Flight Schedules

Last Updated: Fri, 2 May, 2025

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  • 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 Max 8 Passenger
  • United Airlines (UA 2124)
    • -
    • -
    • -
    • -
    • F
    • -
    • -
  • Boeing 737 Max 8 Passenger
  • 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)
    • -
    • -
    • -
    • -
    • -
    • -
    • S
  • Airbus
  • 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 737 900
  • United Airlines (UA 2124)
    • M
    • T
    • W
    • T
    • -
    • -
    • -
  • Boeing 737 900
  • 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)
    • -
    • -
    • -
    • T
    • F
    • S
    • S
  • Airbus
  • 14:15 PNS
    16:55 ORD
    2Hrs, 40m Direct
  • PNSPensacola Municipal Airport 14:15 - ORD 16:55 2h 40m Direct
  • PNSPensacola Municipal Airport 14:15
  • ORDChicago O'Hare International Airport 16:55
  • 2h 40m
  • Direct
  • United Airlines (UA 2179)Boeing 737 800
  • United Airlines (UA 2179)
    • -
    • T
    • -
    • -
    • -
    • -
    • -
  • Boeing 737 800
  • 14:15 PNS
    16:55 ORD
    2Hrs, 40m Direct
  • PNSPensacola Municipal Airport 14:15 - ORD 16:55 2h 40m Direct
  • PNSPensacola Municipal Airport 14:15
  • ORDChicago O'Hare International Airport 16:55
  • 2h 40m
  • Direct
  • United Airlines (UA 2179)Boeing 737 700
  • United Airlines (UA 2179)
    • M
    • -
    • W
    • -
    • -
    • -
    • -
  • Boeing 737 700
  • 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
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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 06:30. The last flight of the day departs at 06:30. See the full list of flight times on Wego.

How many airlines offer direct flights from Pensacola to Chicago?

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