 5424)Canadair Regional
        American Airlines (AA 489)Airbus
      • American Airlines (AA 5424)
        • M
        • -
        • -
        • T
        • F
        • S
        • S
      • 06:08 PNS
        13:14 ORD
        7Hrs, 06m 1 Stop (DCA)
      • PNSPensacola Municipal Airport 06:08 - ORD 13:14 7h 06m 1 Stop (DCA) Washington
      • PNSPensacola Municipal Airport 06:08
        DCAWashington Ronald Reagan National Airport 11:59
      • DCAWashington Ronald Reagan National Airport 09:20
        ORDChicago O'Hare International Airport 13:14
      • 7h 06m (2h 39m)
      • 1 Stop DCA · Washington 2h 39m
      • American Airlines (AA 5424)Canadair Regional
        American Airlines (AA 489)Airbus
      • American Airlines (AA 5424)
        • -
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        • W
        • -
        • -
        • -
        • -
      • 06:50 PNS
        12:25 ORD
        5Hrs, 35m 1 Stop (DFW)
      • PNSPensacola Municipal Airport 06:50 - ORD 12:25 5h 35m 1 Stop (DFW) Dallas
      • PNSPensacola Municipal Airport 06:50
        DFWDallas/Fort Worth Intl Airport 10:00
      • DFWDallas/Fort Worth Intl Airport 09:01
        ORDChicago O'Hare International Airport 12:25
      • 5h 35m (59m)
      • 1 Stop DFW · Dallas 59m
      • American Airlines (AA 851)Airbus
        American Airlines (AA 2754)Boeing 737 800
      • American Airlines (AA 851)
        • M
        • -
        • -
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        • -
        • -
        • -
      • 06:50 PNS
        12:25 ORD
        5Hrs, 35m 1 Stop (DFW)
      • PNSPensacola Municipal Airport 06:50 - ORD 12:25 5h 35m 1 Stop (DFW) Dallas
      • PNSPensacola Municipal Airport 06:50
        DFWDallas/Fort Worth Intl Airport 10:00
      • DFWDallas/Fort Worth Intl Airport 09:03
        ORDChicago O'Hare International Airport 12:25
      • 5h 35m (57m)
      • 1 Stop DFW · Dallas 57m
      • American Airlines (AA 851)Airbus
        American Airlines (AA 2754)Boeing 737 800
      • American Airlines (AA 851)
        • -
        • -
        • -
        • -
        • F
        • -
        • S
      • 06:50 PNS
        12:25 ORD
        5Hrs, 35m 1 Stop (DFW)
      • PNSPensacola Municipal Airport 06:50 - ORD 12:25 5h 35m 1 Stop (DFW) Dallas
      • PNSPensacola Municipal Airport 06:50
        DFWDallas/Fort Worth Intl Airport 10:00
      • DFWDallas/Fort Worth Intl Airport 08:59
        ORDChicago O'Hare International Airport 12:25
      • 5h 35m (1h 01m)
      • 1 Stop DFW · Dallas 1h 01m
      • American Airlines (AA 851)Airbus
        American Airlines (AA 2754)Boeing 737 800
      • American Airlines (AA 851)
        • -
        • -
        • -
        • T
        • -
        • -
        • -
      • 06:50 PNS
        12:29 ORD
        5Hrs, 39m 1 Stop (DFW)
      • PNSPensacola Municipal Airport 06:50 - ORD 12:29 5h 39m 1 Stop (DFW) Dallas
      • PNSPensacola Municipal Airport 06:50
        DFWDallas/Fort Worth Intl Airport 10:00
      • DFWDallas/Fort Worth Intl Airport 09:03
        ORDChicago O'Hare International Airport 12:29
      • 5h 39m (57m)
      • 1 Stop DFW · Dallas 57m
      • American Airlines (AA 851)Airbus
        American Airlines (AA 2754)Boeing 737 800
      • American Airlines (AA 851)
        • -
        • T
        • -
        • -
        • -
        • -
        • -
      • 06:50 PNS
        12:33 ORD
        5Hrs, 43m 1 Stop (DFW)
      • PNSPensacola Municipal Airport 06:50 - ORD 12:33 5h 43m 1 Stop (DFW) Dallas
      • PNSPensacola Municipal Airport 06:50
        DFWDallas/Fort Worth Intl Airport 10:00
      • DFWDallas/Fort Worth Intl Airport 08:59
