Cheap Flights from Pensacola, FL to Chicago, IL from $91

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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 $91, 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: $91 (one-way), $156 (round-trip).

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Best Flights from Pensacola to Chicago Today

Take a look at the list of non stop flights and flights with layovers from Pensacola to Chicago with the lowest price of $91. The fastest direct flight takes 2h 33m and the fastest connecting – 4h 44m.

Price	Departure	Arrival	Flight Duration	Airline	Flight
from $177 Find flight	14:29 Pensacola Pensacola Regional	17:04 Chicago O'Hare International	2h 35m	United Airlines	UA3856
from $221 Find flight	14:24 Pensacola Pensacola Regional	16:57 Chicago O'Hare International	2h 33m	United Airlines	UA3401
from $306 Find flight	14:14 Pensacola Pensacola Regional	16:49 Chicago O'Hare International	2h 35m	United Airlines	UA3953
from $91 Find flight	06:09 Pensacola Pensacola Regional	10:53 Chicago O'Hare International	4h 44m layover 0h 50m - Charlotte	American Airlines	AA5353 AA487
from $91 Find flight	18:57 Pensacola Pensacola Regional	23:56 Chicago O'Hare International	4h 59m layover 1h 18m - Charlotte	American Airlines	AA5463 AA483
from $91 Find flight	09:14 Pensacola Pensacola Regional	14:27 Chicago O'Hare International	5h 13m layover 1h 16m - Charlotte	American Airlines	AA5237 AA1650
from $91 Find flight	16:15 Pensacola Pensacola Regional	23:56 Chicago O'Hare International	7h 41m layover 4h 0m - Charlotte	American Airlines	AA4553 AA483
from $92 Find flight	07:18 Pensacola Pensacola Regional	12:17 Chicago O'Hare International	4h 59m layover 0h 33m - Washington D.C.	American Airlines	AA5082 AA1033
from $92 Find flight	07:08 Pensacola Pensacola Regional	12:14 Chicago O'Hare International	5h 6m layover 0h 40m - Dallas	American Airlines	AA2453 AA1258
from $92 Find flight	19:18 Pensacola Pensacola Regional	00:51+1 день Chicago O'Hare International	5h 33m layover 1h 13m - Dallas	American Airlines	AA3877 AA2585
from $92 Find flight	07:08 Pensacola Pensacola Regional	12:56 Chicago O'Hare International	5h 48m layover 1h 16m - Dallas	American Airlines	AA2453 AA319
from $92 Find flight	06:03 Pensacola Pensacola Regional	12:19 Chicago O'Hare International	6h 16m layover 1h 13m - Miami	American Airlines	AA3508 AA2796
from $92 Find flight	07:18 Pensacola Pensacola Regional	13:55 Chicago O'Hare International	6h 37m layover 2h 10m - Washington D.C.	American Airlines	AA5082 AA985
from $92 Find flight	15:30 Pensacola Pensacola Regional	23:05 Chicago O'Hare International	7h 35m layover 3h 11m - Dallas	American Airlines	AA2389 AA1294
from $107 Find flight	12:49 Pensacola Pensacola Regional	17:46 Chicago O'Hare International	4h 57m layover 1h 1m - Charlotte	American Airlines	AA5298 AA1017
from $125 Find flight	10:38 Pensacola Pensacola Regional	16:30 Chicago O'Hare International	5h 52m layover 0h 51m - Miami	American Airlines	AA3733 AA2367

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*Departure and arrival times - local. Prices indicated for one-way flights. Information updated on November 15, 2024

Flight Schedule Pensacola (Florida) to Chicago (Illinois)

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	Flight Details	Flight Duration	Price
14:14 — 16:49	14:14 — 16:49 UA3953 United Airlines Pensacola — Chicago	2h 35m	Find flight from$306
14:16 — 16:51	14:16 — 16:51 UA5800 United Airlines Pensacola — Chicago	2h 35m	Find flight from$237
14:24 — 16:57	14:24 — 16:57 UA3401 United Airlines Pensacola — Chicago	2h 33m	Find flight from$221
14:27 — 17:04	14:27 — 17:04 UA3937 United Airlines Pensacola — Chicago	2h 37m	Find flight from$221
14:29 — 17:04	14:29 — 17:04 UA3856 United Airlines Pensacola — Chicago	2h 35m	Find flight from$177
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$91
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$91
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$92
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$92
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$199
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$91
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$93
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$92
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$92
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$160
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$155
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$94
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$107
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$109
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$109
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$92
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$94
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$91
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$94
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$212
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$109
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$160
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$91
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$92

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

*Departure and arrival times - local. Updated on November 15, 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 $91. 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

$91

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First class

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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 $ 91 . And the most expensive tickets are offered by American Airlines airline - from $ 610.

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 $177.

UA - United Airlines

from $177

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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 $91.

AA - American Airlines

from $91

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UA - United Airlines

from $155

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Airports

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

Pensacola airports

Ellyson NAS-NDP

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Pensacola Regional-PNS

from $91
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Pensacola NAS-NPA

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Saufley NAS-NUN

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Chicago airports

O'Hare International-ORD

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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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Airplanes

There are flights to Chicago from Pensacola by 2 airlines that use 9 aircraft brands. They range from huge modern airplanes to small-sized.

Canadair RJ 700

from $91

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Canadair 900

from $91

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Embraer 175

from $91

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Embraer RJ145

from $92

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Boeing MD-80

from $92

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Embraer RJ135

from $160

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Canadair JET

from $177

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SAAB SF 340A

from $197

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Embraer 170

from $221

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Top Domestic Destinations from Pensacola

You may also consider searching for discounted plane tickets to some other popular places from Pensacola within United States.

Pensacola — Chicago

from $74

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Pensacola — Denver

from $73

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Pensacola — Dallas

from $69

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Pensacola — Las Vegas

from $73

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Pensacola — Pittsburgh

from $79

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Pensacola — Austin

from $55

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Pensacola — Phoenix

from $76

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Pensacola — Miami

from $54

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Pensacola — Seattle

from $78

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Pensacola — Orlando

from $71

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Top International Destinations from Pensacola

Our state-of-the art metasearch will definitely provide you with the best airfare on international flights. We’re proud to partner with many reliable travel suppliers located outside the US what gives us an opportunity to offer the most competitive prices on far destinations.

Pensacola — Manchester

from $67

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How to book a plane ticket yourself?

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