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Cheap flights from Chicago to Pensacola from $54

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago to Pensacola departing on 2/25. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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Find the cheapest flights from Chicago to Pensacola

Cheap round-trip flights

These are some of the best round-trip flight deals from Chicago to Pensacola that have been recently found on momondo from popular airlines, departing in the coming months.

Cheap one-way flights

Flying one-way? These are some of the best deals recently discovered on momondo for flights from Chicago to Pensacola.

Cheap last minute flights

Planning a quick getaway from Chicago to Pensacola? These are the last-minute flight deals available now.

Cheap direct flights

If you prefer a non-stop journey, check out our latest direct flight deals to Pensacola, so you can enjoy a seamless trip without layovers.

Cheap bus & train deals from Chicago to Pensacola

Find recent round-trip train or bus tickets from Chicago to Pensacola.

All round-trip flight deals to Pensacola

The cheapest plane tickets to Pensacola found on KAYAK recently.
7:25 am - 6:17 pmORD-PNS
10h 52m1 stop
7:17 pm - 12:32 amPNS-ORD
29h 15m1 stop
$118Frontier
Find Deal
Thu, Jan 23 - Thu, Jan 30
7:15 am - 6:17 pmMDW-PNS
11h 02m1 stop
7:17 pm - 12:17 amPNS-MDW
29h 00m1 stop
$118Frontier
Find Deal
Thu, Feb 6 - Mon, Feb 10
5:00 am - 4:09 pmORD-PNS
11h 09m1 stop
7:00 pm - 4:08 pmPNS-ORD
21h 08m1 stop
$184Spirit Airlines
Find Deal
Tue, Dec 31 - Wed, Jan 8
7:45 pm - 6:05 pmORD-PNS
22h 20m1 stop
5:15 pm - 4:06 pmPNS-ORD
22h 51m1 stop
$194Spirit Airlines
Find Deal
Mon, Dec 9 - Fri, Dec 13
10:53 am - 1:23 pmORD-PNS
2h 30mnonstop
2:31 pm - 5:03 pmPNS-ORD
2h 32mnonstop
$209United Airlines
Find Deal
Thu, Jan 23 - Thu, Jan 30
10:53 am - 1:23 pmORD-PNS
2h 30mnonstop
4:55 pm - 12:15 amPNS-ORD
7h 20m1 stop
$219United Airlines
Find Deal
Thu, Jan 23 - Thu, Jan 30
1:51 pm - 9:49 pmORD-PNS
7h 58m1 stop
7:26 am - 2:13 pmPNS-ORD
6h 47m1 stop
$228American Airlines
Find Deal
Wed, Feb 12 - Sun, Feb 16
6:00 am - 11:02 amMDW-PNS
5h 02m1 stop
6:05 pm - 10:20 pmPNS-MDW
4h 15m1 stop
$228Delta
Find Deal
Fri, Jan 3 - Fri, Jan 10
9:30 am - 2:27 pmORD-PNS
4h 57m1 stop
12:38 pm - 8:53 pmPNS-ORD
8h 15m1 stop
$238Delta
Find Deal
Tue, Mar 18 - Tue, Apr 1
5:02 am - 10:29 amORD-PNS
5h 27m1 stop
3:58 pm - 10:05 pmPNS-ORD
6h 07m1 stop
$268American Airlines
Find Deal
Fri, Jan 3 - Fri, Jan 3
6:50 am - 4:23 pmORD-PNS
9h 33m1 stop
$54Frontier
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Tue, Feb 25
7:05 am - 4:23 pmMDW-PNS
9h 18m1 stop
$54Frontier
Find Deal
Wed, Feb 26
5:00 am - 4:09 pmORD-PNS
11h 09m1 stop
$81Spirit Airlines
Find Deal
Wed, Dec 18
5:00 am - 4:09 pmORD-PNS
11h 09m1 stop
$91Spirit Airlines
Find Deal
Wed, Jan 1
10:53 am - 1:23 pmORD-PNS
2h 30mnonstop
$105United Airlines
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Tue, Jan 7
