Cheap Flights from Chicago, IL to Pensacola, FL from $110

Return flight: Pensacola – Chicago

On Cheapflightsplus.com you will find 3 direct and 103 connecting flights from Chicago to Pensacola. You can compare airfare deals from 2 airlines and multiple travel sites from $110, book and save on cheap plane tickets and last minute offers. Also check out CHI-PNS flight schedule to find best flight time, convenient departure and arrival airports.

Flight Information

Below we will explain in detail what the flights cost on the destination from Chicago to Pensacola depends on and how to choose the most interesting flight option for you.

Distance between Chicago and Pensacola is 1269 miles. Time difference between the cities is 0h. Airplanes depart 05:15 to 22:10 from 7 Chicago airports and arrive 05:15 to 22:10 to 4 Pensacola airports. Average flight time is 2h 24m.

  • The fastest flight 2h 15m
  • Average flight time 2h 24m
  • The earliest flight 05:15
  • The latest flight 22:10
  • Distance 789 ml

What is the lowest airfare Chicago to Pensacola?

The cheapest plane ticket found by our users is $110. This airfare is for economy class on one-way AA593 flight by American Airlines for December 7, 2018 which leaves O'Hare International in Chicago at 08:50 am and arrives at Pensacola Pensacola Regional at 15:43.

Economy class
$110
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Business class
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First class
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Flight Schedule Chicago (Illinois) to Pensacola (Florida)

05:15 — 12:04
6h 49m flight time
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from$112
05:15 — 07:49 Chicago — Dallas
AA2429 American Airlines
2h 31m stop
10:20 — 12:04 Dallas — Pensacola
AA3324 American Airlines
05:49 — 12:19
6h 30m flight time
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from$110
05:49 — 08:43 Chicago — Charlotte
AA2523 American Airlines
2h 47m stop
11:30 — 12:19 Charlotte — Pensacola
AA5298 American Airlines
07:00 — 12:59
5h 59m flight time
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from$112
07:00 — 09:47 Chicago — Washington D.C.
AA2378 American Airlines
1h 43m stop
11:30 — 12:59 Washington D.C. — Pensacola
AA3771 American Airlines
07:05 — 12:04
4h 59m flight time
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from$112
07:05 — 09:40 Chicago — Dallas
AA1625 American Airlines
40m stop
10:20 — 12:04 Dallas — Pensacola
AA3324 American Airlines
07:05 — 14:38
7h 33m flight time
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from$112
07:05 — 09:40 Chicago — Dallas
AA1625 American Airlines
3h 20m stop
13:00 — 14:38 Dallas — Pensacola
AA2389 American Airlines
07:24 — 12:19
4h 55m flight time
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from$110
07:24 — 10:24 Chicago — Charlotte
AA2052 American Airlines
1h 6m stop
11:30 — 12:19 Charlotte — Pensacola
AA5298 American Airlines
08:50 — 15:43
6h 53m flight time
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from$110
08:50 — 11:51 Chicago — Charlotte
AA593 American Airlines
3h 4m stop
14:55 — 15:43 Charlotte — Pensacola
AA4553 American Airlines
10:40 — 15:43
5h 3m flight time
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from$110
10:40 — 13:37 Chicago — Charlotte
AA1668 American Airlines
1h 18m stop
14:55 — 15:43 Charlotte — Pensacola
AA4553 American Airlines
11:25 — 13:40
2h 15m flight time
Find flight
from$280
Chicago — Pensacola
UA5803 United Airlines
11:29 — 13:55
2h 26m flight time
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from$264
Chicago — Pensacola
UA3809 United Airlines
11:42 — 14:06
2h 24m flight time
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from$212
Chicago — Pensacola
UA3916 United Airlines
12:11 — 18:27
6h 16m flight time
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from$110
12:11 — 15:10 Chicago — Charlotte
AA2080 American Airlines
2h 31m stop
17:41 — 18:27 Charlotte — Pensacola
AA5463 American Airlines
13:53 — 18:27
4h 34m flight time
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from$110
13:53 — 16:55 Chicago — Charlotte
AA864 American Airlines
46m stop
17:41 — 18:27 Charlotte — Pensacola
AA5463 American Airlines
13:53 — 20:42
6h 49m flight time
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from$110
13:53 — 16:55 Chicago — Charlotte
AA864 American Airlines
3h stop
19:55 — 20:42 Charlotte — Pensacola
AA5103 American Airlines
15:46 — 20:42
4h 56m flight time
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from$110
15:46 — 18:46 Chicago — Charlotte
AA1093 American Airlines
1h 9m stop
19:55 — 20:42 Charlotte — Pensacola
AA5103 American Airlines
Full flight schedule will help you in detecting at what time planes fly from Chicago to Pensacola. You can also specify the concrete flights and airlines on the route and how long the flight actually is. Use the calendar for today, tomorrow or other specific date as some flights are available only on certain days of the week.
*Departure and arrival times - local. Updated on October 15, 2025.

Popular Airlines on the Route

The flight Chicago — Pensacola is served by 2 regular airlines . Most of the flights on this route are operated by American Airlines - 76 departures per week at the price of from $ 110 . And the most expensive tickets are offered by American Airlines airline - from $ 427.

Direct flights

There are 3 nonstop flights on the route. The fastest direct flight is UA5803 by United Airlines takes 2h 15m and the cheapest is AA593 by American Airlines for $212.

  • UA - United Airlines
    from $212
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Connecting Flights

There are 103 flights with layovers on the route. The fastest connecting flight is AA2764 by American Airlines takes 4h 31m and the cheapest is AA593 by American Airlines for $110.

  • AA - American Airlines
    from $110
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  • UA - United Airlines
    from $127
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Airports

You can fly from Chicago to Pensacola from 7 airports (O'Hare International, Midway, Dupage County, Chicago FSS, Merrill C Meigs (closed), Pal-Waukee, Chicago NAS).

Chicago airports

  • O'Hare International-ORD
    from $110
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  • Midway-MDW
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  • Dupage County-DPA
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  • Chicago FSS-CHI
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  • Merrill C Meigs (closed)-CGX
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  • Pal-Waukee-PWK
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  • Chicago NAS-NOH
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Pensacola airports

  • Ellyson NAS-NDP
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  • Pensacola Regional-PNS
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  • Pensacola NAS-NPA
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  • Saufley NAS-NUN
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How to book a plane ticket yourself?

How to book an air ticket yourself?
  • Fill in the search parameters — cities of departure and destination, departure and return dates and click «Find flights»
  • Select the best flight that you like. Please, check the airports of departure and arrival. Select the best fare, but pay attention to the following flight details - airports of departure and arrival, flight duration and layovers. Please use filters and sort to find the best flight.
  • Click «Buy» when you are ready — our system will redirect you to the site that sells the selected flight ticket.
  • Fill in all passenger and payment information — passport and contact information, please double check all passengers’ names and make a payment for your itinerary.
  • That's it — you will receive an email with your e-ticket usually within 10 minutes after your flight is confirmed. Please, print the e-ticket and have it with you at the airport. You would need to have only a passport and/or a required form of ID to travel. Please, check your Visa requirements if you travel outside of the United States or Canada.

    To find a plane ticket, please select dates.

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