PNS - MDW

$89 Find Cheap Flights from Pensacola to Chicago Midway Airport

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Pensacola to Midway departing on 6/8. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult

KAYAK searches hundreds of travel sites at once for deals on flights to Chicago Midway Airport

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Pensacola to Chicago, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Pensacola to Chicago, as well as popular online travel agencies
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Flights Deals

Cheap Flights from Pensacola to Midway

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Pensacola to Midway that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.

Recent round-trip flight deals from Pensacola to Midway

KAYAK's recommended round-trip deals from the most popular airlines that fly from Pensacola to Midway.
Discover the best prices for you by selecting your travel dates on KAYAK.
Southwest Logo
9:35 am - 11:50 amPNS-MDW
2h 15mnonstop
Southwest Logo
5:25 am - 10:15 amMDW-PNS
4h 50m1 stop
$187Southwest
Find Deal
Wed, Jul 9 - Mon, Jul 14
Southwest Logo
4:20 pm - 9:05 pmPNS-MDW
4h 45m1 stop
Southwest Logo
6:45 am - 10:45 amMDW-PNS
4h 00m1 stop
$197Southwest
Find Deal
Tue, May 13 - Tue, May 20
Delta Logo
6:00 am - 11:53 amPNS-MDW
5h 53m1 stop
Delta Logo
6:00 am - 10:35 amMDW-PNS
4h 35m1 stop
$218Delta
Find Deal
Wed, May 21 - Tue, May 27
Southwest Logo
5:30 pm - 11:30 pmPNS-MDW
6h 00m1 stop
Southwest Logo
10:30 am - 12:35 pmMDW-PNS
2h 05mnonstop
$222Southwest
Find Deal
Sat, Jun 28 - Tue, Jul 1
Southwest Logo
2:25 pm - 4:40 pmPNS-MDW
2h 15mnonstop
Southwest Logo
7:50 am - 4:50 pmMDW-PNS
9h 00m1 stop
$228Southwest
Find Deal
Thu, Jul 10 - Sat, Jul 12
Southwest Logo
4:40 pm - 9:25 pmPNS-MDW
4h 45m1 stop
Southwest Logo
5:15 am - 8:55 amMDW-PNS
3h 40m1 stop
$232Southwest
Find Deal
Thu, Jul 17 - Mon, Jul 28
Southwest Logo
6:10 pm - 12:10 amPNS-MDW
6h 00m1 stop
Southwest Logo
10:35 am - 12:40 pmMDW-PNS
2h 05mnonstop
$237Southwest
Find Deal
Fri, Jun 6 - Sun, Jun 8
Southwest Logo
5:30 pm - 11:25 pmPNS-MDW
5h 55m1 stop
Southwest Logo
1:50 pm - 7:40 pmMDW-PNS
5h 50m2 stops
$243Southwest
Find Deal
Wed, Jul 9 - Mon, Jul 14
Delta Logo
6:00 am - 11:53 amPNS-MDW
5h 53m1 stop
Delta Logo
6:00 am - 10:35 amMDW-PNS
4h 35m1 stop
$248Delta
Find Deal
Wed, May 21 - Sun, May 25
Southwest Logo
4:20 pm - 9:05 pmPNS-MDW
4h 45m1 stop
Southwest Logo
2:40 pm - 10:10 pmMDW-PNS
7h 30m2 stops
$252Southwest
Find Deal
Tue, May 13 - Tue, May 20
Useful Info

KAYAK's insights & trends for Pensacola to Midway flights

Get data-powered insights and trends into flights from Pensacola to Midway to help you find the cheapest flights, the best time to fly and much more.

What’s the cheapest day of the week to fly from Pensacola to Chicago Midway Airport?

The average price of all round-trip flights from Pensacola to Chicago Midway Airport clicked on KAYAK for each day over the last 12 months.

If you are looking for a flight deal from Pensacola to Chicago Midway Airport, look for departures on Tuesdays and avoid leaving on a Sunday, as it's usually the priciest day. When flying back from Chicago Midway Airport, Thursday is the cheapest day to fly and Monday is the most expensive.

What is the cheapest month to fly from Pensacola to Chicago Midway Airport?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Pensacola to Chicago Midway Airport, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Pensacola to Chicago Midway Airport is April, where tickets cost $207 (return) on average. On the other hand, the most expensive months are November and July, where the average cost of round-trip tickets is $447 and $436 respectively.

Good to know

Low seasonApril
High seasonSeptember
Cheapest flight$89
Best time to beat the crowds with an average 42% drop in price.
Most popular time to fly and prices are also 7% lower on average.
Flight from Pensacola to Chicago Midway Airport

When to book flights from Pensacola to Midway

Are your dates flexible? Find out the best times to travel from Pensacola to Midway based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking Pensacola to Chicago Midway Airport flights

  • What is the cheapest flight from Pensacola to Chicago Midway Airport?

    In the last 3 days, the lowest price for a flight from Pensacola to Chicago Midway Airport was $89 for a one-way ticket and $187 for a round-trip.

  • Do I need a passport to fly between Pensacola and Chicago Midway Airport?

    A passport is not required to fly from Pensacola to Chicago Midway Airport.

  • Which airports will I be using when flying from Pensacola to Chicago Midway Airport?

    When flying out of Pensacola you will be using Pensacola. You will be landing at Chicago Midway Airport, also known as Chicago Midway.

  • Which airlines offer Wi-Fi service onboard planes from Pensacola to Chicago Midway Airport?

    Only American Airlines offers inflight Wi-Fi service on the Pensacola to Chicago Midway Airport flight route.

  • Which aircraft models fly most regularly from Pensacola to Chicago Midway Airport?