5:45 am - 11:27 amORD-PNS
5h 42m1 stop
$114Delta
Find Deal
Tue, Feb 18
6:00 am - 10:06 amMDW-PNS
4h 06m1 stop
$114Delta
Find Deal
Tue, Dec 17
11:07 am - 1:31 pmORD-PNS
2h 24mnonstop
$125United Airlines
Find Deal
Mon, Feb 17
1:57 pm - 9:10 pmORD-PNS
7h 13m1 stop
$134American Airlines
Find Deal
Fri, Dec 13
8:14 am - 4:11 pmORD-PNS
7h 57m2 stops
$139American Airlines
Find Deal
Sat, Feb 22
11:51 am - 6:05 pmORD-PNS
6h 14m1 stop
7:10 pm - 11:38 pmPNS-ORD
28h 28m2 stops
$315Spirit Airlines
Find Deal
Mon, Nov 25 - Mon, Dec 2
6:00 am - 3:14 pmORD-PNS
33h 14m2 stops
7:10 pm - 11:38 pmPNS-ORD
28h 28m2 stops
Mon, Nov 25 - Mon, Dec 2
4:48 pm - 7:58 pmORD-PNS
27h 10m1 stop
8:58 pm - 12:15 pmPNS-ORD
15h 17m1 stop
$338Frontier
Find Deal
Fri, Nov 22 - Sun, Nov 24
9:48 pm - 7:58 pmMDW-PNS
22h 10m1 stop
8:58 pm - 1:40 pmPNS-MDW
16h 42m1 stop
$338Frontier
Find Deal
Fri, Nov 22 - Sun, Nov 24
3:19 pm - 8:22 pmMDW-PNS
5h 03m1 stop
3:12 pm - 9:46 pmPNS-MDW
6h 34m1 stop
$533Delta
Find Deal
Thu, Nov 21 - Sun, Nov 24
11:14 am - 6:10 pmORD-PNS
6h 56m1 stop
2:20 pm - 4:58 pmPNS-ORD
2h 38mnonstop
$549United Airlines
Find Deal
Sat, Nov 23 - Mon, Nov 25
10:55 am - 1:35 pmORD-PNS
2h 40mnonstop
7:55 pm - 8:03 pmPNS-ORD
24h 08m1 stop
$572United Airlines
Find Deal
Fri, Nov 22 - Mon, Dec 2
6:00 am - 10:15 amMDW-PNS
4h 15m1 stop
5:37 pm - 9:46 pmPNS-MDW
4h 09m1 stop
$593Delta
Find Deal
Fri, Nov 22 - Mon, Dec 2
1:54 pm - 7:27 pmORD-PNS
5h 33m1 stop
5:25 am - 10:48 amPNS-ORD
5h 23m1 stop
$972American Airlines
Find Deal
Mon, Nov 25 - Fri, Nov 29
12:15 pm - 7:27 pmORD-PNS
7h 12m1 stop
5:25 am - 10:48 amPNS-ORD
5h 23m1 stop
$1,077American Airlines
Find Deal
Mon, Nov 25 - Sat, Nov 30
10:53 am - 1:23 pmORD-PNS
2h 30mnonstop
2:31 pm - 5:03 pmPNS-ORD
2h 32mnonstop
$209United Airlines
Find Deal
Thu, Jan 23 - Thu, Jan 30
11:07 am - 1:31 pmORD-PNS
2h 24mnonstop
2:33 pm - 5:10 pmPNS-ORD
2h 37mnonstop
$233United Airlines
Find Deal
Tue, Feb 18 - Mon, Feb 24
10:53 am - 1:23 pmORD-PNS
2h 30mnonstop
2:36 pm - 5:08 pmPNS-ORD
2h 32mnonstop
$239United Airlines
Find Deal
Fri, Jan 17 - Sat, Jan 18
10:50 am - 1:20 pmORD-PNS
2h 30mnonstop
2:36 pm - 5:08 pmPNS-ORD
2h 32mnonstop
$279United Airlines
Find Deal
Sat, Jan 4 - Sat, Jan 11
10:53 am - 1:23 pmORD-PNS
2h 30mnonstop
2:36 pm - 5:08 pmPNS-ORD
2h 32mnonstop
$299United Airlines
Find Deal
Wed, Jan 29 - Sat, Feb 1
10:50 am - 1:20 pmORD-PNS
2h 30mnonstop
2:36 pm - 5:08 pmPNS-ORD
2h 32mnonstop
$309United Airlines
Find Deal
Sat, Jan 4 - Sat, Jan 11
7:10 am - 9:43 amORD-PNS
2h 33mnonstop
1:56 pm - 4:26 pmPNS-ORD
2h 30mnonstop
$312United Airlines
Find Deal
Sat, Mar 15 - Mon, Mar 31
10:50 am - 1:20 pmORD-PNS
2h 30mnonstop
2:31 pm - 5:03 pmPNS-ORD
2h 32mnonstop
$334United Airlines
Find Deal
Tue, Dec 31 - Wed, Jan 8
9:25 am - 11:40 amMDW-PNS
2h 15mnonstop
2:45 pm - 5:00 pmPNS-MDW
2h 15mnonstop
$448Southwest
Find Deal
Sun, Mar 16 - Sat, Mar 22
11:00 am - 1:10 pmMDW-PNS
2h 10mnonstop
4:15 pm - 6:25 pmPNS-MDW
2h 10mnonstop
$500Southwest
Find Deal
Sat, Apr 5 - Sat, Apr 12

