PNS - MDW

$122 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 5/7. 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, 0 bags

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
Travelers love KAYAK
41 299 237 searches in the past 7 days on KAYAK

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Everything you should know

Cheapest round-trip
$220
Typical prices: $442-$390
Multiple Airlines
Thu 5/14Wed 5/20
PNS - MDW • 1 stop
Cheapest non-stop
$369
Southwest
Tue 7/7Sat 7/11
PNS - MDW • Non-stop
Top airlines
Cheapest • from $345 (round-trip)
Best reviews • 8.0 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Nonstop flights
You can fly direct with Southwest. Average duration is 2h 16m
Direct flights
Direct flights
+1
+1
Direct flights
Direct flights
+1
Top layover airports
Cheapest • Avg $371 (round-trip)
Shortest trip • 3h 45m (one-way)
Insights
Insights
Insights
Insights
When to travel
Cheapest • 100% price drop
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
Start a new search
KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Midway!
Flight Deals
Booking Insights
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

Thu, May 14 - Wed, May 20
Multiple Airlines Logo
4:48 pm - 3:57 pm
PNS
-
MDW
23h 09m
1 stop
Multiple Airlines Logo
6:00 am - 3:53 pm
MDW
-
PNS
33h 53m
2 stops
$220Multiple Airlines
Sun, May 17 - Wed, May 20
Multiple Airlines Logo
7:38 pm - 3:57 pm
PNS
-
MDW
20h 19m
1 stop
Multiple Airlines Logo
6:00 am - 3:53 pm
MDW
-
PNS
33h 53m
2 stops
$257Multiple Airlines
Thu, May 14 - Sat, May 16
Multiple Airlines Logo
7:38 pm - 3:57 pm
PNS
-
MDW
20h 19m
1 stop
Multiple Airlines Logo
11:59 am - 1:59 pm
MDW
-
PNS
26h 00m
2 stops
$305Multiple Airlines
Wed, May 27 - Sat, May 30
Southwest Logo
10:10 am - 4:45 pm
PNS
-
MDW
6h 35m
1 stop
Southwest Logo
8:10 am - 10:25 am
MDW
-
PNS
2h 15mnonstop
$345Southwest
Wed, May 27 - Sat, May 30
Southwest Logo
7:40 am - 2:55 pm
PNS
-
MDW
7h 15m
2 stops
Southwest Logo
8:10 am - 10:25 am
MDW
-
PNS
2h 15mnonstop
$350Southwest
Sat, Jun 6 - Sat, Jun 13
Southwest Logo
4:20 pm - 10:25 pm
PNS
-
MDW
6h 05m
1 stop
Southwest Logo
7:05 am - 3:15 pm
MDW
-
PNS
8h 10m
1 stop
$355Southwest
Wed, May 27 - Wed, Jun 3
Southwest Logo
7:40 am - 3:45 pm
PNS
-
MDW
8h 05m
2 stops
Southwest Logo
9:50 am - 2:05 pm
MDW
-
PNS
4h 15m
1 stop
$360Southwest
Mon, Jun 1 - Tue, Jun 16
Delta Logo
4:35 pm - 9:09 pm
PNS
-
MDW
4h 34m
1 stop
Delta Logo
11:05 am - 3:26 pm
MDW
-
PNS
4h 21m
1 stop
$364Delta
Wed, May 27 - Wed, Jun 3
Southwest Logo
7:40 am - 3:45 pm
PNS
-
MDW
8h 05m
2 stops
Southwest Logo
11:35 am - 8:20 pm
MDW
-
PNS
8h 45m
2 stops
$366Southwest
Tue, May 26 - Tue, Jun 2
Southwest Logo
4:25 pm - 10:15 pm
PNS
-
MDW
5h 50m
1 stop
Southwest Logo
11:35 am - 8:20 pm
MDW
-
PNS
8h 45m
2 stops
$369Southwest
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.

How much is a round-trip flight from Pensacola to Chicago Midway Airport?

This analysis is based on the cheapest round-trip price found on KAYAK in the last 12 months by searching for a flight from Pensacola to Chicago Midway Airport departing in May.

