PNS - MDW

$74 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 3/2. 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
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Everything you should know

Cheapest round-trip
$217
Southwest
Thu 3/12Tue 3/17
PNS - MDW • Non-stop
Cheapest non-stop
$227
Southwest
Thu 3/12Tue 3/17
PNS - MDW • Non-stop
Top airlines
Southwest
Cheapest • from $217 (round-trip)
Southwest
Best reviews • 8.0 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
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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, Mar 12 - Tue, Mar 17
Southwest Logo
5:25 pm - 7:40 pm
PNS
-
MDW
2h 15mnonstop
Southwest Logo
2:10 pm - 8:40 pm
MDW
-
PNS
6h 30m
1 stop
$217Southwest
Thu, Mar 12 - Tue, Mar 17
Multiple Airlines Logo
7:00 am - 5:44 pm
PNS
-
MDW
10h 44m
1 stop
Multiple Airlines Logo
11:19 am - 9:14 pm
MDW
-
PNS
9h 55m
1 stop
$221Multiple Airlines
Thu, Mar 5 - Tue, Mar 10
Delta Logo
1:37 pm - 5:45 pm
PNS
-
MDW
4h 08m
1 stop
Delta Logo
12:47 pm - 7:01 pm
MDW
-
PNS
6h 14m
1 stop
$227Delta
Thu, Mar 12 - Tue, Mar 17
Multiple Airlines Logo
7:00 am - 5:44 pm
PNS
-
MDW
10h 44m
1 stop
Multiple Airlines Logo
11:19 am - 9:14 pm
MDW
-
PNS
9h 55m
1 stop
$230Multiple Airlines
Thu, Mar 12 - Tue, Mar 17
Southwest Logo
12:00 pm - 11:00 pm
PNS
-
MDW
11h 00m
1 stop
Southwest Logo
3:35 pm - 8:05 pm
MDW
-
PNS
4h 30m
1 stop
$232Southwest
Fri, Mar 13 - Mon, Mar 16
Multiple Airlines Logo
7:00 am - 1:08 pm
PNS
-
MDW
6h 08m
1 stop
Multiple Airlines Logo
6:15 am - 9:14 pm
MDW
-
PNS
14h 59m
1 stop
$244Multiple Airlines
Thu, Jun 4 - Mon, Jun 8
Southwest Logo
10:40 am - 12:55 pm
PNS
-
MDW
2h 15mnonstop
Southwest Logo
7:45 am - 10:00 am
MDW
-
PNS
2h 15mnonstop
$247Southwest
Fri, May 15 - Sat, May 16
Delta Logo
5:45 pm - 9:45 pm
PNS
-
MDW
4h 00m
1 stop
Delta Logo
4:30 pm - 8:40 pm
MDW
-
PNS
4h 10m
1 stop
$253Delta
Thu, Jun 4 - Mon, Jun 8
Southwest Logo
10:40 am - 12:55 pm
PNS
-
MDW
2h 15mnonstop
Southwest Logo
1:00 pm - 4:40 pm
MDW
-
PNS
3h 40m
1 stop
$257Southwest
Wed, Feb 11 - Sun, Feb 15
Multiple Airlines Logo
5:33 pm - 2:26 pm
PNS
-
MDW
20h 53m
1 stop
Multiple Airlines Logo
7:30 am - 5:42 pm
MDW
-
PNS
10h 12m
1 stop
$260Multiple Airlines
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 Tuesday, 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.

Yes, flying with a layover may cost you more time, but you can also save money on the route, with a 1 stop layover the cheapest option at $289 on average.

Good to know

Low seasonMay
Cheapest flight$74
Best time to beat the crowds with an average 35% drop in price.
Most popular time to fly and prices are also 20% 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 $74 for a one-way ticket and $217 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.

  • 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 Thursday, Friday, and 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 $295 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 $323 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.

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 4268 reviews
8.6Crew
7.5Entertainment
8.0Comfort
7.0Food
8.1Boarding
Airline reviews

All good except once again bags took an hour at Midway Airport Happens all the time. Ridiculous

10.0 ExcellentAnonymous, Jan 2026
PHX - MDW
Read more Southwest reviews

All good except once again bags took an hour at Midway Airport Happens all the time. Ridiculous

The seats were comfortable, and the boarding process was pretty smooth.

Departure was delayed more than 1/2 hour while we waited for luggage (only) transfer from another flight/plane. Once approved for takeoff, the flight was excellent.

Flight was on time. Wi-fi was a little spotty/slow. Boarding and exit were efficient.

It was rough. The staff was unprofessional, the choice of on board drinks terrible, it was cramped in space at every airport, they always ran out of overhead bin space so they pressured people to check bags for free or we couldn’t leave on the plane— so I did check my bag to help, and they nearly lost my bag. My bag did not arrive on the luggage belt, another man on my flight and I had to waste our time going to the baggage office to search for our bags. I would only fly southwest again if it was my last choice. Also, my flights were consistently delayed over and over again— at one point they straight up told us we were waiting for the pilot to arrive.

Excellent. Would encourage Southwest to keep current boarding procedures with free style seating. Makes for a fantastic experience

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.

Excellent flight and got us around tough weather. Only issue was seat TV did not work and crew tried to reboot.

Very large passenger too space from my own seat. Arm board couldn’t be lowered because of his size. It wads very uncomfortable trip, as the flight was full couldn’t move anywhere having back pain because of the position in which I was the entire flight.

Connection through Atlanta was difficult. Mechanical issue on plane caused a two hour delay. New gate was a mile away.

No WiFi. Comfort plus should have alcohol provided, crew only offered water or tea. Who the heck wants tea?

I have diamond medallion status and usually we are in comfort plus . We were in main this time ( which was fine ) and my husband wanted wine . I have at least 10 vouchers for drinks that are good for this year and next! The attendant would not take the picture of the voucher as proof and never came back to check as She asked me to pull it up on delta Wi-Fi. Instead my husband just used his Amex to buy the wine . Disappointing!!!

Food is basically Sun Chips, cookies or Cheezits. I had an exit row seat so I had plenty of room. The crew was very nice and efficient. Pilot kept us informed. Pretty good flight.

The only thing nice I can say is the flight crew was really nice and apologetic about the situation. They shared as much information as they had and advised us on what we could do about missing connecting flights. The boarding process was so slow. The gate agent was working by herself and should have had someone working with her. It took almost an hour to board because she was trying to board a full flight of people and provide customer service to everyone who was flying standby and/or had questions. It was really chaotic. This didn't help the fact that we were delayed and folks were missing connections the longer it took.

The food is terrible. The staff is wonderful. Comfort is good.

I fly Delta all the time, have Platinum Medallion status. But this route seems to have major problems with delays and seems to never leave on time! Have only taken it twice in the last two weeks, and each time it had delays of more than 1 hour... very disappointed!!!!

We had a lot of really rough weather but that was not Delta's fault. Pilot was amazing.

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

Information on your arrival and departure airports