Cheap Flights from Chicago Midway to Pensacola

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Flight deals from Chicago Midway Airport to Pensacola Airport

Looking for a cheap last-minute deal or the best return flight from Chicago Midway Airport to Pensacola Airport? If you want to travel next month, return fares start from ر.ق.‏ 769. Find the lowest prices on one-way and return tickets right here.

Find the cheapest month to fly from Chicago Midway to Pensacola

We’re always keeping an eye on fares, so you can find the best one in seconds. It looks like Chicago Midway to Pensacola flights are currently cheapest in March.

Direct flights from Chicago Midway to Pensacola

Chicago Midway to Pensacola: Alternative routes

Compare routes from Chicago Midway to Pensacola below. You may find an airport to fly into that's cheaper, faster, or easier than Pensacola.

Chicago to Pensacola: Flight information

The things to know before you go.
Cheapest flight foundر.ق.‏ 370
Cheapest month to flyApril
Average flight time2 hrs, 14 mins
Most popular airlineSouthwest Airlines
Average flights per week6

Finding cheap flights from Chicago Midway to Pensacola: Frequently asked questions

The best price we found for a return flight from Chicago Midway to Pensacola is ر.ق.‏ 769. This is an estimate based on information collected from different airlines and travel providers over the last 4 days and is subject to change and availability.
2 hours and 14 minutes is the average flight time from Chicago Midway to Pensacola.
Southwest Airlines flies direct from Chicago Midway to Pensacola.
As of January 2026, there are 6 flights per week flying from Chicago Midway to Pensacola.
The cheapest month to fly from Chicago Midway to Pensacola is usually February.
After crunching the numbers on our flight calendar, we found that it's currently cheapest to fly from Chicago Midway Airport to Pensacola Airport on Tuesday, 17 February 2026.
Yes – the average flight time is 2 hours and 14 minutes.
We show every price from over 1,200 airlines and travel agents, comparing them all so you don’t have to. If you know you want to fly to Pensacola but you’re not ready to book, set up a Price Alert. We’ll track prices for you, and let you know when they rise or fall.
We crunched all the numbers in our flight calendar and it looks like the cheapest time to book a flight to Pensacola is around 40 days in advance, so don’t leave your flight to the last minute.
Currently, Southwest Airlines offers the cheapest flight tickets to Pensacola.

Flying from Chicago Midway International Airport (MDW) to Pensacola International Airport (PNS): what you need to know

  • Hop on a direct flight from Chicago Midway International Airport to Pensacola International Airport and you'll be travelling for an average of 2 hours 5 minutes.

  • Leave enough time to make your MDW to PNS flight. As a general rule, turn up two hours before international departures and an hour ahead for domestic flights.

  • You can expect longer lines in popular months like July. Arriving up to four hours ahead of an international flight and two hours for domestic departures is a wise move.

  • Southwest Airlines has direct flights from Chicago Midway International Airport to Pensacola International Airport. Book with this popular carrier, then get ready to tick off the sights in Pensacola — and maybe even more of United States if you have time.

  • The airline that passengers book most often on this route is Southwest Airlines.

  • We make it a breeze to book a flight with a stopover. To see your options for tickets from Chicago Midway International Airport to Pensacola International Airport, uncheck 'Direct flights only.' Then, pick a flight that has a stop long enough to explore the city of your choice. Stopovers between MDW and PNS include:

    • Nashville International Airport

    • Hartsfield-Jackson Atlanta International Airport

    • Charlotte Douglas International Airport

How to find the cheapest flights from Chicago Midway International Airport (MDW) to Pensacola International Airport (PNS)

  • The lowest price we've found for a one-way Chicago Midway International Airport to Pensacola International Airport flight is ر.ق.‏ 370. A return fare is currently ر.ق.‏ 765. Depending on the availability and when you book, these fares can change.

  • To get cheap tickets from MDW to PNS, book your journey seven months ahead of your departure.

  • Organise your trip for June. That's the cheapest month for flights from Chicago Midway International Airport to Pensacola International Airport. If your travel dates are flexible, try out the 'Whole month' tool to see the lowest airfare across each month.

  • Picking up cheap flights from MDW to PNS is easy with Price Alerts. Simply set up one of these automatic alerts and we'll let you know when a new discounted fare appears.

  • Discover the right flight for you with the help of the filters. To see the 'Cheapest,' 'Fastest' or 'Best' flights from Chicago Midway International Airport to Pensacola International Airport, use the 'Sort by' function. You can also filter results by airline, departure and arrival times, and number of stops.

Handy information about Chicago Midway International Airport (MDW)

  • MDW is located at 5700 South Cicero.

  • Of the flights that depart from Chicago Midway International Airport, 77.88% arrive as scheduled at their destination.

  • To reach Chicago Midway International Airport from central Chicago, it'll take around 20 minutes by car. This depends on traffic, however. It's approximately 19 kilometres from the airport to the city centre.

  • Catching public transport? Expect a trip time of around 45 minutes.

  • Looking for a convenient hotel near MDW? If you've booked an early flight from Chicago Midway International Airport to Pensacola International Airport, these stays will put you moments from your departure gate:

Arriving at Pensacola International Airport (PNS)

Getting from Pensacola International Airport (PNS) to central Pensacola

  • You'll find PNS at 2430 Airport Boulevard.

  • From Pensacola International Airport, Pensacola is approximately 10 kilometres away. It takes around 15 minutes to reach the centre driving.

  • It takes around 1 hour 40 minutes when travelling by public transport.

When to fly to Pensacola International Airport (PNS)

  • The quietest month for a flight from Chicago Midway International Airport to Pensacola International Airport is February, while July is the most popular. Choose the best time to visit Pensacola based on whether you prefer a more fast-paced or easygoing experience.

  • Book your flight from Chicago Midway International Airport to Pensacola International Airport for August if you'd like to explore Pensacola during its warmest month. Expect temperatures of between 24ºC and 35ºC.

  • Search for cheap tickets from MDW to PNS in January if you like travelling in cooler conditions. Temperatures are at their lowest then, ranging between 2ºC and 19ºC on average.

Explore more of United States

  • Atlanta is just one of the many cities in United States waiting to be discovered once you've taken in the sights of Pensacola. Around 451 kilometres away to the north-east, its top attractions include Georgia Aquarium, Centennial Olympic Park and Piedmont Park.

  • New Orleans is another sought-after destination in United States and is around 274 kilometres west of Pensacola. No journey is complete without visiting French Quarter, Jackson Square and Cafe Du Monde.

Prices shown on this page are estimated lowest prices only. Found in the last 45 days.