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Pensacola

$67+ Cheap flights from O'Hare Intl (ORD) to Pensacola (PNS)

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.
ORD — PNS
Oct 11 — Oct 181
Sat 10/11
Sat 10/18
1 adult, Economy
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Cheapflights Tip: The best prices from Chicago O'Hare Intl to Pensacola are usually found in January or May, booked 13 days in advance, depart on a Tuesday or Wednesday and return on a Thursday

Cheap flight deals from O'Hare Intl to Pensacola

Discover tips and strategies to find the most affordable flight options for your journey from O'Hare Intl (ORD) to Pensacola (PNS). 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 11, 2025.

Round-trip from

$203
(United Airlines)

One-way from

$67
(United Airlines)

Popular in

August

Cheapest in

January

Average price

$354

Good round-trip deal

$264 or less

Good one-way deal

$135 or less
From Chicago O'Hare Intl to Pensacola
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One-way flight from Chicago O'Hare Intl to Pensacola
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Highest demand for flights based on searches. 6% potential increase in price ($23 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($9 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 Chicago O'Hare Intl to Pensacola.
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Price to beat on a one-way flight from Chicago O'Hare Intl to Pensacola.
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Find flight deals from O'Hare Intl to Pensacola

Cheapest flights from O'Hare Intl to Pensacola
Explore the most affordable flight options available from O'Hare Intl to Pensacola. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 11, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 9/11. 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 10/105:05 amORD - PNS
1 stop10h 26mSpirit Airlines
Mon 10/204:36 pmPNS - ORD
1 stop7h 09mSpirit Airlines
Deal found 9/11$206
This Booking.com deal was found by Cheapflights users on 9/10. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/86:00 amORD - PNS
1 stop11h 01mSpirit Airlines
Sun 10/124:36 pmPNS - ORD
1 stop7h 09mSpirit Airlines
Deal found 9/10$208
This Booking.com deal was found by Cheapflights users on 9/10. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/165:05 amORD - PNS
1 stop10h 26mSpirit Airlines
Mon 10/204:36 pmPNS - ORD
1 stop7h 09mSpirit Airlines
Deal found 9/10$209
This Kiwi.com deal was found by Cheapflights users on 9/9. 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 10/257:05 amORD - PNS
1 stop8h 52mMultiple Airlines
Sun 11/94:41 pmPNS - ORD
1 stop16h 42mMultiple Airlines
Deal found 9/9$210
This Delta deal was found by Cheapflights users on 9/9. 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.
Sun 10/265:20 amORD - PNS
1 stop5h 19mDelta
Sat 11/87:00 amPNS - ORD
1 stop5h 17mDelta
Deal found 9/9$211
This Cheapflightsfares deal was found by Cheapflights users on 9/8. 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.
Mon 9/156:30 amORD - PNS
1 stop11h 40mSpirit Airlines
Thu 9/184:44 pmPNS - ORD
1 stop6h 04mSpirit Airlines
Deal found 9/8$212
This Frontier deal was found by Cheapflights users on 9/10. 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 10/206:50 amORD - PNS
1 stop8h 03mFrontier
Sat 10/254:52 pmPNS - ORD
1 stop7h 01mFrontier
Deal found 9/10$213
This Cheapflightsfares deal was found by Cheapflights users on 9/10. 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 9/176:30 amORD - PNS
1 stop11h 40mSpirit Airlines
Thu 9/184:44 pmPNS - ORD
1 stop6h 04mSpirit Airlines
Deal found 9/10$214
This United Airlines deal was found by Cheapflights users on 9/10. 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 10/2210:50 amORD - PNS
Nonstop2h 25mUnited Airlines
Sat 10/252:17 pmPNS - ORD
Nonstop2h 37mUnited Airlines
Deal found 9/10$215
This Kiwi.com deal was found by Cheapflights users on 9/10. 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 10/156:58 pmORD - PNS
1 stop14h 16mMultiple Airlines
Fri 10/247:54 pmPNS - ORD
1 stop19h 51mMultiple Airlines
Deal found 9/10$216
This Kiwi.com deal was found by Cheapflights users on 9/10. 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 10/245:05 amORD - PNS
1 stop10h 26mMultiple Airlines
Fri 11/74:30 pmPNS - ORD
1 stop7h 45mMultiple Airlines
Deal found 9/10$217
This Delta deal was found by Cheapflights users on 9/10. 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.
Sat 10/186:45 amORD - PNS
1 stop3h 54mDelta
Wed 10/2212:44 pmPNS - ORD
1 stop6h 41mDelta
Deal found 9/10$218

Cheapflights Fare Finder

 
Customize your flight search to find flights from O'Hare Intl to Pensacola 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 11, 2025.
Use the filters below to find and compare flights from Chicago O'Hare Intl Airport to Pensacola that are best for you.

