O'Hare Intl

$55+ 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 11/17. Fares are subject to change and may not be available on all flights or dates of travel.
PNS — ORD
Nov 28 — Dec 51
We work with more than 300 partners to bring you better travel deals

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

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 Pensacola to Chicago O'Hare Intl are usually found in November or January, booked 51 days in advance, depart on a Thursday or Friday and return on a Tuesday

Cheap 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 October 29, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$209
(United Airlines)

One-way from

$55
(Frontier)

Popular in

June

Cheapest in

November

Average price

$279

Good round-trip deal

$258 or less

Good one-way deal

$125 or less
Provider with most accurate pricing for Pensacola-Chicago O'Hare Intl flight deals.
Provider most trusted by Cheapflights users for Pensacola-Chicago O'Hare Intl flights.
From Pensacola to Chicago O'Hare Intl
One-way flight from Pensacola to Chicago O'Hare Intl
Highest demand for flights based on searches. 4% potential increase in price ($14 potential increase over avg. RT price).
Cheapest flight prices on average. 1% potential price decrease ($6 potential savings vs. average RT price).
Average for round-trip flights in October 2025
Price to beat on a round-trip flight from Pensacola to Chicago O'Hare Intl.
Price to beat on a one-way flight from Pensacola to Chicago O'Hare Intl.

Find 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 October 29, 2025.

This United Airlines deal was found by Cheapflights users on 10/26. 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.
Thu 12/42:15 pmPNS - ORD
Nonstop2h 32mUnited Airlines
Thu 12/1810:55 amORD - PNS
Nonstop2h 36mUnited Airlines
Deal found 10/26$209
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/1411:17 amPNS - ORD
1 stop27h 51mMultiple Airlines
Thu 11/206:48 amORD - PNS
1 stop6h 01mMultiple Airlines
Deal found 10/27$210
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/1711:17 amPNS - ORD
2 stops12h 54mMultiple Airlines
Fri 12/53:14 pmORD - PNS
1 stop24h 50mMultiple Airlines
Deal found 10/27$214
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.
Wed 11/128:16 pmPNS - ORD
2 stops18h 15mSpirit Airlines
Thu 11/2010:12 amORD - PNS
1 stop8h 59mSpirit Airlines
Deal found 10/29$218
This American Airlines 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/111:00 pmPNS - ORD
Nonstop2h 42mAmerican Airlines
Sun 12/149:45 amORD - PNS
Nonstop2h 34mAmerican Airlines
Deal found 10/27$219
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.
Tue 11/118:16 pmPNS - ORD
2 stops18h 15mSpirit Airlines
Sat 11/1510:52 amORD - PNS
1 stop8h 19mSpirit Airlines
Deal found 10/27$220
This Mytrip deal was found by Cheapflights users on 10/26. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/47:09 pmPNS - ORD
1 stop16h 04mSpirit Airlines
Sat 12/137:10 amORD - PNS
1 stop11h 04mSpirit Airlines
Deal found 10/26$223
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.
Wed 11/124:44 pmPNS - ORD
2 stops17h 57mMultiple Airlines
Sun 11/165:25 amORD - PNS
1 stop28h 57mMultiple Airlines
Deal found 10/28$224
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/271:44 pmPNS - ORD
1 stop9h 22mMultiple Airlines
Thu 12/46:15 amORD - PNS
1 stop11h 59mMultiple Airlines
Deal found 10/27$227
This Frontier 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/314:30 pmPNS - ORD
1 stop7h 46mFrontier
Sun 11/25:00 amORD - PNS
1 stop9h 35mFrontier
Deal found 10/28$228
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/247:09 pmPNS - ORD
1 stop4h 53mDelta
Sat 11/295:23 amORD - PNS
1 stop5h 18mDelta
Deal found 10/28$229

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 October 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

