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O'Hare Intl

$78+ 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 11/12. Fares are subject to change and may not be available on all flights or dates of travel.
PNS — ORD
Aug 19 — Aug 261
Tue 8/19
Tue 8/26
1 adult, Economy
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Cheapflights Tip: The best prices from Pensacola to Chicago O'Hare Intl are usually found in January or May, booked 45 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 August 14, 2025.

Round-trip from

$155
(United Airlines)

One-way from

$78
(United Airlines)

Popular in

September

Cheapest in

January

Average price

$303

Good round-trip deal

$294 or less

Good one-way deal

$214 or less
From Pensacola to Chicago O'Hare Intl
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One-way flight from Pensacola to Chicago O'Hare Intl
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Highest demand for flights based on searches. 7% potential increase in price ($26 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($6 potential savings vs. average RT price).
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Average for round-trip flights in August 2025
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Price to beat on a round-trip flight from Pensacola to Chicago O'Hare Intl.
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Price to beat on a one-way flight from Pensacola to Chicago O'Hare Intl.
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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 August 14, 2025.

This United Airlines deal was found by Cheapflights users on 8/12. 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.
Tue 9/162:15 pmPNS - ORD
Nonstop2h 37mUnited Airlines
Wed 9/1710:53 amORD - PNS
Nonstop2h 25mUnited Airlines
Deal found 8/12$155
This Priceline deal was found by Cheapflights users on 8/13. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/164:44 pmPNS - ORD
1 stop6h 04mSpirit Airlines
Wed 9/175:05 amORD - PNS
1 stop10h 34mSpirit Airlines
Deal found 8/13$162
This United Airlines deal was found by Cheapflights users on 8/12. 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 9/102:15 pmPNS - ORD
Nonstop2h 37mUnited Airlines
Mon 9/1510:53 amORD - PNS
Nonstop2h 25mUnited Airlines
Deal found 8/12$166
This Priceline deal was found by Cheapflights users on 8/14. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/184:36 pmPNS - ORD
1 stop7h 09mMultiple Airlines
Thu 10/236:50 amORD - PNS
1 stop8h 03mMultiple Airlines
Deal found 8/14$170
This Cheapflightsfares deal was found by Cheapflights users on 8/12. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/104:44 pmPNS - ORD
1 stop6h 04mSpirit Airlines
Mon 9/156:30 amORD - PNS
1 stop11h 40mSpirit Airlines
Deal found 8/12$171
This Delta deal was found by Cheapflights users on 8/13. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/35:00 pmPNS - ORD
1 stop5h 37mDelta
Wed 9/105:45 amORD - PNS
1 stop5h 05mDelta
Deal found 8/13$177
This Cheapflightsfares deal was found by Cheapflights users on 8/13. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/124:44 pmPNS - ORD
1 stop6h 04mSpirit Airlines
Mon 9/156:30 amORD - PNS
1 stop11h 40mSpirit Airlines
Deal found 8/13$180
This Cheapflightsfares deal was found by Cheapflights users on 8/12. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/194:44 pmPNS - ORD
1 stop6h 04mSpirit Airlines
Sun 9/216:30 amORD - PNS
1 stop11h 40mSpirit Airlines
Deal found 8/12$181
This Priceline deal was found by Cheapflights users on 8/13. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/244:44 pmPNS - ORD
1 stop6h 04mSpirit Airlines
Sat 9/275:05 amORD - PNS
1 stop10h 34mSpirit Airlines
Deal found 8/13$184
This Cheapflightsfares deal was found by Cheapflights users on 8/12. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/2710:50 amPNS - ORD
1 stop8h 17mSpirit Airlines
Wed 9/36:56 amORD - PNS
1 stop10h 11mSpirit Airlines
Deal found 8/12$185
This Delta deal was found by Cheapflights users on 8/12. 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.
Wed 10/112:14 pmPNS - ORD
1 stop7h 03mDelta
Sat 10/46:45 amORD - PNS
1 stop6h 21mDelta
Deal found 8/12$187

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 August 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

