American Airlines Pensacola to Chicago Flights

One way Round trip

Adults

Children under 12

Infants under 2 without place

Economy

Business

First

done

Return flight: Chicago – Pensacola

Page navigation

Best Airfare Price Calendar Flights Schedule

Cheapflightsplus.com will find cheap American Airlines flights from Pensacola to Chicago. Compare airline ticket prices and book air tickets starting from $89 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 Pensacola (FL) — Chicago (IL) 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 january: one-way - $89, two-way – $153.

Direct flights

Check to choose departure date Check to choose departure date

Check prices for return flight

Find flights

Cheap Flights from Pensacola to Chicago by American Airlines

Look at the list of plane tickets for the most connecting flights by American Airlines, their prices start from $89. There’re no direct flights. The fastest connecting flight – 4h 42m.

Price	Departure	Arrival	Flight Time	Airline	Flight
from $89 Find flight	6:09 am Pensacola Pensacola Regional	10:53 am Chicago O'Hare International	4h 44m layover 0h 50m - Charlotte	American Airlines	AA5353 AA487
from $89 Find flight	9:14 am Pensacola Pensacola Regional	2:27 pm Chicago O'Hare International	5h 13m layover 1h 16m - Charlotte	American Airlines	AA5237 AA1650
from $89 Find flight	6:57 pm Pensacola Pensacola Regional	11:56 pm Chicago O'Hare International	4h 59m layover 1h 18m - Charlotte	American Airlines	AA5463 AA483
from $89 Find flight	4:15 pm Pensacola Pensacola Regional	11:56 pm Chicago O'Hare International	7h 41m layover 4h 0m - Charlotte	American Airlines	AA4553 AA483
from $90 Find flight	7:18 am Pensacola Pensacola Regional	1:55 pm Chicago O'Hare International	6h 37m layover 2h 10m - Washington D.C.	American Airlines	AA5082 AA985
from $90 Find flight	6:03 am Pensacola Pensacola Regional	12:19 pm Chicago O'Hare International	6h 16m layover 1h 13m - Miami	American Airlines	AA3508 AA2796
from $90 Find flight	7:18 pm Pensacola Pensacola Regional	0:51 am+1 день Chicago O'Hare International	5h 33m layover 1h 13m - Dallas	American Airlines	AA3877 AA2585
from $90 Find flight	7:08 am Pensacola Pensacola Regional	12:56 pm Chicago O'Hare International	5h 48m layover 1h 16m - Dallas	American Airlines	AA2453 AA319
from $90 Find flight	7:18 am Pensacola Pensacola Regional	3:45 pm Chicago O'Hare International	8h 27m layover 4h 0m - Washington D.C.	American Airlines	AA5082 AA1609
from $90 Find flight	7:08 am Pensacola Pensacola Regional	12:14 pm Chicago O'Hare International	5h 6m layover 0h 40m - Dallas	American Airlines	AA2453 AA1258
from $90 Find flight	6:03 am Pensacola Pensacola Regional	2:19 pm Chicago O'Hare International	8h 16m layover 3h 13m - Miami	American Airlines	AA3508 AA132
from $90 Find flight	7:18 am Pensacola Pensacola Regional	12:17 pm Chicago O'Hare International	4h 59m layover 0h 33m - Washington D.C.	American Airlines	AA5082 AA1033
from $90 Find flight	3:30 pm Pensacola Pensacola Regional	11:05 pm Chicago O'Hare International	7h 35m layover 3h 11m - Dallas	American Airlines	AA2389 AA1294
from $91 Find flight	9:14 am Pensacola Pensacola Regional	3:46 pm Chicago O'Hare International	6h 32m layover 2h 39m - Charlotte	American Airlines	AA5237 AA1883
from $105 Find flight	12:49 pm Pensacola Pensacola Regional	5:46 pm Chicago O'Hare International	4h 57m layover 1h 1m - Charlotte	American Airlines	AA5298 AA1017
from $123 Find flight	10:38 am Pensacola Pensacola Regional	4:30 pm Chicago O'Hare International	5h 52m layover 0h 51m - Miami	American Airlines	AA3733 AA2367

Show All Flights

*Departure and arrival times are local. Prices are for one-way flights. Information refreshed on 12/30/2024

