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

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 $154 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Frontier Airlines
Frontier Airlines
Frontier Airlines
Frontier Airlines
Frontier Airlines
Frontier Airlines
Delta
Southwest Airlines
Delta
Southwest Airlines

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

February is typically the cheapest month to fly

From $128 - $415 per traveler.

Alternative airports near Pensacola

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

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 $154 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)?
October 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.

Travel information

Origin airport
Midway Intl.
Destination airport
Pensacola Intl.
Airlines serving
Delta, Frontier Airlines, Southwest Airlines
Roundtrip price
$154
Distance
782 mi

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*Available to One Key members.