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Pensacola

$89+ Cheap flights from O'Hare Intl (ORD) to Pensacola (PNS)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 2/10. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — PNS
Jan 14 — Jan 211
Wed 1/14
Wed 1/21
1 adult, Economy
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Find cheap flights from O'Hare Intl to Pensacola with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

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3. Compare prices and book

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Cheapflights Tip: The best prices from Chicago O'Hare Intl to Pensacola are usually found in January or November, booked 73 days in advance, depart on a Tuesday or Wednesday and return on a Thursday

Cheap flight deals from O'Hare Intl to Pensacola

Cheapest flights from O'Hare Intl to Pensacola
Explore the most affordable flight options available from O'Hare Intl to Pensacola. Find the lowest fares from popular airlines and budget airlines, with prices last updated on December 15, 2025.

This American Airlines deal was found by Cheapflights users on 12/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/261:27 pmORD - PNS
1 stop8h 02mAmerican Airlines
Tue 12/3011:29 amPNS - ORD
1 stop8h 08mAmerican Airlines
Deal found 12/15$304
This American Airlines deal was found by Cheapflights users on 12/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/2110:34 amORD - PNS
1 stop8h 05mAmerican Airlines
Thu 12/2512:58 pmPNS - ORD
Nonstop2h 42mAmerican Airlines
Deal found 12/14$329
This American Airlines deal was found by Cheapflights users on 12/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/255:00 amORD - PNS
1 stop5h 15mAmerican Airlines
Tue 12/304:19 pmPNS - ORD
1 stop8h 24mAmerican Airlines
Deal found 12/14$339
This American Airlines deal was found by Cheapflights users on 12/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/264:05 pmORD - PNS
1 stop5h 05mAmerican Airlines
Mon 1/56:10 amPNS - ORD
1 stop7h 04mAmerican Airlines
Deal found 12/15$353
This Mytrip deal was found by Cheapflights users on 12/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/297:30 amORD - PNS
1 stop10h 44mSpirit Airlines
Tue 1/61:58 pmPNS - ORD
3 stops30h 06mSpirit Airlines
Deal found 12/14$355
This Super.com deal was found by Cheapflights users on 12/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/247:30 amORD - PNS
1 stop5h 33mSpirit Airlines
Tue 12/301:58 pmPNS - ORD
1 stop10h 32mSpirit Airlines
Deal found 12/14$361
This American Airlines deal was found by Cheapflights users on 12/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/1912:10 amORD - PNS
1 stop7h 48mAmerican Airlines
Sat 12/271:12 pmPNS - ORD
Nonstop2h 42mAmerican Airlines
Deal found 12/12$378
This American Airlines deal was found by Cheapflights users on 12/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/224:07 pmORD - PNS
1 stop5h 22mAmerican Airlines
Sat 12/275:52 pmPNS - ORD
1 stop6h 07mAmerican Airlines
Deal found 12/13$388
This United Airlines deal was found by Cheapflights users on 12/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/2910:55 amORD - PNS
Nonstop2h 36mUnited Airlines
Tue 1/62:13 pmPNS - ORD
Nonstop2h 46mUnited Airlines
Deal found 12/14$391

Find flight deals from O'Hare Intl to Pensacola

Discover tips and strategies to find the most affordable flight options for your journey from O'Hare Intl (ORD) to Pensacola (PNS). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated December 15, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$222
(Expedia)

One-way from

$89
(Kiwi.com)

Popular in

March

Cheapest in

January

Average price

$371

Good round-trip deal

$273 or less

Good one-way deal

$254 or less
Provider with most accurate pricing for Chicago O'Hare Intl-Pensacola flight deals.
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Provider most trusted by Cheapflights users for Chicago O'Hare Intl-Pensacola flights.
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From Chicago O'Hare Intl to Pensacola
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One-way flight from Chicago O'Hare Intl to Pensacola
Search Deals
Highest demand for flights based on searches. 6% potential increase in price ($24 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($4 potential savings vs. average RT price).
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Average for round-trip flights in December 2025
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Price to beat on a round-trip flight from Chicago O'Hare Intl to Pensacola.
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Price to beat on a one-way flight from Chicago O'Hare Intl to Pensacola.
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Cheapflights Fare Finder

