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Cheap flights from Chicago O'Hare Intl Airport to Pensacola from $78

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 9/23. 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

American Airlines Logo
10:30 am - 1:00 pmORD-PNS
2h 30mnonstop
American Airlines Logo
1:32 pm - 4:11 pmPNS-ORD
2h 39mnonstop
$155American Airlines
Find Deal
Wed, Nov 5 - Tue, Nov 11
Spirit Airlines Logo
5:05 am - 3:39 pmORD-PNS
10h 34m1 stop
Spirit Airlines Logo
4:44 pm - 10:48 pmPNS-ORD
6h 04m1 stop
$160Spirit Airlines
Find Deal
Wed, Sep 10 - Wed, Sep 17
United Airlines Logo
10:50 am - 1:15 pmORD-PNS
2h 25mnonstop
United Airlines Logo
2:17 pm - 4:54 pmPNS-ORD
2h 37mnonstop
$166United Airlines
Find Deal
Tue, Sep 30 - Mon, Oct 6
Logo
5:05 am - 3:39 pmORD-PNS
10h 34m1 stop
Logo
5:21 pm - 11:59 pmPNS-ORD
6h 38m1 stop
$170
Find Deal
Fri, Sep 5 - Mon, Sep 8
Logo
5:05 am - 3:39 pmORD-PNS
10h 34m1 stop
Logo
5:21 pm - 9:37 amPNS-ORD
16h 16m1 stop
$173
Find Deal
Wed, Sep 17 - Sat, Sep 20
Delta Logo
9:30 am - 2:26 pmORD-PNS
4h 56m1 stop
Delta Logo
1:59 pm - 9:14 pmPNS-ORD
7h 15m1 stop
$187Delta
Find Deal
Sat, Jan 31 - Wed, Feb 11
United Airlines Logo
10:35 am - 1:00 pmORD-PNS
2h 25mnonstop
United Airlines Logo
2:15 pm - 4:52 pmPNS-ORD
2h 37mnonstop
$190United Airlines
Find Deal
Sat, Sep 20 - Wed, Sep 24
Southwest Logo
7:30 am - 5:05 pmORD-PNS
9h 35m2 stops
Southwest Logo
7:40 am - 12:45 pmPNS-ORD
5h 05m1 stop
$191Southwest
Find Deal
Sat, Oct 25 - Tue, Oct 28
Southwest Logo
7:00 am - 2:10 pmORD-PNS
7h 10m1 stop
Southwest Logo
11:05 am - 9:30 pmPNS-ORD
10h 25m2 stops
$202Southwest
Find Deal
Sat, Sep 6 - Mon, Sep 8
Delta Logo
5:50 am - 12:53 pmORD-PNS
7h 03m1 stop
Delta Logo
5:45 pm - 11:54 pmPNS-ORD
6h 09m1 stop
$203Delta
Find Deal
Tue, Feb 3 - Mon, Feb 9

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
Sep 10
ORD5:05 amChicago O'Hare Intl
10h 34m
1 stop
PNS3:39 pmPensacola
Sep 17
PNS4:44 pmPensacola
6h 04m
1 stop
ORD10:48 pmChicago O'Hare Intl
$160
Find similar
Spirit Airlines
Sep 10
ORD5:05 amChicago O'Hare Intl
10h 34m
1 stop
PNS3:39 pmPensacola
Sep 17
PNS4:44 pmPensacola
6h 04m
1 stop
ORD10:48 pmChicago O'Hare Intl
$162
Find similar
Spirit Airlines
Sep 17
ORD5:05 amChicago O'Hare Intl
10h 34m
1 stop
PNS3:39 pmPensacola
Sep 20
PNS4:44 pmPensacola
6h 04m
1 stop
ORD10:48 pmChicago O'Hare Intl
$171
Find similar

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

Our best United Airlines deals on Chicago O'Hare Intl Airport to Pensacola flight tickets
United Airlines
Sep 30
ORD10:50 amChicago O'Hare Intl
2h 25m
PNS1:15 pmPensacola
Oct 6
PNS2:17 pmPensacola
2h 37m
ORD4:54 pmChicago O'Hare Intl
$166
Find similar
United Airlines
Sep 20
ORD10:35 amChicago O'Hare Intl
2h 25m
PNS1:00 pmPensacola
Sep 24
PNS2:15 pmPensacola
2h 37m
ORD4:52 pmChicago O'Hare Intl
$190
Find similar
United Airlines
Sep 26
ORD10:50 amChicago O'Hare Intl
2h 25m
PNS1:15 pmPensacola
Sep 29
PNS2:17 pmPensacola
2h 37m
ORD4:54 pmChicago O'Hare Intl
$193
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 August 15, 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

