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Cheap Flights from Chicago Midway to Pensacola

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      Travellers and cabin class, 1 Adult, Economy

      Compare Chicago Midway to Pensacola flight deals

      Find the cheapest month or even day of the year to fly to Pensacola

      Book the best Pensacola fare with no extra fees

      Flight deals from Chicago Midway to Pensacola

      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 R 3,938. Find the lowest prices on one-way and return tickets right here.
      Pensacola.R 1,930 per passenger.Departing Tue, 1 Sep.One-way flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departs from Chicago Midway on Tue, 1 Sep, arriving in Pensacola.Price includes taxes and charges.From R 1,930, select.
      Pensacola.R 1,931 per passenger.Departing Wed, 12 Aug.One-way flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departs from Chicago Midway on Wed, 12 Aug, arriving in Pensacola.Price includes taxes and charges.From R 1,931, select.
      Pensacola.R 2,004 per passenger.Departing Sat, 31 Oct.One-way flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departs from Chicago Midway on Sat, 31 Oct, arriving in Pensacola.Price includes taxes and charges.From R 2,004, select.
      Pensacola.R 3,341 per passenger.Departing Tue, 28 Jul.One-way flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Chicago Midway on Tue, 28 Jul, arriving in Pensacola.Price includes taxes and charges.From R 3,341, select.
      Pensacola.R 3,401 per passenger.Departing Sun, 1 Nov.One-way flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Chicago Midway on Sun, 1 Nov, arriving in Pensacola.Price includes taxes and charges.From R 3,401, select.
      Pensacola.R 3,730 per passenger.Departing Fri, 25 Dec.One-way flight with Delta.Outbound indirect flight with Delta, departs from Chicago Midway on Fri, 25 Dec, arriving in Pensacola.Price includes taxes and charges.From R 3,730, select.
      Pensacola.R 3,731 per passenger.Departing Mon, 15 Feb.One-way flight with Delta.Outbound indirect flight with Delta, departs from Chicago Midway on Mon, 15 Feb, arriving in Pensacola.Price includes taxes and charges.From R 3,731, select.
      Pensacola.R 4,025 per passenger.Departing Sat, 1 Aug.One-way flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Sat, 1 Aug, arriving in Pensacola.Price includes taxes and charges.From R 4,025, select.
      Pensacola.R 4,029 per passenger.Departing Wed, 29 Jul.One-way flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Wed, 29 Jul, arriving in Pensacola.Price includes taxes and charges.From R 4,029, select.
      Pensacola.R 4,799 per passenger.Departing Thu, 15 Apr.One-way flight with Delta.Outbound indirect flight with Delta, departs from Chicago Midway on Thu, 15 Apr, arriving in Pensacola.Price includes taxes and charges.From R 4,799, select.

      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 September.
      Jul
      from R 3,341
      Aug
      from R 1,931
      Sep
      from R 1,930
      Oct
      from R 2,004
      Nov
      from R 3,401
      Dec
      from R 3,730
      Jan
      Find prices
      Feb
      from R 3,731
      Mar
      Find prices
      Apr
      from R 4,799
      May
      Find prices
      Jun
      Find prices

      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.

      Pensacola

      7km from central Pensacola
      Closest
      from R 1,930
      Search flights

      Gulf Shores

      45km from central Pensacola
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      Destin-Ft Walton Beach

      66km from central Pensacola
      Cheapest
      from R 653
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      Destin Executive

      71km from central Pensacola
      Search flights

      Chicago to Pensacola: Flight information

      The things to know before you go.
      Cheapest flight foundR 1,930
      Cheapest month to flySeptember
      Average flight time2 hrs, 12 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 R 3,938. 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 12 minutes is the average flight time from Chicago Midway to Pensacola.
      Southwest Airlines flies direct from Chicago Midway to Pensacola.
      As of July 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 August.
      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 Saturday, 22 August 2026.
      Yes – the average flight time is 2 hours and 12 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 Airport (MDW) to Pensacola Airport (PNS): what you need to know

      • The average duration of a direct flight from Chicago Midway Airport to Pensacola Airport is 2 hours 15 minutes.

      • Give yourself plenty of time to catch your MDW to PNS flight. As a general rule, turn up two hours before international departures and an hour ahead for domestic flights.

      • During popular months like July, you'll want to get to the airport earlier than usual. Plan to arrive two hours before domestic departures and four hours ahead of an international flight whenever you're travelling during a high season in general.

      • Getting to Pensacola (and then discovering more of the United States!) is a cinch with Southwest Airlines. This popular carrier has direct flights from Chicago Midway Airport to Pensacola Airport.

      • The airline with the highest booking volume on this route is Southwest Airlines.

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

        • Atlanta Hartsfield-Jackson Airport

        • Charlotte Douglas Airport

        • Nashville Airport

      Handy information about Chicago Midway Airport (MDW)

      • MDW is located at 5700 South Cicero.

      • Of all flights departing from Chicago Midway Airport, 76% touch down on time at their destination.

      • Central Chicago to Chicago Midway Airport is approximately 16 kilometres. Depending on traffic, it'll take you about 25 minutes to get there if you're driving, ride-sharing or catching a taxi.

      • You can expect a journey time of about 30 minutes on public transport.

      • Searching for a convenient hotel near MDW? If you're catching an early flight from Chicago Midway Airport to Pensacola Airport, these accommodation options will have you sleeping moments from your check-in counter:

      Arriving at Pensacola Airport (PNS)

      When to fly to Pensacola Airport (PNS)

      • It's time to choose your travel dates for your flight from Chicago Midway Airport to Pensacola Airport. July is the busiest month to head to Pensacola. If you want a quieter vibe, go in January.

      • The warmest month in Pensacola is August, with the temperature ranging between 24ºC (75ºF) and 35ºC (95ºF). Book your flights from Chicago Midway Airport to Pensacola Airport in this month if this is the kind of weather you like.

      • January has average temperatures of between 2ºC (36ºF) and 19ºC (66ºF). Look for cheap tickets from MDW to PNS around that time if you want to travel in cooler conditions.

      Explore more of the United States

      • Pensacola has plenty to offer, but there are so many other parts of the United States just waiting to be discovered. Around 451 kilometres north-east of Pensacola, a visit to Atlanta will keep your itinerary busy. Check out popular attractions like Georgia Aquarium, Birth Home of Martin Luther King, Jr and Fox Theatre.

      • If you're ready to explore another major stop in the United States, consider New Orleans, about 274 kilometres west of Pensacola. Bourbon St, French Quarter and Cafe Du Monde are the start of reasons to visit.

      Plan the rest of your trip from Chicago to Pensacola

      Prices shown on this page are estimated lowest prices only. Found in the last 12 days.