$59 Cheap Flights from Pensacola (PNS) to Chicago (MDW)

View $59 flight on Thu, Oct 23, 2025Opens in a new window

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

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Cheap Flights from Pensacola to Chicago (PNS-MDW)

Prices were available within the past 7 days and start at $59 for one-way flights and $201 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Frontier Airlines
Thu, Oct 23 - Sun, Oct 26
PNS
Pensacola
MDW
Chicago
$201 Roundtrip, found 2 hours ago
$201
Roundtrip
found 2 hours ago
Select Frontier Airlines flight, departing Thu, Oct 23 from Pensacola to Chicago, returning Sun, Oct 26, priced at $201 found 2 hours ago
Delta
Tue, Dec 16 - Wed, Dec 17
PNS
Pensacola
MDW
Chicago
$217 Roundtrip, just found
$217
Roundtrip
just found
Select Delta flight, departing Tue, Dec 16 from Pensacola to Chicago, returning Wed, Dec 17, priced at $217 just found
Southwest Airlines
Mon, Dec 15 - Tue, Dec 16
PNS
Pensacola
MDW
Chicago
$218 Roundtrip, just found
$218
Roundtrip
just found
Select Southwest Airlines flight, departing Mon, Dec 15 from Pensacola to Chicago, returning Tue, Dec 16, priced at $218 just found
Delta
Wed, Oct 29 - Sun, Nov 2
PNS
Pensacola
MDW
Chicago
$223 Roundtrip, found 3 hours ago
$223
Roundtrip
found 3 hours ago
Select Delta flight, departing Wed, Oct 29 from Pensacola to Chicago, returning Sun, Nov 2, priced at $223 found 3 hours ago
Southwest Airlines
Wed, Dec 10 - Mon, Dec 15
PNS
Pensacola
MDW
Chicago
$224 Roundtrip, found 8 hours ago
$224
Roundtrip
found 8 hours ago
Select Southwest Airlines flight, departing Wed, Dec 10 from Pensacola to Chicago, returning Mon, Dec 15, priced at $224 found 8 hours ago
Southwest Airlines
Thu, Dec 11 - Mon, Dec 15
PNS
Pensacola
MDW
Chicago
$224 Roundtrip, just found
$224
Roundtrip
just found
Select Southwest Airlines flight, departing Thu, Dec 11 from Pensacola to Chicago, returning Mon, Dec 15, priced at $224 just found
Southwest Airlines
Wed, Dec 10 - Mon, Dec 15
PNS
Pensacola
MDW
Chicago
$228 Roundtrip, found 8 hours ago
$228
Roundtrip
found 8 hours ago
Select Southwest Airlines flight, departing Wed, Dec 10 from Pensacola to Chicago, returning Mon, Dec 15, priced at $228 found 8 hours ago
Southwest Airlines
Thu, Dec 11 - Mon, Dec 15
PNS
Pensacola
MDW
Chicago
$230 Roundtrip, just found
$230
Roundtrip
just found
Select Southwest Airlines flight, departing Thu, Dec 11 from Pensacola to Chicago, returning Mon, Dec 15, priced at $230 just found
Southwest Airlines
Sun, Oct 26 - Wed, Oct 29
PNS
Pensacola
MDW
Chicago
$233 Roundtrip, found 3 hours ago
$233
Roundtrip
found 3 hours ago
Select Southwest Airlines flight, departing Sun, Oct 26 from Pensacola to Chicago, returning Wed, Oct 29, priced at $233 found 3 hours ago
Southwest Airlines
Thu, Dec 11 - Mon, Dec 15
PNS
Pensacola
MDW
Chicago
$234 Roundtrip, just found
$234
Roundtrip
just found
Select Southwest Airlines flight, departing Thu, Dec 11 from Pensacola to Chicago, returning Mon, Dec 15, priced at $234 just found

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

February is typically the cheapest month to fly

From $138 - $368 per traveler.

