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 8/4. 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
$265
Typical prices: $373-$278
Southwest
sáb. 8/22mar. 8/25
PNS - MDW • 1 stop
Cheapest non-stop
$355
Southwest
mié. 7/8mié. 7/15
PNS - MDW • Non-stop
Top airlines
Cheapest • from $265 (round-trip)
Best reviews • 7.9 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Nonstop flights
You can fly direct with Southwest. Average duration is 2h 15m
Direct flights
Direct flights
+1
+1
Direct flights
Direct flights
+1
Top layover airports
Cheapest • Avg $378 (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

sáb., ago. 22 - mar., ago. 25
Southwest Logo
10:50 am - 3:55 pm
PNS
-
MDW
5h 05m
1 stop
Southwest Logo
2:00 pm - 5:35 pm
MDW
-
PNS
3h 35m
1 stop
$265Southwest
sáb., ago. 22 - mar., ago. 25
Southwest Logo
10:50 am - 3:55 pm
PNS
-
MDW
5h 05m
1 stop
Southwest Logo
9:05 am - 5:35 pm
MDW
-
PNS
8h 30m
2 stops
$275Southwest
sáb., ago. 22 - mar., ago. 25
Southwest Logo
12:25 pm - 7:10 pm
PNS
-
MDW
6h 45m
2 stops
Southwest Logo
9:25 am - 5:35 pm
MDW
-
PNS
8h 10m
2 stops
$320Southwest
sáb., nov. 7 - mar., nov. 10
Southwest Logo
1:30 pm - 7:35 pm
PNS
-
MDW
6h 05m
1 stop
Southwest Logo
7:05 am - 3:30 pm
MDW
-
PNS
8h 25m
1 stop
$321Southwest
sáb., nov. 7 - mar., nov. 10
Southwest Logo
7:40 am - 2:50 pm
PNS
-
MDW
7h 10m
2 stops
Southwest Logo
8:00 am - 3:30 pm
MDW
-
PNS
7h 30m
2 stops
$326Southwest
mar., nov. 17 - dom., nov. 22
Delta Logo
8:00 am - 11:56 am
PNS
-
MDW
3h 56m
1 stop
Delta Logo
6:00 am - 12:51 pm
MDW
-
PNS
6h 51m
1 stop
$351Delta
vie., oct. 2 - sáb., oct. 3
Delta Logo
9:22 am - 4:11 pm
PNS
-
MDW
6h 49m
1 stop
Delta Logo
4:30 pm - 9:32 pm
MDW
-
PNS
5h 02m
1 stop
$354Delta
mié., jul. 8 - mié., jul. 15
Southwest Logo
3:45 pm - 6:00 pm
PNS
-
MDW
2h 15mnonstop
Southwest Logo
12:55 pm - 3:05 pm
MDW
-
PNS
2h 10mnonstop
$355Southwest
mié., nov. 18 - lun., nov. 23
Southwest Logo
8:00 am - 12:55 pm
PNS
-
MDW
4h 55m
1 stop
Southwest Logo
10:15 am - 5:20 pm
MDW
-
PNS
7h 05m
2 stops
$356Southwest
jue., sep. 10 - lun., sep. 14
Southwest Logo
1:10 pm - 9:00 pm
PNS
-
MDW
7h 50m
2 stops
Southwest Logo
8:00 am - 1:05 pm
MDW
-
PNS
5h 05m
1 stop
$361Southwest
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 Wednesdays 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 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.

No, with an average price for the route of $397, 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 31% drop in price.
Most popular time to fly with an average 6% 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 $265 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 $395 and an overall rating of 7.9, 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 $221 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.
7.9
SouthwestOverall score based on 4237 reviews
7.0Food
8.1Boarding
8.6Crew
7.5Entertainment
8.0Comfort
Airline reviews

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

8.0 ExcellentAnonymous, May 2026
BDL - MDW
Read more Southwest reviews

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.

Truly terrible. Will never willingly fly southwest again. Seats are worse than before they switched to assigned seating. One flight attendant was the opposite of helpful (rude, unhelpful, dismissive, and as my stranger seatmate said unprompted: a total prick). This caused me, 15 minutes into the flight, to book an alternate return flight home on a competing airline (first class 1.2k purchase instead of my existing planned flight) just so I would not have to ever be on that aircraft, with that terrible service person, with those horrific seats ever again.

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

Left /arrived on time. Decent seat space. Like the wifi/plugs and entertainment. Windows and tray table were kinda gross. Attendants didn't start snack service til 40mins before landing. Two rows before us, captain came on to say there's turbulence and recalled staff to seats. So, no drink/snack. Later, attendants didn't stop to see if we had trash nor even look our way. Felt invisible! Almost all pilot announcements were not only unintelligible, but so quiet. We had no idea what she said.

Gate agent was unhelpful for handicapped boarding. Flight attendant seemed untrained.

Clean planes and not take my comfort class seat away.

Weather caused a long delay, but the efficiency and updates from the pilot were helpful. We were able to make our connection fortunately.

Planes were clean, no water or snacks on either flight.

Aside from a completely packed plane, I really have no complaints.

Much better than Latam, the worse airline company ever. I hope I don't have the need to fly Latam ever in my life again.

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.

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

Information on your arrival and departure airports