PNS - MDW

$139 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 7/17. 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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Flights 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

Tue, Jul 1 - Tue, Jul 8
Southwest Logo
9:35 am - 11:50 amPNS-MDW
2h 15mnonstop
Southwest Logo
10:30 am - 12:35 pmMDW-PNS
2h 05mnonstop
$277Southwest
Find Deal
Wed, Jul 2 - Wed, Jul 9
Southwest Logo
5:30 pm - 11:25 pmPNS-MDW
5h 55m1 stop
Southwest Logo
10:30 am - 12:35 pmMDW-PNS
2h 05mnonstop
$287Southwest
Find Deal
Wed, Jul 2 - Wed, Jul 9
Southwest Logo
5:30 pm - 11:25 pmPNS-MDW
5h 55m1 stop
Southwest Logo
5:15 am - 10:00 amMDW-PNS
4h 45m1 stop
$297Southwest
Find Deal
Thu, Jul 10 - Tue, Jul 22
Delta Logo
11:43 am - 6:02 pmPNS-MDW
6h 19m1 stop
Delta Logo
6:00 am - 10:24 amMDW-PNS
4h 24m1 stop
$298Delta
Find Deal
Fri, Jul 4 - Mon, Jul 7
Southwest Logo
6:15 am - 1:20 pmPNS-MDW
7h 05m2 stops
Southwest Logo
5:15 am - 8:55 amMDW-PNS
3h 40m1 stop
$302Southwest
Find Deal
Sat, Aug 2 - Sat, Aug 9
Delta Logo
7:00 am - 11:58 amPNS-MDW
4h 58m1 stop
Delta Logo
4:22 pm - 9:38 pmMDW-PNS
5h 16m1 stop
$303Delta
Find Deal
Fri, Sep 19 - Sun, Sep 21
Delta Logo
3:35 pm - 9:44 pmPNS-MDW
6h 09m1 stop
Delta Logo
6:00 am - 12:50 pmMDW-PNS
6h 50m1 stop
$307Delta
Find Deal
Sat, Jul 12 - Sat, Jul 19
Southwest Logo
9:35 am - 11:50 amPNS-MDW
2h 15mnonstop
Southwest Logo
9:00 am - 4:50 pmMDW-PNS
7h 50m2 stops
$312Southwest
Find Deal
Wed, Jul 2 - Sun, Jul 6
Southwest Logo
5:30 pm - 11:25 pmPNS-MDW
5h 55m1 stop
Southwest Logo
10:35 am - 12:40 pmMDW-PNS
2h 05mnonstop
$317Southwest
Find Deal
Thu, Jul 10 - Mon, Jul 14
 Logo
7:24 pm - 2:04 pmPNS-MDW
18h 40m2 stops
 Logo
10:31 am - 10:41 pmMDW-PNS
12h 10m2 stops
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 Thursdays and avoid leaving on a Sunday, as it's usually the priciest day. When flying back from Chicago Midway Airport, Friday is the cheapest day to fly and Monday 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 $246, prices are generally cheapest when you fly direct.

Good to know

Low seasonMay
High seasonSeptember
Cheapest flight$139
Best time to beat the crowds with an average 38% 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 $139 for a one-way ticket and $277 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 737-800 Passenger/BBJ2 (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?

    There are nonstop flights from Pensacola to Chicago Midway Airport on a daily basis.

  • 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 $358 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 $173 or less one-way and $218 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

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

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 4279 reviews
7.1Food
7.6Entertainment
8.6Crew
8.2Boarding
8.0Comfort
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.

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 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.

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

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