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O'Hare Intl

$69+ 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 5/29. Fares are subject to change and may not be available on all flights or dates of travel.
PNS — ORD
May 5 — May 121
Mon 5/5
Mon 5/12
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 Saturday 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 April 30, 2025.

Most accurate provider

CheapOair
3 stars

Most trusted provider

CheapOair
3 stars

Round-trip from

$140
(FlightHub)

One-way from

$69
(FlightHub)

Popular in

July

Cheapest in

January

Average price

$363

Good round-trip deal

$328 or less

Good one-way deal

$200 or less
Provider with most accurate pricing for Pensacola-Chicago O'Hare Intl flight deals.
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Provider most trusted by Cheapflights users for Pensacola-Chicago O'Hare Intl flights.
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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. 3% potential increase in price ($14 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 April 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 April 30, 2025.

This FlightHub deal was found by Cheapflights users on 4/28. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/294:35 pmPNS - ORD
1 stop7h 30mSpirit Airlines
Sun 6/19:55 amORD - PNS
1 stop5h 35mSpirit Airlines
Deal found 4/28$140
This Delta deal was found by Cheapflights users on 4/29. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/136:10 pmPNS - ORD
1 stop5h 48mDelta
Wed 5/141:30 pmORD - PNS
1 stop4h 45mDelta
Deal found 4/29$197
This American Airlines deal was found by Cheapflights users on 4/29. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/216:15 amPNS - ORD
1 stop6h 26mAmerican Airlines
Sun 5/259:13 amORD - PNS
Nonstop2h 23mAmerican Airlines
Deal found 4/29$228
This Southwest deal was found by Cheapflights users on 4/28. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/1211:05 amPNS - ORD
1 stop5h 20mSouthwest
Sun 9/147:30 amORD - PNS
1 stop5h 15mSouthwest
Deal found 4/28$232
This Mytrip deal was found by Cheapflights users on 4/29. 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.
Sun 6/18:46 pmPNS - ORD
2 stops17h 29mMultiple Airlines
Sat 6/77:37 amORD - PNS
1 stop9h 32mMultiple Airlines
Deal found 4/29$245
This United Airlines deal was found by Cheapflights users on 4/29. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/142:05 pmPNS - ORD
Nonstop2h 41mUnited Airlines
Sun 5/1810:40 amORD - PNS
Nonstop2h 28mUnited Airlines
Deal found 4/29$247
This Frontier deal was found by Cheapflights users on 4/29. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/134:29 pmPNS - ORD
1 stop7h 30mFrontier
Fri 6/205:40 amORD - PNS
1 stop9h 49mFrontier
Deal found 4/29$383

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 April 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