        ORDChicago O'Hare International Airport 12:33
      • 5h 43m (1h 01m)
      • 1 Stop DFW · Dallas 1h 01m
      • American Airlines (AA 851)Airbus
        American Airlines (AA 2754)Airbus
      • American Airlines (AA 851)
        • -
        • -
        • W
        • -
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        • -
        • -
      • 06:50 PNS
        13:25 ORD
        6Hrs, 35m 1 Stop (DFW)
      • PNSPensacola Municipal Airport 06:50 - ORD 13:25 6h 35m 1 Stop (DFW) Dallas
      • PNSPensacola Municipal Airport 06:50
        DFWDallas/Fort Worth Intl Airport 11:00
      • DFWDallas/Fort Worth Intl Airport 09:03
        ORDChicago O'Hare International Airport 13:25
      • 6h 35m (1h 57m)
      • 1 Stop DFW · Dallas 1h 57m
      • American Airlines (AA 851)Airbus
        American Airlines (AA 311)Boeing 737 800
      • American Airlines (AA 851)
        • -
        • -
        • -
        • -
        • F
        • S
        • S
      • 06:50 PNS
        13:25 ORD
        6Hrs, 35m 1 Stop (DFW)
      • PNSPensacola Municipal Airport 06:50 - ORD 13:25 6h 35m 1 Stop (DFW) Dallas
      • PNSPensacola Municipal Airport 06:50
        DFWDallas/Fort Worth Intl Airport 11:00
      • DFWDallas/Fort Worth Intl Airport 09:01
        ORDChicago O'Hare International Airport 13:25
      • 6h 35m (1h 59m)
      • 1 Stop DFW · Dallas 1h 59m
      • American Airlines (AA 851)Airbus
        American Airlines (AA 311)Boeing 737 800
      • American Airlines (AA 851)
        • M
        • -
        • -
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        • -
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        • -
      • 06:50 PNS
        13:25 ORD
        6Hrs, 35m 1 Stop (DFW)
      • PNSPensacola Municipal Airport 06:50 - ORD 13:25 6h 35m 1 Stop (DFW) Dallas
      • PNSPensacola Municipal Airport 06:50
        DFWDallas/Fort Worth Intl Airport 11:00
      • DFWDallas/Fort Worth Intl Airport 08:59
        ORDChicago O'Hare International Airport 13:25
      • 6h 35m (2h 01m)
      • 1 Stop DFW · Dallas 2h 01m
      • American Airlines (AA 851)Airbus
        American Airlines (AA 311)Boeing 737 800
      • American Airlines (AA 851)
        • -
        • -
        • -
        • T
        • -
        • -
        • -
      • 06:50 PNS
        13:26 ORD
        6Hrs, 36m 1 Stop (DFW)
      • PNSPensacola Municipal Airport 06:50 - ORD 13:26 6h 36m 1 Stop (DFW) Dallas
      • PNSPensacola Municipal Airport 06:50
        DFWDallas/Fort Worth Intl Airport 11:00
      • DFWDallas/Fort Worth Intl Airport 09:03
        ORDChicago O'Hare International Airport 13:26
      • 6h 36m (1h 57m)
      • 1 Stop DFW · Dallas 1h 57m
      • American Airlines (AA 851)Airbus
        American Airlines (AA 311)Boeing 737 800
      • American Airlines (AA 851)
        • -
        • T
        • -
        • -
        • -
        • -
        • -
      • 06:50 PNS
        13:26 ORD
        6Hrs, 36m 1 Stop (DFW)
      • PNSPensacola Municipal Airport 06:50 - ORD 13:26 6h 36m 1 Stop (DFW) Dallas
      • PNSPensacola Municipal Airport 06:50
        DFWDallas/Fort Worth Intl Airport 11:00
      • DFWDallas/Fort Worth Intl Airport 08:59
        ORDChicago O'Hare International Airport 13:26
      • 6h 36m (2h 01m)
      • 1 Stop DFW · Dallas 2h 01m
      • American Airlines (AA 851)Airbus
        American Airlines (AA 311)Boeing 737 800
      • American Airlines (AA 851)
        • -
        • -
        • W
        • -
        • -
        • -
        • -
      • 07:00 PNS
        12:31 ORD
        5Hrs, 31m 1 Stop (IAH)
      • PNSPensacola Municipal Airport 07:00 - ORD 12:31 5h 31m 1 Stop (IAH) Houston
