HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Pensacola

$61+ 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 12/8. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — PNS
Nov 29 — Dec 61
Sat 11/29
Sat 12/6
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

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”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

Cheapflights Tip: The best prices from Chicago O'Hare Intl to Pensacola are usually found in January or September, 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

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 October 30, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$209
(American Airlines)

One-way from

$61
(Priceline)

Popular in

December

Cheapest in

January

Average price

$353

Good round-trip deal

$236 or less

Good one-way deal

$136 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.
Search Deals
From Chicago O'Hare Intl to Pensacola
Search Deals
One-way flight from Chicago O'Hare Intl to Pensacola
Search Deals
High demand for flights, 3% potential price rise
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($6 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in October 2025
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

Find 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 October 30, 2025.

This United Airlines deal was found by Cheapflights users on 10/28. 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.
Thu 11/2010:49 amORD - PNS
Nonstop2h 26mUnited Airlines
Mon 11/242:17 pmPNS - ORD
Nonstop2h 31mUnited Airlines
Deal found 10/28$209
This Mytrip deal was found by Cheapflights users on 10/28. 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.
Tue 11/1110:00 amORD - PNS
2 stops9h 11mSpirit Airlines
Fri 11/1411:17 amPNS - ORD
1 stop11h 49mSpirit Airlines
Deal found 10/28$210
This Mytrip deal was found by Cheapflights users on 10/29. 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.
Tue 11/187:34 pmORD - PNS
2 stops23h 37mSpirit Airlines
Thu 11/201:44 pmPNS - ORD
1 stop9h 22mSpirit Airlines
Deal found 10/29$211
This Mytrip deal was found by Cheapflights users on 10/27. 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.
Wed 11/197:34 pmORD - PNS
2 stops17h 15mSpirit Airlines
Mon 11/245:54 pmPNS - ORD
1 stop5h 12mSpirit Airlines
Deal found 10/27$214
This Kiwi.com deal was found by Cheapflights users on 10/29. 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 11/206:23 pmORD - PNS
1 stop22h 36mMultiple Airlines
Mon 11/248:16 pmPNS - ORD
1 stop23h 05mMultiple Airlines
Deal found 10/29$216
This Mytrip deal was found by Cheapflights users on 10/27. 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.
Wed 11/121:48 pmORD - PNS
3 stops29h 23mSpirit Airlines
Mon 11/178:16 pmPNS - ORD
1 stop13h 31mSpirit Airlines
Deal found 10/27$218
This United Airlines deal was found by Cheapflights users on 10/28. 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.
Sat 11/1510:49 amORD - PNS
Nonstop2h 26mUnited Airlines
Tue 11/182:17 pmPNS - ORD
Nonstop2h 31mUnited Airlines
Deal found 10/28$219
This Kiwi.com deal was found by Cheapflights users on 10/28. 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 11/158:00 amORD - PNS
1 stop26h 22mMultiple Airlines
Wed 11/198:16 pmPNS - ORD
1 stop20h 55mMultiple Airlines
Deal found 10/28$221
This United Airlines deal was found by Cheapflights users on 10/28. 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.
Wed 12/310:50 amORD - PNS
Nonstop2h 27mUnited Airlines
Sun 12/72:15 pmPNS - ORD
Nonstop2h 32mUnited Airlines
Deal found 10/28$223
This Mytrip deal was found by Cheapflights users on 10/28. 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 12/117:10 amORD - PNS
1 stop11h 04mSpirit Airlines
Sun 12/147:09 pmPNS - ORD
1 stop16h 04mSpirit Airlines
Deal found 10/28$224
This Mytrip deal was found by Cheapflights users on 10/28. 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.
Wed 11/127:34 pmORD - PNS
2 stops23h 37mSpirit Airlines
Fri 11/1411:17 amPNS - ORD
1 stop11h 49mSpirit Airlines
Deal found 10/28$225

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 October 30, 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

