Cheap Flights from Pensacola, FL to Chicago, IL from $97

Return flight: Chicago – Pensacola

On Cheapflightsplus.com you will find 5 direct and 136 connecting flights from Pensacola to Chicago. You can compare airfare deals from 2 airlines and multiple travel sites from $97, book and save on cheap plane tickets and last minute offers. Also check out PNS-CHI flight schedule to find best flight time, convenient departure and arrival airports.

Find One-Way and Round-Trip Pensacola to Chicago Flight Deals

To find the cheapest one way airline ticket select the date with the lowest price on the calendar below and click «Find Flights». To search for round-trip flight deals click on the link «Check prices for return flights» and select the date of the return flight. Cheapest flights in November: $97 (one-way), $166 (round-trip).
Direct flights
  • Check to choose departure date Check to choose departure date
Check prices for return flight
Find flights
Full flight schedule will help you in detecting at what time planes fly from Pensacola to Chicago. 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 Arrival Flight Details Flight Duration Price
14:14 — 16:49
14:14 — 16:49 UA3953 United Airlines
Pensacola — Chicago
2h 35m
Find flight
from$325
14:16 — 16:51
14:16 — 16:51 UA5800 United Airlines
Pensacola — Chicago
2h 35m
Find flight
from$252
14:24 — 16:57
14:24 — 16:57 UA3401 United Airlines
Pensacola — Chicago
2h 33m
Find flight
from$235
14:27 — 17:04
14:27 — 17:04 UA3937 United Airlines
Pensacola — Chicago
2h 37m
Find flight
from$235
14:29 — 17:04
14:29 — 17:04 UA3856 United Airlines
Pensacola — Chicago
2h 35m
Find flight
from$188
06:09 — 10:53
06:09 — 08:50 AA5353 American Airlines
Pensacola — Charlotte
50m stop
09:40 — 10:53 AA487 American Airlines
Charlotte — Chicago
4h 44m
including layover
Find flight
from$97
06:09 — 12:33
06:09 — 08:50 AA5353 American Airlines
Pensacola — Charlotte
2h 32m stop
11:22 — 12:33 AA864 American Airlines
Charlotte — Chicago
6h 24m
including layover
Find flight
from$97
07:08 — 12:14
07:08 — 09:15 AA2453 American Airlines
Pensacola — Dallas
40m stop
09:55 — 12:14 AA1258 American Airlines
Dallas — Chicago
5h 6m
including layover
Find flight
from$98
07:08 — 12:56
07:08 — 09:15 AA2453 American Airlines
Pensacola — Dallas
1h 16m stop
10:31 — 12:56 AA319 American Airlines
Dallas — Chicago
5h 48m
including layover
Find flight
from$98
08:25 — 14:24
08:25 — 11:15 UA3071 United Airlines
Pensacola — Tampa
1h 25m stop
12:40 — 14:24 UA2191 United Airlines
Tampa — Chicago
5h 59m
including layover
Find flight
from$212
09:14 — 14:27
09:14 — 12:01 AA5237 American Airlines
Pensacola — Charlotte
1h 16m stop
13:17 — 14:27 AA1650 American Airlines
Charlotte — Chicago
5h 13m
including layover
Find flight
from$97
09:14 — 15:46
09:14 — 12:01 AA5237 American Airlines
Pensacola — Charlotte
2h 39m stop
14:40 — 15:46 AA1883 American Airlines
Charlotte — Chicago
6h 32m
including layover
Find flight
from$99
10:38 — 16:30
10:38 — 13:20 AA3733 American Airlines
Pensacola — Miami
51m stop
14:11 — 16:30 AA2361 American Airlines
Miami — Chicago
5h 52m
including layover
Find flight
from$98
10:38 — 18:43
10:38 — 13:20 AA3733 American Airlines
Pensacola — Miami
2h 59m stop
16:19 — 18:43 AA2303 American Airlines
Miami — Chicago
8h 5m
including layover
Find flight
from$98
11:50 — 16:57
11:50 — 13:38 UA6228 United Airlines
Pensacola — Houston
42m stop
14:20 — 16:57 UA1899 United Airlines
Houston — Chicago
5h 7m
including layover
Find flight
from$170
11:51 — 19:27
11:51 — 13:38 UA6217 United Airlines
Pensacola — Houston
3h 8m stop
16:46 — 19:27 UA2153 United Airlines
Houston — Chicago
7h 36m
including layover
Find flight
from$165
12:48 — 20:18
12:48 — 15:59 AA3822 American Airlines
Pensacola — Washington D.C.
3h 1m stop
19:00 — 20:18 AA1015 American Airlines
Washington D.C. — Chicago
7h 30m
including layover
Find flight
from$100
12:49 — 17:46
12:49 — 15:30 AA5298 American Airlines
Pensacola — Charlotte
1h 1m stop
16:31 — 17:46 AA1017 American Airlines
Charlotte — Chicago
4h 57m
including layover
Find flight
from$114
13:33 — 18:59
13:33 — 15:36 AA3488 American Airlines
Pensacola — Dallas
56m stop
16:32 — 18:59 AA2418 American Airlines
Dallas — Chicago
5h 26m
including layover
Find flight
from$115
13:33 — 20:49
13:33 — 15:36 AA3488 American Airlines
Pensacola — Dallas
2h 54m stop
18:30 — 20:49 AA2520 American Airlines
Dallas — Chicago
7h 16m
including layover
Find flight
from$115
15:30 — 23:05
15:30 — 17:34 AA2389 American Airlines
Pensacola — Dallas
3h 11m stop
20:45 — 23:05 AA1294 American Airlines
Dallas — Chicago
7h 35m
including layover
Find flight
from$98
15:30 — 20:49
15:30 — 17:34 AA2389 American Airlines
Pensacola — Dallas
56m stop
18:30 — 20:49 AA2520 American Airlines
Dallas — Chicago
5h 19m
including layover
Find flight
from$100
16:15 — 23:56
16:15 — 18:55 AA4553 American Airlines
Pensacola — Charlotte
4h stop
22:55 — 23:56 AA483 American Airlines
Charlotte — Chicago
7h 41m
including layover
Find flight
from$97
16:27 — 22:56
16:27 — 20:00 AA4537 American Airlines
Pensacola — Philadelphia
1h 25m stop
21:25 — 22:56 AA1680 American Airlines
Philadelphia — Chicago
6h 29m
including layover
Find flight
from$100
17:43 — 16:30
+1 day
17:43 — 20:30 AA3427 American Airlines
Pensacola — Miami
17h 41m stop
14:11 — 16:30 AA2367 American Airlines
Miami — Chicago
22h 47m
including layover
Find flight
from$225
17:47 — 00:02
+1 day
17:47 — 20:30 AA3427 American Airlines
Pensacola — Miami
1h 10m stop
21:40 — 00:02 AA1627 American Airlines
Miami — Chicago
6h 15m
including layover
Find flight
from$115
18:50 — 00:09
+1 day
18:50 — 20:35 UA6036 United Airlines
Pensacola — Houston
1h 6m stop
21:41 — 00:09 UA1854 United Airlines
Houston — Chicago
5h 19m
including layover
Find flight
from$170
18:57 — 23:56
18:57 — 21:37 AA5463 American Airlines
Pensacola — Charlotte
1h 18m stop
22:55 — 23:56 AA483 American Airlines
Charlotte — Chicago
4h 59m
including layover
Find flight
from$97
19:18 — 00:51
+1 day
19:18 — 21:22 AA3877 American Airlines
Pensacola — Dallas
1h 13m stop
22:35 — 00:51 AA2585 American Airlines
Dallas — Chicago
5h 33m
including layover
Find flight
from$98
*Departure and arrival times - local. Updated on May 20, 2024