      • PNSPensacola Municipal Airport 07:00
        IAHHouston George Bush Intercontinental Airport 09:49
      • IAHHouston George Bush Intercontinental Airport 08:48
        ORDChicago O'Hare International Airport 12:31
      • 5h 31m (1h 01m)
      • 1 Stop IAH · Houston 1h 01m
      • United Airlines (UA 2174)Airbus
        United Airlines (UA 1321)Boeing 737 900
      • United Airlines (UA 2174)
        • M
        • T
        • W
        • T
        • F
        • S
        • S
      • 07:24 PNS
        12:11 ORD
        4Hrs, 47m 1 Stop (CLT)
      • PNSPensacola Municipal Airport 07:24 - ORD 12:11 4h 47m 1 Stop (CLT) Charlotte
      • PNSPensacola Municipal Airport 07:24
        CLTCharlotte Airport 10:59
      • CLTCharlotte Airport 10:09
        ORDChicago O'Hare International Airport 12:11
      • 4h 47m (50m)
      • 1 Stop CLT · Charlotte 50m
      • American Airlines (AA 5353)Canadair Regional
        American Airlines (AA 2279)Boeing 737 800
      • American Airlines (AA 5353)
        • -
        • -
        • -
        • T
        • F
        • -
        • S
      • 07:24 PNS
        12:15 ORD
        4Hrs, 51m 1 Stop (CLT)
      • PNSPensacola Municipal Airport 07:24 - ORD 12:15 4h 51m 1 Stop (CLT) Charlotte
      • PNSPensacola Municipal Airport 07:24
        CLTCharlotte Airport 11:10
      • CLTCharlotte Airport 10:09
        ORDChicago O'Hare International Airport 12:15
      • 4h 51m (1h 01m)
      • 1 Stop CLT · Charlotte 1h 01m
      • American Airlines (AA 5353)Canadair Regional
        American Airlines (AA 2279)Boeing 737 800
      • American Airlines (AA 5353)
        • M
        • -
        • -
        • -
        • -
        • -
        • -
      • 07:24 PNS
        12:24 ORD
        5Hrs, 00m 1 Stop (CLT)
      • PNSPensacola Municipal Airport 07:24 - ORD 12:24 5h 1 Stop (CLT) Charlotte
      • PNSPensacola Municipal Airport 07:24
        CLTCharlotte Airport 11:13
      • CLTCharlotte Airport 10:09
        ORDChicago O'Hare International Airport 12:24
      • 5h (1h 04m)
      • 1 Stop CLT · Charlotte 1h 04m
      • American Airlines (AA 5353)Canadair Regional
        American Airlines (AA 2279)Boeing 737 800
      • American Airlines (AA 5353)
        • -
        • T
        • W
        • -
        • -
        • -
        • -
      • 07:24 PNS
        13:10 ORD
        5Hrs, 46m 1 Stop (CLT)
      • PNSPensacola Municipal Airport 07:24 - ORD 13:10 5h 46m 1 Stop (CLT) Charlotte
      • PNSPensacola Municipal Airport 07:24
        CLTCharlotte Airport 11:40
      • CLTCharlotte Airport 10:09
        ORDChicago O'Hare International Airport 13:10
      • 5h 46m (1h 31m)
      • 1 Stop CLT · Charlotte 1h 31m
      • American Airlines (AA 5353)Canadair Regional
        American Airlines (AA 2279)Boeing 737 800
      • American Airlines (AA 5353)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • 07:24 PNS
        14:10 ORD
        6Hrs, 46m 1 Stop (CLT)
      • PNSPensacola Municipal Airport 07:24 - ORD 14:10 6h 46m 1 Stop (CLT) Charlotte
      • PNSPensacola Municipal Airport 07:24
        CLTCharlotte Airport 13:00
      • CLTCharlotte Airport 10:09
        ORDChicago O'Hare International Airport 14:10
      • 6h 46m (2h 51m)
      • 1 Stop CLT · Charlotte 2h 51m
      • American Airlines (AA 5353)Canadair Regional
        American Airlines (AA 1052)Boeing 737 800
      • American Airlines (AA 5353)
        • -
        • T
        • -
        • -
        • -
        • -
        • -
      • 07:24 PNS
        14:15 ORD
        6Hrs, 51m 1 Stop (CLT)
      • PNSPensacola Municipal Airport 07:24 - ORD 14:15 6h 51m 1 Stop (CLT) Charlotte
      • PNSPensacola Municipal Airport 07:24
