PNS - MDW

$123 Find Cheap Flights from Pensacola to Chicago Midway Airport - Compare and Save

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 9/8. 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
1 adult, Economy, 0 bags

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Everything you should know

Cheapest round-trip
$241
Typical prices: $368-$556
Southwest
Tue 8/18Wed 8/19
PNS - MDW • 1 stop
Cheapest non-stop
$461
Southwest
Fri 7/31Mon 8/3
PNS - MDW • Non-stop
Nonstop flights
4 days a week
Mon, Thu, Fri, Sun
You can fly direct with Southwest. Average duration is 2h 15m
Direct flights
Direct flights
+1
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Direct flights
Direct flights
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Top airlines
Cheapest • from $241 (round-trip)
Best reviews • 8.0 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
When to travel
Cheapest • 100% price drop
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
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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

Tue, Aug 18 - Wed, Aug 19
Southwest Logo
3:00 pm - 8:40 pm
PNS
-
MDW
5h 40m
1 stop
Southwest Logo
2:00 pm - 5:35 pm
MDW
-
PNS
3h 35m
1 stop
$241Southwest
Tue, Oct 27 - Wed, Nov 4
Delta Logo
6:00 am - 9:52 am
PNS
-
MDW
3h 52m
1 stop
Delta Logo
6:00 am - 12:34 pm
MDW
-
PNS
6h 34m
1 stop
$245Delta
Tue, Aug 18 - Wed, Aug 19
Southwest Logo
3:00 pm - 11:10 pm
PNS
-
MDW
8h 10m
2 stops
Southwest Logo
2:00 pm - 5:35 pm
MDW
-
PNS
3h 35m
1 stop
$246Southwest
Tue, Aug 18 - Wed, Aug 19
Southwest Logo
7:55 am - 3:25 pm
PNS
-
MDW
7h 30m
2 stops
Southwest Logo
10:10 am - 6:35 pm
MDW
-
PNS
8h 25m
2 stops
$256Southwest
Mon, Oct 26 - Wed, Nov 4
Delta Logo
6:00 am - 12:05 pm
PNS
-
MDW
6h 05m
1 stop
Delta Logo
6:00 am - 10:53 am
MDW
-
PNS
4h 53m
1 stop
$269Delta
Tue, Aug 25 - Thu, Aug 27
Southwest Logo
3:00 pm - 8:40 pm
PNS
-
MDW
5h 40m
1 stop
Southwest Logo
5:30 am - 12:30 pm
MDW
-
PNS
7h 00m
1 stop
$270Southwest
Fri, Oct 30 - Wed, Nov 4
Delta Logo
7:05 am - 12:05 pm
PNS
-
MDW
5h 00m
1 stop
Delta Logo
10:58 am - 3:04 pm
MDW
-
PNS
4h 06m
1 stop
$271Delta
Tue, Aug 25 - Thu, Aug 27
Southwest Logo
4:20 pm - 10:20 pm
PNS
-
MDW
6h 00m
1 stop
Southwest Logo
5:30 am - 1:05 pm
MDW
-
PNS
7h 35m
2 stops
$275Southwest
Fri, Sep 11 - Mon, Sep 14
Southwest Logo
7:45 am - 3:30 pm
PNS
-
MDW
7h 45m
2 stops
Southwest Logo
5:55 am - 9:30 am
MDW
-
PNS
3h 35m
1 stop
$276Southwest
Tue, Aug 25 - Thu, Aug 27
Southwest Logo
7:55 am - 3:25 pm
PNS
-
MDW
7h 30m
2 stops
Southwest Logo
5:30 am - 1:05 pm
MDW
-
PNS
7h 35m
2 stops
$280Southwest
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 August.

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 Saturdays and avoid leaving on a Monday, as it's usually the priciest day. When flying back from Chicago Midway Airport, Wednesday is the cheapest day to fly and Sunday 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.

No, with an average price for the route of $423, prices are generally cheapest when you fly direct.

Good to know

Low seasonJune
Cheapest flight$123
Best time to beat the crowds with an average 35% drop in price.
Most popular time to fly with an average 5% 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 5 days, the lowest price for a flight from Pensacola to Chicago Midway Airport was $123 for a one-way ticket and $241 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?

    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 $397 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 $388 and an overall rating of 7.8.

  • 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 $209 or less one-way and $425 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

Thursday

Southwest

Southwest

Friday

Southwest

Southwest

Sunday

Southwest

Southwest

See more direct flights

Direct returns

Chicago Midway to Pensacola

Monday

Southwest

Southwest

Thursday

Southwest

Southwest

Friday

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 4246 reviews
8.0Comfort
7.5Entertainment
7.0Food
8.6Crew
8.1Boarding
Airline reviews

Flight was delayed over 3 hours. Planes were dirty. Staff indifferent. And they serve vegan pretzels as snacks.

2.0 MediocreMatthew, Jun 2026
CVG - MDW
Read more Southwest reviews

Flight was delayed over 3 hours. Planes were dirty. Staff indifferent. And they serve vegan pretzels as snacks.

The flight was smooth. The Southwest experience has degraded overall, but this one was okay.

The checking experience in Orlando was terrible, almost missed the flight. Too many travelers and Southwest completely understaffed.

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.

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.

The flight was great. We were not offered any beverages though. And there was no real turbulence, so not sure why.

Not good.,At first delayed due to weather, then still had to load all the luggage, then a mechanical issue. Upon finally arriving, clothes wet as suitcases sat out in the rain. In a hard side suitcase! Ruined some paper items inside. Not happy!

The flight itself was good. We were delayed 1 1/2 hours which was not good.

Flight was fine but new boarding policy was a drag Xtra time passenger group And Waiting until entire bridge empties before calling a list preferred... Waste of time

Wish that they would space out the boarding a little. COVID is still around and is real. No entertainment. Miss the peanuts.

It was as good as it could be. Flying is not a pleasant experience these days.

There was an unruly family behind us that made the short flight miserable!!! The cabin crew did nothing to contain it.

Flight delay was frustrating, also you cannot checkin online without delta app, web browser check-in throw errors

Got on the plane and sat there for an hour before departure.

Cramped seating for me. Luckily it wasn’t a long flight

It’s was good. There’s so much room for improvement though. Since the plane was small, there was no entertainment but for years now, the most jarring aspect of travel is the lack of tasty snacks.

5 hour delay. They blamed the weather but it was the computer issues they had been dealing with for days.

I liked the ease of checking in, luggage check in, wheel chair assistance, boarding and flight.

I usually have a positive experience with Delta. Complimentary upgrades are always nice!

The captain was amazing and kept us informed throughout that there would be some rough air. The flight also got delayed but we were able to actually leave on time, which was great.

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

Information on your arrival and departure airports