Wed 9/10

2:15 pm-4:52 pm

Nonstop2h 37m

Chicago O'Hare Intl

Wed 9/17

10:53 am-1:18 pm

Nonstop2h 25m

$155

PensacolaChicago

PNS - ORD

PNSORD

Pensacola

Tue 9/16

2:15 pm-4:52 pm

Nonstop2h 37m

Chicago O'Hare Intl

Wed 9/17

10:53 am-1:18 pm

Nonstop2h 25m

$155

PensacolaChicago

PNS - ORD

PNSORD

Pensacola

Tue 9/16

4:44 pm-10:48 pm

1 stop6h 04m

Chicago O'Hare Intl

Wed 9/17

5:05 am-3:39 pm

1 stop10h 34m

$162

PensacolaChicago

PNS - ORD

PNSORD

Pensacola

Wed 9/10

2:15 pm-4:52 pm

Nonstop2h 37m

Chicago O'Hare Intl

Mon 9/15

10:53 am-1:18 pm

Nonstop2h 25m

$166

PensacolaChicago

PNS - ORD

PNSORD

Pensacola

Sat 10/18

4:36 pm-11:45 pm

1 stop7h 09m

Chicago O'Hare Intl

Thu 10/23

6:50 am-2:53 pm

1 stop8h 03m

$170

PensacolaChicago

PNS - ORD

PNSORD

Pensacola

Wed 9/10

4:44 pm-10:48 pm

1 stop6h 04m

Chicago O'Hare Intl

Sun 9/14

6:30 am-6:10 pm

1 stop11h 40m

$171

PensacolaChicago

PNS - ORD

PNSORD

Pensacola

Wed 9/17

4:44 pm-10:48 pm

1 stop6h 04m

Chicago O'Hare Intl

Wed 9/24

5:05 am-3:39 pm

1 stop10h 34m

$171

PensacolaChicago

PNS - ORD

PNSORD

Pensacola

Thu 9/4

4:44 pm-10:48 pm

1 stop6h 04m

Chicago O'Hare Intl

Tue 9/9

6:30 am-6:10 pm

1 stop11h 40m

$171

PensacolaChicago

PNS - ORD

PNSORD

Pensacola

Sun 9/7

4:44 pm-10:48 pm

1 stop6h 04m

Chicago O'Hare Intl

Wed 9/10

5:05 am-3:39 pm

1 stop10h 34m

$171

PensacolaChicago

PNS - ORD

PNSORD

Pensacola

Tue 9/16

4:44 pm-10:48 pm

1 stop6h 04m

Chicago O'Hare Intl

Thu 9/25

5:05 am-3:39 pm

1 stop10h 34m

$171

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/13

Showing 1-10 of 19 results
1
2

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 August 8, 2025.

Booking 45 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, August is the cheapest month in which you can book a flight from Pensacola to Chicago O'Hare Intl Airport (average of $245). Flying from Pensacola to Chicago O'Hare Intl Airport in March is currently the most expensive (average of $321). 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 August 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 52% 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 August 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
8.0
Very good
4,244 reviews

Overall

8.0

Entertainment

7.5

Boarding

8.1

Crew

8.6

Comfort

8.0

Food

7.0

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
8.0
Very good
4,244 reviews
Southwest
8.0
Very good
4,244 reviews

Overall

8.0

Entertainment

7.5

Boarding

8.1

Crew

8.6

Comfort

8.0

Food

7.0

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
8.0
Very good
7,980 reviews
Southwest
8.0
Very good
4,244 reviews

Overall

8.0

Entertainment

7.5

Boarding

8.1

Crew

8.6

Comfort

8.0

Food

7.0

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
8,916 reviews
Southwest
8.0
Very good
4,244 reviews

Overall

8.0

Entertainment

7.5

Boarding

8.1

Crew

8.6

Comfort

8.0

Food

7.0

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
10,000 reviews
Southwest
8.0
Very good
4,244 reviews

Overall

8.0

Entertainment

7.5

Boarding

8.1

Crew

8.6

Comfort

8.0

Food

7.0

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
8,046 reviews
Southwest
8.0
Very good
4,244 reviews

Overall

8.0

Entertainment

7.5

Boarding

8.1

Crew

8.6

Comfort

8.0

Food

7.0

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 3 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.

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

    Currently priced at $152, 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 53% cheaper than the average price of flights available within the next 90 days to this destination.

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

    Consider Emirates (72%), United Airlines (72%) or Air New Zealand (72%) 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 $316 for a flight from Pensacola to Chicago O'Hare Intl Airport. The cheapest flight overall is $138 while the most popular route, (Pensacola - Chicago O'Hare Intl) is currently priced at $155.

  • 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, August is the cheapest month in which you can book a flight from Pensacola to Chicago O'Hare Intl Airport (average of $245). Flying from Pensacola to Chicago O'Hare Intl Airport in March is currently the most expensive (average of $321). 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
Beloit
Hoffman Estates
Skokie
Des Plaines
Elgin
Gurnee
Arlington Heights
Racine
Rockford
Great Lakes
Orland Park
Merrillville
Naperville
Waukegan
Elk Grove Village
Downers Grove
Tinley Park
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 August 14, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$152Average$201FlexibilityNo cancel feeOn-time65%
SouthwestCheapest$173Average$370FlexibilityNo cancel feeOn-time63%
DeltaCheapest$194Average$260FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$220Average$401FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$228Average$316FlexibilityNo cancel feeOn-time71%

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