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 Fridays 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 Thursday 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 February, where tickets cost $0 (return) on average. On the other hand, the most expensive months are March and October, where the average cost of round-trip tickets is $502 and $448 respectively.

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.

Yes, flying with a layover may cost you more time, but you can also save money on the route, with a 2 stops layover the cheapest option at $348 on average.

Good to know

Low seasonJune
Cheapest flight$116
Best time to beat the crowds with an average 30% drop in price.
Most popular time to fly with an average 11% increase in price.
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 $116 for a one-way ticket and $220 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 is the aircraft model that flies most regularly on the Pensacola to Chicago Midway Airport flight route.

  • Which airline alliances offer flights from Pensacola to Chicago Midway Airport?

    SkyTeam is the only airline alliance operating flights between Pensacola and Chicago Midway Airport.

  • 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, 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 $326 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 $373 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 $218 or less one-way and $397 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 4314 reviews
8.6Crew
8.0Comfort
7.5Entertainment
8.1Boarding
7.0Food
Airline reviews

no service at all due to turbulence. they should've at least given us snacks, there were only 10 people on the entire flight.

4.0 OkayCrystal, Apr 2026
MSY - MDW
Read more Southwest reviews

no service at all due to turbulence. they should've at least given us snacks, there were only 10 people on the entire flight.

For the first time in a long time, the Wi-Fi actually worked the entire flight! The flight crew was amazing as usual.

Great flight. I didn't get a drink because I was asleep whole on the flight.

Communication about the delayed flight was poor. We were told to move gates three times but that was bad information. We went from gate 128 to gate 126 and then to gate 123 and back to gate 126. Communication about the delay was bad. Ended up being 1 1/2 hour late getting home.

Love them will get a Southwest card to track my points and keep flying with them. My family and I were pleased with the services.

Southwest continues to do less for more money. Flight attendants used to be fun and friendly. But now it’s like they don’t even see you. Such a shame.

I liked it better when you were truer to your roots Am paying more for less fun

I was supposed to be on a later flight. When I showed up at the gate, the woman working there was extremely helpful getting moved up to this earlier flight.

Long layover between flights to Long Island from BWI - need better coordination between flights

I realize they are still working out kinks with the new boarding process, but by the time I boarded in group 5, most of the bins were full. All airlines should better enforce small bags and jackets going under the seats until everyone has boarded.

Flight was delayed it was hot while sitting on the plane, one engine was working on the plane until they had to do some jimmy rigging down the runway in order for the other engine to charge up. It was ridiculous

The flight was very good and the staff was very friendly and helpful!

Landed without a gate ready. Plane is extremely old and dirty.

All the amenities was wonderful, if they could keep their prices that low. I'd fly with them all the time.

The WiFi was horrific. I fly delta often and love their (usually reliable and free) WiFi. On this flight it was intermittent and when it did connect was extremely slow. I couldn’t get any work done while I was on the flight which was extremely frustrating. I was also in the exit row seat where there is now immediate seat in front of you, so while the leg room was nice, I couldn’t even watch the TV when the internet wasn’t working. Finally, for the last 20 mins of the flight, the announcement indicator came on the TV screens and took them over, even though no announcement was being made. Really disappointed.

Crew was great. Near on time departure and early arrival. Snacks are always meh. Not a fan of the "pay for everything including miles " proposal unless base flight rate going to be 100 bucks.

On the return flight, flight attendant Britt went out of her way to inform passengers that several of us had tight connections.

Too many people are taking up space in the overhead bins with their extra piece of luggage. Since they cannot fit their backpacks or extra luggage piece under the seat in front of them, they store it in the overheads and thus taking up room for other passengers. It wasn’t only one or two persons; more like 12 or 13 passengers.

Kayak botched up the booking, i had to call delta and fix. In the process Delta failed to honor my comfort plus seat assignment that i had previously.

Perhaps when you’re sitting in 1st class and the crew closes the bathroom for the pilots, there could be a notification other than holding your hands up as a blockade when you get there and you’re told the restrooms are closed please turn around … especially at night when visibility is poor and you’re met by a flight attendants with their arms up

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

Information on your arrival and departure airports