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Pensacola

$64+ 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 3/3. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — PNS
Feb 27 — Mar 61
Fri 2/27
Fri 3/6
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

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

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 January 28, 2026.

This Kiwi.com deal was found by Cheapflights users on 1/26. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/74:23 pm
ORD
-
PNS
1 stop24h 19m
Multiple Airlines
Wed 3/116:37 pm
PNS
-
ORD
2 stops16h 44m
Multiple Airlines
Deal found 1/26$212
This Cheapflightsfares deal was found by Cheapflights users on 1/26. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/297:05 am
ORD
-
PNS
1 stop5h 47m
Spirit Airlines
Sat 5/21:47 pm
PNS
-
ORD
1 stop6h 01m
Spirit Airlines
Deal found 1/26$213
This CheapOair deal was found by Cheapflights users on 1/26. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/175:15 am
ORD
-
PNS
1 stop7h 37m
Spirit Airlines
Fri 4/241:47 pm
PNS
-
ORD
1 stop6h 01m
Spirit Airlines
Deal found 1/26$214
This CheapOair deal was found by Cheapflights users on 1/27. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/710:48 am
ORD
-
PNS
1 stop5h 49m
Spirit Airlines
Sat 2/145:20 pm
PNS
-
ORD
1 stop6h 27m
Spirit Airlines
Deal found 1/27$215
This CheapOair deal was found by Cheapflights users on 1/27. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/1910:44 am
ORD
-
PNS
1 stop6h 58m
Spirit Airlines
Sun 2/226:37 pm
PNS
-
ORD
1 stop23h 09m
Spirit Airlines
Deal found 1/27$216
This Kiwi.com deal was found by Cheapflights users on 1/26. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/1610:44 am
ORD
-
PNS
1 stop6h 58m
Spirit Airlines
Mon 2/236:37 pm
PNS
-
ORD
2 stops16h 45m
Spirit Airlines
Deal found 1/26$217
This Kiwi.com deal was found by Cheapflights users on 1/26. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/1910:44 am
ORD
-
PNS
1 stop6h 58m
Spirit Airlines
Mon 2/236:37 pm
PNS
-
ORD
2 stops16h 45m
Spirit Airlines
Deal found 1/26$218
This Mytrip deal was found by Cheapflights users on 1/27. 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.
Thu 3/510:44 am
ORD
-
PNS
1 stop6h 58m
Spirit Airlines
Tue 3/106:37 pm
PNS
-
ORD
2 stops24h 34m
Spirit Airlines
Deal found 1/27$221
This Kiwi.com deal was found by Cheapflights users on 1/26. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/1710:44 am
ORD
-
PNS
1 stop6h 58m
Multiple Airlines
Sat 2/216:37 pm
PNS
-
ORD
2 stops22h 31m
Multiple Airlines
Deal found 1/26$222
This United Airlines deal was found by Cheapflights users on 1/26. 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.
Fri 3/136:05 pm
ORD
-
PNS
Nonstop2h 25m
United Airlines
Mon 3/167:00 am
PNS
-
ORD
Nonstop2h 38m
United Airlines
Deal found 1/26$223

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 January 28, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$212
(Kiwi.com)

One-way from

$64
(Trip.com)

Popular in

March

Cheapest in

November

Average price

$319

Good round-trip deal

$303 or less

Good one-way deal

$194 or less
Provider with most accurate pricing for Chicago O'Hare Intl-Pensacola flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago O'Hare Intl-Pensacola flights.
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From Chicago O'Hare Intl to Pensacola
Search Deals
One-way flight from Chicago O'Hare Intl to Pensacola
Search Deals
Highest demand for flights based on searches. 2% potential increase in price ($10 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($4 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
Search Deals
Price to beat on a round-trip flight from Chicago O'Hare Intl to Pensacola.
Search Deals
Price to beat on a one-way flight from Chicago O'Hare Intl to Pensacola.
Search Deals

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 January 28, 2026.
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