 
Customize your flight search to find flights from O'Hare Intl 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, Cheapflights users made 2,558,603 searches. Data last updated December 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

O'Hare Intl

Fly to

Pensacola

Route

Depart

Return

Price

ChicagoPensacola

ORD - PNS

ORDPNS

Chicago O'Hare Intl

Fri 3/6

10:50 am-1:16 pm

Nonstop2h 26m

Pensacola

Mon 3/9

7:00 am-9:38 am

Nonstop2h 38m

$229

ChicagoPensacola

ORD - PNS

ORDPNS

Chicago O'Hare Intl

Fri 3/13

7:05 am-11:34 am

1 stop4h 29m

Pensacola

Tue 3/17

12:39 pm-7:52 pm

1 stop7h 13m

$229

ChicagoPensacola

ORD - PNS

ORDPNS

Chicago O'Hare Intl

Mon 1/12

9:55 am-1:53 pm

1 stop3h 58m

Pensacola

Tue 2/3

9:23 am-1:40 pm

1 stop4h 17m

$229

ChicagoPensacola

ORD - PNS

ORDPNS

Chicago O'Hare Intl

Sat 2/28

5:25 am-12:30 pm

1 stop7h 05m

Pensacola

Sat 3/7

9:03 am-2:10 pm

1 stop5h 07m

$229

ChicagoPensacola

ORD - PNS

ORDPNS

Chicago O'Hare Intl

Tue 1/13

9:55 am-1:53 pm

1 stop3h 58m

Pensacola

Tue 2/3

9:23 am-1:40 pm

1 stop4h 17m

$229

ChicagoPensacola

ORD - PNS

ORDPNS

Chicago O'Hare Intl

Wed 2/18

5:25 am-12:30 pm

1 stop7h 05m

Pensacola

Tue 2/24

6:00 am-10:08 am

1 stop4h 08m

$229

ChicagoPensacola

ORD - PNS

ORDPNS

Chicago O'Hare Intl

Tue 1/13

7:05 am-11:39 am

1 stop4h 34m

Pensacola

Sat 1/31

9:23 am-1:49 pm

1 stop4h 26m

$229

ChicagoPensacola

ORD - PNS

ORDPNS

Chicago O'Hare Intl

Tue 3/10

11:15 am-3:09 pm

1 stop3h 54m

Pensacola

Fri 3/13

12:39 pm-6:46 pm

1 stop6h 07m

$229

ChicagoPensacola

ORD - PNS

ORDPNS

Chicago O'Hare Intl

Sat 3/14

5:40 am-11:34 am

1 stop5h 54m

Pensacola

Sat 3/21

5:23 pm-11:56 pm

1 stop6h 33m

$229

ChicagoPensacola

ORD - PNS

ORDPNS

Chicago O'Hare Intl

Sun 3/15

7:05 am-11:34 am

1 stop4h 29m

Pensacola

Sun 3/22

7:24 pm-11:56 pm

1 stop4h 32m

$229

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/13

Showing 1-10 of 22 results
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Compare providers for flights from O'Hare Intl to Pensacola

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from O'Hare Intl to Pensacola in December.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star
eDreamsPrice Accuracy3 starsTrust Score*3 stars
CheapflightsfaresPrice Accuracy3 starsTrust Score*2 stars
PricelinePrice Accuracy1 starTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Chicago O'Hare Intl Airport-Pensacola flights, users find the pricing of eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Chicago O'Hare Intl Airport-Pensacola flight deals on Cheapflights vs. eDreams >95% of the time. Price accuracy is based on data collected from Chicago O'Hare Intl Airport-Pensacola flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Chicago O'Hare Intl Airport-Pensacola flights, Cheapflights users trust eDreams the most. eDreams has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Chicago O'Hare Intl Airport-Pensacola flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Best time to book a flight from O'Hare Intl to Pensacola

Have a flexible travel schedule? Discover the best time to fly to Pensacola from O'Hare Intl with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Chicago O'Hare Intl Airport to Pensacola

How far ahead should I book a flight from Chicago O'Hare Intl Airport to Pensacola?

