$104 Cheap Flights from Chicago (MDW) to Pensacola (PNS)

View $104 flight on Tue, Nov 4, 2025Opens in a new window

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

Cheap Flights from Chicago to Pensacola (MDW-PNS)

Prices were available within the past 7 days and start at $104 for one-way flights and $218 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Southwest Airlines
Wed, Dec 10 - Sat, Dec 13
MDW
Chicago
PNS
Pensacola
$218 Roundtrip, found 3 days ago
$218
Roundtrip
found 3 days ago
Select Southwest Airlines flight, departing Wed, Dec 10 from Chicago to Pensacola, returning Sat, Dec 13, priced at $218 found 3 days ago
Southwest Airlines
Sat, Sep 20 - Sat, Sep 27
MDW
Chicago
PNS
Pensacola
$219 Roundtrip, found 3 days ago
$219
Roundtrip
found 3 days ago
Select Southwest Airlines flight, departing Sat, Sep 20 from Chicago to Pensacola, returning Sat, Sep 27, priced at $219 found 3 days ago
Southwest Airlines
Sat, Sep 13 - Sat, Sep 20
MDW
Chicago
PNS
Pensacola
$219 Roundtrip, found 2 days ago
$219
Roundtrip
found 2 days ago
Select Southwest Airlines flight, departing Sat, Sep 13 from Chicago to Pensacola, returning Sat, Sep 20, priced at $219 found 2 days ago
Southwest Airlines
Tue, Sep 23 - Sat, Sep 27
MDW
Chicago
PNS
Pensacola
$239 Roundtrip, found 20 hours ago
$239
Roundtrip
found 20 hours ago
Select Southwest Airlines flight, departing Tue, Sep 23 from Chicago to Pensacola, returning Sat, Sep 27, priced at $239 found 20 hours ago
Southwest Airlines
Sat, Nov 15 - Tue, Nov 18
MDW
Chicago
PNS
Pensacola
$243 Roundtrip, found 2 days ago
$243
Roundtrip
found 2 days ago
Select Southwest Airlines flight, departing Sat, Nov 15 from Chicago to Pensacola, returning Tue, Nov 18, priced at $243 found 2 days ago
Southwest Airlines
Wed, Dec 10 - Sat, Dec 13
MDW
Chicago
PNS
Pensacola
$247 Roundtrip, found 3 days ago
$247
Roundtrip
found 3 days ago
Select Southwest Airlines flight, departing Wed, Dec 10 from Chicago to Pensacola, returning Sat, Dec 13, priced at $247 found 3 days ago
Southwest Airlines
Sat, Sep 20 - Sat, Sep 27
MDW
Chicago
PNS
Pensacola
$248 Roundtrip, found 3 days ago
$248
Roundtrip
found 3 days ago
Select Southwest Airlines flight, departing Sat, Sep 20 from Chicago to Pensacola, returning Sat, Sep 27, priced at $248 found 3 days ago
Southwest Airlines
Wed, Sep 17 - Sat, Sep 20
MDW
Chicago
PNS
Pensacola
$249 Roundtrip, found 2 hours ago
$249
Roundtrip
found 2 hours ago
Select Southwest Airlines flight, departing Wed, Sep 17 from Chicago to Pensacola, returning Sat, Sep 20, priced at $249 found 2 hours ago
Frontier Airlines
Fri, Nov 7 - Sat, Nov 15
MDW
Chicago
PNS
Pensacola
$284 Roundtrip, found 2 hours ago
$284
Roundtrip
found 2 hours ago
Select Frontier Airlines flight, departing Fri, Nov 7 from Chicago to Pensacola, returning Sat, Nov 15, priced at $284 found 2 hours ago
Delta
Wed, Sep 24 - Tue, Sep 30
MDW
Chicago
PNS
Pensacola
$287 Roundtrip, found 6 hours ago
$287
Roundtrip
found 6 hours ago
Select Delta flight, departing Wed, Sep 24 from Chicago to Pensacola, returning Tue, Sep 30, priced at $287 found 6 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

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 $259
PNS
Pensacola Intl.
CheapestClosest
Average driving time to city center8 min
Flights from $259
Flights from Chicago (MDW) to Pensacola (PNS)
Origin airport
Midway Intl.
Destination airport
Pensacola Intl.
Airlines serving
Delta, Southwest Airlines
Roundtrip price
$218
Distance
782 mi
Average flight time
2 hours 10 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 December. 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 $104 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?
Secure a cheap one-way flight from $104 or cheap return flight from $218 from Midway Intl. Airport (MDW) to Pensacola Intl. Airport (PNS) 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 Midway Intl. Airport (MDW) to Pensacola Intl. Airport (PNS)?
December is the least expensive month to fly from MDW to PNS. Traveling outside of peak seasons is often the key to landing a great deal.
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 Midway Intl. Airport (MDW) to Pensacola Intl. Airport (PNS)?
To find the cheapest airline flying from MDW to PNS, use Expedia's filter tool. Customize your search based on what matters most to you, such as preferred carriers and flight duration. You can then sort your results by "Price (lowest to highest)" to see the cheapest fares upfront.
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.