MDW - PNS

$139 Find Cheap Flights from Chicago Midway Airport to Pensacola

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Midway to Pensacola departing on 7/15. 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 Pensacola

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Pensacola, 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 Chicago to Pensacola, as well as popular online travel agencies
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Flights Deals

Cheap Flights from Midway to Pensacola (MDW-PNS)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Midway to Pensacola 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 Midway to Pensacola

Fri, Jul 11 - Mon, Jul 21
Southwest Logo
1:50 pm - 3:55 pmMDW-PNS
2h 05mnonstop
Southwest Logo
2:25 pm - 4:40 pmPNS-MDW
2h 15mnonstop
$277Southwest
Find Deal
Sat, Sep 13 - Thu, Sep 18
Southwest Logo
8:20 am - 10:30 amMDW-PNS
2h 10mnonstop
Southwest Logo
1:45 pm - 8:25 pmPNS-MDW
6h 40m1 stop
$287Southwest
Find Deal
Sat, Sep 13 - Thu, Sep 18
Southwest Logo
8:15 am - 3:05 pmMDW-PNS
6h 50m1 stop
Southwest Logo
4:35 pm - 10:50 pmPNS-MDW
6h 15m1 stop
$297Southwest
Find Deal
Thu, Aug 14 - Thu, Aug 21
Southwest Logo
5:40 am - 9:15 amMDW-PNS
3h 35m1 stop
Southwest Logo
1:45 pm - 10:00 pmPNS-MDW
8h 15m2 stops
$302Southwest
Find Deal
Sun, Jul 13 - Thu, Jul 17
Southwest Logo
10:35 am - 12:40 pmMDW-PNS
2h 05mnonstop
Southwest Logo
2:25 pm - 4:40 pmPNS-MDW
2h 15mnonstop
$307Southwest
Find Deal
Wed, Jul 9 - Thu, Jul 10
Delta Logo
6:00 am - 10:38 amMDW-PNS
4h 38m1 stop
Delta Logo
1:54 pm - 6:02 pmPNS-MDW
4h 08m1 stop
$328Delta
Find Deal
Fri, Jul 11 - Wed, Jul 16
Delta Logo
6:47 pm - 11:24 pmMDW-PNS
4h 37m1 stop
Delta Logo
4:37 pm - 9:42 pmPNS-MDW
5h 05m1 stop
$333Delta
Find Deal
Fri, Aug 22 - Mon, Aug 25
Frontier Logo
6:31 pm - 3:05 pmMDW-PNS
20h 34m1 stop
Frontier Logo
4:00 pm - 12:24 amPNS-MDW
8h 24m1 stop
$462Frontier
Find Deal
Thu, Oct 9 - Sun, Oct 12
 Logo
5:40 pm - 7:51 amMDW-PNS
38h 11m3 stops
 Logo
8:46 am - 4:33 pmPNS-MDW
31h 47m2 stops
Thu, Oct 9 - Sun, Oct 12
 Logo
5:40 pm - 7:51 amMDW-PNS
38h 11m3 stops
 Logo
3:50 pm - 4:33 pmPNS-MDW
24h 43m3 stops
Useful Info

KAYAK's insights & trends for Midway to Pensacola flights

Get data-powered insights and trends into flights from Midway to Pensacola 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 Chicago Midway Airport to Pensacola?

The average price of all round-trip flights from Chicago Midway Airport to Pensacola clicked on KAYAK for each day over the last 12 months.

Your flight ticket price will generally be cheaper if you fly to Pensacola on a Friday and more expensive on a Monday. On your return trip to Chicago Midway Airport, you should consider flying back on a Thursday, and avoid Sundays for better deals.

What is the cheapest month to fly from Chicago Midway Airport to Pensacola?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Chicago Midway Airport to Pensacola, 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 Chicago Midway Airport to Pensacola is January, where tickets cost $228 (return) on average. On the other hand, the most expensive months are March and November, where the average cost of round-trip tickets is $468 and $458 respectively.

Good to know

Low seasonFebruary
High seasonMarch
Cheapest flight$139
Best time to beat the crowds but there is an average 4% increase in price.
Most popular time to fly with an average 34% increase in price.
Flight from Chicago Midway Airport to Pensacola

When to book flights from Midway to Pensacola

Are your dates flexible? Find out the best times to travel from Midway to Pensacola 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 Chicago Midway Airport to Pensacola flights

  • What is the cheapest flight from Chicago Midway Airport to Pensacola?

    In the last 3 days, the lowest price for a flight from Chicago Midway Airport to Pensacola was $139 for a one-way ticket and $277 for a round-trip.

  • Do I need a passport to fly between Chicago Midway Airport and Pensacola?

    No, a passport isn't needed to fly from Chicago Midway Airport to Pensacola. However, local authorities might ask for an official ID.

  • Which airlines offer Wi-Fi service onboard planes from Chicago Midway Airport to Pensacola?

    Only American Airlines offers inflight Wi-Fi service on the Chicago Midway Airport to Pensacola flight route.

  • Which aircraft models fly most regularly from Chicago Midway Airport to Pensacola?

    The Airbus A320-100/200 is the aircraft model that flies most regularly on the Chicago Midway Airport to Pensacola flight route.

