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O'Hare Intl

$81+ Cheap flights from Pensacola (PNS) to O'Hare Intl (ORD)

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 3/12. Fares are subject to change and may not be available on all flights or dates of travel.
PNS — ORD
Jan 13 — Jan 201
Tue 1/13
Tue 1/20
1 adult, Economy
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Find cheap flights from Pensacola to O'Hare Intl 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

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3. Compare prices and book

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Cheapflights Tip: The best prices from Pensacola to Chicago O'Hare Intl are usually found in October or January, booked 55 days in advance, depart on a Thursday or Friday and return on a Tuesday

Cheap flight deals from Pensacola to O'Hare Intl

Cheapest flights from Pensacola to O'Hare Intl
Explore the most affordable flight options available from Pensacola to O'Hare Intl. Find the lowest fares from popular airlines and budget airlines, with prices last updated on December 14, 2025.

This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/297:16 pmPNS - ORD
1 stop4h 46mDelta
Thu 1/15:30 amORD - PNS
1 stop4h 50mDelta
Deal found 12/12$269
This United 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/242:33 pmPNS - ORD
Nonstop2h 34mUnited Airlines
Wed 12/3110:55 amORD - PNS
Nonstop2h 36mUnited Airlines
Deal found 12/12$284
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.
Mon 12/295:52 pmPNS - ORD
1 stop5h 50mAmerican Airlines
Thu 1/110:13 amORD - PNS
Nonstop2h 25mAmerican Airlines
Deal found 12/12$294
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.
Tue 12/304:19 pmPNS - ORD
1 stop8h 24mAmerican Airlines
Thu 1/15:00 amORD - PNS
1 stop5h 15mAmerican Airlines
Deal found 12/14$304
This Priceline 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/241:58 pmPNS - ORD
1 stop10h 32mSpirit Airlines
Wed 12/315:00 amORD - PNS
1 stop8h 03mSpirit Airlines
Deal found 12/12$309
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.
Wed 12/2412:58 pmPNS - ORD
Nonstop2h 42mAmerican Airlines
Wed 12/315:00 amORD - PNS
1 stop5h 15mAmerican Airlines
Deal found 12/12$329
This United 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/262:33 pmPNS - ORD
Nonstop2h 34mUnited Airlines
Mon 1/510:55 amORD - PNS
Nonstop2h 36mUnited Airlines
Deal found 12/13$334
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 12/215:52 pmPNS - ORD
1 stop5h 50mAmerican Airlines
Fri 12/261:27 pmORD - PNS
1 stop8h 02mAmerican Airlines
Deal found 12/14$339
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/311:58 pmPNS - ORD
2 stops28h 35mMultiple Airlines
Sun 1/44:44 pmORD - PNS
1 stop25h 30mMultiple Airlines
Deal found 12/13$341
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.
Sun 12/285:19 amPNS - ORD
1 stop5h 26mAmerican Airlines
Thu 1/110:13 amORD - PNS
Nonstop2h 25mAmerican Airlines
Deal found 12/13$343

Find flight deals from Pensacola to O'Hare Intl

Discover tips and strategies to find the most affordable flight options for your journey from Pensacola (PNS) to O'Hare Intl (ORD). 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 14, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$181
(Kiwi.com)

One-way from

$81
(Frontier)

Popular in

June

Cheapest in

October

Average price

$319

Good round-trip deal

$288 or less

Good one-way deal

$219 or less
Provider with most accurate pricing for Pensacola-Chicago O'Hare Intl flight deals.
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Provider most trusted by Cheapflights users for Pensacola-Chicago O'Hare Intl flights.
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From Pensacola to Chicago O'Hare Intl
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One-way flight from Pensacola to Chicago O'Hare Intl
Search Deals
Highest demand for flights based on searches. 4% potential increase in price ($13 potential increase over avg. RT price).
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 December 2025
Search Deals
Price to beat on a round-trip flight from Pensacola to Chicago O'Hare Intl.
Search Deals
Price to beat on a one-way flight from Pensacola to Chicago O'Hare Intl.
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Pensacola to O'Hare Intl 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 14, 2025.
Use the filters below to find and compare flights from Pensacola to Chicago O'Hare Intl Airport that are best for you.