American Airlines Flight Schedule Pensacola to Chicago

Below is a detailed 2025 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	Flight Details	Flight Time	Price
10:38 am — 6:43 pm	10:38 am — 1:20 pm AA3733 American Airlines Pensacola — Miami 2h 59m stop 4:19 pm — 6:43 pm AA2303 American Airlines Miami — Chicago	8h 5m including layover	Find flight from$90
10:38 am — 4:30 pm	10:38 am — 1:20 pm AA3733 American Airlines Pensacola — Miami 51m stop 2:11 pm — 4:30 pm AA2361 American Airlines Miami — Chicago	5h 52m including layover	Find flight from$90
12:48 pm — 8:18 pm	12:48 pm — 3:59 pm AA3822 American Airlines Pensacola — Washington D.C. 3h 1m stop 7:00 pm — 8:18 pm AA1015 American Airlines Washington D.C. — Chicago	7h 30m including layover	Find flight from$92
12:49 pm — 5:46 pm	12:49 pm — 3:30 pm AA5298 American Airlines Pensacola — Charlotte 1h 1m stop 4:31 pm — 5:46 pm AA1017 American Airlines Charlotte — Chicago	4h 57m including layover	Find flight from$105
1:33 pm — 6:59 pm	1:33 pm — 3:36 pm AA3488 American Airlines Pensacola — Dallas 56m stop 4:32 pm — 6:59 pm AA2418 American Airlines Dallas — Chicago	5h 26m including layover	Find flight from$106
1:33 pm — 8:49 pm	1:33 pm — 3:36 pm AA3488 American Airlines Pensacola — Dallas 2h 54m stop 6:30 pm — 8:49 pm AA2520 American Airlines Dallas — Chicago	7h 16m including layover	Find flight from$106
3:30 pm — 11:05 pm	3:30 pm — 5:34 pm AA2389 American Airlines Pensacola — Dallas 3h 11m stop 8:45 pm — 11:05 pm AA1294 American Airlines Dallas — Chicago	7h 35m including layover	Find flight from$90
3:30 pm — 8:49 pm	3:30 pm — 5:34 pm AA2389 American Airlines Pensacola — Dallas 56m stop 6:30 pm — 8:49 pm AA2520 American Airlines Dallas — Chicago	5h 19m including layover	Find flight from$92
4:15 pm — 11:56 pm	4:15 pm — 6:55 pm AA4553 American Airlines Pensacola — Charlotte 4h stop 10:55 pm — 11:56 pm AA483 American Airlines Charlotte — Chicago	7h 41m including layover	Find flight from$89
4:27 pm — 10:56 pm	4:27 pm — 8:00 pm AA4537 American Airlines Pensacola — Philadelphia 1h 25m stop 9:25 pm — 10:56 pm AA1680 American Airlines Philadelphia — Chicago	6h 29m including layover	Find flight from$92
5:47 pm — 0:02 am +1 day	5:47 pm — 8:30 pm AA3427 American Airlines Pensacola — Miami 1h 10m stop 9:40 pm — 0:02 am AA1627 American Airlines Miami — Chicago	6h 15m including layover	Find flight from$106
5:56 pm — 11:52 pm	5:56 pm — 8:45 pm AA3427 American Airlines Pensacola — Miami 45m stop 9:30 pm — 11:52 pm AA1627 American Airlines Miami — Chicago	5h 56m including layover	Find flight from$111
6:09 am — 10:53 am	6:09 am — 8:50 am AA5353 American Airlines Pensacola — Charlotte 50m stop 9:40 am — 10:53 am AA487 American Airlines Charlotte — Chicago	4h 44m including layover	Find flight from$89
6:09 am — 12:33 pm	6:09 am — 8:50 am AA5353 American Airlines Pensacola — Charlotte 2h 32m stop 11:22 am — 12:33 pm AA864 American Airlines Charlotte — Chicago	6h 24m including layover	Find flight from$89
7:18 am — 1:55 pm	7:18 am — 10:30 am AA5082 American Airlines Pensacola — Washington D.C. 2h 10m stop 12:40 pm — 1:55 pm AA985 American Airlines Washington D.C. — Chicago	6h 37m including layover	Find flight from$90
7:18 pm — 0:51 am +1 day	7:18 pm — 9:22 pm AA3877 American Airlines Pensacola — Dallas 1h 13m stop 10:35 pm — 0:51 am AA2585 American Airlines Dallas — Chicago	5h 33m including layover	Find flight from$90
9:14 am — 2:27 pm	9:14 am — 12:01 pm AA5237 American Airlines Pensacola — Charlotte 1h 16m stop 1:17 pm — 2:27 pm AA1650 American Airlines Charlotte — Chicago	5h 13m including layover	Find flight from$89
9:14 am — 3:46 pm	9:14 am — 12:01 pm AA5237 American Airlines Pensacola — Charlotte 2h 39m stop 2:40 pm — 3:46 pm AA1883 American Airlines Charlotte — Chicago	6h 32m including layover	Find flight from$91

Departure	Arrival	Flight Details	Flight Time	Price
		stop stop	including layover	Find flight from$

*Departure and arrival times are local. Last updated on 12/30/2024

Flight Information

There are 132 flights by American Airlines from Pensacola to Chicago every week with departures from Ellyson NAS, Pensacola Regional, Pensacola NAS, Saufley NAS. All flights arrive at Chicago FSS, Midway, O'Hare International, Chicago NAS, Merrill C Meigs (closed), Dupage County, Pal-Waukee.

Departures start from 10:35 am to 9:14 am. Nonstop flight is 4h 42m. The time difference between Pensacola and Chicago is 0h.

The fastest flight 4h 42m
Average flight time 9h 30m
The earliest flight 10:35 am
The latest flight 9:14 am
Distance 789 ml

The cheapest flight by American Airlines that our users were able to find is $89. This airfare is economy class on one-way AA5353 flight for December 6, 2018 leaving Pensacola Regional in Pensacola at 6:09 am, it includes all taxes and additional fees.

Find same flight?

American Airlines Airplanes on the Route

List of the most popular American Airlines airplanes flying from Pensacola to Chicago:

Canadair RJ 700

from $89

Find
Canadair 900

from $89

Find
Embraer 175

from $89

Find
Embraer RJ145

from $90

Find
Boeing MD-80

from $90

Find

Other Popular Airlines on the Route

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

Nonstop flights

There are 5 direct flights every day from Pensacola. Airlines and fares are below:

UA - United Airlines

from $173

Find

See more direct flights

Connecting Flights

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

UA - United Airlines

from $152

Find

See more connecting flights

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.