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O'Hare Intl

$84+ 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 1/17. Fares are subject to change and may not be available on all flights or dates of travel.
PNS — ORD
Jan 28 — Feb 41
Wed 1/28
Wed 2/4
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

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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 Friday or Thursday 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 29, 2025.

This Super.com deal was found by Cheapflights users on 12/27. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/301:58 pmPNS - ORD
1 stop10h 32mSpirit Airlines
Thu 1/85:45 amORD - PNS
1 stop10h 52mSpirit Airlines
Deal found 12/27$262
This Expedia deal was found by Cheapflights users on 12/26. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/301:58 pmPNS - ORD
1 stop10h 32mMultiple Airlines
Sat 1/37:00 amORD - PNS
1 stop11h 31mMultiple Airlines
Deal found 12/26$303
This Super.com deal was found by Cheapflights users on 12/27. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/301:58 pmPNS - ORD
1 stop10h 32mSpirit Airlines
Thu 1/17:30 amORD - PNS
1 stop10h 44mSpirit Airlines
Deal found 12/27$318
This Delta deal was found by Cheapflights users on 12/27. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/288:20 amPNS - ORD
1 stop6h 53mDelta
Sat 1/105:59 pmORD - PNS
1 stop5h 14mDelta
Deal found 12/27$364
This American Airlines deal was found by Cheapflights users on 12/26. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/281:12 pmPNS - ORD
Nonstop2h 42mAmerican Airlines
Mon 1/510:13 amORD - PNS
Nonstop2h 25mAmerican Airlines
Deal found 12/26$379
This Delta deal was found by Cheapflights users on 12/27. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/3011:45 amPNS - ORD
1 stop4h 34mDelta
Sun 1/115:30 amORD - PNS
1 stop6h 09mDelta
Deal found 12/27$384
This American Airlines deal was found by Cheapflights users on 12/26. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/261:12 pmPNS - ORD
Nonstop2h 42mAmerican Airlines
Fri 1/211:35 amORD - PNS
1 stop5h 45mAmerican Airlines
Deal found 12/26$389
This Delta deal was found by Cheapflights users on 12/26. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/2910:26 amPNS - ORD
1 stop5h 53mDelta
Mon 1/55:30 amORD - PNS
1 stop6h 09mDelta
Deal found 12/26$399
This Southwest deal was found by Cheapflights users on 12/26. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/287:20 amPNS - ORD
1 stop4h 55mSouthwest
Wed 1/76:05 amORD - PNS
2 stops12h 20mSouthwest
Deal found 12/26$410
This Delta deal was found by Cheapflights users on 12/27. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/3011:45 amPNS - ORD
1 stop4h 34mDelta
Wed 1/77:05 amORD - PNS
1 stop4h 34mDelta
Deal found 12/27$419
This United Airlines deal was found by Cheapflights users on 12/27. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/302:33 pmPNS - ORD
Nonstop2h 34mUnited Airlines
Thu 1/810:45 amORD - PNS
Nonstop2h 47mUnited Airlines
Deal found 12/27$425
This Kiwi.com deal was found by Cheapflights users on 12/27. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/297:09 pmPNS - ORD
1 stop20h 33mMultiple Airlines
Thu 1/85:53 pmORD - PNS
2 stops40h 45mMultiple Airlines
Deal found 12/27$435

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 29, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$178
(Kiwi.com)

One-way from

$84
(Kiwi.com)

Popular in

June

Cheapest in

October

Average price

$326

Good round-trip deal

$303 or less

Good one-way deal

$219 or less
Provider with most accurate pricing for Pensacola-Chicago O'Hare Intl flight deals.
Search Deals
Provider most trusted by Cheapflights users for Pensacola-Chicago O'Hare Intl flights.
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From Pensacola to Chicago O'Hare Intl
Search Deals
One-way flight from Pensacola to Chicago O'Hare Intl
Search Deals
Highest demand for flights based on searches. 4% potential increase in price ($15 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($5 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 29, 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