Fly from

Pensacola

Fly to

O'Hare Intl

Route

Depart

Return

Price

PensacolaChicago

PNS - ORD

PNSORD

Pensacola

Fri 1/9

4:03 pm-11:46 pm

1 stop7h 43m

Chicago O'Hare Intl

Thu 1/15

5:15 am-3:08 pm

1 stop9h 53m

$184

PensacolaChicago

PNS - ORD

PNSORD

Pensacola

Wed 1/21

5:33 pm-10:41 am

1 stop17h 08m

Chicago O'Hare Intl

Thu 1/29

8:43 pm-3:08 pm

1 stop18h 25m

$205

PensacolaChicago

PNS - ORD

PNSORD

Pensacola

Fri 2/20

5:59 pm-11:27 am

2 stops17h 28m

Chicago O'Hare Intl

Mon 2/23

7:05 am-3:54 pm

1 stop8h 49m

$223

PensacolaChicago

PNS - ORD

PNSORD

Pensacola

Sat 1/17

12:35 pm-4:44 pm

1 stop4h 09m

Chicago O'Hare Intl

Fri 1/30

5:59 pm-11:13 pm

1 stop5h 14m

$229

PensacolaChicago

PNS - ORD

PNSORD

Pensacola

Fri 1/16

5:54 pm-11:59 pm

1 stop6h 05m

Chicago O'Hare Intl

Mon 1/19

5:30 am-12:35 pm

1 stop7h 05m

$229

PensacolaChicago

PNS - ORD

PNSORD

Pensacola

Tue 1/13

8:00 am-1:40 pm

1 stop5h 40m

Chicago O'Hare Intl

Thu 1/15

7:05 am-1:53 pm

1 stop6h 48m

$229

PensacolaChicago

PNS - ORD

PNSORD

Pensacola

Wed 1/21

9:23 am-1:40 pm

1 stop4h 17m

Chicago O'Hare Intl

Sat 1/31

5:59 pm-11:13 pm

1 stop5h 14m

$229

PensacolaChicago

PNS - ORD

PNSORD

Pensacola

Sat 2/21

7:00 am-2:10 pm

1 stop7h 10m

Chicago O'Hare Intl

Wed 2/25

5:25 am-10:26 am

1 stop5h 01m

$229

PensacolaChicago

PNS - ORD

PNSORD

Pensacola

Fri 1/23

11:25 am-4:55 pm

1 stop5h 30m

Chicago O'Hare Intl

Sat 1/31

5:30 am-10:26 am

1 stop4h 56m

$229

PensacolaChicago

PNS - ORD

PNSORD

Pensacola

Tue 1/6

12:55 pm-8:47 pm

1 stop7h 52m

Chicago O'Hare Intl

Sun 1/11

7:05 am-1:53 pm

1 stop6h 48m

$229

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/12

Showing 1-10 of 21 results
1
2
3

Compare providers for flights from Pensacola to O'Hare Intl

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 Pensacola to O'Hare Intl 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 Pensacola-Chicago O'Hare Intl Airport flights, users find the pricing of eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Pensacola-Chicago O'Hare Intl Airport flight deals on Cheapflights vs. eDreams >95% of the time. Price accuracy is based on data collected from Pensacola-Chicago O'Hare Intl Airport flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Pensacola-Chicago O'Hare Intl Airport 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 Pensacola-Chicago O'Hare Intl Airport 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 Pensacola to O'Hare Intl

Have a flexible travel schedule? Discover the best time to fly to O'Hare Intl from Pensacola 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 Pensacola to Chicago O'Hare Intl Airport

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

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

Booking 50 days in advance of your planned departure date is, on average, the best time to get cheap flights from Pensacola to Chicago O'Hare Intl Airport. The general trend is that the closer you book to the departure date, the more expensive your flight will be.

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

Currently, June is the cheapest month in which you can book a flight from Pensacola to Chicago O'Hare Intl Airport (average of $118). Flying from Pensacola to Chicago O'Hare Intl Airport in April is currently the most expensive (average of $232). 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 PNS to ORD?

Find hourly flight availability from Pensacola to O'Hare Intl. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated December 14, 2025.

When flying from Pensacola to Chicago O'Hare Intl Airport, the time of day you fly usually plays a role in the price. Save by searching for a flight in the evening, which can drop the price by up to 40% versus a flight at noon.

