PNS - MDW

$87 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 10/26. 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
1 adult, Economy

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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Flight Deals

Cheap Flights from Pensacola to Midway (PNS-MDW)

 
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.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Pensacola to Midway

Fri, Sep 19 - Tue, Sep 23
Southwest Logo
3:20 pm - 8:50 pmPNS-MDW
5h 30m1 stop
Southwest Logo
6:25 am - 10:35 amMDW-PNS
4h 10m1 stop
$223Southwest
Find Deal
Wed, Oct 15 - Mon, Oct 20
Southwest Logo
5:15 pm - 11:35 pmPNS-MDW
6h 20m1 stop
Southwest Logo
9:40 am - 5:30 pmMDW-PNS
7h 50m1 stop
$228Southwest
Find Deal
Fri, Oct 24 - Mon, Oct 27
Delta Logo
4:27 pm - 10:14 pmPNS-MDW
5h 47m1 stop
Delta Logo
10:35 am - 3:01 pmMDW-PNS
4h 26m1 stop
$229Delta
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Thu, Oct 2 - Sun, Oct 5
Southwest Logo
7:35 pm - 11:15 pmPNS-MDW
3h 40m1 stop
Southwest Logo
6:50 am - 10:25 amMDW-PNS
3h 35m1 stop
$239Southwest
Find Deal
Fri, Nov 14 - Mon, Nov 17
Southwest Logo
4:30 pm - 9:50 pmPNS-MDW
5h 20m1 stop
Southwest Logo
9:20 am - 6:35 pmMDW-PNS
9h 15m2 stops
$244Southwest
Find Deal
Sat, Sep 20 - Sun, Sep 21
Southwest Logo
4:45 pm - 6:55 pmPNS-MDW
2h 10mnonstop
Southwest Logo
5:30 am - 12:45 pmMDW-PNS
7h 15m1 stop
$248Southwest
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Sun, Sep 7 - Tue, Sep 9
Southwest Logo
6:45 pm - 10:55 pmPNS-MDW
4h 10m1 stop
Southwest Logo
6:25 am - 12:50 pmMDW-PNS
6h 25m1 stop
$249Southwest
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Thu, Sep 25 - Mon, Sep 29
 Logo
7:10 pm - 8:53 amPNS-MDW
13h 43m1 stop
 Logo
8:19 am - 6:10 pmMDW-PNS
9h 51m1 stop
Fri, Sep 19 - Mon, Sep 22
Delta Logo
4:03 pm - 9:36 pmPNS-MDW
5h 33m1 stop
Delta Logo
6:30 pm - 11:08 pmMDW-PNS
4h 38m1 stop
$254Delta
Find Deal
Fri, Oct 31 - Tue, Nov 4
Delta Logo
4:27 pm - 10:14 pmPNS-MDW
5h 47m1 stop
Delta Logo
6:00 am - 10:42 amMDW-PNS
4h 42m1 stop
$268Delta
Find Deal
Booking Insights

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 Thursdays and avoid leaving on a Sunday, as it's usually the priciest day. When flying back from Chicago Midway Airport, Tuesday is the cheapest day to fly and Sunday is the most expensive.

Can I save money by flying with a layover from Pensacola to Chicago Midway Airport?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

No, with an average price for the route of $297, prices are generally cheapest when you fly direct.

Good to know

Low seasonMay
Cheapest flight$87
Best time to beat the crowds with an average 36% 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 $87 for a one-way ticket and $223 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 Airbus A319 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 Saturday.

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

    The two airlines most popular with KAYAK users for flights from Pensacola to Chicago are Southwest and Delta. With an average price for the route of $329 and an overall rating of 8.0, Southwest is the most popular choice. Delta is also a great choice for the route, with an average price of $320 and an overall rating of 7.9.

  • 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 $232 or less one-way and $487 or less round-trip.

Prefer to fly direct from Pensacola to Chicago Midway Airport?

 
Direct data is based off flight results for the next 60 days. Find direct flights from all airlines flying direct from Pensacola to Chicago Midway.
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

Saturday

Southwest

Southwest

See more direct flights

Direct returns

Chicago Midway to Pensacola

Saturday

Southwest

Southwest

See more direct flights

Reviews of the 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 4242 reviews
8.1Boarding
7.5Entertainment
8.6Crew
8.0Comfort
7.0Food
Airline reviews

Near 4 hour flight with only 1 service. Had to use call button to request water. Internet and power not working until into flight. Internet would stop working during flight.

6.0 GoodDavid, Aug 2025MCO - DEN
Read more Southwest reviews

Near 4 hour flight with only 1 service. Had to use call button to request water. Internet and power not working until into flight. Internet would stop working during flight.

My flight was delayed 50 minutes and we were rushed to board to then sit for 15 minutes until the pilot arrived. Unacceptable since we could have waited to board. Also the delayed flight was updated AFTER we boarded to more than the 10 minutes as originally stated.

If we are going to have to pay for luggage, make it easier to do. Put something on the app during check-in so I don't need to do it at the kiosk. I've done it twice recently and I ended up having to pay at the desk because something went wrong at the kiosk in Tampa.

Worst experience I had on Southwest. Still better than most, but the seating was barely tolerable.

It was okay. The plane was delayed from earlier in the day, but they kept updating the departure time, sometimes later, sometimes earlier. That was stressful. Once we finally got on and took off, it was fine. I was supposed to have a connection in Chicago to Los Angeles, and the time for so late I was rebooked to arrive in LA 3 hours late. The departure time to Chicago later became early enough to have taken my original connection and arrive earlier but that wasn't an option.

Everything was on time. I was disappointed by the front section female, African American flight attendant. I did not see her name tag or would have identified by name not race. As passengers moved to the bathroom early in flight, she would say with a disdainful tone “I have to say the seat belt light is on” then go back to her book. Better trained flight attendants say something like be careful the seat belt light is on.

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

For a 69 year old with health problems I had the worse experience, no wheelchair when I entered a lady told me to sit and wait while a gentleman told me I had to walk to the Delta station, which I did. I had a carry on and a bag, and I was traveling with my service dog, which was on his carrier and the lady charged me for my carry on luggage, beside all the waiting cause of the delay, I had to walk to get my luggage cause no wheelchair showed up, I am so disappointed. I will get in touch with the company. I got home at 3:00 am, not good for my health situation.

Flight was an hour late, who knows why. It was OK, nothing outstanding.

Excellent check-in. Crew was good. Excellent communication from flight deck.

Amazing flight! I have never noticed the uniforms of the attendants before in twenty years of flying except today when one female had the most amazing dress on. It was beautifully designed and showed she was in charge. I never dreamed I would google who designed Delta uniforms . The ultimate compliment is when another woman admires your outfit. . I hope your designer puts it on the market

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 you need to know for your flight from Pensacola to Midway

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