Cheap Flights from Chicago, IL to Pensacola, FL from $111

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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 $111, 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.

Find One-Way and Round-Trip Chicago to Pensacola 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: $111 (one-way), $190 (round-trip).

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Best Flights from Chicago to Pensacola Today

Take a look at the list of non stop flights and flights with layovers from Chicago to Pensacola with the lowest price of $111. The fastest direct flight takes 2h 15m and the fastest connecting – 4h 31m.

Price	Departure	Arrival	Flight Duration	Airline	Flight
from $213 Find flight	11:42 Chicago O'Hare International	14:06 Pensacola Pensacola Regional	2h 24m	United Airlines	UA3916
from $265 Find flight	11:29 Chicago O'Hare International	13:55 Pensacola Pensacola Regional	2h 26m	United Airlines	UA3809
from $111 Find flight	13:53 Chicago O'Hare International	18:27 Pensacola Pensacola Regional	4h 34m layover 0h 46m - Charlotte	American Airlines	AA864 AA5463
from $128 Find flight	15:46 Chicago O'Hare International	20:40 Pensacola Pensacola Regional	4h 54m layover 1h 8m - Charlotte	American Airlines	AA1195 AA5103

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*Departure and arrival times - local. Prices indicated for one-way flights. Information updated on September 14, 2025

Flight Schedule Chicago (Illinois) to Pensacola (Florida)

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	Flight Details	Flight Duration	Price
05:15 — 12:04	05:15 — 07:49 AA2429 American Airlines Chicago — Dallas 2h 31m stop 10:20 — 12:04 AA3324 American Airlines Dallas — Pensacola	6h 49m including layover	Find flight from$112
05:49 — 12:19	05:49 — 08:43 AA2523 American Airlines Chicago — Charlotte 2h 47m stop 11:30 — 12:19 AA5298 American Airlines Charlotte — Pensacola	6h 30m including layover	Find flight from$111
07:00 — 12:59	07:00 — 09:47 AA2378 American Airlines Chicago — Washington D.C. 1h 43m stop 11:30 — 12:59 AA3771 American Airlines Washington D.C. — Pensacola	5h 59m including layover	Find flight from$112
07:05 — 12:04	07:05 — 09:40 AA1625 American Airlines Chicago — Dallas 40m stop 10:20 — 12:04 AA3324 American Airlines Dallas — Pensacola	4h 59m including layover	Find flight from$112
07:05 — 14:38	07:05 — 09:40 AA1625 American Airlines Chicago — Dallas 3h 20m stop 13:00 — 14:38 AA2389 American Airlines Dallas — Pensacola	7h 33m including layover	Find flight from$112
07:24 — 12:19	07:24 — 10:24 AA2052 American Airlines Chicago — Charlotte 1h 6m stop 11:30 — 12:19 AA5298 American Airlines Charlotte — Pensacola	4h 55m including layover	Find flight from$111
08:50 — 15:43	08:50 — 11:51 AA593 American Airlines Chicago — Charlotte 3h 4m stop 14:55 — 15:43 AA4553 American Airlines Charlotte — Pensacola	6h 53m including layover	Find flight from$111
10:40 — 15:43	10:40 — 13:37 AA1668 American Airlines Chicago — Charlotte 1h 18m stop 14:55 — 15:43 AA4553 American Airlines Charlotte — Pensacola	5h 3m including layover	Find flight from$111
11:25 — 13:40	11:25 — 13:40 UA5803 United Airlines Chicago — Pensacola	2h 15m	Find flight from$281
11:29 — 13:55	11:29 — 13:55 UA3809 United Airlines Chicago — Pensacola	2h 26m	Find flight from$265
11:42 — 14:06	11:42 — 14:06 UA3916 United Airlines Chicago — Pensacola	2h 24m	Find flight from$213
12:11 — 18:27	12:11 — 15:10 AA2080 American Airlines Chicago — Charlotte 2h 31m stop 17:41 — 18:27 AA5463 American Airlines Charlotte — Pensacola	6h 16m including layover	Find flight from$111
13:53 — 18:27	13:53 — 16:55 AA864 American Airlines Chicago — Charlotte 46m stop 17:41 — 18:27 AA5463 American Airlines Charlotte — Pensacola	4h 34m including layover	Find flight from$111
13:53 — 20:42	13:53 — 16:55 AA864 American Airlines Chicago — Charlotte 3h stop 19:55 — 20:42 AA5103 American Airlines Charlotte — Pensacola	6h 49m including layover	Find flight from$111
15:46 — 20:42	15:46 — 18:46 AA1093 American Airlines Chicago — Charlotte 1h 9m stop 19:55 — 20:42 AA5103 American Airlines Charlotte — Pensacola	4h 56m including layover	Find flight from$111

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

*Departure and arrival times - local. Updated on September 14, 2025

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 $111. 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

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First class

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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 $ 111 . And the most expensive tickets are offered by American Airlines airline - from $ 429.

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 $213.

UA - United Airlines

from $213

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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 $111.

AA - American Airlines

from $111

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UA - United Airlines

from $128

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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 $111
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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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Airplanes

There are flights to Pensacola from Chicago by 2 airlines that use 8 aircraft brands. They range from huge modern airplanes to small-sized.

Boeing 737

from $111

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Airbus A321

from $111

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Boeing 787

from $112

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Boeing 757

from $131

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Canadair JET

from $213

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Airbus A320

from $239

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Airbus A319

from $268

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Boeing 767

from $268

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Top Domestic Destinations from Chicago

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

Chicago — Las Vegas

from $508

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from $61

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Top International Destinations from Chicago

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.

Chicago — London

from $60

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Chicago — Cancun

from $72

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Chicago — Toronto

from $73

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Chicago — Paris

from $61

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from $79

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Chicago — Hyderabad

from $73

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Chicago — Mexico City

from $76

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Chicago — Tokyo

from $60

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Chicago — Dublin

from $59

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Chicago — Mumbai

from $74

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How to book a plane ticket yourself?

Fill in the search parameters — cities of departure and destination, departure and return dates and click «Find flights»
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Click «Buy» when you are ready — our system will redirect you to the site that sells the selected flight ticket.
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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.
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