        CLTCharlotte Airport 13:07
      • CLTCharlotte Airport 10:09
        ORDChicago O'Hare International Airport 14:15
      • 6h 51m (2h 58m)
      • 1 Stop CLT · Charlotte 2h 58m
      • American Airlines (AA 5353)Canadair Regional
        American Airlines (AA 1052)Boeing 737 800
      • American Airlines (AA 5353)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • 07:24 PNS
        14:17 ORD
        6Hrs, 53m 1 Stop (CLT)
      • PNSPensacola Municipal Airport 07:24 - ORD 14:17 6h 53m 1 Stop (CLT) Charlotte
      • PNSPensacola Municipal Airport 07:24
        CLTCharlotte Airport 13:07
      • CLTCharlotte Airport 10:09
        ORDChicago O'Hare International Airport 14:17
      • 6h 53m (2h 58m)
      • 1 Stop CLT · Charlotte 2h 58m
      • American Airlines (AA 5353)Canadair Regional
        American Airlines (AA 1052)Boeing 737 800
      • American Airlines (AA 5353)
        • -
        • -
        • W
        • -
        • -
        • -
        • -
      • 07:24 PNS
        14:24 ORD
        7Hrs, 00m 1 Stop (CLT)
      • PNSPensacola Municipal Airport 07:24 - ORD 14:24 7h 1 Stop (CLT) Charlotte
      • PNSPensacola Municipal Airport 07:24
        CLTCharlotte Airport 13:16
      • CLTCharlotte Airport 10:09
        ORDChicago O'Hare International Airport 14:24
      • 7h (3h 07m)
      • 1 Stop CLT · Charlotte 3h 07m
      • American Airlines (AA 5353)Canadair Regional
        American Airlines (AA 1052)Boeing 737 800
      • American Airlines (AA 5353)
        • M
        • -
        • -
        • T
        • F
        • -
        • S
      • 07:25 PNS
        14:21 ORD
        6Hrs, 56m 1 Stop (TPA)
      • PNSPensacola Municipal Airport 07:25 - ORD 14:21 6h 56m 1 Stop (TPA) Tampa
      • PNSPensacola Municipal Airport 07:25
        TPATampa International Airport 12:25
      • TPATampa International Airport 10:05
        ORDChicago O'Hare International Airport 14:21
      • 6h 56m (2h 20m)
      • 1 Stop TPA · Tampa 2h 20m
      • Silver Airways (3M 82)Aerospatiale Alenia Atr 42
        United Airlines (UA 2184)Boeing 737 Max 8 Passenger
      • Silver Airways (3M 82)
        • -
        • -
        • -
        • -
        • -
        • -
        • S
      • 07:25 PNS
        14:21 ORD
        6Hrs, 56m 1 Stop (TPA)
      • PNSPensacola Municipal Airport 07:25 - ORD 14:21 6h 56m 1 Stop (TPA) Tampa
      • PNSPensacola Municipal Airport 07:25
        TPATampa International Airport 12:25
      • TPATampa International Airport 10:05
        ORDChicago O'Hare International Airport 14:21
      • 6h 56m (2h 20m)
      • 1 Stop TPA · Tampa 2h 20m
      • Silver Airways (3M 82)Aerospatiale Alenia Atr 42
        United Airlines (UA 2184)Boeing 737 800
      • Silver Airways (3M 82)
        • M
        • T
        • W
        • T
        • F
        • -
        • -
      • 07:30 PNS
        13:00 ORD
        5Hrs, 30m 1 Stop (BNA)
      • PNSPensacola Municipal Airport 07:30 - ORD 13:00 5h 30m 1 Stop (BNA) Nashville
      • PNSPensacola Municipal Airport 07:30
        BNANashville Airport 11:15
      • BNANashville Airport 08:55
        ORDChicago O'Hare International Airport 13:00
      • 5h 30m (2h 20m)
      • 1 Stop BNA · Nashville 2h 20m
      • Southwest Airlines (WN 1106)Boeing 737 800
        Southwest Airlines (WN 467)Boeing 737 800
      • Southwest Airlines (WN 1106)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • 07:30 PNS
        14:00 MDW
        6Hrs, 30m 1 Stop (BNA)
      • PNSPensacola Municipal Airport 07:30 - MDW 14:00 6h 30m 1 Stop (BNA) Nashville
      • PNSPensacola Municipal Airport 07:30
        BNANashville Airport 12:25
      • BNANashville Airport 08:55
