$60 Cheap flights from Midway Intl. to Pensacola Intl. (MDW to PNS)

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Find The Best Dates To Fly from Midway Intl. to Pensacola Intl.

Amazing MDW to PNS Flight Deals

The cheapest flights to Pensacola Intl. found within the past 7 days were $108 round trip and $60 one way. Prices and availability subject to change. Additional terms may apply.

Thu, May 9 - Mon, May 13
MDW
Chicago
PNS
Pensacola
$108 Roundtrip, found 6 days ago
$108
Roundtrip
found 6 days ago
Select Frontier Airlines flight, departing Thu, May 9 from Chicago to Pensacola, returning Mon, May 13, priced at $108 found 6 days ago
Thu, May 9 - Fri, May 17
MDW
Chicago
PNS
Pensacola
$118 Roundtrip, found 6 days ago
$118
Roundtrip
found 6 days ago
Select Frontier Airlines flight, departing Thu, May 9 from Chicago to Pensacola, returning Fri, May 17, priced at $118 found 6 days ago
Fri, May 17 - Wed, May 22
MDW
Chicago
PNS
Pensacola
$138 Roundtrip, found 6 days ago
$138
Roundtrip
found 6 days ago
Select Frontier Airlines flight, departing Fri, May 17 from Chicago to Pensacola, returning Wed, May 22, priced at $138 found 6 days ago
Sat, May 18 - Sat, May 25
MDW
Chicago
PNS
Pensacola
$139 Roundtrip, found 6 days ago
$139
Roundtrip
found 6 days ago
Select Frontier Airlines flight, departing Sat, May 18 from Chicago to Pensacola, returning Sat, May 25, priced at $139 found 6 days ago
Sat, May 11 - Fri, May 17
MDW
Chicago
PNS
Pensacola
$144 Roundtrip, found 6 days ago
$144
Roundtrip
found 6 days ago
Select Frontier Airlines flight, departing Sat, May 11 from Chicago to Pensacola, returning Fri, May 17, priced at $144 found 6 days ago
Sat, May 18 - Wed, May 29
MDW
Chicago
PNS
Pensacola
$147 Roundtrip, found 6 days ago
$147
Roundtrip
found 6 days ago
Select Frontier Airlines flight, departing Sat, May 18 from Chicago to Pensacola, returning Wed, May 29, priced at $147 found 6 days ago
Sat, May 4 - Sat, May 11
MDW
Chicago
PNS
Pensacola
$148 Roundtrip, found 6 days ago
$148
Roundtrip
found 6 days ago
Select Frontier Airlines flight, departing Sat, May 4 from Chicago to Pensacola, returning Sat, May 11, priced at $148 found 6 days ago
Fri, May 3 - Sat, May 11
MDW
Chicago
PNS
Pensacola
$158 Roundtrip, found 6 days ago
$158
Roundtrip
found 6 days ago
Select Frontier Airlines flight, departing Fri, May 3 from Chicago to Pensacola, returning Sat, May 11, priced at $158 found 6 days ago
Sat, May 11 - Wed, May 22
MDW
Chicago
PNS
Pensacola
$160 Roundtrip, found 1 day ago
$160
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Sat, May 11 from Chicago to Pensacola, returning Wed, May 22, priced at $160 found 1 day ago
Fri, May 17 - Wed, May 22
MDW
Chicago
PNS
Pensacola
$164 Roundtrip, found 1 day ago
$164
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Fri, May 17 from Chicago to Pensacola, returning Wed, May 22, priced at $164 found 1 day ago

Best Pensacola Intl. Flight and Hotel Packages

Pensacola Intl. flight + hotel packages - economy flights

Price found within the past 48 hours. Click for updated prices.
The Island Resort at Fort Walton Beach

The Island Resort at Fort Walton Beach

4 out of 5
per person
Jun 13 - Jun 16
Roundtrip flight included
Chicago (ORD) to Pensacola (PNS)
Super 8 by Wyndham Ft Walton Beach

Super 8 by Wyndham Ft Walton Beach

2 out of 5
per person
Jun 6 - Jun 9
Roundtrip non-stop flight included
Chicago (ORD) to Pensacola (PNS)
Hampton Inn & Suites Navarre

Hampton Inn & Suites Navarre

2.5 out of 5
per person
Jun 6 - Jun 9
Roundtrip non-stop flight included
Chicago (ORD) to Pensacola (PNS)
The Pensacola Beach Resort

The Pensacola Beach Resort

4 out of 5
per person
Jun 13 - Jun 16
Roundtrip flight included
Chicago (ORD) to Pensacola (PNS)
Quality Inn

Quality Inn

2.5 out of 5
per person
Jun 6 - Jun 9
Roundtrip non-stop flight included
Chicago (ORD) to Pensacola (PNS)
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Frequently asked questions

