$67 Cheap Flights from Chicago (MDW) to Pensacola (PNS)

View $67 flight on Sat, Sep 27, 2025Opens in a new window

Popular airlines from Chicago Midway Airport (MDW) to Pensacola Intl. Airport (PNS)

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Cheap Flights from Chicago to Pensacola (MDW-PNS)

Prices were available within the past 7 days and start at $67 for one-way flights and $171 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Southwest Airlines
Wed, Sep 3 - Sat, Sep 6
MDW
Chicago
PNS
Pensacola
$171 Roundtrip, found 5 days ago
$171
Roundtrip
found 5 days ago
Select Southwest Airlines flight, departing Wed, Sep 3 from Chicago to Pensacola, returning Sat, Sep 6, priced at $171 found 5 days ago
Southwest Airlines
Mon, Aug 11 - Tue, Aug 12
MDW
Chicago
PNS
Pensacola
$181 Roundtrip, found 5 days ago
$181
Roundtrip
found 5 days ago
Select Southwest Airlines flight, departing Mon, Aug 11 from Chicago to Pensacola, returning Tue, Aug 12, priced at $181 found 5 days ago
Delta
Wed, Sep 3 - Sat, Sep 6
MDW
Chicago
PNS
Pensacola
$187 Roundtrip, found 5 days ago
$187
Roundtrip
found 5 days ago
Select Delta flight, departing Wed, Sep 3 from Chicago to Pensacola, returning Sat, Sep 6, priced at $187 found 5 days ago
Southwest Airlines
Sat, Oct 4 - Mon, Oct 6
MDW
Chicago
PNS
Pensacola
$196 Roundtrip, found 5 days ago
$196
Roundtrip
found 5 days ago
Select Southwest Airlines flight, departing Sat, Oct 4 from Chicago to Pensacola, returning Mon, Oct 6, priced at $196 found 5 days ago
Delta
Fri, Aug 22 - Sat, Aug 23
MDW
Chicago
PNS
Pensacola
$199 Roundtrip, found 6 days ago
$199
Roundtrip
found 6 days ago
Select Delta flight, departing Fri, Aug 22 from Chicago to Pensacola, returning Sat, Aug 23, priced at $199 found 6 days ago
Southwest Airlines
Sat, Aug 23 - Sat, Aug 30
MDW
Chicago
PNS
Pensacola
$217 Roundtrip, found 22 hours ago
$217
Roundtrip
found 22 hours ago
Select Southwest Airlines flight, departing Sat, Aug 23 from Chicago to Pensacola, returning Sat, Aug 30, priced at $217 found 22 hours ago
Southwest Airlines
Sat, Aug 16 - Sat, Aug 23
MDW
Chicago
PNS
Pensacola
$227 Roundtrip, found 17 hours ago
$227
Roundtrip
found 17 hours ago
Select Southwest Airlines flight, departing Sat, Aug 16 from Chicago to Pensacola, returning Sat, Aug 23, priced at $227 found 17 hours ago
Delta
Sat, Aug 23 - Sat, Aug 30
MDW
Chicago
PNS
Pensacola
$228 Roundtrip, found 22 hours ago
$228
Roundtrip
found 22 hours ago
Select Delta flight, departing Sat, Aug 23 from Chicago to Pensacola, returning Sat, Aug 30, priced at $228 found 22 hours ago
Southwest Airlines
Sun, Aug 17 - Sat, Aug 23
MDW
Chicago
PNS
Pensacola
$234 Roundtrip, found 17 hours ago
$234
Roundtrip
found 17 hours ago
Select Southwest Airlines flight, departing Sun, Aug 17 from Chicago to Pensacola, returning Sat, Aug 23, priced at $234 found 17 hours ago
Frontier Airlines
Thu, Aug 14 - Mon, Aug 25
MDW
Chicago
PNS
Pensacola
$284 Roundtrip, found 4 hours ago
$284
Roundtrip
found 4 hours ago
Select Frontier Airlines flight, departing Thu, Aug 14 from Chicago to Pensacola, returning Mon, Aug 25, priced at $284 found 4 hours ago

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

February is typically the cheapest month to fly

From $128 - $409 per traveler.