Thu 11/27

10:49 am-1:15 pm

Nonstop2h 26m

Pensacola

Thu 12/4

2:15 pm-4:47 pm

Nonstop2h 32m

$209

ChicagoPensacola

ORD - PNS

ORDPNS

Chicago O'Hare Intl

Fri 1/23

7:05 am-12:45 pm

1 stop5h 40m

Pensacola

Fri 2/6

6:07 pm-11:57 pm

1 stop5h 50m

$229

ChicagoPensacola

ORD - PNS

ORDPNS

Chicago O'Hare Intl

Tue 1/27

7:05 am-12:45 pm

1 stop5h 40m

Pensacola

Sat 2/7

6:00 am-10:15 am

1 stop4h 15m

$229

ChicagoPensacola

ORD - PNS

ORDPNS

Chicago O'Hare Intl

Wed 1/28

5:33 am-10:28 am

1 stop4h 55m

Pensacola

Thu 2/5

1:40 pm-8:59 pm

1 stop7h 19m

$229

ChicagoPensacola

ORD - PNS

ORDPNS

Chicago O'Hare Intl

Fri 1/23

5:54 pm-11:12 pm

1 stop5h 18m

Pensacola

Tue 2/10

7:00 am-1:39 pm

1 stop6h 39m

$229

ChicagoPensacola

ORD - PNS

ORDPNS

Chicago O'Hare Intl

Sun 1/25

5:54 pm-11:12 pm

1 stop5h 18m

Pensacola

Sat 2/7

1:59 pm-7:21 pm

1 stop5h 22m

$229

ChicagoPensacola

ORD - PNS

ORDPNS

Chicago O'Hare Intl

Tue 1/27

5:33 am-10:28 am

1 stop4h 55m

Pensacola

Thu 2/5

1:40 pm-6:49 pm

1 stop5h 09m

$229

ChicagoPensacola

ORD - PNS

ORDPNS

Chicago O'Hare Intl

Thu 1/22

5:33 am-12:35 pm

1 stop7h 02m

Pensacola

Sun 2/8

6:00 am-10:08 am

1 stop4h 08m

$229

ChicagoPensacola

ORD - PNS

ORDPNS

Chicago O'Hare Intl

Tue 1/27

5:33 am-10:28 am

1 stop4h 55m

Pensacola

Wed 2/11

6:00 am-10:08 am

1 stop4h 08m

$229

ChicagoPensacola

ORD - PNS

ORDPNS

Chicago O'Hare Intl

Tue 1/27

2:49 pm-6:42 pm

1 stop3h 53m

Pensacola

Tue 2/10

12:55 pm-8:47 pm

1 stop7h 52m

$229

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/30

Showing 1-10 of 22 results
1
2
3

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 October.
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 October 24, 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 $137). Flying from Chicago O'Hare Intl Airport to Pensacola in December is currently the most expensive (average of $228). 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 October 30, 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 60% 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 October 26, 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 October 30, 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
8.0
Very good
4,243 reviews

Entertainment

7.5

Overall

8.0

Food

7.0

Comfort

8.0

Crew

8.6

Boarding

8.1

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
4,243 reviews
Southwest
8.0
Very good
4,243 reviews

Entertainment

7.5

Overall

8.0

Food

7.0

Comfort

8.0

Crew

8.6

Boarding

8.1

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
7,998 reviews
Southwest
8.0
Very good
4,243 reviews

Entertainment

7.5

Overall

8.0

Food

7.0

Comfort

8.0

Crew

8.6

Boarding

8.1

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
8,998 reviews
Southwest
8.0
Very good
4,243 reviews

Entertainment

7.5

Overall

8.0

Food

7.0

Comfort

8.0

Crew

8.6

Boarding

8.1

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
11,035 reviews
Southwest
8.0
Very good
4,243 reviews

Entertainment

7.5

Overall

8.0

Food

7.0

Comfort

8.0

Crew

8.6

Boarding

8.1

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
8,116 reviews
Southwest
8.0
Very good
4,243 reviews

Entertainment

7.5

Overall

8.0

Food

7.0

Comfort

8.0

Crew

8.6

Boarding

8.1

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 0 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 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 3h 14m. 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 $118. Other airlines that can offer you cheap pricing are Delta, from $177, and American Airlines, from $217. Users have found that Spirit Airlines is 65% cheaper than the other options available to this destination.

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

    Looking at all options, your cheapest flight can be booked for $104. While the most popular route (Chicago O'Hare Intl - Pensacola) can be booked for $162 on average, our data indicates $269 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 December is currently the most expensive (average of $228). 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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for O'Hare Intl to Pensacola

See prices for flight routes from nearby airports that may be better suited for you.
O'Hare Intl to Orlando flights
O'Hare Intl to Miami flights
O'Hare Intl to Fort Lauderdale flights
O'Hare Intl to Tampa flights
O'Hare Intl to Fort Myers flights
Midway to Miami flights
O'Hare Intl to West Palm Beach flights
Midway to Orlando flights
Midway to Tampa flights
O'Hare Intl to Sarasota flights
Midway to Fort Lauderdale flights
Midway to Fort Myers flights
O'Hare Intl to Jacksonville flights
O'Hare Intl to Key West flights
Midway to West Palm Beach flights
Midway to Sarasota flights
O'Hare Intl to Panama City flights
Rockford to Orlando Sanford Intl flights
Midway to Key West flights
Midway to Jacksonville flights
Rockford to St Petersburg flights
O'Hare Intl to Daytona Beach flights
Midway to Pensacola flights
Rockford to Punta Gorda flights
O'Hare Intl to Melbourne flights
Midway to Panama City flights
O'Hare Intl to St Petersburg flights
O'Hare Intl to Valparaiso flights
Midway to Daytona Beach flights
Midway to Melbourne flights
Midway to Orlando Sanford Intl flights
Midway to Valparaiso flights
O'Hare Intl to Tallahassee flights
O'Hare Intl to Punta Gorda flights
Midway to Punta Gorda flights
O'Hare Intl to Gainesville flights
Midway to Tallahassee flights
O'Hare Intl to Orlando Sanford Intl flights
Midway to Gainesville flights
O'Hare Intl to Valdosta flights
Midway to Valdosta flights
O'Hare Intl to Destin flights

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 October 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$118Average$210FlexibilityNo cancel feeOn-time65%
DeltaCheapest$177Average$296FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$217Average$318FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$219Average$379FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$232Average$412FlexibilityNo cancel feeOn-time63%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.
Site
Cookie settings©2025 Cheapflights