$81 Cheap Flights from Chicago (ORD) to Pensacola (PNS)

View $81 flight on Tue, Aug 5, 2025Opens in a new window

Popular airlines from Chicago O'Hare Intl. Airport (ORD) to Pensacola Intl. Airport (PNS)

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Cheap Flights from Chicago to Pensacola (ORD-PNS)

Prices were available within the past 7 days and start at $81 for one-way flights and $155 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

United
Tue, Nov 18 - Sun, Nov 23
ORD
Chicago
PNS
Pensacola
$155 Roundtrip, found 4 days ago
$155
Roundtrip
found 4 days ago
Select United flight, departing Tue, Nov 18 from Chicago to Pensacola, returning Sun, Nov 23, priced at $155 found 4 days ago
Delta
Sat, Nov 1 - Wed, Nov 5
ORD
Chicago
PNS
Pensacola
$156 Roundtrip, found 1 day ago
$156
Roundtrip
found 1 day ago
Select Delta flight, departing Sat, Nov 1 from Chicago to Pensacola, returning Wed, Nov 5, priced at $156 found 1 day ago
Southwest Airlines
Sat, Nov 1 - Wed, Nov 5
ORD
Chicago
PNS
Pensacola
$166 Roundtrip, found 1 day ago
$166
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Sat, Nov 1 from Chicago to Pensacola, returning Wed, Nov 5, priced at $166 found 1 day ago
Southwest Airlines
Thu, Oct 30 - Mon, Nov 3
ORD
Chicago
PNS
Pensacola
$169 Roundtrip, found 1 day ago
$169
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Thu, Oct 30 from Chicago to Pensacola, returning Mon, Nov 3, priced at $169 found 1 day ago
Southwest Airlines
Mon, Oct 27 - Sat, Nov 1
ORD
Chicago
PNS
Pensacola
$171 Roundtrip, found 3 days ago
$171
Roundtrip
found 3 days ago
Select Southwest Airlines flight, departing Mon, Oct 27 from Chicago to Pensacola, returning Sat, Nov 1, priced at $171 found 3 days ago
Spirit Airlines
Tue, Aug 5 - Fri, Aug 8
ORD
Chicago
PNS
Pensacola
$173 Roundtrip, found 1 hour ago
$173
Roundtrip
found 1 hour ago
Select Spirit Airlines flight, departing Tue, Aug 5 from Chicago to Pensacola, returning Fri, Aug 8, priced at $173 found 1 hour ago
United
Tue, Oct 21 - Mon, Oct 27
ORD
Chicago
PNS
Pensacola
$176 Roundtrip, found 1 day ago
$176
Roundtrip
found 1 day ago
Select United flight, departing Tue, Oct 21 from Chicago to Pensacola, returning Mon, Oct 27, priced at $176 found 1 day ago
Southwest Airlines
Thu, Oct 30 - Mon, Nov 3
ORD
Chicago
PNS
Pensacola
$181 Roundtrip, found 1 day ago
$181
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Thu, Oct 30 from Chicago to Pensacola, returning Mon, Nov 3, priced at $181 found 1 day ago
Spirit Airlines
Tue, Aug 12 - Fri, Aug 15
ORD
Chicago
PNS
Pensacola
$184 Roundtrip, just found
$184
Roundtrip
just found
Select Spirit Airlines flight, departing Tue, Aug 12 from Chicago to Pensacola, returning Fri, Aug 15, priced at $184 just found
Frontier Airlines
Sat, Nov 1 - Sat, Nov 8
ORD
Chicago
PNS
Pensacola
$192 Roundtrip, found 12 hours ago
$192
Roundtrip
found 12 hours ago
Select Frontier Airlines flight, departing Sat, Nov 1 from Chicago to Pensacola, returning Sat, Nov 8, priced at $192 found 12 hours ago

Find the cheapest month to fly from Chicago (ORD) to Pensacola (PNS)

March is typically the cheapest month to fly

From $121 - $470 per traveler.

Graph displaying average flight prices per month

Alternative airports near Pensacola

Prices were available within the past 7 days. Prices and availability are subject to change.

Select flight to Pensacola Intl. PNS. Cheapest and Closest option available. Average driving time to city center is 8 minutes. Flights from $267
PNS
Pensacola Intl.
CheapestClosest
Average driving time to city center8 min
Flights from $267
Flights from Chicago (ORD) to Pensacola (PNS)
Origin airport
O'Hare Intl.
Destination airport
Pensacola Intl.
Airlines serving
American Airlines, Delta, Frontier Airlines, Southwest Airlines, Spirit Airlines, United
Roundtrip price
$154
Distance
795 mi
Average flight time
2 hours 27 mins

Chicago to Pensacola Flights

The cheapest times to fly from Chicago to Pensacola

On average, Thursday can be the cheapest time to fly, according to data from the Airlines Reporting Corporation (ARC), one of the world's biggest databases for global airline sales. The data reveals that you could save up to 16% by flying on a Thursday—the cheapest day to travel on average—instead of a Sunday—the most expensive. Some of the most affordable flights from Chicago to Pensacola are during the month of November. You can find some of the cheapest flights from Chicago to Pensacola with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Chicago to Pensacola

Sunday is one of the best days to book for cheap flights from Chicago to Pensacola: Tickets reserved on a Sunday cost between 6% and 13% less than those reserved on a Friday, according to ARC data. The data also suggests booking early can also lead to cheaper airfares. You could save 24% by buying your tickets for domestic flights at least a month in advance and 10% by booking international flights 2 months in advance.

