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O'Hare Intl

$88+ 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 10/6. Fares are subject to change and may not be available on all flights or dates of travel.
PNS — ORD
Oct 17 — Oct 241
Fri 10/17
Fri 10/24
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 Friday or Thursday 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 September 17, 2025.

Round-trip from

$166
(Frontier)

One-way from

$88
(Booking.com)

Popular in

June

Cheapest in

January

Average price

$349

Good round-trip deal

$273 or less

Good one-way deal

$156 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. 1% potential increase in price ($4 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($5 potential savings vs. average RT price).
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Average for round-trip flights in September 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 September 17, 2025.

This Frontier deal was found by Cheapflights users on 9/15. 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 11/144:30 pmPNS - ORD
1 stop7h 45mFrontier
Sun 11/166:00 amORD - PNS
1 stop9h 35mFrontier
Deal found 9/15$166
This Kiwi.com deal was found by Cheapflights users on 9/16. 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 11/14:30 pmPNS - ORD
1 stop7h 42mFrontier
Thu 12/117:39 pmORD - PNS
1 stop22h 52mFrontier
Deal found 9/16$176
This Cheapflightsfares deal was found by Cheapflights users on 9/15. 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 10/244:36 pmPNS - ORD
1 stop7h 09mSpirit Airlines
Wed 10/296:00 amORD - PNS
1 stop11h 01mSpirit Airlines
Deal found 9/15$182
This Priceline deal was found by Cheapflights users on 9/17. 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.
Thu 10/910:28 amPNS - ORD
1 stop7h 25mSpirit Airlines
Mon 10/275:05 amORD - PNS
1 stop10h 26mSpirit Airlines
Deal found 9/17$184
This Cheapflightsfares deal was found by Cheapflights users on 9/16. 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.
Sat 10/44:44 pmPNS - ORD
1 stop6h 04mSpirit Airlines
Wed 10/86:00 amORD - PNS
1 stop11h 01mSpirit Airlines
Deal found 9/16$186
This Kiwi.com deal was found by Cheapflights users on 9/16. 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 11/14:30 pmPNS - ORD
1 stop7h 42mFrontier
Fri 12/127:39 pmORD - PNS
1 stop22h 52mFrontier
Deal found 9/16$189
This Cheapflightsfares deal was found by Cheapflights users on 9/15. 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 11/144:41 pmPNS - ORD
1 stop7h 01mSpirit Airlines
Mon 11/175:05 amORD - PNS
1 stop10h 31mSpirit Airlines
Deal found 9/15$197
This United Airlines deal was found by Cheapflights users on 9/15. 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 10/152:17 pmPNS - ORD
Nonstop2h 37mUnited Airlines
Mon 10/2010:50 amORD - PNS
Nonstop2h 25mUnited Airlines
Deal found 9/15$203
This Frontier deal was found by Cheapflights users on 9/16. 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.
Sat 10/254:52 pmPNS - ORD
1 stop7h 01mFrontier
Mon 11/176:00 amORD - PNS
1 stop10h 17mFrontier
Deal found 9/16$204
This Cheapflightsfares deal was found by Cheapflights users on 9/15. 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 10/104:36 pmPNS - ORD
1 stop7h 09mSpirit Airlines
Mon 10/135:05 amORD - PNS
1 stop10h 26mSpirit Airlines
Deal found 9/15$206
This United Airlines deal was found by Cheapflights users on 9/17. 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 10/92:17 pmPNS - ORD
Nonstop2h 37mUnited Airlines
Mon 10/2710:49 amORD - PNS
Nonstop2h 26mUnited Airlines
Deal found 9/17$209
This Cheapflightsfares deal was found by Cheapflights users on 9/15. 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 10/34:44 pmPNS - ORD
1 stop6h 04mSpirit Airlines
Sun 10/55:05 amORD - PNS
1 stop10h 26mSpirit Airlines
Deal found 9/15$211

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 September 17, 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 10/17

