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Cheap flights from Chicago O'Hare Intl Airport to Pensacola from $61

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 12/8. 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.
American Airlines Logo
8:25 am - 10:47 amORD-PNS
2h 22mnonstop
American Airlines Logo
1:16 pm - 3:55 pmPNS-ORD
2h 39mnonstop
$209American Airlines
Find Deal
水, 2月 18 - 月, 2月 23
Multiple Airlines Logo
6:15 am - 6:14 pmORD-PNS
11h 59m1 stop
Multiple Airlines Logo
7:09 pm - 11:08 amPNS-ORD
15h 59m1 stop
$212Multiple Airlines
Find Deal
木, 12月 11 - 月, 12月 15
Spirit Airlines Logo
6:48 am - 12:49 pmORD-PNS
6h 01m1 stop
Spirit Airlines Logo
5:54 pm - 11:06 pmPNS-ORD
5h 12m1 stop
$213Spirit Airlines
Find Deal
木, 11月 20 - 水, 11月 26
Spirit Airlines Logo
10:52 am - 7:11 pmORD-PNS
8h 19m1 stop
Spirit Airlines Logo
5:54 pm - 11:06 pmPNS-ORD
5h 12m1 stop
$214Spirit Airlines
Find Deal
水, 11月 19 - 水, 11月 26
Multiple Airlines Logo
5:25 am - 10:22 amORD-PNS
28h 57m1 stop
Multiple Airlines Logo
1:44 pm - 11:06 pmPNS-ORD
9h 22m1 stop
$219Multiple Airlines
Find Deal
日, 11月 16 - 木, 11月 20
Multiple Airlines Logo
5:25 am - 10:22 amORD-PNS
28h 57m1 stop
Multiple Airlines Logo
8:16 pm - 7:21 pmPNS-ORD
23h 05m1 stop
$220Multiple Airlines
Find Deal
日, 11月 16 - 土, 11月 22
United Airlines Logo
10:50 am - 1:17 pmORD-PNS
2h 27mnonstop
United Airlines Logo
2:15 pm - 4:47 pmPNS-ORD
2h 32mnonstop
$228United Airlines
Find Deal
水, 12月 3 - 日, 12月 7
Delta Logo
5:25 am - 12:32 pmORD-PNS
7h 07m1 stop
Delta Logo
7:00 am - 1:39 pmPNS-ORD
6h 39m1 stop
$229Delta
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土, 2月 14 - 水, 2月 25
Delta Logo
11:15 am - 4:34 pmORD-PNS
5h 19m1 stop
Delta Logo
11:46 am - 6:43 pmPNS-ORD
6h 57m1 stop
$254Delta
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金, 12月 12 - 土, 12月 13
United Airlines Logo
10:55 am - 1:31 pmORD-PNS
2h 36mnonstop
United Airlines Logo
6:35 am - 1:00 pmPNS-ORD
6h 25m1 stop
$258United Airlines
Find Deal
日, 1月 4 - 日, 1月 11

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

Our best American Airlines deals on Chicago O'Hare Intl Airport to Pensacola flight tickets
American Airlines
Feb 18
ORD8:25 amChicago O'Hare Intl
2h 22m
PNS10:47 amPensacola
Feb 23
PNS1:16 pmPensacola
2h 39m
ORD3:55 pmChicago O'Hare Intl
$209
Find similar
American Airlines
Feb 18
ORD12:32 pmChicago O'Hare Intl
6h 18m
1 stop
PNS6:50 pmPensacola
Feb 23
PNS1:16 pmPensacola
2h 39m
ORD3:55 pmChicago O'Hare Intl
$239
Find similar
American Airlines
Feb 28
ORD10:16 amChicago O'Hare Intl
2h 22m
PNS12:38 pmPensacola
Mar 7
PNS1:16 pmPensacola
2h 39m
ORD3:55 pmChicago O'Hare Intl
$249
Find similar

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
Nov 20
ORD6:48 amChicago O'Hare Intl
6h 01m
1 stop
PNS12:49 pmPensacola
Nov 26
PNS5:54 pmPensacola
5h 12m
1 stop
ORD11:06 pmChicago O'Hare Intl
$213
Find similar
Spirit Airlines
Nov 19
ORD10:52 amChicago O'Hare Intl
8h 19m
1 stop
PNS7:11 pmPensacola
Nov 26
PNS5:54 pmPensacola
5h 12m
1 stop
ORD11:06 pmChicago O'Hare Intl
$214
Find similar
Spirit Airlines
Dec 2
ORD10:12 amChicago O'Hare Intl
8h 59m
1 stop
PNS7:11 pmPensacola
Dec 6
PNS7:09 pmPensacola
15h 59m
1 stop
ORD11:08 amChicago O'Hare Intl
$222
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 11月 4, 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