Fly from

O'Hare Intl

Fly to

Pensacola

Route

Depart

Return

Price

ChicagoPensacola

ORD - PNS

ORDPNS

Chicago O'Hare Intl

Sat 10/18

6:45 am-10:39 am

1 stop3h 54m

Pensacola

Wed 10/22

12:44 pm-7:25 pm

1 stop6h 41m

$218

ChicagoPensacola

ORD - PNS

ORDPNS

Chicago O'Hare Intl

Mon 10/27

10:49 am-1:15 pm

Nonstop2h 26m

Pensacola

Tue 11/11

2:17 pm-4:48 pm

Nonstop2h 31m

$219

ChicagoPensacola

ORD - PNS

ORDPNS

Chicago O'Hare Intl

Wed 10/1

10:50 am-1:15 pm

Nonstop2h 25m

Pensacola

Wed 10/8

2:17 pm-4:54 pm

Nonstop2h 37m

$219

ChicagoPensacola

ORD - PNS

ORDPNS

Chicago O'Hare Intl

Wed 10/1

10:50 am-1:15 pm

Nonstop2h 25m

Pensacola

Mon 10/13

2:17 pm-4:54 pm

Nonstop2h 37m

$226

ChicagoPensacola

ORD - PNS

ORDPNS

Chicago O'Hare Intl

Tue 10/21

6:00 am-12:04 pm

1 stop6h 04m

Pensacola

Wed 10/29

7:00 am-12:16 pm

1 stop5h 16m

$229

ChicagoPensacola

ORD - PNS

ORDPNS

Chicago O'Hare Intl

Sat 10/18

5:20 am-10:39 am

1 stop5h 19m

Pensacola

Sat 10/25

7:00 am-9:19 pm

2 stops14h 19m

$233

ChicagoPensacola

ORD - PNS

ORDPNS

Chicago O'Hare Intl

Sun 10/19

10:50 am-1:15 pm

Nonstop2h 25m

Pensacola

Wed 10/22

2:17 pm-4:54 pm

Nonstop2h 37m

$235

ChicagoPensacola

ORD - PNS

ORDPNS

Chicago O'Hare Intl

Wed 10/15

6:00 am-12:04 pm

1 stop6h 04m

Pensacola

Tue 10/28

11:47 am-4:41 pm

1 stop4h 54m

$248

ChicagoPensacola

ORD - PNS

ORDPNS

Chicago O'Hare Intl

Wed 10/15

6:00 am-12:04 pm

1 stop6h 04m

Pensacola

Sat 10/25

11:44 am-6:49 pm

1 stop7h 05m

$248

ChicagoPensacola

ORD - PNS

ORDPNS

Chicago O'Hare Intl

Fri 10/10

10:50 am-1:15 pm

Nonstop2h 25m

Pensacola

Wed 10/15

2:17 pm-4:54 pm

Nonstop2h 37m

$255

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/9

Showing 1-10 of 21 results
1
2
3

Best time to book a flight from O'Hare Intl to Pensacola

Have a flexible travel schedule? Discover the best time to fly to Pensacola from O'Hare Intl 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 Chicago O'Hare Intl Airport to Pensacola

How far ahead should I book a flight from Chicago O'Hare Intl Airport to Pensacola?

Use this chart to determine the optimal time to book a round-trip flight from O'Hare Intl to Pensacola. Price data was last updated on August 29, 2025.

The best time to book flights from Chicago O'Hare Intl Airport to Pensacola is 13 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.

What is the cheapest month to book a flight from Chicago O'Hare Intl Airport to Pensacola?

Currently, September is the cheapest month in which you can book a flight from Chicago O'Hare Intl Airport to Pensacola (average of $303). Flying from Chicago O'Hare Intl Airport to Pensacola in March is currently the most expensive (average of $415). 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 ORD to PNS?

Find hourly flight availability from O'Hare Intl to Pensacola. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated September 11, 2025.

One of the essential ways to save on airfare from Chicago O'Hare Intl Airport to Pensacola is to remain as flexible as possible. Flights that are in the morning tend to be the most expensive. A flight in the afternoon could potentially save you up to 32% on airfare.

What is the cheapest day to fly from Chicago O'Hare Intl Airport to Pensacola?

Use this chart to determine the cheapest time to fly round-trip from O'Hare Intl to Pensacola. Price data was last updated on September 7, 2025.

Travelers seeking maximum savings on their Chicago O'Hare Intl Airport to Pensacola flight should consider departing on Wednesday evenings when fares are most often at their lowest. Friday mornings flights should be avoided if possible as fares are typically the most expensive at this time.

