$61 Cheap Flights from Pensacola (PNS) to Chicago (ORD)

View $61 flight on Mon, Nov 17, 2025Opens in a new window

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

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Cheap Flights from Pensacola to Chicago (PNS-ORD)

Prices were available within the past 7 days and start at $61 for one-way flights and $110 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Frontier Airlines
Sat, Nov 15 - Mon, Nov 17
PNS
Pensacola
ORD
Chicago
$110 Roundtrip, found 1 day ago
$110
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Sat, Nov 15 from Pensacola to Chicago, returning Mon, Nov 17, priced at $110 found 1 day ago
Spirit Airlines
Fri, Nov 14 - Mon, Nov 17
PNS
Pensacola
ORD
Chicago
$145 Roundtrip, found 2 days ago
$145
Roundtrip
found 2 days ago
Select Spirit Airlines flight, departing Fri, Nov 14 from Pensacola to Chicago, returning Mon, Nov 17, priced at $145 found 2 days ago
Frontier Airlines
Mon, Nov 17 - Fri, Nov 28
PNS
Pensacola
ORD
Chicago
$153 Roundtrip, found 2 days ago
$153
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Mon, Nov 17 from Pensacola to Chicago, returning Fri, Nov 28, priced at $153 found 2 days ago
Spirit Airlines
Thu, Nov 13 - Mon, Nov 17
PNS
Pensacola
ORD
Chicago
$158 Roundtrip, found 1 day ago
$158
Roundtrip
found 1 day ago
Select Spirit Airlines flight, departing Thu, Nov 13 from Pensacola to Chicago, returning Mon, Nov 17, priced at $158 found 1 day ago
Frontier Airlines
Sat, Nov 15 - Mon, Nov 17
PNS
Pensacola
ORD
Chicago
$162 Roundtrip, found 1 day ago
$162
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Sat, Nov 15 from Pensacola to Chicago, returning Mon, Nov 17, priced at $162 found 1 day ago
Spirit Airlines
Thu, Nov 13 - Tue, Nov 18
PNS
Pensacola
ORD
Chicago
$165 Roundtrip, found 4 days ago
$165
Roundtrip
found 4 days ago
Select Spirit Airlines flight, departing Thu, Nov 13 from Pensacola to Chicago, returning Tue, Nov 18, priced at $165 found 4 days ago
Frontier Airlines
Mon, Nov 17 - Thu, Nov 20
PNS
Pensacola
ORD
Chicago
$168 Roundtrip, found 5 days ago
$168
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Mon, Nov 17 from Pensacola to Chicago, returning Thu, Nov 20, priced at $168 found 5 days ago
Southwest Airlines
Fri, Nov 14 - Mon, Nov 17
PNS
Pensacola
ORD
Chicago
$195 Roundtrip, found 2 days ago
$195
Roundtrip
found 2 days ago
Select Southwest Airlines flight, departing Fri, Nov 14 from Pensacola to Chicago, returning Mon, Nov 17, priced at $195 found 2 days ago
American Airlines
Wed, Dec 3 - Sun, Dec 7
PNS
Pensacola
ORD
Chicago
$197 Roundtrip, found 11 hours ago
$197
Roundtrip
found 11 hours ago
Select American Airlines flight, departing Wed, Dec 3 from Pensacola to Chicago, returning Sun, Dec 7, priced at $197 found 11 hours ago
United
Tue, Feb 3 - Sun, Feb 8
PNS
Pensacola
ORD
Chicago
$208 Roundtrip, found 11 hours ago
$208
Roundtrip
found 11 hours ago
Select United flight, departing Tue, Feb 3 from Pensacola to Chicago, returning Sun, Feb 8, priced at $208 found 11 hours ago

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

March is typically the cheapest month to fly

From $115 - $369 per traveler.

Alternative airports near Chicago

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

Select flight to Midway Intl. MDW. Closest option available. Average driving time to city center is 16 minutes. Flights from $384
MDW
Midway Intl.
Closest
Average driving time to city center16 min
Flights from $384