    The Boeing 737-700 Passenger/BBJ1 (winglets) is the aircraft model that flies most regularly on the Pensacola to Chicago Midway Airport flight route.

  • On which days can I fly direct from Pensacola to Chicago Midway Airport?

    You can catch a nonstop flight from Pensacola to Chicago Midway Airport on Monday, Thursday, Friday, Saturday, and Sunday.

  • Which is the best airline for flights from Pensacola to Chicago, Delta or Southwest?

    The two airlines most popular with KAYAK users for flights from Pensacola to Chicago are Delta and Southwest. With an average price for the route of $358 and an overall rating of 8.0, Delta is the most popular choice. Southwest is also a great choice for the route, with an average price of $334 and an overall rating of 8.0.

  • How does KAYAK find such low prices on flights from Pensacola to Chicago Midway Airport?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Pensacola to Chicago Midway Airport.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Pensacola to Chicago Midway Airport?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago Midway Airport from Pensacola is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Pensacola to Chicago Midway Airport?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Chicago Midway Airport with an airline and back to Pensacola with another airline. Booking your flights between Pensacola and MDW can sometimes prove cheaper using this method.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Pensacola to Chicago Midway Airport?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Chicago Midway Airport from Pensacola up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

KAYAK’s top tips for finding a cheap flight from Pensacola to Chicago Midway Airport

  • Looking for a cheap flight? 25% of our users found flights on this route for $138 or less one-way and $337 or less round-trip.

Prefer to fly direct from Pensacola to Chicago Midway Airport?

Find which airlines fly direct from Pensacola Airport to Chicago Midway Airport, which days they fly and book direct flights.

Direct departures

Pensacola to Chicago Midway

Monday

Southwest

Southwest

Tuesday

Southwest

Southwest

Wednesday

Southwest

Southwest

Thursday

Southwest

Southwest

Friday

Southwest

Southwest

Saturday

Southwest

Southwest

Sunday

Southwest

Southwest

See more direct flights

Direct returns

Chicago Midway to Pensacola

Monday

Southwest

Southwest

Tuesday

Southwest

Southwest

Wednesday

Southwest

Southwest

Thursday

Southwest

Southwest

Friday

Southwest

Southwest

Saturday

Southwest

Southwest

Sunday

Southwest

Southwest

See more direct flights
See more direct flights

Top airlines flying from Pensacola to Midway

 
See real verified KAYAK customer reviews for airlines flying from Pensacola to Chicago. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Pensacola to Midway? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
8.0
SouthwestOverall score based on 4294 reviews
8.0Comfort
8.2Boarding
7.6Entertainment
7.1Food
8.6Crew
Airline reviews

The price of the tickets isn't matching the flight experience. No matter how long the flight is, you're only getting pretzels. The flight attendants looked unkept and over it.

6.0 GoodJennifer, Apr 2025FLL - RDU
Read more Southwest reviews

The price of the tickets isn't matching the flight experience. No matter how long the flight is, you're only getting pretzels. The flight attendants looked unkept and over it.

WiFi on the flight was not working. Thus, entertainment options were limited.

Flight was awfully bumpy and landing was a bit jolting. I was in the restroom when snacks and drinks were served and was not asked if i wanted any. I had to ask for water finally.

Crew was great flight was great baggage claim was a failure. It took over 1 hour for bags to arrive. Poor communication poor effort when I spoke to the supervisor about the delay

Planes are aged. The wifi is unreliable and on many fights, no-existent. The flight attendants were very good.

I had a wonderful flight, but the only thing that annoyed me was how crowded TSA was. I still believe airports and all planes work together to bunch everyone together to drive up cost.

Easy to book and to get check in and get on and off.

Everything worked well. Crew was as entertaining as is possible on a plane flight. Southwest still has good legroom:

I like that it was on time and the staff was friendly.

Glad flight made it out. So many delays due to hurricane. everyone did a great job.

This had nothing to do with Delta… The flights were on time and flawless. The service was excellent. We purchased seats in (aisle/middle) comfort plus since this was a cross country flight. Unfortunately, the woman seated at the window was 300+ pounds and, as might be expected, covered up about a third of the middle seat also. there was absolutely nothing that Delta could have done about that… I just don’t know what the answer should be. If you purchase a seat, you should should be able to use the entire seat and not just the portion that someone else is not sitting/oozing in. Disappointing…there should be something that could be done….I'm just not sure what solution could be.

The worst part was I was NOT allowed in the lounge even though I was holding a first class ticket and have a premium American Express card. I have flown Business or First Class with many airlines. Delta is the ONLY one who does not extend this courtesy to anyone except people who hold the very expensive American Express card. As a result, I won’t fly Delta if I have any other choice.

The Dekta Rep that checked us in was great. She's very personable, pleasant, and can tell she enjoys her job.

The young man who was our flight attendant in first class was lazy and did not do his job well at all. Never offered drinks upon boarding - actually I take that back... said "are you okay with water" as if I do not want to get you anything else, only passed the snacks around once, got my drink order wrong and then never offered a second round of drinks. He was the worst I have ever seen on Delta and we fly a lot.

Flight left early and arrived early. the whole trip was excellent.

Newer plane, relatively easy boarding, not a full flight and was told that we could not be moved up because of weight and balance issues. Otherwise, a very good experience.

Everything was great. Great service, excellent communication, and early arrival

I sat in comfort plus. It was fine. Seats were comfortable. I got drinks and snacks.

Good and consistent Printer in lounge did not work for me :(

Great - This was the last flight before hurricane closures and did a quick turnaround to get the plane heading north. Much appreciated.

Everything you need to know for your flight from Pensacola to Midway

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