4:36 pm-11:45 pm

1 stop7h 09m

Chicago O'Hare Intl

Mon 10/20

5:05 am-3:31 pm

1 stop10h 26m

$182

PensacolaChicago

PNS - ORD

PNSORD

Pensacola

Fri 11/14

4:41 pm-11:42 pm

1 stop7h 01m

Chicago O'Hare Intl

Mon 11/17

8:41 am-3:36 pm

1 stop6h 55m

$182

PensacolaChicago

PNS - ORD

PNSORD

Pensacola

Wed 10/15

2:17 pm-4:54 pm

Nonstop2h 37m

Chicago O'Hare Intl

Mon 10/20

10:50 am-1:15 pm

Nonstop2h 25m

$203

PensacolaChicago

PNS - ORD

PNSORD

Pensacola

Sat 11/8

2:17 pm-4:48 pm

Nonstop2h 31m

Chicago O'Hare Intl

Wed 11/12

10:49 am-1:15 pm

Nonstop2h 26m

$203

PensacolaChicago

PNS - ORD

PNSORD

Pensacola

Tue 9/30

4:44 pm-10:48 pm

1 stop6h 04m

Chicago O'Hare Intl

Fri 10/3

6:30 am-6:10 pm

1 stop11h 40m

$221

PensacolaChicago

PNS - ORD

PNSORD

Pensacola

Tue 10/21

12:44 pm-7:25 pm

1 stop6h 41m

Chicago O'Hare Intl

Thu 11/20

5:32 am-10:41 am

1 stop5h 09m

$223

PensacolaChicago

PNS - ORD

PNSORD

Pensacola

Wed 10/15

7:40 am-12:45 pm

1 stop5h 05m

Chicago O'Hare Intl

Mon 10/20

2:50 pm-9:55 pm

1 stop7h 05m

$228

PensacolaChicago

PNS - ORD

PNSORD

Pensacola

Thu 11/27

1:26 pm-6:47 pm

1 stop5h 21m

Chicago O'Hare Intl

Mon 12/1

4:21 pm-11:09 pm

1 stop6h 48m

$229

PensacolaChicago

PNS - ORD

PNSORD

Pensacola

Mon 10/6

1:51 pm-6:49 pm

1 stop4h 58m

Chicago O'Hare Intl

Tue 10/21

6:45 am-10:39 am

1 stop3h 54m

$233

PensacolaChicago

PNS - ORD

PNSORD

Pensacola

Sat 10/4

6:00 am-10:10 am

1 stop4h 10m

Chicago O'Hare Intl

Tue 10/7

6:45 am-12:37 pm

1 stop5h 52m

$233

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/16

Showing 1-10 of 21 results
1
2
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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 September 12, 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 September 17, 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 48% 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 September 17, 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
4,242 reviews

Boarding

8.1

Comfort

8.0

Food

7.0

Overall

8.0

Crew

8.6

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
4,242 reviews
Southwest
8.0
Very good
4,242 reviews

Boarding

8.1

Comfort

8.0

Food

7.0

Overall

8.0

Crew

8.6

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
8.0
Very good
7,961 reviews
Southwest
8.0
Very good
4,242 reviews

Boarding

8.1

Comfort

8.0

Food

7.0

Overall

8.0

Crew

8.6

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
8,926 reviews
Southwest
8.0
Very good
4,242 reviews

Boarding

8.1

Comfort

8.0

Food

7.0

Overall

8.0

Crew

8.6

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
10,000 reviews
Southwest
8.0
Very good
4,242 reviews

Boarding

8.1

Comfort

8.0

Food

7.0

Overall

8.0

Crew

8.6

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
8,023 reviews
Southwest
8.0
Very good
4,242 reviews

Boarding

8.1

Comfort

8.0

Food

7.0

Overall

8.0

Crew

8.6

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 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.

  • 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 37m. Spirit Airlines provides one of the quickest options available for as low as $203. 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 51% 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 Lufthansa (81%), Emirates (80%) or United Airlines (80%) 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 $291 for a flight from Pensacola to Chicago O'Hare Intl Airport. The cheapest flight overall is $125 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, 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
Skokie
Gurnee
Hoffman Estates
Des Plaines
Elgin
Arlington Heights
Orland Park
Beloit
Racine
Rockford
Oak Brook
Elk Grove Village
Downers Grove
Naperville
Evanston
Merrillville
Bridgeview
Warrenville

Browse thousands of different options on Cheapflights for your next trip

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Alternative routes for Pensacola to O'Hare Intl

See prices for flight routes from nearby airports that may be better suited for you.
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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 September 17, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$155Average$213FlexibilityNo cancel feeOn-time65%
SouthwestCheapest$173Average$326FlexibilityNo cancel feeOn-time63%
DeltaCheapest$194Average$248FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$211Average$382FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$228Average$309FlexibilityNo cancel feeOn-time71%

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