Use this chart to determine the optimal time to book a round-trip flight from O'Hare Intl to Pensacola. Price data was last updated on December 12, 2025.

The best time to book flights from Chicago O'Hare Intl Airport to Pensacola is 73 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.

What is the cheapest month to book a flight from Chicago O'Hare Intl Airport to Pensacola?

Currently, April is the cheapest month in which you can book a flight from Chicago O'Hare Intl Airport to Pensacola (average of $133). Flying from Chicago O'Hare Intl Airport to Pensacola in December is currently the most expensive (average of $215). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from ORD to PNS?

Find hourly flight availability from O'Hare Intl to Pensacola. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated December 15, 2025.

One of the essential ways to save on airfare from Chicago O'Hare Intl Airport to Pensacola is to remain as flexible as possible. Flights that are in the afternoon tend to be the most expensive. A flight at noon could potentially save you up to 46% on airfare.

What is the cheapest day to fly from Chicago O'Hare Intl Airport to Pensacola?

Use this chart to determine the cheapest time to fly round-trip from O'Hare Intl to Pensacola. Price data was last updated on December 13, 2025.

Travelers seeking maximum savings on their Chicago O'Hare Intl Airport to Pensacola flight should consider departing on Tuesday evenings when fares are most often at their lowest. Saturday afternoons flights should be avoided if possible as fares are typically the most expensive at this time.

Reviews of airlines servicing Pensacola

Get insights into the airlines that provide service to Pensacola. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Pensacola. Reviews last updated December 15, 2025.
See what other customers who have flown with Southwest, Delta, and United Airlines from Chicago O'Hare Intl Airport to Pensacola have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
7.9
Good
4,250 reviews

Comfort

8.0

Crew

8.6

Boarding

8.1

Overall

7.9

Food

7.0

Entertainment

7.5

Reviews

1 / 20
10.0
Excellent

Sarah,Aug 2024

MDW - AUS

My first time, surprisingly good! It was a good ride overall. Coming from Singapore, this budget flight is better than the budget airline for our national carrier Singapore Airlines.
Southwest
7.9
Good
4,250 reviews
Southwest
7.9
Good
4,250 reviews

Comfort

8.0

Crew

8.6

Boarding

8.1

Overall

7.9

Food

7.0

Entertainment

7.5

Reviews

1 / 20
10.0
Excellent

Sarah,Aug 2024

MDW - AUS

My first time, surprisingly good! It was a good ride overall. Coming from Singapore, this budget flight is better than the budget airline for our national carrier Singapore Airlines.
Delta
7.9
Good
8,007 reviews
Southwest
7.9
Good
4,250 reviews

Comfort

8.0

Crew

8.6

Boarding

8.1

Overall

7.9

Food

7.0

Entertainment

7.5

Reviews

1 / 20
10.0
Excellent

Sarah,Aug 2024

MDW - AUS

My first time, surprisingly good! It was a good ride overall. Coming from Singapore, this budget flight is better than the budget airline for our national carrier Singapore Airlines.
United Airlines
7.4
Good
9,092 reviews
Southwest
7.9
Good
4,250 reviews

Comfort

8.0

Crew

8.6

Boarding

8.1

Overall

7.9

Food

7.0

Entertainment

7.5

Reviews

1 / 20
10.0
Excellent

Sarah,Aug 2024

MDW - AUS

My first time, surprisingly good! It was a good ride overall. Coming from Singapore, this budget flight is better than the budget airline for our national carrier Singapore Airlines.
American Airlines
7.2
Good
11,052 reviews
Southwest
7.9
Good
4,250 reviews