Can I catch a flight from MDW to Pensacola Intl. Airport (PNS) right now?
For information on any present Pensacola Airport travel advice and quarantine requirements, go to our Covid-19 Travel Advisor. Look before you book your flight, so you don’t get caught up en route.
Are there direct flights from Midway Airport to PNS?
The only thing standing between you and your next memorable adventure is a single flight. Southwest Airlines is the only airline that offers nonstop services between Chicago Airport and Pensacola Airport, so it’s smart to book ahead.
If I am not able to travel due to COVID-19, can I change my booking to a later date?
For more info about changing your flight to Pensacola Intl. Airport (PNS), please visit our Customer Service Portal.
How long is the flight from Chicago Airport to Pensacola Intl. Airport (PNS)?
Step off the plane feeling rested and relaxed by having a snooze and a few snacks during your flight to Pensacola Airport. With a general travel time of 3 hours and 18 minutes from Midway Intl. Airport (MDW), you’ll have more than enough time to indulge in both.
What is the flight distance from Chicago Airport to Pensacola Airport?
From Midway Airport, you’ll cover 780 mi before landing at Pensacola Intl. Airport (PNS). That should give you enough time to read a couple of chapters of your book and perhaps even manage a power nap.
What airlines fly from Chicago Airport to Pensacola Airport?
Ready to lock in the airfare for your next grand adventure? Eager to travel from Chicago to Pensacola in the shortest possible time? Hop on one of the 4 nonstop flights offered by Southwest Airlines every month, and you’ll be hitting the runway before you can ask ‘Are we there yet?’
What airlines have practices regarding COVID-19 in place and use social distancing?
From the moment you enter the departure terminal to when you leave the arrivals terminal, if you’re flying with American Airlines, United Airlines or Southwest Airlines you can be sure that COVID-19 measures and social distancing rules have been adhered to. Many airlines have introduced capped capacity flights and keeping the middle seat empty.
What is the best day to buy a plane ticket?
This just in! Airfares offered on Thursdays tend to be the cheapest, according to flight demand on Travelocity in 2021. Tuesday and Wednesday prices are also good, but you may want to prepare your budget if booking during the weekend, as data shows that is when prices are generally at their highest.
What are the cheapest days to fly?
Frequent travelers may already know this, but earlier in the week can be the cheapest time to fly. In 2021, flights departing on a Monday were generally the cheapest of the week, whereas you may pay a premium for weekend flights when demand is usually high. On average, tickets were most expensive for Saturday departures, so if you need to fly out on a weekend, you might look for deals ahead of time.
How far in advance can you book a flight?
Trying to figure out how early you should book your flight? It’s possible to start comparing international airfares on Travelocity up to 12 months in advance. However, it does depend on the carrier as not all airlines release their prices that far out. According to our 2021 flight demand trends, last minute planners can still bag a bargain with some of the cheapest fares appearing 0-2 weeks prior to their travel dates.*According to flight demand on Travelocity.com from January to December 2021. Savings are subject to change based on departure location, date and destination.

 

Traveling From
Midway Intl.
Traveling To
Pensacola Intl.
Shortest Flight Time
 hours mins
Earliest Departure Time
Latest Departure Time
Lowest Flight Price
$108

Route Info

Flight path for flights from Chicago Midway International Airport to Pensacola International Airport.


Origin:
MDW - Chicago Midway International Airport
Destination:
PNS - Pensacola International Airport
Distance:
867.00 miles


Discover our best flights from Chicago MDW to Pensacola PNS. 

With 20 airlines to choose from on Travelocity, you can easily find the best option for you. Use our filters to sort by price, compare airlines, and find the most convenient flight times. 

 

Find our best return flights from Chicago MDW to Pensacola PNS at the right price  

Airfares to Pensacola PNS from Chicago MDW currently cost between $108 and $164. It’s usually cheaper to book a round trip than two separate one-way flights. Prices and availability subject to change. Additional terms may apply. 

 

Book one-way flights from Chicago MDW to Pensacola PNS 

If you want to be flexible about when you return, or keep your travel options open ended, a one-way flight could be just the ticket! You’ll find one-way airfares from Chicago MDW to Pensacola PNS on Travelocity starting at $60. Prices and availability subject to change. Additional terms may apply. 

 

Get to Pensacola PNS from Chicago MDW quicker with direct flights. 

Get to Pensacola faster, without the hassle of changing planes and moving baggage, by booking a direct flight. Expect your direct flight to PNS from MDW to take around hour(s) min(s).  

 

Find our cheapest airfares for flights from Chicago MDW to Pensacola PNS

Find cheap flight deals by using our search filters to sort results starting with the lowest price airfares to PNS from MDW. Our Price Match Promise means if you find a lower rate on Travelocity.com or on another US-based website within 24 hours of booking, we’ll credit or refund the difference.  

 

Get our best airfare deals for your flight from Chicago MDW to Pensacola PNS today 

If you’re flexible about when you travel, May is usually the cheapest month to fly from Chicago MDW to Pensacola PNS. If you need to be more specific, search by date and arrival and departure times.Then, compare prices across different airlines, and sort results by lowest price first. 

 

Book flexible airline tickets for flights to Pensacola PNS from Chicago MDW 

Some airlines let you change your travel dates without charging a fee. Use our ‘no change fee’ filter to see which flights to PNS from MDW have this option.  

 

Travel with confidence when you book flights to Pensacola PNS from Chicago MDW with Travelocity 

We’ve secured fantastic deals with all the main airline carriers and it’s easy to compare, choose, and book with Travelocity. With 24/7 customer service and our free 'App', we’ll always keep you moving. 

*Price based on the lowest price found within past 24 hours and based upon one night stay for two adults over the next thirty days. Prices and availability subject to change. Additional terms may apply.