Thu 12/4

2:15 pm-4:47 pm

Nonstop2h 32m

Chicago O'Hare Intl

Thu 12/18

10:55 am-1:31 pm

Nonstop2h 36m

$209

PensacolaChicago

PNS - ORD

PNSORD

Pensacola

Wed 11/12

8:16 pm-11:12 am

1 stop14h 56m

Chicago O'Hare Intl

Thu 11/20

10:12 am-7:11 pm

1 stop8h 59m

$218

PensacolaChicago

PNS - ORD

PNSORD

Pensacola

Sun 12/7

6:00 am-10:14 am

1 stop4h 14m

Chicago O'Hare Intl

Mon 12/8

5:30 am-10:41 am

1 stop5h 11m

$229

PensacolaChicago

PNS - ORD

PNSORD

Pensacola

Wed 11/12

2:17 pm-4:48 pm

Nonstop2h 31m

Chicago O'Hare Intl

Thu 11/20

10:49 am-1:15 pm

Nonstop2h 26m

$229

PensacolaChicago

PNS - ORD

PNSORD

Pensacola

Sat 2/14

6:00 am-10:06 am

1 stop4h 06m

Chicago O'Hare Intl

Tue 2/17

5:50 am-12:53 pm

1 stop7h 03m

$229

PensacolaChicago

PNS - ORD

PNSORD

Pensacola

Fri 1/16

2:58 pm-7:35 pm

1 stop4h 37m

Chicago O'Hare Intl

Mon 1/19

5:33 am-12:45 pm

1 stop7h 12m

$229

PensacolaChicago

PNS - ORD

PNSORD

Pensacola

Fri 2/13

1:59 pm-6:57 pm

1 stop4h 58m

Chicago O'Hare Intl

Wed 2/18

7:10 am-12:53 pm

1 stop5h 43m

$229

PensacolaChicago

PNS - ORD

PNSORD

Pensacola

Mon 11/24

7:09 pm-12:02 am

1 stop4h 53m

Chicago O'Hare Intl

Sat 11/29

5:23 am-10:41 am

1 stop5h 18m

$229

PensacolaChicago

PNS - ORD

PNSORD

Pensacola

Sat 3/7

6:00 am-10:06 am

1 stop4h 06m

Chicago O'Hare Intl

Mon 3/9

5:55 pm-10:02 pm

1 stop4h 07m

$229

PensacolaChicago

PNS - ORD

PNSORD

Pensacola

Fri 12/5

6:00 am-10:14 am

1 stop4h 14m

Chicago O'Hare Intl

Sat 12/6

6:45 am-12:41 pm

1 stop5h 56m

$229

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/29

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 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 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 October 24, 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 December is currently the most expensive (average of $263). 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 October 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 42% versus a flight at noon.

How much does it cost to fly round-trip from Pensacola to Chicago O'Hare Intl Airport?

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 October 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.

Food

7.0

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Overall

8.0

Crew

8.6

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.

Food

7.0

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Overall

8.0

Crew

8.6

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.

Food

7.0

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Overall

8.0

Crew

8.6

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.

Food

7.0

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Overall

8.0

Crew

8.6

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.

Food

7.0

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Overall

8.0

Crew

8.6

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.

Food

7.0

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Overall

8.0

Crew

8.6

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 2h 32m. United Airlines provides one of the quickest options available for as low as $209. 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 United Airlines. According to our data, you can fly for as low as $105. Users have also found prices from $114 and $115 on Frontier and Delta, respectively.

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

    Consider United Airlines (88%), Lufthansa (86%) or Emirates (85%) 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 $265 for a flight from Pensacola to Chicago O'Hare Intl Airport. The cheapest flight overall is $104 while the most popular route, (Pensacola - Chicago O'Hare Intl) is currently priced at $175.

  • 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 December is currently the most expensive (average of $263). 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
Skokie
Des Plaines
Gurnee
Hoffman Estates
Beloit
Elgin
Oak Brook
Elk Grove Village
Naperville
Racine
Downers Grove
Rockford
Orland Park
Merrillville
Bridgeview
Warrenville
Waukegan
Aurora

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.

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 October 29, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$155Average$213FlexibilityNo cancel feeOn-time65%
SouthwestCheapest$173Average$326FlexibilityNo cancel feeOn-time63%
DeltaCheapest$194Average$238FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$209Average$347FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$238Average$310FlexibilityNo cancel feeOn-time71%

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.