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Cheap flights from Chicago O'Hare Intl Airport to Pensacola from $75

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 O'Hare Intl Airport to Pensacola departing on 1/13. 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 O'Hare Intl Airport to Pensacola

Cheap round-trip flights

Enter your travel dates to find the best prices.
Spirit Airlines Logo
5:15 am - 3:08 pm
ORD
-
PNS
9h 53m1 stop
Spirit Airlines Logo
4:03 pm - 11:47 am
PNS
-
ORD
19h 44m2 stops
$226Spirit Airlines
Thu, Jan 15 - Mon, Jan 19
Multiple Airlines Logo
8:27 pm - 4:37 pm
ORD
-
PNS
20h 10m1 stop
Multiple Airlines Logo
5:33 pm - 1:13 pm
PNS
-
ORD
19h 40m1 stop
$227Multiple Airlines
Fri, Jan 9 - Tue, Jan 13
Multiple Airlines Logo
7:30 am - 3:08 pm
ORD
-
PNS
7h 38m1 stop
Multiple Airlines Logo
7:31 pm - 6:24 pm
PNS
-
ORD
22h 53m2 stops
$228Multiple Airlines
Sun, Jan 11 - Fri, Jan 16
Delta Logo
5:30 am - 10:26 am
ORD
-
PNS
4h 56m1 stop
Delta Logo
6:00 am - 10:05 am
PNS
-
ORD
4h 05m1 stop
$229Delta
Fri, Jan 30 - Sun, Feb 1
Multiple Airlines Logo
4:49 pm - 10:38 am
ORD
-
PNS
17h 49m2 stops
Multiple Airlines Logo
5:33 pm - 1:13 pm
PNS
-
ORD
19h 40m1 stop
$231Multiple Airlines
Fri, Jan 9 - Tue, Jan 13
Multiple Airlines Logo
5:24 pm - 5:42 pm
ORD
-
PNS
24h 18m2 stops
Multiple Airlines Logo
5:20 pm - 11:24 pm
PNS
-
ORD
30h 04m1 stop
$232Multiple Airlines
Fri, Feb 13 - Wed, Feb 18
Multiple Airlines Logo
8:43 pm - 2:32 pm
ORD
-
PNS
17h 49m2 stops
Multiple Airlines Logo
4:03 pm - 11:46 pm
PNS
-
ORD
7h 43m1 stop
$233Multiple Airlines
Sun, Jan 11 - Thu, Jan 15
Spirit Airlines Logo
5:15 am - 4:37 pm
ORD
-
PNS
11h 22m2 stops
Spirit Airlines Logo
4:03 pm - 1:13 pm
PNS
-
ORD
21h 10m2 stops
$234Spirit Airlines
Sat, Jan 10 - Mon, Jan 12
Spirit Airlines Logo
5:15 am - 3:08 pm
ORD
-
PNS
9h 53m1 stop
Spirit Airlines Logo
4:03 pm - 11:46 pm
PNS
-
ORD
7h 43m1 stop
$235Spirit Airlines
Fri, Jan 16 - Sun, Jan 18
United Airlines Logo
10:45 am - 1:32 pm
ORD
-
PNS
2h 47mnonstop
United Airlines Logo
6:35 am - 1:00 pm
PNS
-
ORD
6h 25m1 stop
$236United Airlines
Sun, Jan 18 - Tue, Jan 20

Spirit Airlines flights from Chicago O'Hare Intl Airport to Pensacola

Our best Spirit Airlines deals on Chicago O'Hare Intl Airport to Pensacola flight tickets
Spirit Airlines
Jan 15
ORD5:15 amChicago O'Hare Intl
9h 53m
1 stop
PNS3:08 pmPensacola
Jan 19
PNS4:03 pmPensacola
19h 44m
2 stops
ORD11:47 amChicago O'Hare Intl
$226
Find similar
Spirit Airlines
Jan 10
ORD5:15 amChicago O'Hare Intl
11h 22m
2 stops
PNS4:37 pmPensacola
Jan 12
PNS4:03 pmPensacola
21h 10m
2 stops
ORD1:13 pmChicago O'Hare Intl
$234
Find similar
Spirit Airlines
Jan 16
ORD5:15 amChicago O'Hare Intl
9h 53m
1 stop
PNS3:08 pmPensacola
Jan 18
PNS4:03 pmPensacola
7h 43m
1 stop
ORD11:46 pmChicago O'Hare Intl
$235
Find similar