Reviews of airlines servicing O'Hare Intl

Get insights into the airlines that provide service to O'Hare Intl. 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 O'Hare Intl. Reviews last updated December 14, 2025.
Peruse reviews from past customers who have flown with Southwest, Delta, and United Airlines from Pensacola to Chicago O'Hare Intl Airport to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
7.9
Good
4,250 reviews

Entertainment

7.5

Food

7.0

Boarding

8.1

Crew

8.6

Overall

7.9

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.
Southwest
7.9
Good
4,250 reviews
Southwest
7.9
Good
4,250 reviews

Entertainment

7.5

Food

7.0

Boarding

8.1

Crew

8.6

Overall

7.9

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.
Delta
7.9
Good
8,007 reviews
Southwest
7.9
Good
4,250 reviews

Entertainment

7.5

Food

7.0

Boarding

8.1

Crew

8.6

Overall

7.9

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.
United Airlines
7.4
Good
9,092 reviews
Southwest
7.9
Good
4,250 reviews

Entertainment

7.5

Food

7.0

Boarding

8.1

Crew

8.6

Overall

7.9

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.
American Airlines
7.2
Good
11,052 reviews
Southwest
7.9
Good
4,250 reviews

Entertainment

7.5

Food

7.0

Boarding

8.1

Crew

8.6

Overall

7.9

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.
Spirit Airlines
6.3
Okay
8,185 reviews
Southwest
7.9
Good
4,250 reviews

Entertainment

7.5

Food

7.0

Boarding

8.1

Crew

8.6

Overall

7.9

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Related info for your journey

Find useful and relevant information for your journey from Pensacola to O'Hare Intl. 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 from for flights from Pensacola to Chicago O'Hare Intl?

    Most people fly from Pensacola (PNS) if they book a flight from Pensacola to Chicago O'Hare Intl. On average, Pensacola has 2 outbound flights to 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 Pensacola to Chicago O'Hare Intl Airport?

    A quick flight from Pensacola to Chicago O'Hare Intl Airport can take about 4h 09m. Spirit Airlines provides one of the quickest options available for as low as $229. The distance from Pensacola to Chicago O'Hare Intl Airport is about 795 mi. This flight may include one or multiple stops.

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

    Currently priced at $155, Spirit Airlines will fly you from Pensacola to Chicago O'Hare Intl Airport and back. In addition to Spirit Airlines, many other airlines offer competitively priced options for your trip. Search Cheapflights for deals from Southwest and Delta - these airlines can fly you to your destination from $173 and $194, respectively. Spirit Airlines is 49% cheaper than the average price of flights available within the next 90 days to this destination.

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

    For one-way options, check prices for Spirit Airlines. According to our data, you can fly for as low as $87. Users have also found prices from $98 and $104 on Delta and United Airlines, respectively.

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

    Consider Lufthansa (96%), Emirates (81%) or American Airlines (79%) when booking your flight. These represent the most reliable airlines when flying from Pensacola to Chicago O'Hare Intl Airport.

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

    On average you can expect to pay $402 for a flight from Pensacola to Chicago O'Hare Intl Airport. The cheapest flight overall is $122 while the most popular route, (Pensacola - Chicago O'Hare Intl) is currently priced at $182.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Pensacola to O'Hare Intl 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 Pensacola to Chicago O'Hare Intl Airport?

    Currently, June is the cheapest month in which you can book a flight from Pensacola to Chicago O'Hare Intl Airport (average of $118). Flying from Pensacola to Chicago O'Hare Intl Airport in April is currently the most expensive (average of $232). 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 Chicago O'Hare Intl Airport?

Book flights to Chicago O'Hare Intl Airport if you plan to visit one of these locations
Schaumburg
Rosemont
Gurnee
Elgin
Naperville
Hoffman Estates
Beloit
Delavan
Oak Brook
Downers Grove
Des Plaines
Elk Grove Village
Skokie
Lake Geneva
Bridgeview
Warrenville
Waukegan
Aurora
Kenosha
Evanston

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Top 5 airlines flying from Pensacola to O'Hare Intl

Discover the top 5 airlines that operate flights from Pensacola to O'Hare Intl. 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 14, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$155Average$213FlexibilityNo cancel feeOn-time65%
SouthwestCheapest$173Average$326FlexibilityNo cancel feeOn-time63%
DeltaCheapest$194Average$237FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$209Average$310FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$228Average$320FlexibilityNo cancel feeOn-time71%

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