American Airlines Chicago to Pensacola Flights

Return flight: Pensacola – Chicago

Cheapflightsplus.com will find cheap American Airlines flights from Chicago to Pensacola. Compare airline ticket prices and book air tickets starting from $94 from trusted online travel agencies, web sites and directly from airlines. Check flights schedule of American Airlines, arrivals and departure details below.

Find Cheap Airfare Chicago (IL) — Pensacola (FL) by American Airlines

To find cheap tickets choose a day of your departure with attractive price on the graph below and click «Find flights». For round trip flights please click «Check prices for return flight». The cheapest airfare is in november: one-way - $94, two-way – $161.
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Below is a detailed 2024 flight schedule for today, tomorrow and all other days. It may vary depending on season and a day of the week of your desired trip. We recommend booking your itinerary at least 2 weeks prior your travel to get the best price and availability by the airline.
Departure Arrival Flight Details Flight Time Price
10:40 am — 3:43 pm
10:40 am — 1:37 pm AA1668 American Airlines
Chicago — Charlotte
1h 18m stop
2:55 pm — 3:43 pm AA4553 American Airlines
Charlotte — Pensacola
5h 3m
including layover
Find flight
from$94
10:50 am — 6:44 pm
10:50 am — 1:16 pm AA1408 American Airlines
Chicago — Dallas
3h 39m stop
4:55 pm — 6:44 pm AA3877 American Airlines
Dallas — Pensacola
7h 54m
including layover
Find flight
from$95
11:15 am — 6:35 pm
11:15 am — 1:37 pm AA2223 American Airlines
Chicago — Dallas
3h 8m stop
4:45 pm — 6:35 pm AA3877 American Airlines
Dallas — Pensacola
7h 20m
including layover
Find flight
from$227
12:11 pm — 6:27 pm
12:11 pm — 3:10 pm AA2080 American Airlines
Chicago — Charlotte
2h 31m stop
5:41 pm — 6:27 pm AA5463 American Airlines
Charlotte — Pensacola
6h 16m
including layover
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from$94
12:30 pm — 6:20 pm
12:30 pm — 3:33 pm AA2080 American Airlines
Chicago — Charlotte
2h 8m stop
5:41 pm — 6:20 pm AA5463 American Airlines
Charlotte — Pensacola
5h 50m
including layover
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from$163
1:53 pm — 6:27 pm
1:53 pm — 4:55 pm AA864 American Airlines
Chicago — Charlotte
46m stop
5:41 pm — 6:27 pm AA5463 American Airlines
Charlotte — Pensacola
4h 34m
including layover
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from$94
1:53 pm — 8:42 pm
1:53 pm — 4:55 pm AA864 American Airlines
Chicago — Charlotte
3h stop
7:55 pm — 8:42 pm AA5103 American Airlines
Charlotte — Pensacola
6h 49m
including layover
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from$94
2:05 pm — 8:40 pm
2:05 pm — 5:08 pm AA864 American Airlines
Chicago — Charlotte
2h 47m stop
7:55 pm — 8:40 pm AA5103 American Airlines
Charlotte — Pensacola
6h 35m
including layover
Find flight
from$184
2:23 pm — 10:30 pm
2:23 pm — 4:50 pm AA2346 American Airlines
Chicago — Dallas
3h 55m stop
8:45 pm — 10:30 pm AA2641 American Airlines
Dallas — Pensacola
8h 7m
including layover
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from$164
3:12 pm — 9:07 pm
3:12 pm — 6:02 pm AA2679 American Airlines
Chicago — Washington D.C.
1h 33m stop
7:35 pm — 9:07 pm AA5597 American Airlines
Washington D.C. — Pensacola
5h 55m
including layover
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from$95
3:46 pm — 8:42 pm
3:46 pm — 6:46 pm AA1093 American Airlines
Chicago — Charlotte
1h 9m stop
7:55 pm — 8:42 pm AA5103 American Airlines
Charlotte — Pensacola
4h 56m
including layover
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from$94
4:45 pm — 10:49 pm
4:45 pm — 8:51 pm AA160 American Airlines
Chicago — Miami
1h stop
9:51 pm — 10:49 pm AA4109 American Airlines
Miami — Pensacola
6h 4m
including layover
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from$112
4:55 pm — 10:17 pm
4:55 pm — 7:31 pm AA2501 American Airlines
Chicago — Dallas
1h 9m stop
8:40 pm — 10:17 pm AA2641 American Airlines
Dallas — Pensacola
5h 22m
including layover
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from$112
5:15 am — 12:04 pm
5:15 am — 7:49 am AA2429 American Airlines
Chicago — Dallas
2h 31m stop
10:20 am — 12:04 pm AA3324 American Airlines
Dallas — Pensacola
6h 49m
including layover
Find flight
from$95
5:49 am — 12:19 pm
5:49 am — 8:43 am AA2523 American Airlines
Chicago — Charlotte
2h 47m stop
11:30 am — 12:19 pm AA5298 American Airlines
Charlotte — Pensacola
6h 30m
including layover
Find flight
from$94
6:25 pm — 11:08 pm
6:25 pm — 9:20 pm AA354 American Airlines
Chicago — Charlotte
1h 4m stop
10:24 pm — 11:08 pm AA5103 American Airlines
Charlotte — Pensacola
4h 43m
including layover
Find flight
from$252
6:30 am — 10:49 pm
6:30 am — 10:34 am AA2498 American Airlines
Chicago — Miami
11h 17m stop
9:51 pm — 10:49 pm AA4109 American Airlines
Miami — Pensacola
16h 19m
including layover
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from$227
7:00 am — 12:59 pm
7:00 am — 9:47 am AA2378 American Airlines
Chicago — Washington D.C.
1h 43m stop
11:30 am — 12:59 pm AA3771 American Airlines
Washington D.C. — Pensacola
5h 59m
including layover
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from$95
7:24 am — 12:19 pm
7:24 am — 10:24 am AA2052 American Airlines
Chicago — Charlotte
1h 6m stop
11:30 am — 12:19 pm AA5298 American Airlines
Charlotte — Pensacola
4h 55m
including layover
Find flight
from$94
8:30 am — 2:38 pm
8:30 am — 11:05 am AA2428 American Airlines
Chicago — Dallas
1h 55m stop
1:00 pm — 2:38 pm AA2389 American Airlines
Dallas — Pensacola
6h 8m
including layover
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from$95
8:50 am — 3:43 pm
8:50 am — 11:51 am AA593 American Airlines
Chicago — Charlotte
3h 4m stop
2:55 pm — 3:43 pm AA4553 American Airlines
Charlotte — Pensacola
6h 53m
including layover
Find flight
from$94
9:00 am — 2:38 pm
9:00 am — 11:40 am AA2412 American Airlines
Chicago — Dallas
1h 20m stop
1:00 pm — 2:38 pm AA2389 American Airlines
Dallas — Pensacola
5h 38m
including layover
Find flight
from$95
9:05 am — 2:45 pm
9:05 am — 11:36 am AA2412 American Airlines
Chicago — Dallas
1h 24m stop
1:00 pm — 2:45 pm AA2389 American Airlines
Dallas — Pensacola
5h 40m
including layover
Find flight
from$164
*Departure and arrival times are local. Last updated on 11/15/2024