Wed 1/21

5:33 pm-6:29 pm

2 stops24h 56m

Chicago O'Hare Intl

Wed 1/28

10:48 am-4:37 pm

1 stop5h 49m

$214

PensacolaChicago

PNS - ORD

PNSORD

Pensacola

Tue 2/3

5:33 pm-7:41 pm

1 stop26h 08m

Chicago O'Hare Intl

Fri 2/6

8:43 pm-4:37 pm

2 stops19h 54m

$224

PensacolaChicago

PNS - ORD

PNSORD

Pensacola

Thu 3/19

8:15 am-1:38 pm

1 stop5h 23m

Chicago O'Hare Intl

Tue 3/24

11:10 am-3:09 pm

1 stop3h 59m

$229

PensacolaChicago

PNS - ORD

PNSORD

Pensacola

Mon 1/26

6:07 pm-11:56 pm

1 stop5h 49m

Chicago O'Hare Intl

Sat 1/31

5:59 pm-11:13 pm

1 stop5h 14m

$229

PensacolaChicago

PNS - ORD

PNSORD

Pensacola

Thu 3/5

5:20 pm-5:24 pm

1 stop24h 04m

Chicago O'Hare Intl

Mon 3/9

8:15 am-2:32 pm

1 stop6h 17m

$244

PensacolaChicago

PNS - ORD

PNSORD

Pensacola

Thu 1/15

6:00 am-10:59 am

1 stop4h 59m

Chicago O'Hare Intl

Thu 1/22

5:30 am-10:26 am

1 stop4h 56m

$249

PensacolaChicago

PNS - ORD

PNSORD

Pensacola

Wed 1/21

6:35 am-1:00 pm

1 stop6h 25m

Chicago O'Hare Intl

Wed 1/28

10:45 am-1:32 pm

Nonstop2h 47m

$254

PensacolaChicago

PNS - ORD

PNSORD

Pensacola

Tue 1/13

5:33 pm-9:12 am

2 stops15h 39m

Chicago O'Hare Intl

Fri 1/16

7:20 am-3:08 pm

1 stop7h 48m

$276

PensacolaChicago

PNS - ORD

PNSORD

Pensacola

Tue 2/3

7:50 am-9:50 pm

2 stops14h 00m

Chicago O'Hare Intl

Fri 2/6

6:05 am-6:50 pm

2 stops12h 45m

$319

PensacolaChicago

PNS - ORD

PNSORD

Pensacola

Sat 2/14

1:15 pm-4:00 pm

Nonstop2h 45m

Chicago O'Hare Intl

Wed 2/18

10:16 am-12:39 pm

Nonstop2h 23m

$319

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/28

Showing 1-10 of 22 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

*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 26, 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 29, 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 39% 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 29, 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
8.0
Very good
4,252 reviews

Food

7.0

Crew

8.6

Boarding

8.1

Comfort

8.0

Overall

8.0

Entertainment

7.5

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
8.0
Very good
4,252 reviews
Southwest
8.0
Very good
4,252 reviews

Food

7.0

Crew

8.6

Boarding

8.1

Comfort

8.0

Overall

8.0

Entertainment

7.5

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
8,014 reviews
Southwest
8.0
Very good
4,252 reviews

Food

7.0

Crew

8.6

Boarding

8.1

Comfort

8.0

Overall

8.0

Entertainment

7.5

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
9,120 reviews
Southwest
8.0
Very good
4,252 reviews

Food

7.0

Crew

8.6

Boarding

8.1

Comfort

8.0

Overall

8.0

Entertainment

7.5

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
11,072 reviews
Southwest
8.0
Very good
4,252 reviews

Food

7.0

Crew

8.6

Boarding

8.1

Comfort

8.0

Overall

8.0

Entertainment

7.5

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
8,221 reviews
Southwest
8.0
Very good
4,252 reviews

Food

7.0

Crew

8.6

Boarding

8.1

Comfort

8.0

Overall

8.0

Entertainment

7.5

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 5 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 5h 23m. 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 $196, 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 (82%), Qatar Airways (80%) or Envoy Air (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 $408 for a flight from Pensacola to Chicago O'Hare Intl Airport. The cheapest flight overall is $159 while the most popular route, (Pensacola - Chicago O'Hare Intl) is currently priced at $179.

  • 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
Kenosha
Warrenville
Waukegan
Aurora
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 29, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$155Average$213FlexibilityNo cancel feeOn-time65%
SouthwestCheapest$173Average$326FlexibilityNo cancel feeOn-time63%
DeltaCheapest$196Average$237FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$209Average$313FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$238Average$339FlexibilityNo cancel feeOn-time71%

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