Frontier flights from Chicago to Pensacola

Our best Frontier deals on Chicago to Pensacola flight tickets
Frontier
Feb 6
MDW7:15 amChicago Midway
11h 02m
1 stop
PNS6:17 pmPensacola
Feb 10
PNS7:17 pmPensacola
29h 00m
1 stop
MDW12:17 amChicago Midway
Frontier
Jan 10
MDW7:15 amChicago Midway
11h 20m
1 stop
PNS6:35 pmPensacola
Jan 13
PNS7:17 pmPensacola
28h 56m
1 stop
MDW12:13 amChicago Midway
Frontier
Feb 22
ORD6:30 pmChicago O'Hare Intl
23h 57m
1 stop
PNS6:27 pmPensacola
Feb 26
PNS5:23 pmPensacola
20h 02m
1 stop
ORD1:25 pmChicago O'Hare Intl

Southwest flights from Chicago to Pensacola

Our best Southwest deals on Chicago to Pensacola flight tickets
Southwest
Feb 10
ORD7:30 amChicago O'Hare Intl
7h 35m
2 stops
PNS3:05 pmPensacola
Feb 16
PNS7:35 amPensacola
5h 25m
1 stop
ORD1:00 pmChicago O'Hare Intl
Southwest
Feb 12
MDW6:25 amChicago Midway
4h 35m
1 stop
PNS11:00 amPensacola
Feb 16
PNS6:05 pmPensacola
6h 20m
1 stop
MDW12:25 amChicago Midway
Southwest
Feb 10
MDW6:10 amChicago Midway
10h 05m
2 stops
PNS4:15 pmPensacola
Feb 16
PNS6:05 pmPensacola
6h 20m
1 stop
MDW12:25 amChicago Midway

See travel insights to Pensacola from

How to get the cheapest flight ticket from Chicago to Pensacola

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest month to fly from Chicago to Pensacola?

January. The cheapest time of year to fly to Pensacola from Chicago is January. Most expensive is March

What is the cheapest day to depart Chicago for Pensacola?

Tuesday. The cheapest day of the week is typically Tuesday. The most expensive is typically Monday

When is the cheapest time to fly from Chicago to Pensacola?

In the evening. Chicago to Pensacola flights are approximately 45% more expensive in the morning than in the evening

What is the cheapest Chicago to Pensacola flight route?

Chicago Midway - Pensacola. Fly from Chicago Midway to Pensacola for the best Chicago - Pensacola flight prices

How far in advance should you book Chicago to Pensacola flights?