Flight Information

There are 111 flight by American Airlines from Chicago to Pensacola every week with departures from Chicago FSS, Midway, O'Hare International, Chicago NAS, Merrill C Meigs (closed), Dupage County, Pal-Waukee. All flights arrive at Ellyson NAS, Pensacola Regional, Pensacola NAS, Saufley NAS.

Departures start from 10:05 pm to 9:05 am. Nonstop flight is 4h 31m. The time difference between Chicago and Pensacola is 0h.

  • The fastest flight 4h 31m
  • Average flight time 8h 12m
  • The earliest flight 10:05 pm
  • The latest flight 9:05 am
  • Distance 789 ml

The cheapest flight by American Airlines that our users were able to find is $94. This airfare is economy class on one-way AA593 flight for December 7, 2018 leaving O'Hare International in Chicago at 8:50 am, it includes all taxes and additional fees.

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Other Popular Airlines on the Route

Besides American Airlines there are other 1 airline carriers between Chicago and Pensacola. Please review schedules and prices from the most popular airlines to find the best airfare deals from Chicago to Pensacola.

Nonstop flights

There are 3 direct flights every day from Chicago. Airlines and fares are below:

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Connecting Flights

List of flights with layovers (1 and more stops):

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How to book an air 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 airfare.
  • 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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