 

How to find cheap round-trip tickets from Chicago to Pensacola

Being flexible with your dates and using Expedia's Price Drop Protection and Price Tracking features are some of the best ways of finding a cheap ticket from Chicago to Pensacola in 2025. You can also book with separate airlines for your outbound and return journeys, from $81 one-way. Expedia also offers Price Drop Protection, so if the cost of your airfare goes down after booking, you'll receive a credit for the difference*. This is available for a small fee, and is free to One Key Gold and Platinum tier members.

 

Expedia's Price Tracking feature means you can stay on top of airfares without manually checking every day. It sends you automated price alerts for cheap Chicago to Pensacola flights and uses historical data to indicate when the best time to book is. Download Expedia's free app to activate this handy tool in a few easy taps.

 

You could also save big by booking one of Expedia's vacation packages. Bundling together your Chicago to Pensacola airfare with your accommodations and car rental is often cheaper than booking everything separately. There’s also One Key, Expedia's generous rewards program. Join for free and you could earn One Key cash on most bookings to save on future adventures.

 

*Terms apply.

 

Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023. The percentages you see are averages.

 

Frequently asked questions

How much does a flight from O'Hare Intl. Airport (ORD) to Pensacola Intl. Airport (PNS) cost?
Cheap round-trip fares from O'Hare Intl. Airport (ORD) to Pensacola Intl. Airport (PNS) start at $197. This information is based on the cheapest price found on Expedia for this return journey departing within the next three months. This airfare is for a United flight leaving ORD on July 29 2025 and touching down at PNS. The price was last updated on July 8 2025 and has not changed since.
What is the cheapest month to fly from ORD to PNS?
The cheapest flights from ORD to PNS are usually during off-peak season, when demand is lower. To save money, avoid flying during public holidays, school breaks and major local events.
Which airlines fly direct from O'Hare Intl. Airport (ORD) to Pensacola Intl. Airport (PNS)?
Fly directly from O'Hare Intl. Airport (ORD) to Pensacola Intl. Airport (PNS) on a United Airlines flight.
What is the cheapest airline that flies from ORD to PNS?
With fares starting at $99 for a one-way journey from ORD to PNS, United is currently the cheapest carrier flying this route. This fare is based on the lowest price found on Expedia departing within the next three months. The flight takes off from ORD on September 3 2025. Prices were last updated on July 8 2025 and have not changed since.
How many flights per day from O'Hare Intl. Airport (ORD) to Pensacola Intl. Airport (PNS)?
On average, there is just 1 nonstop flight leaving from O'Hare Intl. Airport (ORD) to Pensacola Intl. Airport (PNS) per day. If this doesn't fit your plans, consider flights with layovers. Just filter your search results on Expedia to include one stop or more to discover the next best option.
What are the most popular departure times for flights from O'Hare Intl. Airport (ORD) to Pensacola Intl. Airport (PNS)?
The 10 AM departures from ORD to PNS are the most sought after. Prices can be higher for these popular slots. If you want to save money, choose a less crowded time to fly.
What day of the week has the most flights from ORD to PNS?
Jet off on a Sunday if you're after the largest selection of flights from O'Hare Intl. Airport (ORD) to Pensacola Intl. Airport (PNS).
What is the earliest flight from O'Hare Intl. Airport (ORD) to Pensacola Intl. Airport (PNS)?
Take the earliest flight at around 10:53AM UTC-6, departing from O'Hare Intl. Airport (ORD). You'll be flying for roughly 2h 30m, touching down at Pensacola Intl. Airport (PNS) at approximately 1:23PM UTC-6.
How long does it take to fly from O'Hare Intl. Airport (ORD) to Pensacola Intl. Airport (PNS)?
Flights from ORD to PNS have an average travel time of 2 hours and 30 minutes. The distance between the two airports is 800 mi.
What airline has the least delays from ORD to PNS?
With 89% of flights usually arriving as scheduled, American Airlines has the best on-time performance for direct flights from O'Hare Intl. Airport (ORD) to Pensacola Intl. Airport (PNS). To monitor your flight status and get notified about any changes, use the Expedia App.
What is the best time to fly from O'Hare Intl. Airport (ORD) to Pensacola Intl. Airport (PNS)?
Opt for a flight from O'Hare Intl. Airport (ORD) to Pensacola Intl. Airport (PNS) that takes off before 3 PM to reduce the risk of cancellations. Departures after this time have a 22% higher chance of being canceled, on average.**Most reliable time of the day and month to travel recommendation is based on January through August 2024 flight status data sourced from OAG's global flight data platform.
What airports do you fly into for Pensacola from O'Hare Intl. Airport (ORD)?
Browse your flight options from O'Hare Intl. Airport (ORD) to Pensacola Intl. Airport (PNS). This is the only airport in Pensacola you can land at if you're taking a direct flight.
Is it cheaper to buy a plane ticket from O'Hare Intl. Airport (ORD) to Pensacola Intl. Airport (PNS) last-minute?
Last-minute bookings from ORD to PNS are generally more expensive. For the lowest prices, start looking for flights ahead of time. That said, if you're flexible with your travel plans, it's possible to find a cheap fare just before your departure.
Is it cheaper to book an ORD to PNS flight and hotel package?
Securing an ORD to PNS flight and hotel package is typically cheaper than booking separately. With Expedia, you can enjoy the ease of organizing your travels in one place. Pick from our extensive range of hotels and then add car rentals, flights and activities to your booking. Bundle everything together, and you could save hundreds of dollars.
Can I cancel or change the date of my flight from O'Hare Intl. Airport (ORD) to Pensacola Intl. Airport (PNS)?
In most cases, you can cancel or modify your ORD to PNS flight. However, there may be additional fees, especially if you booked over 24 hours ago. Double-check your itinerary for the airline's policies and fees on flight changes, or if you want more information, visit our Customer Service portal.

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