Delta flights from Chicago O'Hare Intl Airport to Pensacola

Our best Delta deals on Chicago O'Hare Intl Airport to Pensacola flight tickets
Delta
Jan 30
ORD5:30 amChicago O'Hare Intl
4h 56m
1 stop
PNS10:26 amPensacola
Feb 1
PNS6:00 amPensacola
4h 05m
1 stop
ORD10:05 amChicago O'Hare Intl
$229
Find similar
Delta
Jan 7
ORD7:05 amChicago O'Hare Intl
4h 34m
1 stop
PNS11:39 amPensacola
Jan 14
PNS12:55 pmPensacola
7h 52m
1 stop
ORD8:47 pmChicago O'Hare Intl
$249
Find similar
Delta
Mar 7
ORD5:25 amChicago O'Hare Intl
5h 01m
1 stop
PNS10:26 amPensacola
Mar 14
PNS8:15 amPensacola
5h 03m
1 stop
ORD1:18 pmChicago O'Hare Intl
$274
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Chicago O'Hare Intl Airport to Pensacola that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, momondo users made 832,500 searches. Data last updated December 21, 2025.
Use the filters below to find and compare flights from Chicago O'Hare Intl Airport to Pensacola that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

ChicagoPensacola

ORD - PNS

ORDPNS

Chicago O'Hare Intl

Thu 1/15

5:15 am-3:08 pm

1 stop9h 53m

Pensacola

Mon 1/19

4:03 pm-11:47 am

2 stops19h 44m

$226

ChicagoPensacola

ORD - PNS

ORDPNS

Chicago O'Hare Intl

Fri 1/9

8:27 pm-4:37 pm

1 stop20h 10m

Pensacola

Tue 1/13

5:33 pm-1:13 pm

1 stop19h 40m

$227

ChicagoPensacola

ORD - PNS

ORDPNS

Chicago O'Hare Intl

Sun 1/11

7:30 am-3:08 pm

1 stop7h 38m

Pensacola

Fri 1/16

7:31 pm-6:24 pm

2 stops22h 53m

$228

ChicagoPensacola

ORD - PNS

ORDPNS

Chicago O'Hare Intl

Fri 1/30

5:30 am-10:26 am

1 stop4h 56m

Pensacola

Sun 2/1

6:00 am-10:05 am

1 stop4h 05m

$229

ChicagoPensacola

ORD - PNS

ORDPNS

Chicago O'Hare Intl

Fri 1/9

4:49 pm-10:38 am

2 stops17h 49m

Pensacola

Tue 1/13

5:33 pm-1:13 pm

1 stop19h 40m

$231

ChicagoPensacola

ORD - PNS

ORDPNS

Chicago O'Hare Intl

Fri 2/13

5:24 pm-5:42 pm

2 stops24h 18m

Pensacola

Wed 2/18

5:20 pm-11:24 pm

1 stop30h 04m

$232

ChicagoPensacola

ORD - PNS

ORDPNS

Chicago O'Hare Intl

Sun 1/11

8:43 pm-2:32 pm

2 stops17h 49m

Pensacola

Thu 1/15

4:03 pm-11:46 pm

1 stop7h 43m

$233

ChicagoPensacola

ORD - PNS

ORDPNS

Chicago O'Hare Intl

Sat 1/10

5:15 am-4:37 pm

2 stops11h 22m

Pensacola

Mon 1/12

4:03 pm-1:13 pm

2 stops21h 10m

$234

ChicagoPensacola

ORD - PNS

ORDPNS

Chicago O'Hare Intl

Fri 1/16

5:15 am-3:08 pm

1 stop9h 53m

Pensacola

Sun 1/18

4:03 pm-11:46 pm

1 stop7h 43m

$235

ChicagoPensacola

ORD - PNS

ORDPNS

Chicago O'Hare Intl

Sun 1/18

10:45 am-1:32 pm

Nonstop2h 47m

Pensacola

Tue 1/20

6:35 am-1:00 pm

1 stop6h 25m

$236

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to Pensacola from

How to get the cheapest flight ticket from Chicago O'Hare Intl Airport 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 O'Hare Intl Airport is in January. Flight prices, which tend to average around $291, 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 O'Hare Intl Airport during November instead. Flights to Pensacola in November, while not as cheap as those in January, still average around $298.

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

On average, the least expensive day to fly to Pensacola from Chicago O'Hare Intl Airport is on a Tuesday. momondo users have found tickets for Tuesday departures for as low as $322. However, this price may fluctuate depending on the airline, the season, and holidays. On the other hand, Friday is the most expensive day to depart from Chicago O'Hare Intl Airport because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $385.

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

The cheapest time of day to fly to Pensacola is at noon when flights can be purchased for as low as $323. Flights to Pensacola are more costly in the afternoon, with an average ticket price of $587. Departure times in the afternoon fall within the peak daily travel times, which is why tickets can be more expensive.

What is the cheapest Chicago O'Hare Intl to Pensacola flight route?

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

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

You are more likely to see cheaper flights to Pensacola from Chicago O'Hare Intl Airport when booking weeks ahead of your departure date. In general, you can expect to find flights to Pensacola for around $332 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Pensacola from Chicago O'Hare Intl Airport for as low as $255 on momondo.