        MDWChicago Midway Airport 14:00
      • 6h 30m (3h 30m)
      • 1 Stop BNA · Nashville 3h 30m
      • Southwest Airlines (WN 1106)Boeing 737 800
        Southwest Airlines (WN 2412)Boeing 737 700
      • Southwest Airlines (WN 1106)
        • -
        • -
        • -
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        • -
      • 08:39 PNS
        14:31 ORD
        5Hrs, 52m 1 Stop (FLL)
      • PNSPensacola Municipal Airport 08:39 - ORD 14:31 5h 52m 1 Stop (FLL) Miami
      • PNSPensacola Municipal Airport 08:39
        FLLFort Lauderdale/Hollywood Intl Airport 12:11
      • FLLFort Lauderdale/Hollywood Intl Airport 11:24
        ORDChicago O'Hare International Airport 14:31
      • 5h 52m (47m)
      • 1 Stop FLL · Miami 47m
      • Spirit Airlines (NK 1051)Airbus A320 Neo
        Spirit Airlines (NK 395)Airbus Industrie A320 Sharklets
      • Spirit Airlines (NK 1051)
        • -
        • -
        • -
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        • F
        • S
        • S
      • 08:39 PNS
        15:16 ORD
        6Hrs, 37m 1 Stop (FLL)
      • PNSPensacola Municipal Airport 08:39 - ORD 15:16 6h 37m 1 Stop (FLL) Miami
      • PNSPensacola Municipal Airport 08:39
        FLLFort Lauderdale/Hollywood Intl Airport 12:56
      • FLLFort Lauderdale/Hollywood Intl Airport 11:24
        ORDChicago O'Hare International Airport 15:16
      • 6h 37m (1h 32m)
      • 1 Stop FLL · Miami 1h 32m
      • Spirit Airlines (NK 1051)Airbus A320 Neo
        Spirit Airlines (NK 2)Airbus Industrie A321 Sharklets
      • Spirit Airlines (NK 1051)
        • -
        • T
        • -
        • -
        • -
        • -
        • -
      • 08:45 PNS
        13:00 ORD
        4Hrs, 15m 1 Stop (BNA)
      • PNSPensacola Municipal Airport 08:45 - ORD 13:00 4h 15m 1 Stop (BNA) Nashville
      • PNSPensacola Municipal Airport 08:45
        BNANashville Airport 11:15
      • BNANashville Airport 10:10
        ORDChicago O'Hare International Airport 13:00
      • 4h 15m (1h 05m)
      • 1 Stop BNA · Nashville 1h 05m
      • Southwest Airlines (WN 1106)Boeing 737 800
        Southwest Airlines (WN 983)Boeing 737 800
      • Southwest Airlines (WN 1106)
        • -
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        • -
        • -
        • -
        • -
      • 14:00 CMH
        10:10 BNA
        5Hrs, 30m 1 Stop (MDW)
      • CMHColumbus Port Columbus Intl Airport 14:00 - BNA 10:10 5h 30m 1 Stop (MDW) Chicago
      • CMHColumbus Port Columbus Intl Airport 14:00
        PNSPensacola Municipal Airport 08:45
      • MDWChicago Midway Airport 14:15
        BNANashville Airport 10:10
      • 5h 30m (1h 30m)
      • 1 Stop MDW · Chicago 1h 30m
      • Southwest Airlines (WN 2328)Boeing 737 700
        Southwest Airlines (WN 1106)Boeing 737 800
      • Southwest Airlines (WN 2328)
        • -
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        • -
        • -
        • -
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      • 14:10 PIT
        10:10 BNA
        5Hrs, 50m 1 Stop (MDW)
      • PITPittsburgh International Airport 14:10 - BNA 10:10 5h 50m 1 Stop (MDW) Chicago
      • PITPittsburgh International Airport 14:10
        PNSPensacola Municipal Airport 08:45
      • MDWChicago Midway Airport 14:35
        BNANashville Airport 10:10
      • 5h 50m (1h 30m)
      • 1 Stop MDW · Chicago 1h 30m
      • Southwest Airlines (WN 3286)Boeing 737 Max 8 Passenger
        Southwest Airlines (WN 1106)Boeing 737 800
      • Southwest Airlines (WN 3286)
        • -
        • T
        • W
        • -
        • -
        • -
        • -
      • 08:45 PNS
        15:10 MDW
        6Hrs, 25m 1 Stop (BNA)
