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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
$127Frontier
Find Deal
Sun, Jan 26 - Thu, Jan 30
7:15 am - 6:17 pmMDW-PNS
11h 02m1 stop
7:17 pm - 12:17 amPNS-MDW
29h 00m1 stop
$127Frontier
Find Deal
Sun, Jan 26 - Thu, Jan 30
8:00 am - 1:23 pmORD-PNS
5h 23m1 stop
10:20 am - 8:13 pmPNS-ORD
9h 53m1 stop
$174Spirit Airlines
Find Deal
Tue, Jan 21 - Mon, Jan 27
8:00 am - 1:23 pmORD-PNS
5h 23m1 stop
2:18 pm - 4:10 pmPNS-ORD
25h 52m1 stop
$182Spirit Airlines
Find Deal
Wed, Jan 15 - Wed, Jan 22
11:07 am - 1:31 pmORD-PNS
2h 24mnonstop
2:33 pm - 5:10 pmPNS-ORD
2h 37mnonstop
$209United Airlines
Find Deal
Tue, Feb 18 - Tue, Mar 4
7:35 am - 1:54 pmORD-PNS
6h 19m1 stop
2:31 pm - 5:03 pmPNS-ORD
2h 32mnonstop
$219United Airlines
Find Deal
Thu, Jan 9 - Tue, Feb 4
5:10 am - 10:33 amORD-PNS
5h 23m1 stop
5:30 am - 12:30 pmPNS-ORD
7h 00m1 stop
$228American Airlines
Find Deal
Thu, Jan 16 - Tue, Jan 21
6:00 am - 11:27 amMDW-PNS
5h 27m1 stop
9:41 am - 4:21 pmPNS-MDW
6h 40m1 stop
$228Delta
Find Deal
Tue, Jan 21 - Tue, Jan 28
1:33 pm - 9:39 pmORD-PNS
8h 06m1 stop
5:30 am - 10:24 amPNS-ORD
4h 54m1 stop
$238American Airlines
Find Deal
Mon, Jan 6 - Sat, Jan 11
1:05 pm - 6:04 pmMDW-PNS
4h 59m1 stop
1:59 pm - 6:00 pmPNS-MDW
4h 01m1 stop
$238Delta
Find Deal
Sat, May 10 - Sat, May 17
6:50 am - 4:23 pmORD-PNS
9h 33m1 stop
$54Frontier
Find Deal
Tue, Feb 25
7:05 am - 4:23 pmMDW-PNS
9h 18m1 stop
$54Frontier
Find Deal
Tue, Mar 4
8:00 am - 1:23 pmORD-PNS
5h 23m1 stop
$80Spirit Airlines
Find Deal
Tue, Jan 21
8:00 am - 1:23 pmORD-PNS
5h 23m1 stop
$82Spirit Airlines
Find Deal
Wed, Jan 22
7:05 am - 1:43 pmORD-PNS
6h 38m1 stop
$114Delta
Find Deal
Tue, Jan 21
6:00 am - 11:27 amMDW-PNS
5h 27m1 stop
$114Delta
Find Deal
Mon, Jan 20
8:00 am - 10:24 amORD-PNS
2h 24mnonstop
$135American Airlines
Find Deal
Sat, Jun 14
5:29 am - 9:44 amORD-PNS
4h 15m1 stop
$144American Airlines
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Sun, Apr 27
10:45 am - 1:12 pmORD-PNS
2h 27mnonstop
$204United Airlines
Find Deal
Sun, Apr 27
10:53 am - 1:23 pmORD-PNS
2h 30mnonstop
$214United Airlines
Find Deal
Sun, Jan 26
10:05 am - 5:25 pmORD-PNS
7h 20m1 stop
6:00 am - 2:00 pmPNS-ORD
8h 00m1 stop
$333American Airlines
Find Deal
Fri, Dec 20 - Wed, Jan 1
5:35 pm - 11:53 pmORD-PNS
6h 18m1 stop
4:33 pm - 9:52 pmPNS-ORD