Wed 11/5

10:30 am-1:00 pm

Nonstop2h 30m

Pensacola

Tue 11/11

1:32 pm-4:11 pm

Nonstop2h 39m

$155

ChicagoPensacola

ORD - PNS

ORDPNS

Chicago O'Hare Intl

Wed 9/10

5:05 am-3:39 pm

1 stop10h 34m

Pensacola

Wed 9/17

4:44 pm-10:48 pm

1 stop6h 04m

$160

ChicagoPensacola

ORD - PNS

ORDPNS

Chicago O'Hare Intl

Tue 9/30

10:50 am-1:15 pm

Nonstop2h 25m

Pensacola

Mon 10/6

2:17 pm-4:54 pm

Nonstop2h 37m

$166

ChicagoPensacola

ORD - PNS

ORDPNS

Chicago O'Hare Intl

Fri 9/5

5:05 am-3:39 pm

1 stop10h 34m

Pensacola

Mon 9/8

5:21 pm-11:59 pm

1 stop6h 38m

$170

ChicagoPensacola

ORD - PNS

ORDPNS

Chicago O'Hare Intl

Wed 9/17

5:05 am-3:39 pm

1 stop10h 34m

Pensacola

Sat 9/20

5:21 pm-9:37 am

1 stop16h 16m

$173

ChicagoPensacola

ORD - PNS

ORDPNS

Chicago O'Hare Intl

Sat 1/31

9:30 am-2:26 pm

1 stop4h 56m

Pensacola

Wed 2/11

1:59 pm-9:14 pm

1 stop7h 15m

$187

ChicagoPensacola

ORD - PNS

ORDPNS

Chicago O'Hare Intl

Sat 9/20

10:35 am-1:00 pm

Nonstop2h 25m

Pensacola

Wed 9/24

2:15 pm-4:52 pm

Nonstop2h 37m

$190

ChicagoPensacola

ORD - PNS

ORDPNS

Chicago O'Hare Intl

Sat 10/25

7:30 am-5:05 pm

2 stops9h 35m

Pensacola

Tue 10/28

7:40 am-12:45 pm

1 stop5h 05m

$191

ChicagoPensacola

ORD - PNS

ORDPNS

Chicago O'Hare Intl

Sat 9/6

7:00 am-2:10 pm

1 stop7h 10m

Pensacola

Mon 9/8

11:05 am-9:30 pm

2 stops10h 25m

$202

ChicagoPensacola

ORD - PNS

ORDPNS

Chicago O'Hare Intl

Tue 2/3

5:50 am-12:53 pm

1 stop7h 03m

Pensacola

Mon 2/9

5:45 pm-11:54 pm

1 stop6h 09m

$203

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 $290, 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 May instead. Flights to Pensacola in May, while not as cheap as those in January, still average around $314.

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 $319. 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 $454.

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 afternoon when flights can be purchased for as low as $293. Flights to Pensacola are more costly in the morning, with an average ticket price of $399. 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 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 $361 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 $271 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 40% 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 August 2025, prices for Chicago O'Hare Intl Airport to Pensacola flights are approximately 34% 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

$78

Fastest flight time

2h 25m

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 $78. The best round-trip flight deal from Chicago O'Hare Intl Airport to Pensacola found on momondo in the last 72 hours is $155.
The fastest flight from Chicago O'Hare Intl Airport to Pensacola takes 2h 25m
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 25m.

  • 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
8,046 reviews
Search Spirit Airlines flights
DeltaPriceFrom $196Free CancellationRating
8.0
7,982 reviews
Search Delta flights
SouthwestPriceFrom $222Free CancellationRating
8.0
4,244 reviews
Search Southwest flights
American AirlinesPriceFrom $228Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
United AirlinesPriceFrom $233Free CancellationRating
7.4
8,915 reviews
Search United Airlines 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 $233 round-trip. Over the 5 United Airlines flights for this route in a normal week, average airfare is usually $404 round-trip - but some users have found much cheaper deals with momondo.

Traveling to a place near Pensacola?

Book flights to Pensacola if you plan to visit one of these locations
Orange Beach
Pensacola Beach
Foley
Navarre Beach
Perdido Key
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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