水 2/18

8:25 am-10:47 am

Nonstop2h 22m

Pensacola

月 2/23

1:16 pm-3:55 pm

Nonstop2h 39m

$209

ChicagoPensacola

ORD - PNS

ORDPNS

Chicago O'Hare Intl

木 12/11

6:15 am-6:14 pm

1 stop11h 59m

Pensacola

月 12/15

7:09 pm-11:08 am

1 stop15h 59m

$212

ChicagoPensacola

ORD - PNS

ORDPNS

Chicago O'Hare Intl

木 11/20

6:48 am-12:49 pm

1 stop6h 01m

Pensacola

水 11/26

5:54 pm-11:06 pm

1 stop5h 12m

$213

ChicagoPensacola

ORD - PNS

ORDPNS

Chicago O'Hare Intl

水 11/19

10:52 am-7:11 pm

1 stop8h 19m

Pensacola

水 11/26

5:54 pm-11:06 pm

1 stop5h 12m

$214

ChicagoPensacola

ORD - PNS

ORDPNS

Chicago O'Hare Intl

日 11/16

5:25 am-10:22 am

1 stop28h 57m

Pensacola

木 11/20

1:44 pm-11:06 pm

1 stop9h 22m

$219

ChicagoPensacola

ORD - PNS

ORDPNS

Chicago O'Hare Intl

日 11/16

5:25 am-10:22 am

1 stop28h 57m

Pensacola

土 11/22

8:16 pm-7:21 pm

1 stop23h 05m

$220

ChicagoPensacola

ORD - PNS

ORDPNS

Chicago O'Hare Intl

水 12/3

10:50 am-1:17 pm

Nonstop2h 27m

Pensacola

日 12/7

2:15 pm-4:47 pm

Nonstop2h 32m

$228

ChicagoPensacola

ORD - PNS

ORDPNS

Chicago O'Hare Intl

土 2/14

5:25 am-12:32 pm

1 stop7h 07m

Pensacola

水 2/25

7:00 am-1:39 pm

1 stop6h 39m

$229

ChicagoPensacola

ORD - PNS

ORDPNS

Chicago O'Hare Intl

金 12/12

11:15 am-4:34 pm

1 stop5h 19m

Pensacola

土 12/13

11:46 am-6:43 pm

1 stop6h 57m

$254

ChicagoPensacola

ORD - PNS

ORDPNS

Chicago O'Hare Intl

日 1/4

10:55 am-1:31 pm

Nonstop2h 36m

Pensacola

日 1/11

6:35 am-1:00 pm

1 stop6h 25m

$258

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 $279, 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 September instead. Flights to Pensacola in September, while not as cheap as those in January, still average around $300.

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 $309. 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 $399.

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 evening, with an average ticket price of $379. Departure times in the evening 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 $338 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 $302 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.

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

As of November 2025, prices for Chicago O'Hare Intl Airport to Pensacola flights are approximately 39% more expensive 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

$136

Fastest flight time

2h 22m

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 $136. The best round-trip flight deal from Chicago O'Hare Intl Airport to Pensacola found on momondo in the last 72 hours is $236.
The fastest flight from Chicago O'Hare Intl Airport to Pensacola takes 2h 22m
Direct flights go from Chicago O'Hare Intl Airport to Pensacola every day.
There is 1 airport near Pensacola: 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 22m.

  • 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
8,113 reviews
Search Spirit Airlines flights
DeltaPriceFrom $177Free CancellationRating
7.9
8,003 reviews
Search Delta flights
American AirlinesPriceFrom $217Free CancellationRating
7.2
11,040 reviews
Search American Airlines flights
United AirlinesPriceFrom $218Free CancellationRating
7.4
9,002 reviews
Search United Airlines flights
SouthwestPriceFrom $232Free CancellationRating
8.0
4,239 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 $218 round-trip. Over the 4 United Airlines flights for this route in a normal week, average airfare is usually $377 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 11,040 reviews) operates around 7 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 $217 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 Beach
Navarre
Milton
Atmore
Gulf Breeze
Warrington
Evergreen

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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