Flight Information

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

Distance between Pensacola and Chicago is 1269 miles. Time difference between the cities is 0h. Airplanes depart 06:02 to 19:18 from 4 Pensacola airports and arrive 06:02 to 19:18 to 7 Chicago airports. Average flight time is 2h 35m.

  • The fastest flight 2h 33m
  • Average flight time 2h 35m
  • The earliest flight 06:02
  • The latest flight 19:18
  • Distance 789 ml

What is the lowest airfare Pensacola to Chicago?

The cheapest plane ticket found by our users is $97. This airfare is for economy class on one-way AA5353 flight by American Airlines for December 6, 2018 which leaves Pensacola Regional in Pensacola at 06:09 am and arrives at Chicago O'Hare International at 10:53.

Economy class
$97
Find
Business class
?
Find
First class
?
Find

Popular Airlines on the Route

The flight Pensacola — Chicago is served by 2 regular airlines . Most of the flights on this route are operated by American Airlines - 87 departures per week at the price of from $ 97 . And the most expensive tickets are offered by American Airlines airline - from $ 649.

Direct flights

There are 5 nonstop flights on the route. The fastest direct flight is UA3401 by United Airlines takes 2h 33m and the cheapest is AA5353 by American Airlines for $188.

See more direct flights

Connecting Flights

There are 136 flights with layovers on the route. The fastest connecting flight is AA5353 by American Airlines takes 4h 44m and the cheapest is AA5353 by American Airlines for $97.

See more connecting flights

Airports

You can fly from Pensacola to Chicago from 4 airports (Ellyson NAS, Pensacola Regional, Pensacola NAS, Saufley NAS).

Pensacola airports

  • Ellyson NAS-NDP
    Find
  • Pensacola Regional-PNS
    from $97
    Find
  • Pensacola NAS-NPA
    Find
  • Saufley NAS-NUN
    Find

Chicago airports

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

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.

Back