5h 19m1 stop
$358American Airlines
Find Deal
Sun, Dec 22 - Thu, Dec 26
6:55 am - 11:55 amORD-PNS
29h 00m1 stop
9:37 pm - 7:34 pmPNS-ORD
21h 57m1 stop
$400Frontier
Find Deal
Tue, Dec 24 - Sat, Jan 4
5:35 pm - 11:53 pmORD-PNS
6h 18m1 stop
5:30 am - 11:01 amPNS-ORD
5h 31m1 stop
$408American Airlines
Find Deal
Sun, Dec 22 - Sat, Dec 28
8:57 am - 4:15 pmORD-PNS
7h 18m1 stop
2:21 pm - 4:53 pmPNS-ORD
2h 32mnonstop
$559United Airlines
Find Deal
Fri, Dec 20 - Wed, Jan 1
11:05 am - 7:10 pmORD-PNS
8h 05m1 stop
2:21 pm - 4:53 pmPNS-ORD
2h 32mnonstop
$623United Airlines
Find Deal
Sun, Dec 22 - Thu, Dec 26
6:00 am - 11:02 amMDW-PNS
5h 02m1 stop
5:40 pm - 10:06 pmPNS-MDW
4h 26m1 stop
$668Delta
Find Deal
Sun, Dec 22 - Fri, Dec 27
8:14 pm - 1:53 pmORD-PNS
17h 39m2 stops
7:00 pm - 12:33 amPNS-ORD
29h 33m3 stops
$673Spirit Airlines
Find Deal
Sun, Dec 22 - Sat, Dec 28
5:03 pm - 11:02 pmMDW-PNS
5h 59m1 stop
5:40 pm - 10:06 pmPNS-MDW
4h 26m1 stop
$728Delta
Find Deal
Sun, Dec 22 - Fri, Dec 27
9:15 pm - 4:09 pmORD-PNS
18h 54m2 stops
7:00 pm - 10:07 amPNS-ORD
15h 07m2 stops
$825Spirit Airlines
Find Deal
Tue, Dec 24 - Sat, Jan 4
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
2:31 pm - 5:03 pmPNS-ORD
2h 32mnonstop
$279United Airlines
Find Deal
Tue, Jan 21 - Tue, Jan 28
10:51 am - 1:21 pmORD-PNS
2h 30mnonstop
2:36 pm - 5:08 pmPNS-ORD
2h 32mnonstop
$299United Airlines
Find Deal
Sun, Jan 5 - Sat, Jan 11
7:10 am - 9:43 amORD-PNS
2h 33mnonstop
2:10 pm - 4:48 pmPNS-ORD
2h 38mnonstop
$314United Airlines
Find Deal
Sat, Mar 15 - Sat, Mar 22
10:53 am - 1:23 pmORD-PNS
2h 30mnonstop
2:31 pm - 5:03 pmPNS-ORD
2h 32mnonstop
$339United Airlines
Find Deal
Sun, Feb 2 - Sun, Feb 9
11:10 am - 1:40 pmORD-PNS
2h 30mnonstop
2:31 pm - 5:03 pmPNS-ORD
2h 32mnonstop
$369United Airlines
Find Deal
Sat, Feb 1 - Tue, Feb 4
10:53 am - 1:23 pmORD-PNS
2h 30mnonstop
2:31 pm - 5:03 pmPNS-ORD
2h 32mnonstop
$397United Airlines
Find Deal
Mon, Jan 13 - Thu, Jan 16
1:30 pm - 3:35 pmMDW-PNS
2h 05mnonstop
4:15 pm - 6:25 pmPNS-MDW
2h 10mnonstop
$398Southwest
Find Deal
Sat, May 10 - Sat, May 17
11:10 am - 1:40 pmORD-PNS
2h 30mnonstop
2:31 pm - 5:03 pmPNS-ORD
2h 32mnonstop
$399United Airlines
Find Deal
Sat, Feb 1 - Mon, Feb 10
11:00 am - 1:10 pmMDW-PNS
2h 10mnonstop
2:45 pm - 5:00 pmPNS-MDW
2h 15mnonstop
$470Southwest
Find Deal
Sat, Mar 15 - Sat, Mar 22