  • On which days can I fly direct from Chicago Midway Airport to Pensacola?

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

  • Which is the best airline for flights from Chicago to Pensacola, Southwest or Delta?

    The two airlines most popular with KAYAK users for flights from Chicago to Pensacola are Southwest and Delta. With an average price for the route of $381 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 $340 and an overall rating of 8.0.

  • How does KAYAK find such low prices on flights from Chicago Midway Airport to Pensacola?

    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 Chicago Midway Airport to Pensacola.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Chicago Midway Airport to Pensacola?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Pensacola from Chicago Midway Airport 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 Chicago Midway Airport to Pensacola?

    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 Pensacola with an airline and back to Chicago Midway Airport with another airline. Booking your flights between Chicago Midway Airport and PNS 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 Chicago Midway Airport to Pensacola?

    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 Pensacola from Chicago Midway Airport 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 Chicago Midway Airport to Pensacola

  • Looking for a cheap flight? 25% of our users found flights on this route for $138 or less one-way and $268 or less round-trip.

Prefer to fly direct from Chicago Midway Airport to Pensacola?

 
Direct data is based off flight results for the next 60 days. Find direct flights from all airlines flying direct from Chicago Midway to Pensacola.
Find which airlines fly direct from Chicago Midway Airport to Pensacola Airport, which days they fly and book direct flights.

Direct departures

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

Direct returns

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

Top airlines flying from Midway to Pensacola

 
See real verified KAYAK customer reviews for airlines flying from Chicago to Pensacola. 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 Midway to Pensacola? 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 4278 reviews
8.0Comfort
8.2Boarding
7.6Entertainment
7.1Food
8.6Crew
Airline reviews

I'm not a fan of Southwest's model. I don't like the herding style of boarding.

6.0 GoodVincent, May 2025MDW - MCO
Read more Southwest reviews

I'm not a fan of Southwest's model. I don't like the herding style of boarding.

It is southwest seat was ok. Not the most comfortable seat

Plz don't take away free bags and free seating

My flight to Chicago left and landed early. My return flight left two minutes late and arrived 2 minutes late. My seat selections were ideal! There were no snacks going to Chicago and no snacks on the return trip. There are no charging outlets on board.

Excellent! Only question is how we check in at exactly 24 hours in advance and end up at the end of the B boarding group

It went well. Plane wasn't full. Will be great when assigned seating is in place

One of the crew performed a hilarious skit to accompany the standard instructions. Passengers enjoyed it so much they applauded at the end!

Excellent experience. WiFi worked on this leg of My trip

Flight was great, but golf bag never made it until later in the day. Even though I had a nonstop flight it was placed on a different one. They made it right with flight credits and I was able to get it the same day.

Pretty standard flight. We left late, but arrived early. The wifi entertainment is always nice. The free snacks and beverages are simple, but appreciated. I'm tall and the seats are an issue. I can deal with a short flight, but any longer, I have to find another airline where I know beforehand I have extra legroom.

The flight was scheduled for 2:30 PM. Early in the morning we got a text message saying the flight was delayed and rescheduled for 3:00 PM. We got to the airport with that in mind. Then we got a message during check-in at the flight was rescheduled again for 2:30 PM. We almost missed our flight. In fact, our bags Were told that they would not make it. At the end, everything worked out. But it is very stressful.

Most aspects were good however if they assign boarding zones they ought to enforce them or why bother? My luggage from SAN-JFK-MAD was lost in NY so I without my main bag for two days upon arrival in Spain. They were helpful in tracking it and eventually delivered it to my hotel. The flub was because of a delay upon arrival in NYC. I had booked 2 1/2 hours between flights but we had to hold on the taxiway for an hour after landing while waiting for a clear gate which likely caused the baggage error.

Excellent check-in. Crew was good. Excellent communication from flight deck.

Great overall. There was a bit of turbulence so they could only serve water because too much turbulence for the carts. Was glad they prioritized safety though

Excellent flight, the planes were newer, they did a nice job with boarding, great service overall.

I am very bothered by the events today. I can't believe the flight attendants allowed someone to take my seat and made me move. It was embarrassing. I was in the right. The lady just didn't want move. I can't believe delta would allow this to stand and disrespect my rights as a passenger. The lady complained about her leg and that she couldn't move. Firstly somehow she was able to make it to row 24. Not sure how much her leg could have hurt. Secondly, I'm in plenty of pain myself. I just finished chemotherapy a several weeks ago. My body is constantly sore. Yet deltas flight attendants didn't appropriately protect my rights. In the end they found me a seat on the plane but I want to understand how delta can operate this way. They in essence allowed a bully to get their way.

Crew was friendly Love the entertainment in the seat head rest.

Other then mechanical/ computer problem and 3.5 hours flight delay the flight was great. I guess that what happened when you fly an old airplane now a day.

This was a code share Latam Airlines flight - everything very good except there was no seatback entertainment

Don't waste your money or points on first class. Delta first class is a joke. The seats were rickety, the food was awful, and nothing worked, wifi, my light, the power plug - and it was dirty - the fold out table was gross. For 2-3 hours, tough it out in Economy.

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

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