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O'Hare Intl

$80+ 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 8/30. Fares are subject to change and may not be available on all flights or dates of travel.
PNS — ORD
Jul 5 — Jul 121
Sat 7/5
Sat 7/12
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 June 30, 2025.

Round-trip from

$187
(Priceline)

One-way from

$80
(Priceline)

Popular in

September

Cheapest in

January

Average price

$379

Good round-trip deal

$374 or less

Good one-way deal

$235 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. 10% potential increase in price ($40 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($4 potential savings vs. average RT price).
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Average for round-trip flights in June 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 June 30, 2025.

This Priceline deal was found by Cheapflights users on 6/28. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/304:00 pmPNS - ORD
1 stop7h 39mMultiple Airlines
Mon 9/16:56 amORD - PNS
1 stop10h 11mMultiple Airlines
Deal found 6/28$187
This Kiwi.com deal was found by Cheapflights users on 6/28. 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.
Mon 8/184:52 pmPNS - ORD
1 stop7h 07mSpirit Airlines
Tue 8/266:30 amORD - PNS
1 stop10h 37mSpirit Airlines
Deal found 6/28$194
This Frontier deal was found by Cheapflights users on 6/28. 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.
Mon 8/184:29 pmPNS - ORD
1 stop8h 03mFrontier
Sat 8/237:00 amORD - PNS
1 stop8h 05mFrontier
Deal found 6/28$204
This Delta deal was found by Cheapflights users on 6/28. 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.
Tue 8/195:00 pmPNS - ORD
1 stop4h 36mDelta
Sat 8/237:05 amORD - PNS
1 stop3h 45mDelta
Deal found 6/28$234
This Southwest deal was found by Cheapflights users on 6/29. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/303:50 pmPNS - ORD
1 stop6h 10mSouthwest
Wed 9/37:00 amORD - PNS
2 stops11h 55mSouthwest
Deal found 6/29$245
This American Airlines deal was found by Cheapflights users on 6/30. 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 10/286:11 amPNS - ORD
1 stop4h 55mAmerican Airlines
Thu 11/131:30 pmORD - PNS
1 stop8h 02mAmerican Airlines
Deal found 6/30$251
This United Airlines deal was found by Cheapflights users on 6/28. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/201:56 pmPNS - ORD
Nonstop2h 37mUnited Airlines
Mon 9/2210:53 amORD - PNS
Nonstop2h 25mUnited Airlines
Deal found 6/28$266

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 June 30, 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

Sat 8/30

4:00 pm-11:39 pm

1 stop7h 39m

Chicago O'Hare Intl

Mon 9/1

6:56 am-5:07 pm

1 stop10h 11m

$187

PensacolaChicago

PNS - ORD

PNSORD

Pensacola

Mon 8/18

4:52 pm-11:59 pm

1 stop7h 07m

Chicago O'Hare Intl

Tue 8/26

6:30 am-5:07 pm

1 stop10h 37m

$194

PensacolaChicago

PNS - ORD

PNSORD

Pensacola

Mon 8/18

4:29 pm-12:32 am

1 stop8h 03m

Chicago O'Hare Intl

Sat 8/23

7:00 am-3:05 pm

1 stop8h 05m

$204

PensacolaChicago

PNS - ORD

PNSORD

Pensacola

Tue 8/19

5:00 pm-9:36 pm

1 stop4h 36m

Chicago O'Hare Intl

Sat 8/23

7:05 am-10:50 am

1 stop3h 45m

$234

PensacolaChicago

PNS - ORD

PNSORD

Pensacola

Sat 8/30

3:50 pm-10:00 pm

1 stop6h 10m

Chicago O'Hare Intl

Wed 9/3

7:00 am-6:55 pm

2 stops11h 55m

$245

PensacolaChicago

PNS - ORD

PNSORD

Pensacola

Sat 9/20

1:56 pm-4:33 pm

Nonstop2h 37m

Chicago O'Hare Intl

Mon 9/22

10:53 am-1:18 pm

Nonstop2h 25m

$266

PensacolaChicago

PNS - ORD

PNSORD

Pensacola

Sun 8/3

11:19 am-1:58 pm

Nonstop2h 39m

Chicago O'Hare Intl

Wed 8/6

11:54 am-7:35 pm

1 stop7h 41m

$282

PensacolaChicago

PNS - ORD

PNSORD

Pensacola

Sat 8/16

4:29 pm-12:32 am

1 stop8h 03m

$80

PensacolaChicago

PNS - ORD

PNSORD

Pensacola

Fri 9/19

4:52 pm-10:48 pm

1 stop5h 56m

$90

PensacolaChicago

PNS - ORD

PNSORD

Pensacola

Tue 8/5

2:08 pm-4:47 pm

Nonstop2h 39m

$99

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/28

Showing 1-10 of 13 results
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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 June 27, 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 June 30, 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 June 30, 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
4,278 reviews

Food

7.0

Entertainment

7.6

Overall

8.0

Boarding

8.2

Crew

8.6

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
8.0
Very good
4,278 reviews
Southwest
8.0
Very good
4,278 reviews

Food

7.0

Entertainment

7.6

Overall

8.0

Boarding

8.2

Crew

8.6

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
8.0
Very good
7,969 reviews
Southwest
8.0
Very good
4,278 reviews

Food

7.0

Entertainment

7.6

Overall

8.0

Boarding

8.2

Crew

8.6

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
8,852 reviews
Southwest
8.0
Very good
4,278 reviews

Food

7.0

Entertainment

7.6

Overall

8.0

Boarding

8.2

Crew

8.6

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
10,000 reviews
Southwest
8.0
Very good
4,278 reviews

Food

7.0

Entertainment

7.6

Overall

8.0

Boarding

8.2

Crew

8.6

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
8,096 reviews
Southwest
8.0
Very good
4,278 reviews

Food

7.0

Entertainment

7.6

Overall

8.0

Boarding

8.2

Crew

8.6

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 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 $193, 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 Frontier and Delta - these airlines can fly you to your destination from $204 and $234, respectively. Spirit Airlines is 43% 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 Frontier. According to our data, you can fly for as low as $80. Users have also found prices from $90 and $99 on Spirit Airlines and United Airlines, respectively.

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

    Consider Envoy Air (88%), Emirates (87%) or United Airlines (87%) 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 $457 for a flight from Pensacola to Chicago O'Hare Intl Airport. The cheapest flight overall is $164 while the most popular route, (Pensacola - Chicago O'Hare Intl) is currently priced at $166.

  • 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 Pensacola?

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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 June 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$152Average$188FlexibilityNo cancel feeOn-time65%
SouthwestCheapest$192Average$402FlexibilityNo cancel feeOn-time63%
DeltaCheapest$194Average$277FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$227Average$405FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$228Average$324FlexibilityNo cancel feeOn-time71%

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