      • PNSPensacola Municipal Airport 08:45 - MDW 15:10 6h 25m 1 Stop (BNA) Nashville
      • PNSPensacola Municipal Airport 08:45
        BNANashville Airport 13:35
      • BNANashville Airport 10:10
        MDWChicago Midway Airport 15:10
      • 6h 25m (3h 25m)
      • 1 Stop BNA · Nashville 3h 25m
      • Southwest Airlines (WN 1106)Boeing 737 800
        Southwest Airlines (WN 1622)Boeing 737 700
      • Southwest Airlines (WN 1106)
        • -
        • T
        • W
        • -
        • -
        • -
        • -
      • 09:00 PNS
        14:37 ORD
        5Hrs, 37m 1 Stop (IAH)
      • PNSPensacola Municipal Airport 09:00 - ORD 14:37 5h 37m 1 Stop (IAH) Houston
      • PNSPensacola Municipal Airport 09:00
        IAHHouston George Bush Intercontinental Airport 11:55
      • IAHHouston George Bush Intercontinental Airport 10:56
        ORDChicago O'Hare International Airport 14:37
      • 5h 37m (59m)
      • 1 Stop IAH · Houston 59m
      • United Airlines (UA 4290)Embraer
        United Airlines (UA 1168)Boeing 737 Max 9 Passenger
      • United Airlines (UA 4290)
        • M
        • T
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        • T
        • F
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        • S
      • 09:00 PNS
        14:37 ORD
        5Hrs, 37m 1 Stop (IAH)
      • PNSPensacola Municipal Airport 09:00 - ORD 14:37 5h 37m 1 Stop (IAH) Houston
      • PNSPensacola Municipal Airport 09:00
        IAHHouston George Bush Intercontinental Airport 11:55
      • IAHHouston George Bush Intercontinental Airport 10:56
        ORDChicago O'Hare International Airport 14:37
      • 5h 37m (59m)
      • 1 Stop IAH · Houston 59m
      • United Airlines (UA 4290)Embraer
        United Airlines (UA 1168)Boeing 737 900
      • United Airlines (UA 4290)
        • -
        • -
        • -
        • -
        • -
        • S
        • -
      • 09:50 PNS
        14:55 MDW
        5Hrs, 05m 1 Stop (BNA)
      • PNSPensacola Municipal Airport 09:50 - MDW 14:55 5h 05m 1 Stop (BNA) Nashville
      • PNSPensacola Municipal Airport 09:50
        BNANashville Airport 13:20
      • BNANashville Airport 11:15
        MDWChicago Midway Airport 14:55
      • 5h 05m (2h 05m)
      • 1 Stop BNA · Nashville 2h 05m
      • Southwest Airlines (WN 5253)Boeing 737 700
        Southwest Airlines (WN 2191)Boeing 737 Max 8 Passenger
      • Southwest Airlines (WN 5253)
        • M
        • -
        • -
        • T
        • F
        • -
        • S
      • 09:50 PNS
        16:15 MDW
        6Hrs, 25m 1 Stop (BNA)
      • PNSPensacola Municipal Airport 09:50 - MDW 16:15 6h 25m 1 Stop (BNA) Nashville
      • PNSPensacola Municipal Airport 09:50
        BNANashville Airport 14:40
      • BNANashville Airport 11:15
        MDWChicago Midway Airport 16:15
      • 6h 25m (3h 25m)
      • 1 Stop BNA · Nashville 3h 25m
      • Southwest Airlines (WN 5253)Boeing 737 700
        Southwest Airlines (WN 6432)Boeing 737 Max 8 Passenger
      • Southwest Airlines (WN 5253)
        • M
        • -
        • -
        • T
        • F
        • -
        • S
      • 10:35 PNS
        15:45 MDW
        5Hrs, 10m 1 Stop (DAL)
      • PNSPensacola Municipal Airport 10:35 - MDW 15:45 5h 10m 1 Stop (DAL) Dallas
      • PNSPensacola Municipal Airport 10:35
        DALDallas/Fort Worth Love Field Airport 13:35
      • DALDallas/Fort Worth Love Field Airport 12:30
        MDWChicago Midway Airport 15:45
      • 5h 10m (1h 05m)
      • 1 Stop DAL · Dallas 1h 05m
      • Southwest Airlines (WN 1164)Boeing 737 700
        Southwest Airlines (WN 2564)Boeing 737 Max 8 Passenger
      • Southwest Airlines (WN 1164)