What cabin class options are available on Chicago O'Hare Intl to Pensacola flights?

There are 4 cabin classes available to choose from on Chicago O'Hare Intl 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 O'Hare Intl Airport to Pensacola flights?

You could potentially save up to 15% on your flight if you consider stops on a Chicago O'Hare Intl Airport to Pensacola flight.

How have Chicago O'Hare Intl Airport to Pensacola flight prices changed over time?

As of December 2025, prices for Chicago O'Hare Intl Airport to Pensacola flights are approximately 52% cheaper when compared to flights at the same time last year.

When to book flights from Chicago O'Hare Intl Airport to Pensacola

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

Cheap Chicago O'Hare Intl Airport to Pensacola (ORD to PNS) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago O'Hare Intl Airport to Pensacola

Best Price Found

$243

Fastest flight time

2h 19m

Direct flights

Every day

Airports in Pensacola

1 airport
The best one-way flight to Pensacola from Chicago O'Hare Intl Airport in the past 72 hours is $243. The best round-trip flight deal from Chicago O'Hare Intl Airport to Pensacola found on momondo in the last 72 hours is $284.
The fastest flight from Chicago O'Hare Intl Airport to Pensacola takes 2h 19m
Direct flights go from Chicago O'Hare Intl Airport to Pensacola every day.
There is 1 airport in Pensacola. From Chicago O'Hare Intl Airport there are direct flights to Pensacola (PNS).
Search flight deals

  • How far is Chicago O'Hare Intl to Pensacola by plane?

    A flight from Chicago O'Hare Intl to Pensacola will travel around 799.0 mi. In terms of flight time, this usually takes a little over 2h 19m.

  • When did momondo last update prices for flights from Chicago O'Hare Intl Airport to Pensacola Airport?

    Prices for flights from Chicago O'Hare Intl Airport to Pensacola Airport are updated daily.

  • How many operators does momondo search for flights from Chicago O'Hare Intl Airport to Pensacola Airport?

  • How old do you have to be to fly from Chicago O'Hare Intl Airport 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 O'Hare Intl Airport to Pensacola Airport.

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

    The travel and health documents you'll need for your trip to Pensacola Airport may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Pensacola Airport. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

  • What is the most popular plane model from Chicago O'Hare Intl Airport to Pensacola?

  • What is the most popular airline from Chicago O'Hare Intl Airport to Pensacola?

Best airlines flying from Chicago O'Hare Intl Airport to Pensacola

Compare and see reviews for airlines that fly from Chicago O'Hare Intl Airport to Pensacola with momondo
Airline
Rating
Free Cancellation
Price
Spirit AirlinesPriceFrom $118Free CancellationRating
6.3
8,192 reviews
Search Spirit Airlines flights
DeltaPriceFrom $177Free CancellationRating
7.9
8,014 reviews
Search Delta flights
United AirlinesPriceFrom $214Free CancellationRating
7.4
9,102 reviews
Search United Airlines flights
American AirlinesPriceFrom $218Free CancellationRating
7.2
11,051 reviews
Search American Airlines flights
SouthwestPriceFrom $232Free CancellationRating
8.0
4,254 reviews
Search Southwest flights

  • United Airlines Flights From Chicago O'Hare Intl Airport to Pensacola

    United Airlines flight deals from Chicago O'Hare Intl Airport to Pensacola start from $214 round-trip. Over the 5 United Airlines flights for this route in a normal week, average airfare is usually $372 round-trip - but some users have found much cheaper deals with momondo.

  • American Airlines Flights From Chicago O'Hare Intl Airport to Pensacola

    American Airlines (7.2/10 from 11,051 reviews) operates around 5 flights from Chicago O'Hare Intl Airport to Pensacola in any given week. The average American Airlines airfare for this route is around $318, with deals from around $218 rare but found on momondo. Referenced prices are for round-trip Chicago O'Hare Intl Airport to Pensacola flight searches in the last 72 hours.

Traveling to a place near Pensacola?

Book flights to Pensacola if you plan to visit one of these locations
Orange Beach
Pensacola Beach
Foley
Perdido Key
Navarre
Navarre Beach
Atmore
Milton
Gulf Breeze
Evergreen
Warrington

Why use momondo?

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

It is quick and easy to find Chicago to Pensacola flights on momondo. We search and return numerous flight options from various airlines and agents. You can then use our filters to narrow your search until you have found the most convenient flight to Pensacola that suits you.

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

momondo does allow users to show only those flights to Pensacola from Chicago which offer a flexible booking policy as well as other useful filters and features.

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

Once you have performed a search in the form on the page, momondo provides useful filters and insights. We can show you the cheapest days and times to fly as well as help filter your options to help you make an informed choice when booking flights to Pensacola from Chicago.

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

Of course. momondo tracks the price of Chicago to Pensacola flights. All you need is a valid email address and we will do the rest; it is that quick and easy.

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