Thu 5/29

4:35 pm-12:05 am

1 stop7h 30m

Chicago O'Hare Intl

Sun 6/1

9:55 am-3:30 pm

1 stop5h 35m

$140

PensacolaChicago

PNS - ORD

PNSORD

Pensacola

Tue 5/13

6:10 pm-11:58 pm

1 stop5h 48m

Chicago O'Hare Intl

Wed 5/14

1:30 pm-6:15 pm

1 stop4h 45m

$197

PensacolaChicago

PNS - ORD

PNSORD

Pensacola

Wed 5/21

6:15 am-12:41 pm

1 stop6h 26m

Chicago O'Hare Intl

Sun 5/25

9:13 am-11:36 am

Nonstop2h 23m

$228

PensacolaChicago

PNS - ORD

PNSORD

Pensacola

Wed 7/9

6:50 am-12:45 pm

1 stop5h 55m

Chicago O'Hare Intl

Mon 7/14

4:00 pm-10:55 pm

1 stop6h 55m

$238

PensacolaChicago

PNS - ORD

PNSORD

Pensacola

Sun 6/1

8:46 pm-2:15 pm

2 stops17h 29m

Chicago O'Hare Intl

Sat 6/7

7:37 am-5:09 pm

1 stop9h 32m

$245

PensacolaChicago

PNS - ORD

PNSORD

Pensacola

Wed 5/14

2:05 pm-4:46 pm

Nonstop2h 41m

Chicago O'Hare Intl

Sun 5/18

10:40 am-1:08 pm

Nonstop2h 28m

$247

PensacolaChicago

PNS - ORD

PNSORD

Pensacola

Fri 6/13

4:29 pm-11:59 pm

1 stop7h 30m

Chicago O'Hare Intl

Fri 6/20

5:40 am-3:29 pm

1 stop9h 49m

$383

PensacolaChicago

PNS - ORD

PNSORD

Pensacola

Fri 5/30

4:35 pm-12:05 am

1 stop7h 30m

$69

PensacolaChicago

PNS - ORD

PNSORD

Pensacola

Sun 6/8

11:11 am-1:43 pm

Nonstop2h 32m

$89

PensacolaChicago

PNS - ORD

PNSORD

Pensacola

Fri 6/27

4:07 pm-9:24 pm

1 stop5h 17m

$99

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/29

Showing 1-10 of 13 results
1
2

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 April.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*2 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars
PricelinePrice Accuracy2 starsTrust Score*3 stars
CheapOairPrice 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 CheapOair to be most consistent on Cheapflights vs. CheapOair Users can find the same prices on Pensacola-Chicago O'Hare Intl Airport flight deals on Cheapflights vs. CheapOair >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 CheapOair the most. CheapOair 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 April 25, 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 April 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 54% versus a flight at noon.

Rainfall in O'Hare Intl by month

Plan your trip to O'Hare Intl by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Chicago O'Hare Intl Airport ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago O'Hare Intl Airport when rainfall is around 1.7 in.

Temperature in O'Hare Intl by month

Plan your trip to O'Hare Intl by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Chicago O'Hare Intl Airport, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

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 April 30, 2025.
Get a feel of what it's like to fly with Southwest, Delta and United Airlines from Pensacola to Chicago by reading reviews from past customers. 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
4,295 reviews

Boarding

8.2

Comfort

8.0

Food

7.1

Entertainment

7.6

Crew

8.6

Overall

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
4,295 reviews
Southwest
8.0
Very good
4,295 reviews

Boarding

8.2

Comfort

8.0

Food

7.1

Entertainment

7.6

Crew

8.6

Overall

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
7,929 reviews
Southwest
8.0
Very good
4,295 reviews

Boarding

8.2

Comfort

8.0

Food

7.1

Entertainment

7.6

Crew

8.6

Overall

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
8,696 reviews
Southwest
8.0
Very good
4,295 reviews

Boarding

8.2

Comfort

8.0

Food

7.1

Entertainment

7.6

Crew

8.6

Overall

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
4,295 reviews

Boarding

8.2

Comfort

8.0

Food

7.1

Entertainment

7.6

Crew

8.6

Overall

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
7,956 reviews
Southwest
8.0
Very good
4,295 reviews

Boarding

8.2

Comfort

8.0

Food

7.1

Entertainment

7.6

Crew

8.6

Overall

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 1 outbound flight 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 $140, 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 Delta and American Airlines - these airlines can fly you to your destination from $197 and $203, respectively. Spirit Airlines is 58% 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 $69. Users have also found prices from $89 and $99 on United Airlines and Delta, respectively.

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

    Consider American Airlines (100%), Qatar Airways (100%) or Envoy Air (100%) 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 $806 for a flight from Pensacola to Chicago O'Hare Intl Airport. The cheapest flight overall is $92 while the most popular route, (Pensacola - Chicago O'Hare Intl) is currently priced at $140.

  • 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

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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 April 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$98Average$188FlexibilityNo cancel feeOn-time65%
SouthwestCheapest$192Average$424FlexibilityNo cancel feeOn-time63%
DeltaCheapest$196Average$281FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$228Average$324FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$253Average$409FlexibilityNo cancel feeOn-time69%

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