Book cheap flights from Chicago (Midway) to Pensacola with Southwest Airlines®. It’s easy to find the Chicago Midway International Airport to Pensacola International Airport flight to make your booking and travel a breeze. Whether you’re traveling for business or pleasure, solo or with the whole family, you’ll enjoy flying Southwest®. Have flexible travel dates? Plug them into the Low Fare Calendar and see the lowest fares available within your travel window. You may also want to browse Southwest Vacations® to see special offers and package deals on flights, hotels, rental cars, and more.
Explore your options and book your Chicago (Midway) to Pensacola flight with Southwest today!
Chicago (Midway), IL to Pensacola, FL
departing on 10/27
one-way starting at*$103
*Restrictions and exclusions apply. Seats and dates are limited. Select markets. 36 travel days available.
Middle seats open through November 30
Full exchange of fresh, outdoor air every 2-3 minutes while inflight
Face coverings required
Average flight time: 2 hours 10 minutes
Departing from: Chicago Midway International Airport (MDW)
Arriving at: Pensacola International Airport (PNS)
Other popular flights from ChicagoView our interactive map
†Based on DOT published scheduled average flights Monday-Friday between 8/20/2020 and 4/11/2021, as of 8/20/2020.
One child over 14 days and under two (2) years of age, not occupying a seat, may be carried free of charge when traveling with an adult (12 years of age or older). Learn more.
Customers flying with a pet are subject to a pet fare. To learn more about traveling with your furry friend, explore the Southwest® pet policy.
Minors under the age of 18 are not permitted to fly unaccompanied on international flights or any itinerary that includes an international flight. Learn more.
Start packing! Every ticketed Customer’s first two checked bags are free. Learn more.
Pensacola International Airport is the start of your Pensacola adventure. The Florida Panhandle is calling!
At Southwest, we know it takes more than great deals on Pensacola airfares and convenient scheduling options to make your trip memorable. So from booking to boarding, we offer services and features designed to make your travel from Chicago (Midway) to Pensacola the best it can be. Find out more about the Southwest® Experience before you book your Chicago Midway International Airport to Pensacola International Airport flight.
Flying with Southwest is simple and fun, no matter which of our dozens of exciting destinations you choose. And when you search for your next flight to Pensacola, you know you won’t be surprised at checkout. Low fares, no hidden fees. That’s our Transfarency® promise. And, as always, bags fly free. Enroll in our Click 'N Save® emails and stay up to date on our latest flight deals. Looking for tours, activities, and more hidden gems to add to your Pensacola adventure? Explore Southwest Airlines® Experiences and earn Rapid Rewards® points when you fly.
1First and second checked bags. Weight and size limits apply.
2Fare difference may apply.
How many Southwest flights from Chicago (Midway) to Pensacola occur daily?
There are 7 flights daily from Chicago (Midway) to Pensacola on Southwest Airlines.
What day is it cheapest to fly from Chicago (Midway) to Pensacola?
To find the cheapest day and time to fly Chicago (Midway) to Pensacola with Southwest, check out our Low Fare Calendar.
Can I rent a car at Pensacola International Airport?
You can rent a car at Pensacola International Airport—book yours with your flight.
Can I change my flight reservation for my flight from Chicago (Midway) to Pensacola?
Yes! Flights from Chicago (Midway) to Pensacola—or from here or there to anywhere—can be changed with no change fees. Fare difference may apply.
Where can I find the status of my flight from Chicago (Midway) to Pensacola?
Check the status of your upcoming Southwest flight here.
Where can I find answers to other questions about flying from Chicago (Midway) to Pensacola with Southwest?
Check out the Southwest Airlines® FAQs for answers about everything Southwest.