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Pensacola

$88+ 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 8/27. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — PNS
Aug 2 — Aug 91
Sat 8/2
Sat 8/9
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 July 28, 2025.

Round-trip from

$238
(Frontier)

One-way from

$88
(CheapOair)

Popular in

August

Cheapest in

January

Average price

$333

Good round-trip deal

$293 or less

Good one-way deal

$233 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 ($24 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 July 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 July 28, 2025.

This Frontier deal was found by Cheapflights users on 7/27. 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 9/126:00 amORD - PNS
1 stop10h 26mFrontier
Mon 9/155:21 pmPNS - ORD
1 stop6h 38mFrontier
Deal found 7/27$238
This Mytrip deal was found by Cheapflights users on 7/27. 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.
Wed 9/175:17 pmORD - PNS
2 stops22h 22mSpirit Airlines
Sun 9/214:44 pmPNS - ORD
1 stop6h 04mSpirit Airlines
Deal found 7/27$240
This United Airlines deal was found by Cheapflights users on 7/26. 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 11/1910:49 amORD - PNS
Nonstop2h 26mUnited Airlines
Mon 11/242:17 pmPNS - ORD
Nonstop2h 31mUnited Airlines
Deal found 7/26$247
This American Airlines deal was found by Cheapflights users on 7/27. 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 11/510:30 amORD - PNS
Nonstop2h 30mAmerican Airlines
Tue 11/116:00 amPNS - ORD
1 stop6h 07mAmerican Airlines
Deal found 7/27$257
This Delta deal was found by Cheapflights users on 7/27. 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.
Mon 9/85:45 amORD - PNS
1 stop5h 05mDelta
Tue 9/1612:14 pmPNS - ORD
1 stop7h 03mDelta
Deal found 7/27$267
This CheapOair deal was found by Cheapflights users on 7/27. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/27:00 amORD - PNS
1 stop8h 34mMultiple Airlines
Sat 8/93:06 pmPNS - ORD
1 stop8h 21mMultiple Airlines
Deal found 7/27$271
This Southwest deal was found by Cheapflights users on 7/28. 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.
Wed 11/56:05 amORD - PNS
2 stops12h 30mSouthwest
Tue 11/117:20 amPNS - ORD
1 stop4h 55mSouthwest
Deal found 7/28$272

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 July 28, 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

Fri 9/12

6:00 am-4:26 pm

1 stop10h 26m

Pensacola

Sun 9/14

5:21 pm-11:59 pm

1 stop6h 38m

$238

ChicagoPensacola

ORD - PNS

ORDPNS

Chicago O'Hare Intl

Wed 9/17

5:17 pm-3:39 pm

2 stops22h 22m

Pensacola

Sun 9/21

4:44 pm-10:48 pm

1 stop6h 04m

$240

ChicagoPensacola

ORD - PNS

ORDPNS

Chicago O'Hare Intl

Mon 9/8

5:45 am-10:50 am

1 stop5h 05m

Pensacola

Tue 9/16

12:14 pm-7:17 pm

1 stop7h 03m

$267

ChicagoPensacola

ORD - PNS

ORDPNS

Chicago O'Hare Intl

Sat 8/2

7:00 am-3:34 pm

1 stop8h 34m

Pensacola

Sat 8/9

3:06 pm-11:27 pm

1 stop8h 21m

$271

ChicagoPensacola

ORD - PNS

ORDPNS

Chicago O'Hare Intl

Tue 9/9

10:53 am-1:18 pm

Nonstop2h 25m

Pensacola

Wed 9/10

2:15 pm-4:52 pm

Nonstop2h 37m

$287

ChicagoPensacola

ORD - PNS

ORDPNS

Chicago O'Hare Intl

Thu 9/18

2:55 pm-7:00 pm

1 stop4h 05m

Pensacola

Mon 9/22

11:05 am-9:30 pm

2 stops10h 25m

$302

ChicagoPensacola

ORD - PNS

ORDPNS

Chicago O'Hare Intl

Sat 9/27

5:05 am-3:39 pm

1 stop10h 34m

$90

ChicagoPensacola

ORD - PNS

ORDPNS

Chicago O'Hare Intl

Sat 9/27

10:50 am-1:15 pm

Nonstop2h 25m

$109

ChicagoPensacola

ORD - PNS

ORDPNS

Chicago O'Hare Intl

Tue 9/23

7:20 am-1:06 pm

1 stop5h 46m

$119

ChicagoPensacola

ORD - PNS

ORDPNS

Chicago O'Hare Intl

Sat 10/25

7:30 am-5:05 pm

2 stops9h 35m

$124

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/27

Showing 1-10 of 12 results
1
2

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 July 25, 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 $306). Flying from Chicago O'Hare Intl Airport to Pensacola in March is currently the most expensive (average of $416). 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 July 28, 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 34% 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 July 27, 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.

Weekly flight availability from Chicago O'Hare Intl Airport to Pensacola

Explore weekly flight availability from O'Hare Intl to Pensacola. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated July 28, 2025.

The most flights from ORD to PNS are scheduled on a Saturday (3 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (1 on average).

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 July 28, 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
4,237 reviews

Comfort

8.0

Boarding

8.1

Entertainment

7.5

Crew

8.6

Overall

8.0

Food

7.0

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
4,237 reviews
Southwest
8.0
Very good
4,237 reviews

Comfort

8.0

Boarding

8.1

Entertainment

7.5

Crew

8.6

Overall

8.0

Food

7.0

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
7,971 reviews
Southwest
8.0
Very good
4,237 reviews

Comfort

8.0

Boarding

8.1

Entertainment

7.5

Crew

8.6

Overall

8.0

Food

7.0

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
8,893 reviews
Southwest
8.0
Very good
4,237 reviews

Comfort

8.0

Boarding

8.1

Entertainment

7.5

Crew

8.6

Overall

8.0

Food

7.0

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
4,237 reviews

Comfort

8.0

Boarding

8.1

Entertainment

7.5

Crew

8.6

Overall

8.0

Food

7.0

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
8,034 reviews
Southwest
8.0
Very good
4,237 reviews

Comfort

8.0

Boarding

8.1

Entertainment

7.5

Crew

8.6

Overall

8.0

Food

7.0

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.

  • 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 $238. Other airlines that can offer you cheap pricing are Spirit Airlines, from $240, and United Airlines, from $266. Users have found that Frontier is 34% cheaper than the other options available to this destination.

  • What are the cheapest airlines to fly from Chicago O'Hare Intl Airport to Pensacola one-way?

    The cheapest airlines for a one-way flight from Chicago O'Hare Intl Airport to Pensacola are Spirit Airlines ($88), United Airlines ($109), and Delta ($119).

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

    Consider United Airlines (90%), Air New Zealand (90%) or Envoy Air (83%) 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 $168. While the most popular route (Chicago O'Hare Intl - Pensacola) can be booked for $177 on average our data indicates $332 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 $306). Flying from Chicago O'Hare Intl Airport to Pensacola in March is currently the most expensive (average of $416). 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
Milton
Navarre Beach
Warrington

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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 July 28, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$118Average$211FlexibilityNo cancel feeOn-time65%
DeltaCheapest$196Average$300FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$222Average$378FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$228Average$322FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$235Average$405FlexibilityNo cancel feeOn-time69%

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