Sat 4/11

5:30 am-11:11 am

1 stop5h 41m

Pensacola

Sat 4/18

7:02 am-1:14 pm

1 stop6h 12m

$225

ChicagoPensacola

ORD - PNS

ORDPNS

Chicago O'Hare Intl

Sat 3/14

2:59 pm-7:01 pm

1 stop4h 02m

Pensacola

Sat 3/21

6:00 am-10:06 am

1 stop4h 06m

$225

ChicagoPensacola

ORD - PNS

ORDPNS

Chicago O'Hare Intl

Mon 3/9

7:10 am-11:11 am

1 stop4h 01m

Pensacola

Wed 3/11

12:16 pm-6:53 pm

1 stop6h 37m

$225

ChicagoPensacola

ORD - PNS

ORDPNS

Chicago O'Hare Intl

Wed 3/11

10:50 am-1:16 pm

Nonstop2h 26m

Pensacola

Sun 3/15

2:18 pm-4:57 pm

Nonstop2h 39m

$227

ChicagoPensacola

ORD - PNS

ORDPNS

Chicago O'Hare Intl

Thu 3/12

10:50 am-1:16 pm

Nonstop2h 26m

Pensacola

Mon 3/16

7:00 am-9:38 am

Nonstop2h 38m

$227

ChicagoPensacola

ORD - PNS

ORDPNS

Chicago O'Hare Intl

Wed 4/22

5:10 am-11:53 am

1 stop6h 43m

Pensacola

Sun 4/26

6:00 am-10:09 am

1 stop4h 09m

$227

ChicagoPensacola

ORD - PNS

ORDPNS

Chicago O'Hare Intl

Mon 4/6

5:59 pm-10:04 pm

1 stop4h 05m

Pensacola

Thu 4/9

7:34 pm-11:54 pm

1 stop4h 20m

$227

ChicagoPensacola

ORD - PNS

ORDPNS

Chicago O'Hare Intl

Thu 5/28

9:30 am-2:23 pm

1 stop4h 53m

Pensacola

Mon 6/1

7:15 pm-11:55 pm

1 stop4h 40m

$227

ChicagoPensacola

ORD - PNS

ORDPNS

Chicago O'Hare Intl

Wed 3/11

7:10 am-11:11 am

1 stop4h 01m

Pensacola

Mon 3/16

7:34 pm-11:54 pm

1 stop4h 20m

$227

ChicagoPensacola

ORD - PNS

ORDPNS

Chicago O'Hare Intl

Fri 4/24

7:14 am-11:55 am

1 stop4h 41m

Pensacola

Wed 4/29

1:00 pm-6:48 pm

1 stop5h 48m

$227

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/26

Showing 1-10 of 23 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 January.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
CheapflightsfaresPrice Accuracy2 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 FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago O'Hare Intl Airport-Pensacola flight deals on Cheapflights vs. FlightHub >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 FlightHub the most. FlightHub 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 January 23, 2026.

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 $137). Flying from Chicago O'Hare Intl Airport to Pensacola in August is currently the most expensive (average of $217). 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 January 28, 2026.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Chicago O'Hare Intl Airport to Pensacola as you normally would.

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 January 28, 2026.
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
8.0
Very good
4,267 reviews

Crew

8.6

Comfort

8.0

Food

7.0

Boarding

8.1

Overall

8.0

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
8.0
Very good
4,267 reviews
Southwest
8.0
Very good
4,267 reviews

Crew

8.6

Comfort

8.0

Food

7.0

Boarding

8.1

Overall

8.0

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
8,124 reviews
Southwest
8.0
Very good
4,267 reviews

Crew

8.6

Comfort

8.0

Food

7.0

Boarding

8.1

Overall

8.0

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
9,212 reviews
Southwest
8.0
Very good
4,267 reviews

Crew

8.6

Comfort

8.0

Food

7.0

Boarding

8.1

Overall

8.0

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
11,201 reviews
Southwest
8.0
Very good
4,267 reviews

Crew

8.6

Comfort

8.0

Food

7.0

Boarding

8.1

Overall

8.0

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
8,387 reviews
Southwest
8.0
Very good
4,267 reviews

Crew

8.6

Comfort

8.0

Food

7.0

Boarding

8.1

Overall

8.0

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 2 inbound flights 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 Delta fly from Chicago O'Hare Intl Airport to Pensacola in about 5h 41m. The time it takes to get you to your destination can typically vary by up to . Chicago O'Hare Intl Airport and Pensacola are separated by a distance of 795 mi.

  • 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 $154, and United Airlines, from $209. Users have found that Spirit Airlines is 64% 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 ($73), Delta ($88), and Southwest ($98).

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

    Consider United Airlines (80%), Air New Zealand (80%) or Republic Airways (67%) 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 $159. While the most popular route (Chicago O'Hare Intl - Pensacola) can be booked for $147 on average, our data indicates $494 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 $137). Flying from Chicago O'Hare Intl Airport to Pensacola in August is currently the most expensive (average of $217). 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
Navarre Beach
Perdido Key
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 January 28, 2026.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$116Average$210FlexibilityNo cancel feeOn-time65%
DeltaCheapest$154Average$266FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$209Average$370FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$209Average$321FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$232Average$348FlexibilityNo cancel feeOn-time63%

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