Comfort

8.0

Crew

8.6

Boarding

8.1

Overall

7.9

Food

7.0

Entertainment

7.5

Reviews

1 / 20
10.0
Excellent

Sarah,Aug 2024

MDW - AUS

My first time, surprisingly good! It was a good ride overall. Coming from Singapore, this budget flight is better than the budget airline for our national carrier Singapore Airlines.
Spirit Airlines
6.3
Okay
8,185 reviews
Southwest
7.9
Good
4,250 reviews

Comfort

8.0

Crew

8.6

Boarding

8.1

Overall

7.9

Food

7.0

Entertainment

7.5

Reviews

1 / 20
10.0
Excellent

Sarah,Aug 2024

MDW - AUS

My first time, surprisingly good! It was a good ride overall. Coming from Singapore, this budget flight is better than the budget airline for our national carrier Singapore Airlines.

Related info for your journey

Find useful and relevant information for your journey from O'Hare Intl to Pensacola. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly into for flights to Pensacola from Chicago O'Hare Intl?

    Most people fly into Pensacola (PNS) if they book a flight to Pensacola from Chicago O'Hare Intl. On average, Pensacola has 1 inbound flight from Chicago O'Hare Intl per day from 5 airlines. Pensacola is conveniently located just 4.0 mi from Pensacola’s city center.

  • How long is the flight from Chicago O'Hare Intl Airport to Pensacola?

    Airlines like United Airlines and Delta fly from Chicago O'Hare Intl Airport to Pensacola in about 2h 26m. The time it takes to get you to your destination can typically vary by up to 2h 03m. Chicago O'Hare Intl Airport and Pensacola are separated by a distance of 795 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • What are the cheapest airlines flying from Chicago O'Hare Intl Airport to Pensacola round-trip?

    Cheapflights users have booked flights from Chicago O'Hare Intl Airport to Pensacola round-trip from $116. Other airlines that can offer you cheap pricing are Delta, from $176, and United Airlines, from $210. Users have found that Spirit Airlines is 65% cheaper than the other options available to this destination.

  • What are the cheapest airlines to fly from Chicago O'Hare Intl Airport to Pensacola one-way?

    The cheapest airlines for a one-way flight from Chicago O'Hare Intl Airport to Pensacola are Spirit Airlines ($62), Delta ($88), and Southwest ($98).

  • What are the most reliable airlines from Chicago O'Hare Intl Airport to Pensacola?

    Consider United Airlines (82%), Air New Zealand (78%) or American Airlines (70%) when booking your flight. These represent the most reliable airlines when flying from Chicago O'Hare Intl Airport to Pensacola.

  • What are the cheapest flights from Chicago O'Hare Intl Airport to Pensacola?

    Looking at all options, your cheapest flight can be booked for $153. While the most popular route (Chicago O'Hare Intl - Pensacola) can be booked for $169 on average, our data indicates $311 when flying from Chicago O'Hare Intl Airport to Pensacola.

  • Can I find deals for flights from O'Hare Intl to Pensacola that include hotel bookings?

    Yes. In addition to deals on O'Hare Intl to Pensacola flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from O'Hare Intl to Pensacola?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from O'Hare Intl to Pensacola.

  • Can I find deals for business class flights from O'Hare Intl to Pensacola?

    Yes. Cheapflights offers flight deals from O'Hare Intl to Pensacola by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Chicago O'Hare Intl Airport to Pensacola?

    Currently, April is the cheapest month in which you can book a flight from Chicago O'Hare Intl Airport to Pensacola (average of $133). Flying from Chicago O'Hare Intl Airport to Pensacola in December is currently the most expensive (average of $215). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Traveling to a place near Pensacola?

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

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Alternative routes for O'Hare Intl to Pensacola

See prices for flight routes from nearby airports that may be better suited for you.
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Top 5 airlines flying from O'Hare Intl to Pensacola

Discover the top 5 airlines that operate flights from O'Hare Intl to Pensacola. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated December 15, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$118Average$211FlexibilityNo cancel feeOn-time65%
DeltaCheapest$177Average$268FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$214Average$373FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$218Average$318FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$232Average$375FlexibilityNo cancel feeOn-time63%

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