Frequently asked questions

How much does a flight from Pensacola Intl. Airport (PNS) to O'Hare Intl. Airport (ORD) cost?
Secure a cheap one-way flight from $61 or cheap return flight from $110 from Pensacola Intl. Airport (PNS) to O'Hare Intl. Airport (ORD) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to find our cheapest flight deals on this route.
What is the cheapest month to fly from Pensacola Intl. Airport (PNS) to O'Hare Intl. Airport (ORD)?
Traveling in November can help you save, as it's the cheapest month for flights between PNS and ORD. You'll usually find the lowest fares during off-peak months.
Which airlines fly direct from Pensacola Intl. Airport (PNS) to O'Hare Intl. Airport (ORD)?
Board a direct flight with United Airlines and travel straight from Pensacola Intl. Airport (PNS) to O'Hare Intl. Airport (ORD).
What is the cheapest airline that flies from Pensacola Intl. Airport (PNS) to O'Hare Intl. Airport (ORD)?
To find the cheapest airline that'll fly you from PNS to ORD, use Expedia's filter tool. Tailor your search based on your travel style, such as preferred carriers and cabin class. You can then sort your results by "Price (lowest to highest)" to list the most affordable options first.
How many flights per day from Pensacola Intl. Airport (PNS) to O'Hare Intl. Airport (ORD)?
On average, there's only 1 nonstop flight departing from Pensacola Intl. Airport (PNS) to O'Hare Intl. Airport (ORD) every day. If this doesn't work with your itinerary, 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 Pensacola Intl. Airport (PNS) to O'Hare Intl. Airport (ORD)?
Flights between PNS and ORD are their busiest at 2 PM. If you want a quieter experience and possibly cheaper tickets, look for a time when demand is lower.
What day of the week has the most flights from PNS to ORD?
Friday has the most flights from Pensacola Intl. Airport (PNS) to O'Hare Intl. Airport (ORD). Consider jetting off on this day and you'll have the best chance of finding a departure that fits your itinerary.
What is the earliest flight from Pensacola Intl. Airport (PNS) to O'Hare Intl. Airport (ORD)?
Catch the earliest flight at around 2:31PM UTC-6, heading out of Pensacola Intl. Airport (PNS). You'll be traveling for approximately 2h 32m, touching down at O'Hare Intl. Airport (ORD) at approximately 5:03PM UTC-6.
How long does it take to fly from Pensacola Intl. Airport (PNS) to O'Hare Intl. Airport (ORD)?
Flights from PNS to ORD have an average travel time of 2 hours and 32 minutes. The distance between these two airports is 800 mi.
What airline has the least delays from PNS to ORD?
With 100% of journeys generally landing on schedule, Frontier Airlines has the best on-time performance for direct flights from Pensacola Intl. Airport (PNS) to O'Hare Intl. Airport (ORD). To keep track of your flight status and get notifications if anything changes, simply head to the Expedia App.
What is the best time to fly from Pensacola Intl. Airport (PNS) to O'Hare Intl. Airport (ORD)?
To reach O'Hare Intl. Airport (ORD) on time, choose a flight that leaves Pensacola Intl. Airport (PNS) before 3 PM. The likelihood of cancellations is 22% higher, on average, for departures after this time.**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 Chicago from Pensacola Intl. Airport (PNS)?
If you're boarding a direct flight from Pensacola Intl. Airport (PNS) to Chicago, O'Hare Intl. Airport (ORD) is the only airport you can touch down at.
Is it cheaper to buy a plane ticket from Pensacola Intl. Airport (PNS) to O'Hare Intl. Airport (ORD) last-minute?
Last-minute fares from PNS to ORD are typically more expensive. For the lowest rates, start looking for flights as soon as possible. That said, if you can play around with your travel dates, you may land a cheap fare just before your departure.
Is it cheaper to book a PNS to ORD flight and hotel package?
You'll generally save money by booking a PNS to ORD flight and hotel package compared to booking separately. In fact, travelers could save hundreds of dollars by bundling with Expedia. And it's simple to manage it all in one convenient place. Once you've chosen your preferred flights and accommodations, consider adding extras like car rentals, activities and tours.
Can I cancel or change the date of my flight from Pensacola Intl. Airport (PNS) to O'Hare Intl. Airport (ORD)?
If you reserved your PNS to ORD flight within the last 24 hours, you may be able to modify or cancel it without fees. Depending on the airline and the type of fare you purchased, additional charges may apply for changes beyond this timeframe. Airline policies and contact information can be found in your itinerary or confirmation email. Or, head to our Customer Service portal if you'd like more information.

Travel information

Origin airport
Pensacola Intl.
Destination airport
O'Hare Intl.
Airlines serving
American Airlines, Delta, Frontier Airlines, Southwest Airlines, Spirit Airlines, United
Roundtrip price
$110
Distance
795 mi
Average flight time
2 hours 34 mins

Book with confidence

Pensacola to Chicago Flights

The cheapest times to fly from Pensacola to Chicago

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 Pensacola to Chicago are during the month of November. You can find some of the cheapest flights from Pensacola to Chicago with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Pensacola to Chicago

Sunday is one of the best days to book for cheap flights from Pensacola to Chicago: 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 Pensacola to Chicago

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 Pensacola to Chicago in 2025. You can also book with separate airlines for your outbound and return journeys, from $61 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 Pensacola to Chicago 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 Pensacola to Chicago 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.

 

Pensacola to Chicago Flights

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