Alternative airports near Chicago

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

Select flight to O'Hare Intl. ORD. Cheapest option available. Average driving time to city center is 23 minutes. Flights from $118
ORD
O'Hare Intl.
Cheapest
Average driving time to city center23 min
Flights from $118

Frequently asked questions

How much does a flight from Pensacola Intl. Airport (PNS) to Midway Intl. Airport (MDW) cost?
Snag a cheap one-way flight from $59 or cheap return flight from $201 from Pensacola Intl. Airport (PNS) to Midway Intl. Airport (MDW) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to see our cheapest flight offers on this route.
What is the cheapest month to fly from Pensacola Intl. Airport (PNS) to Midway Intl. Airport (MDW)?
The cheapest month to fly from PNS to MDW is October, when there's less demand. Off-peak season is usually when airlines offer better prices between these airports.
Which airlines fly direct from Pensacola Intl. Airport (PNS) to Midway Intl. Airport (MDW)?
You can't catch a nonstop flight to Midway Intl. Airport (MDW) from Pensacola, FL (PNS-Pensacola Intl.). However, you can arrive in Chicago without any layovers by departing from Northwest Florida Regional Airport (VPS).
What is the cheapest airline that flies from Pensacola Intl. Airport (PNS) to Midway Intl. Airport (MDW)?
Use the filters on Expedia to compare airlines and find the most affordable carrier that'll fly you from PNS to MDW. Then, sort your results by "Price (lowest to highest)" to score a great deal.
How many flights per day from Pensacola Intl. Airport (PNS) to Midway Intl. Airport (MDW)?
You'll need to catch a flight with a layover if you're traveling from Pensacola Intl. Airport (PNS) to Midway Intl. Airport (MDW). There are no daily direct flights on this route. However, just filter your search to include one or two stops to discover an option that works for you.
What day of the week has the most flights from PNS to MDW?
Generally you'll find the greatest selection of flight options on a Friday. Tuesdays are often the quietest.* However, this can change based on the season, carrier and other factors.*Busiest/quietest day to travel is based on Expedia flight demand through January to December 2024.
What airline has the least delays from PNS to MDW?
Consider traveling with Southwest Airlines if you'd like to go straight from Pensacola Intl. Airport (PNS) to Midway Intl. Airport (MDW) without any interruptions. This airline has the strongest track record for punctuality, with an on-time score of 93%. Want to get notified of any changes? You can check your flight status using the Expedia App.
What is the best time to fly from Pensacola Intl. Airport (PNS) to Midway Intl. Airport (MDW)?
Opt for a flight from Pensacola Intl. Airport (PNS) to Midway Intl. Airport (MDW) that leaves before 3 PM to reduce the likelihood of delays. Departures later than this 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 Chicago from Pensacola Intl. Airport (PNS)?
If you've booked a direct flight from Pensacola Intl. Airport (PNS) to Chicago, O'Hare Intl. Airport (ORD) is the only airport you can land at.
Is it cheaper to buy a plane ticket from Pensacola Intl. Airport (PNS) to Midway Intl. Airport (MDW) last-minute?
Booking your plane ticket from PNS to MDW just before your getaway is typically more expensive. However, if you're flexible with your travel times and dates, you could bag a cheap last-minute fare.
Is it cheaper to book a PNS to MDW flight and hotel package?
Compared with arranging hotels and flights separately, booking a PNS to MDW flight and hotel package with Expedia could lead to significant savings. Better still, having it all in one place will take the hassle out of travel planning. Simply secure your flights and select from our wide range of stays, then customize your trip with other add-ons like tours, activities and car rentals.
Can I cancel or change the date of my flight from Pensacola Intl. Airport (PNS) to Midway Intl. Airport (MDW)?
Usually, it's possible to cancel or reschedule your PNS to MDW flight. However, if the booking was 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 further details on our Customer Service portal.

Travel information

Travel information

Origin airport
Pensacola Intl.
Destination airport
Midway Intl.
Airlines serving
Delta, Frontier Airlines, Southwest Airlines
Roundtrip price
$201
Distance
782 mi

Book with confidence

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 October. 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 $59 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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*Available to One Key members.