Frontier flights from Chicago to Pensacola

Our best Frontier deals on Chicago to Pensacola flight tickets
Frontier
Jan 26
ORD7:25 amChicago O'Hare Intl
10h 52m
1 stop
PNS6:17 pmPensacola
Jan 30
PNS7:17 pmPensacola
29h 15m
1 stop
ORD12:32 amChicago O'Hare Intl
Frontier
Feb 24
MDW6:40 amChicago Midway
11h 47m
1 stop
PNS6:27 pmPensacola
Mar 4
PNS5:23 pmPensacola
6h 54m
1 stop
MDW12:17 amChicago Midway
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

American Airlines flights from Chicago to Pensacola

Our best American Airlines deals on Chicago to Pensacola flight tickets
American Airlines
Jan 16
ORD5:10 amChicago O'Hare Intl
5h 23m
1 stop
PNS10:33 amPensacola
Jan 21
PNS5:30 amPensacola
7h 00m
1 stop
ORD12:30 pmChicago O'Hare Intl
American Airlines
Jan 6
ORD1:33 pmChicago O'Hare Intl
8h 06m
1 stop
PNS9:39 pmPensacola
Jan 11
PNS5:30 amPensacola
4h 54m
1 stop
ORD10:24 amChicago O'Hare Intl
American Airlines
Apr 19
ORD3:25 pmChicago O'Hare Intl
6h 56m
1 stop
PNS10:21 pmPensacola
Apr 23
PNS3:54 pmPensacola
5h 17m
1 stop
ORD9:11 pmChicago O'Hare Intl

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 to Pensacola?

The cheapest month to fly to Pensacola from Chicago is in January. Flight prices, which tend to average around $281, are often lower during this time because this is during the off-season. If you aren’t able to travel during the month of January, then book flights to Pensacola from Chicago during April instead. Flights to Pensacola in April, while not as cheap as those in January, still average around $304.

What is the cheapest day to depart on your flight to Pensacola?

On average, the least expensive day to fly to Pensacola from Chicago is on a Tuesday. momondo users have found tickets for Tuesday departures for as low as $315. However, this price may fluctuate depending on the airline, the season, and holidays. On the other hand, Sunday is the most expensive day to depart from Chicago because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $430.

What is the cheapest time of day to depart on your flight to Pensacola?

The cheapest time of day to fly to Pensacola is in the evening when flights can be purchased for as low as $212. Flights to Pensacola are more costly in the morning, with an average ticket price of $378. Departure times in the morning fall within the peak daily travel times, which is why tickets can be more expensive.

What is the cheapest Chicago to Pensacola flight route?

Fly from Chicago O'Hare Intl to Pensacola for the best Chicago - Pensacola flight prices

How far in advance should I book a flight to Pensacola?

Most flyers found that booking tickets 45 days in advance of their planned departure date is the best time to get cheap flights to Pensacola. During this timeframe, flight prices are around $364. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Pensacola from Chicago for as low as $205 on momondo.

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

There are 4 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 60% 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 December 2024, prices for Chicago to Pensacola flights are approximately 209% more expensive when compared to flights at the same time last year.

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 $127.
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
8,120 reviews
Search Spirit Airlines flights
SouthwestPriceFrom $143Free CancellationRating
8.1
4,836 reviews
Search Southwest flights
DeltaPriceFrom $204Free CancellationRating
8.0
8,600 reviews
Search Delta flights
American AirlinesPriceFrom $204Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
United AirlinesPriceFrom $241Free CancellationRating
7.4
9,048 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 3 flights/week on average for this route. A good United Airlines flight deal for Chicago to Pensacola starts from $241 round-trip, up to an average price of $419. 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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