$89 Cheap Flights from Pensacola (PNS) to Chicago (MDW)

View $89 flight on Thu, Jul 10, 2025Opens in a new window

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Find available prices by choosing your travel dates.

Cheap Flights from Pensacola to Chicago (PNS-MDW)

Prices were available within the past 7 days and start at $89 for one-way flights and $177 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Southwest Airlines
Tue, Jun 24 - Sun, Jun 29
PNS
Pensacola
MDW
Chicago
$177 Roundtrip, found 2 hours ago
$177
Roundtrip
found 2 hours ago
Select Southwest Airlines flight, departing Tue, Jun 24 from Pensacola to Chicago, returning Sun, Jun 29, priced at $177 found 2 hours ago
Southwest Airlines
Tue, Jun 24 - Sun, Jun 29
PNS
Pensacola
MDW
Chicago
$187 Roundtrip, found 2 hours ago
$187
Roundtrip
found 2 hours ago
Select Southwest Airlines flight, departing Tue, Jun 24 from Pensacola to Chicago, returning Sun, Jun 29, priced at $187 found 2 hours ago
Southwest Airlines
Tue, Sep 30 - Mon, Oct 6
PNS
Pensacola
MDW
Chicago
$197 Roundtrip, found 6 hours ago
$197
Roundtrip
found 6 hours ago
Select Southwest Airlines flight, departing Tue, Sep 30 from Pensacola to Chicago, returning Mon, Oct 6, priced at $197 found 6 hours ago
Delta
Thu, May 8 - Sun, May 11
PNS
Pensacola
MDW
Chicago
$197 Roundtrip, found 1 hour ago
$197
Roundtrip
found 1 hour ago
Select Delta flight, departing Thu, May 8 from Pensacola to Chicago, returning Sun, May 11, priced at $197 found 1 hour ago
Southwest Airlines
Wed, May 14 - Sat, May 17
PNS
Pensacola
MDW
Chicago
$202 Roundtrip, found 15 hours ago
$202
Roundtrip
found 15 hours ago
Select Southwest Airlines flight, departing Wed, May 14 from Pensacola to Chicago, returning Sat, May 17, priced at $202 found 15 hours ago
Southwest Airlines
Wed, Jun 25 - Wed, Jul 2
PNS
Pensacola
MDW
Chicago
$207 Roundtrip, found 2 hours ago
$207
Roundtrip
found 2 hours ago
Select Southwest Airlines flight, departing Wed, Jun 25 from Pensacola to Chicago, returning Wed, Jul 2, priced at $207 found 2 hours ago
Southwest Airlines
Thu, Jul 17 - Sat, Jul 19
PNS
Pensacola
MDW
Chicago
$208 Roundtrip, found 6 hours ago
$208
Roundtrip
found 6 hours ago
Select Southwest Airlines flight, departing Thu, Jul 17 from Pensacola to Chicago, returning Sat, Jul 19, priced at $208 found 6 hours ago
Delta
Wed, Sep 24 - Tue, Sep 30
PNS
Pensacola
MDW
Chicago
$213 Roundtrip, found 1 day ago
$213
Roundtrip
found 1 day ago
Select Delta flight, departing Wed, Sep 24 from Pensacola to Chicago, returning Tue, Sep 30, priced at $213 found 1 day ago
Southwest Airlines
Wed, Jun 25 - Wed, Jul 2
PNS
Pensacola
MDW
Chicago
$217 Roundtrip, found 2 hours ago
$217
Roundtrip
found 2 hours ago
Select Southwest Airlines flight, departing Wed, Jun 25 from Pensacola to Chicago, returning Wed, Jul 2, priced at $217 found 2 hours ago
Frontier Airlines
Sun, May 11 - Thu, May 15
PNS
Pensacola
MDW
Chicago
$248 Roundtrip, found 1 day ago
$248
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Sun, May 11 from Pensacola to Chicago, returning Thu, May 15, priced at $248 found 1 day ago
Flights from Pensacola (PNS) to Chicago (MDW)
Origin airport
Pensacola Intl.
Destination airport
Midway Intl.
Airlines serving
Delta, Frontier Airlines, Southwest Airlines
Roundtrip price
$177
Distance
782 mi

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 June. 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 $89 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.

Frequently asked questions

How much does a flight from Pensacola Intl. Airport (PNS) to Midway Intl. Airport (MDW) cost?
Score cheap return flights from Pensacola Intl. Airport (PNS) to Midway Intl. Airport (MDW) starting from $177. Grab a seat and get ready for takeoff. 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 and American Airlines flight leaving PNS on April 26 2025 and touching down at MDW. The price was last updated on April 23 2025 and has not changed since.
What is the cheapest month to fly from PNS to MDW?
The cheapest flights from PNS to MDW 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 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 PNS to MDW?
Right now, the cheapest carrier operating one-way flights from PNS to MDW is Southwest Airlines. You can jet off on this route from $89. This fare is based on the lowest price found on Expedia departing within the next three months. The flight takes off from PNS on June 25 2025. Prices were last updated on April 23 2025 and have not changed since.
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.

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*Available to One Key members.