36 days before. The cheapest time to buy a flight from Chicago to Pensacola is approximately 36 days to departure

What cabin class options are available on Chicago to Pensacola flights?

There are 2 cabin classes available to choose from on Chicago to Pensacola flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Can stopping save me money on Chicago to Pensacola flights?

You could potentially save up to 48% on your flight if you consider stops on a Chicago to Pensacola flight.

How have Chicago to Pensacola flight prices changed over time?

As of November 2024, prices for Chicago to Pensacola flights are approximately 50% cheaper when compared to flights at the same time last year.

What is the typical price of a round-trip flight between Chicago and Pensacola?


When to book flights from Chicago to Pensacola

Are you open to changing your travel dates? Check out the ideal times to fly from Chicago to Pensacola according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Chicago to Pensacola (CHI to PNS) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago to Pensacola

Best Price Found

$54

Fastest flight time

2h 05m

Direct flights

Every day

Airports in Pensacola

1 airport
The best one-way flight to Pensacola from Chicago in the past 72 hours is $54. The best round-trip flight deal from Chicago to Pensacola found on momondo in the last 72 hours is $118.
The fastest flight from Chicago to Pensacola takes 2h 05m
Direct flights go from Chicago to Pensacola every day.
There is 1 airport near Pensacola: Pensacola (PNS)

  • How far is Chicago to Pensacola by plane?

    The distance between Chicago and Pensacola is about 791.2 mi. A reasonable flight in good conditions will take 2h 05m.

  • When did momondo last update prices for flights from Chicago to Pensacola Airport?

    Prices for flights from Chicago to Pensacola Airport refresh daily.

  • How many operators does momondo search for flights from Chicago to Pensacola Airport?

  • How old do you have to be to fly from Chicago to Pensacola Airport?

    The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Chicago to Pensacola Airport.

  • What documentation or ID do you need to fly to Pensacola Airport?

    The travel and health documents required for your trip to Pensacola Airport can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Pensacola Airport. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

  • What is the most popular plane model from Chicago to Pensacola?

  • What is the most popular airline from Chicago to Pensacola?


Best airlines flying from Chicago to Pensacola

Compare and see reviews for airlines that fly from Chicago to Pensacola with momondo
Airline
Rating
Free Cancellation
Price
Spirit AirlinesPriceFrom $100Free CancellationRating
6.3
8,174 reviews
Search Spirit Airlines flights
SouthwestPriceFrom $143Free CancellationRating
8.1
5,014 reviews
Search Southwest flights
DeltaPriceFrom $204Free CancellationRating
8.0
8,756 reviews
Search Delta flights
American AirlinesPriceFrom $204Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
United AirlinesPriceFrom $231Free CancellationRating
7.4
9,171 reviews
Search United Airlines flights
  • United Airlines Flights From Chicago to Pensacola

    United Airlines is one of the most popular airlines flying from Chicago to Pensacola, operating 5 flights/week on average for this route. A good United Airlines flight deal for Chicago to Pensacola starts from $231 round-trip, up to an average price of $416. Our users have rated United Airlines at 7.4/10.


Why use momondo?

Why should I use momondo to find a flight deal from Chicago to Pensacola?

momondo compares prices from hundreds of airlines and agents so you can find and book the best deal on flights from Chicago to Pensacola. Millions of users trust and use momondo every year so you are in good hands.

Can I find flights from Chicago to Pensacola with flexible booking policies on momondo?

All flight searches from Chicago to Pensacola on momondo can be filtered to show those which offer flexible booking policies.

How can momondo help me find flights from Chicago to Pensacola?

momondo helps you find the best flight between Chicago and Pensacola by providing filters to narrow your choice of flights to those matching your criteria. You can select flights based on numerous factors such as price, departure and landing times, airport and airline.

I’m not ready to book a flight from Chicago to Pensacola right now. Can momondo alert me if prices change?

If you are simply researching potential flights to Pensacola, momondo offers a useful price alert feature which will track prices for flights to Pensacola from Chicago and alert you when they change.


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