Reviews of airlines servicing Pensacola

Get insights into the airlines that provide service to Pensacola. 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 Pensacola. Reviews last updated September 11, 2025.
See what other customers who have flown with Southwest, Delta, and United Airlines from Chicago O'Hare Intl Airport to Pensacola have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,248 reviews

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Crew

8.6

Food

7.0

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Sarah,Aug 2024

MDW - AUS

My first time, surprisingly good! It was a good ride overall. Coming from Singapore, this budget flight is better than the budget airline for our national carrier Singapore Airlines.
Southwest
8.0
Very good
4,248 reviews
Southwest
8.0
Very good
4,248 reviews

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Crew

8.6

Food

7.0

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Sarah,Aug 2024

MDW - AUS

My first time, surprisingly good! It was a good ride overall. Coming from Singapore, this budget flight is better than the budget airline for our national carrier Singapore Airlines.
Delta
8.0
Very good
7,960 reviews
Southwest
8.0
Very good
4,248 reviews

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Crew

8.6

Food

7.0

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Sarah,Aug 2024

MDW - AUS

My first time, surprisingly good! It was a good ride overall. Coming from Singapore, this budget flight is better than the budget airline for our national carrier Singapore Airlines.
United Airlines
7.4
Good
8,937 reviews
Southwest
8.0
Very good
4,248 reviews

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Crew

8.6

Food

7.0

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Sarah,Aug 2024

MDW - AUS

My first time, surprisingly good! It was a good ride overall. Coming from Singapore, this budget flight is better than the budget airline for our national carrier Singapore Airlines.
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,248 reviews

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Crew

8.6

Food

7.0

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Sarah,Aug 2024

MDW - AUS

My first time, surprisingly good! It was a good ride overall. Coming from Singapore, this budget flight is better than the budget airline for our national carrier Singapore Airlines.
Spirit Airlines
6.3
Okay
8,023 reviews
Southwest
8.0
Very good
4,248 reviews

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Crew

8.6

Food

7.0

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Sarah,Aug 2024

MDW - AUS

My first time, surprisingly good! It was a good ride overall. Coming from Singapore, this budget flight is better than the budget airline for our national carrier Singapore Airlines.

Related info for your journey

Find useful and relevant information for your journey from O'Hare Intl to Pensacola. 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 into for flights to Pensacola from Chicago O'Hare Intl?

    Most people fly into Pensacola (PNS) if they book a flight to Pensacola from Chicago O'Hare Intl. On average, Pensacola has 1 inbound flight from 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 Chicago O'Hare Intl Airport to Pensacola?

    Airlines like Delta and United Airlines fly from Chicago O'Hare Intl Airport to Pensacola in about 2h 26m. The time it takes to get you to your destination can typically vary by up to 1h 28m. Chicago O'Hare Intl Airport and Pensacola are separated by a distance of 795 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

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

    Cheapflights users have booked flights from Chicago O'Hare Intl Airport to Pensacola round-trip from $118. Other airlines that can offer you cheap pricing are Delta, from $196, and Southwest, from $222. Users have found that Spirit Airlines is 66% cheaper than the other options available to this destination.

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

    Consider United Airlines (90%), Air New Zealand (90%) or American Airlines (80%) when booking your flight. These represent the most reliable airlines when flying from Chicago O'Hare Intl Airport to Pensacola.

  • What are the cheapest flights from Chicago O'Hare Intl Airport to Pensacola?

    Looking at all options, your cheapest flight can be booked for $104. While the most popular route (Chicago O'Hare Intl - Pensacola) can be booked for $133 on average, our data indicates $407 when flying from Chicago O'Hare Intl Airport to Pensacola.

  • Can I find deals for flights from O'Hare Intl to Pensacola that include hotel bookings?

    Yes. In addition to deals on O'Hare Intl to Pensacola flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from O'Hare Intl to Pensacola?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from O'Hare Intl to Pensacola.

  • Can I find deals for business class flights from O'Hare Intl to Pensacola?

    Yes. Cheapflights offers flight deals from O'Hare Intl to Pensacola 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 Chicago O'Hare Intl Airport to Pensacola?

    Currently, September is the cheapest month in which you can book a flight from Chicago O'Hare Intl Airport to Pensacola (average of $303). Flying from Chicago O'Hare Intl Airport to Pensacola in March is currently the most expensive (average of $415). 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?

Book flights to Pensacola if you plan to visit one of these locations
Gulf Breeze
Navarre
Foley
Perdido Key
Navarre Beach
Warrington

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Alternative routes for O'Hare Intl to Pensacola

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Top 5 airlines flying from O'Hare Intl to Pensacola

Discover the top 5 airlines that operate flights from O'Hare Intl to Pensacola. 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 11, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$118Average$212FlexibilityNo cancel feeOn-time65%
DeltaCheapest$196Average$297FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$222Average$392FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$223Average$318FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$229Average$393FlexibilityNo cancel feeOn-time69%

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