        • -
        • T
        • W
        • -
        • -
        • -
        • -
      • 10:59 PNS
        16:55 ORD
        5Hrs, 56m 1 Stop (MIA)
      • PNSPensacola Municipal Airport 10:59 - ORD 16:55 5h 56m 1 Stop (MIA) Miami
      • PNSPensacola Municipal Airport 10:59
        MIAMiami International Airport 14:25
      • MIAMiami International Airport 13:41
        ORDChicago O'Hare International Airport 16:55
      • 5h 56m (44m)
      • 1 Stop MIA · Miami 44m
      • American Airlines (AA 3613)Embraer Emb 175
        American Airlines (AA 1003)Boeing 737 Max 8 Passenger
      • American Airlines (AA 3613)
        • -
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        • -
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        • -
      • 10:59 PNS
        17:44 ORD
        6Hrs, 45m 1 Stop (MIA)
      • PNSPensacola Municipal Airport 10:59 - ORD 17:44 6h 45m 1 Stop (MIA) Miami
      • PNSPensacola Municipal Airport 10:59
        MIAMiami International Airport 15:17
      • MIAMiami International Airport 13:41
        ORDChicago O'Hare International Airport 17:44
      • 6h 45m (1h 36m)
      • 1 Stop MIA · Miami 1h 36m
      • American Airlines (AA 3613)Embraer Emb 175
        American Airlines (AA 3143)Boeing 737 800
      • American Airlines (AA 3613)
        • M
        • -
        • -
        • -
        • -
        • -
        • -
      • 10:59 PNS
        17:45 ORD
        6Hrs, 46m 1 Stop (MIA)
      • PNSPensacola Municipal Airport 10:59 - ORD 17:45 6h 46m 1 Stop (MIA) Miami
      • PNSPensacola Municipal Airport 10:59
        MIAMiami International Airport 15:17
      • MIAMiami International Airport 13:41
        ORDChicago O'Hare International Airport 17:45
      • 6h 46m (1h 36m)
      • 1 Stop MIA · Miami 1h 36m
      • American Airlines (AA 3613)Embraer Emb 175
        American Airlines (AA 3143)Boeing 737 800
      • American Airlines (AA 3613)
        • -
        • T
        • W
        • -
        • -
        • -
        • -
      • 10:59 PNS
        17:59 ORD
        7Hrs, 00m 1 Stop (MIA)
      • PNSPensacola Municipal Airport 10:59 - ORD 17:59 7h 1 Stop (MIA) Miami
      • PNSPensacola Municipal Airport 10:59
        MIAMiami International Airport 15:30
      • MIAMiami International Airport 13:41
        ORDChicago O'Hare International Airport 17:59
      • 7h (1h 49m)
      • 1 Stop MIA · Miami 1h 49m
      • American Airlines (AA 3613)Embraer Emb 175
        American Airlines (AA 3143)Boeing 737 800
      • American Airlines (AA 3613)
        • -
        • -
        • -
        • T
        • F
        • S
        • -
      • 11:14 PNS
        15:40 ORD
        4Hrs, 26m 1 Stop (CLT)
      • PNSPensacola Municipal Airport 11:14 - ORD 15:40 4h 26m 1 Stop (CLT) Charlotte
      • PNSPensacola Municipal Airport 11:14
        CLTCharlotte Airport 14:32
      • CLTCharlotte Airport 13:51
        ORDChicago O'Hare International Airport 15:40
      • 4h 26m (41m)
      • 1 Stop CLT · Charlotte 41m
      • American Airlines (AA 2737)Airbus
        American Airlines (AA 614)Boeing 737 800
      • American Airlines (AA 2737)
        • M
        • T
        • W
        • T
        • F
        • -
        • 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 38 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 05:25. The last flight of the day departs at 18:25. See the full list of flight times on Wego.

      How many airlines offer direct flights from Pensacola to Chicago?

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

      All Airports in Pensacola

      Pensacola Municipal Airport PNS

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