Graph displaying average flight prices per month

Flights from Chicago (MDW) to Pensacola (PNS)
Origin airport
Midway Intl.
Destination airport
Pensacola Intl.
Airlines serving
Delta, Frontier Airlines, Southwest Airlines
Roundtrip price
$171
Distance
782 mi
Average flight time
3 hours 20 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 September. 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 $67 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 Midway Intl. Airport (MDW) to Pensacola Intl. Airport (PNS) cost?
You'll find cheap return tickets from Midway Intl. Airport (MDW) to Pensacola Intl. Airport (PNS) starting at $154. Grab a seat and take off on your trip. 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 Southwest Airlines flight leaving MDW on August 1 2025 and touching down at PNS. The price was last updated on July 11 2025 and has not changed since.
What is the cheapest month to fly from MDW to PNS?
The cheapest flights from MDW 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 Midway Intl. Airport (MDW) to Pensacola Intl. Airport (PNS)?
Although Chicago, IL (MDW-Midway Intl.) has no direct flights to Pensacola Intl. Airport (PNS), other airports have nonstop routes. Leaving from O'Hare Intl. Airport (ORD) will get you to Pensacola without any detours.
What is the cheapest airline that flies from MDW to PNS?
At the moment, the cheapest carrier offering one-way flights from MDW to PNS is Southwest Airlines. You can jet off on this route from $139. This fare is based on the lowest price found on Expedia departing within the next three months. The flight takes off from MDW on July 31 2025. Prices were last updated on July 11 2025 and have not changed since.
How many flights per day from Midway Intl. Airport (MDW) to Pensacola Intl. Airport (PNS)?
Nonstop flights from Midway Intl. Airport (MDW) to Pensacola Intl. Airport (PNS) aren't available daily, so you'll have to take a flight with a layover. Explore your options with Expedia's filter tool. Enter your travel dates and pick either "1 Stop" or "2+ Stops."
What day of the week has the most flights from MDW to PNS?
You'll typically find Tuesday the quietest day for flights, while Fridays tend to be the busiest.* However this can change from season to season and during peak travel times or public holidays.*Busiest/quietest day to travel is based on Expedia flight demand through January to December 2024.
What is the best time to fly from Midway Intl. Airport (MDW) to Pensacola Intl. Airport (PNS)?
Book a flight from Midway Intl. Airport (MDW) to Pensacola Intl. Airport (PNS) that takes off before 3 PM to reduce the risk of cancellations. Departures after this time are on average 22% more likely to be canceled.**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 Midway Intl. Airport (MDW)?
Explore your flight options from Midway Intl. Airport (MDW) to Northwest Florida Regional Airport (VPS). This is the only airport in Pensacola you can arrive at if you're taking a direct flight.
Is it cheaper to buy a plane ticket from Midway Intl. Airport (MDW) to Pensacola Intl. Airport (PNS) last-minute?
Last-minute fares from MDW to PNS are generally more expensive. For the best prices, start looking for flights well in advance. That being said, if you can play around with your travel dates, you may land a cheap fare right before your journey.
Is it cheaper to book a MDW to PNS flight and hotel package?
You can save money by securing a MDW to PNS flight and hotel package compared to booking separately. In fact, you could save hundreds of dollars by bundling with Expedia. And it's easy to manage it all in one convenient place. Once you've chosen your preferred flights and accommodations, consider adding extras including car rentals, tours and activities.
Can I cancel or change the date of my flight from Midway Intl. Airport (MDW) to Pensacola Intl. Airport (PNS)?
Typically, it's possible to reschedule or cancel your MDW to PNS flight. However, for bookings made more than 24 hours ago, additional fees may apply. Refer to your airline's policies in your itinerary to see what changes are allowed and whether any costs are involved. You'll also find more information on our Customer Service portal.

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*Available to One Key members.