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MDW - PNS

$81 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 5/11. 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
0 bags
Mon 6/3
Mon 6/10

Search 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
In the last 7 days travelers have searched 43,369,418 times on KAYAK, and here is why:

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Cheap flight deals 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 and deals for you by selecting your travel dates.
Choose your dates
6:00 am - 7:13 pmMDW-PNS
13h 13m1 stop
8:10 pm - 11:52 amPNS-MDW
15h 42m1 stop
$148Frontier
Find Deal
Sat, Sep 7 - Wed, Sep 11
6:00 am - 7:13 pmMDW-PNS
13h 13m1 stop
8:10 pm - 11:52 amPNS-MDW
15h 42m1 stop
$158Frontier
Find Deal
Wed, Sep 4 - Mon, Sep 9
10:01 pm - 3:19 pmMDW-PNS
17h 18m1 stop
6:24 pm - 11:12 amPNS-MDW
16h 48m1 stop
$164Frontier
Find Deal
Sat, Jun 1 - Sat, Jun 8
6:00 am - 7:13 pmMDW-PNS
13h 13m1 stop
8:10 pm - 11:52 amPNS-MDW
15h 42m1 stop
$182Frontier
Find Deal
Fri, Aug 23 - Sun, Aug 25
5:01 am - 8:33 pmMDW-PNS
15h 32m1 stop
6:24 pm - 11:12 amPNS-MDW
16h 48m1 stop
$184Frontier
Find Deal
Thu, Jun 6 - Sat, Jun 8
6:00 am - 10:23 amMDW-PNS
4h 23m1 stop
11:28 am - 5:59 pmPNS-MDW
6h 31m1 stop
$208Delta
Find Deal
Wed, Jul 10 - Wed, Jul 17
6:49 pm - 11:45 pmMDW-PNS
4h 56m1 stop
5:40 pm - 9:46 pmPNS-MDW
4h 06m1 stop
$218Delta
Find Deal
Mon, Jun 17 - Mon, Jun 24
6:00 am - 12:44 pmMDW-PNS
6h 44m1 stop
5:40 pm - 9:46 pmPNS-MDW
4h 06m1 stop
$243Delta
Find Deal
Fri, May 31 - Fri, Jun 7
3:45 pm - 8:10 pmMDW-PNS
4h 25m1 stop
5:43 pm - 9:41 pmPNS-MDW
3h 58m1 stop
$283Delta
Find Deal
Mon, Jul 29 - Sat, Aug 3
6:15 pm - 5:31 pmMDW-PNS
23h 16m2 stops
10:39 am - 6:30 pmPNS-MDW
31h 51m3 stops
Fri, May 31 - Fri, Jun 7

Flights from Midway to Pensacola - Travel Insights & Trends

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 flights from Chicago Midway Airport to Pensacola clicked on KAYAK for each day over the last 12 months.
For Chicago Midway Airport to Pensacola, Monday is the cheapest day to fly on average and Friday is the most expensive. Flying from Pensacola back to Chicago Midway Airport, the best deals are generally found on Monday, with Sunday being the most expensive.

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 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 $340 on average. On the other hand, the most expensive months are March and April, where the average cost of tickets is $506 and $489 respectively.

How far in advance should I book a flight from Chicago Midway Airport to Pensacola?

To calculate daily average prices, KAYAK takes all prices for each day before departure over the last year for flights from Chicago Midway Airport to Pensacola, removes the top 0.1% to account for outliers, and then takes the average of all the values for each month.
To get a below average price on the flight from Chicago Midway Airport to Pensacola, you should book around 1 week before departure. For the absolute cheapest price, our data suggests you should book 24 days before departure.

Which airlines provide the cheapest flights from Chicago Midway Airport to Pensacola?

The cheapest price for the route for each airline clicked by KAYAK users in the last 72 hours.
In the last 72 hours, the best return deals on flights connecting Chicago Midway Airport to Pensacola were found on Frontier ($148) and Delta ($208). Frontier proposed the cheapest one-way flight at $81.

How many flights are there between Chicago Midway Airport and Pensacola per day?

There is a maximum of 1 nonstop flight a day that takes off from Chicago Midway Airport and lands in Pensacola, with an average flight time of 2h 05m. The most common departure time is 9:00 am and most flights take off in the morning. Each week, there are 3 flights.

What’s the earliest departure time from Chicago Midway Airport to Pensacola?

Early birds can take the earliest flight from Chicago Midway Airport at 9:05 am and will be landing in Pensacola at 11:10 am.

What’s the latest departure time from Chicago Midway Airport to Pensacola?

If you prefer to fly at night, the latest flight from Chicago Midway Airport to Pensacola jets off at 2:40 pm and lands at 4:45 pm.

Good to know

Low season

November

High season

March

Cheapest flight

$81
Best time to beat the crowds with an average 23% drop in price.
Most popular time to fly with an average 92% 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 $81 for a one-way ticket and $148 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 aircraft models fly most regularly from Chicago Midway Airport to Pensacola?

    We unfortunately don’t have that data for this specific 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.

  • 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.

See more FAQs

Prefer to fly non-stop from Chicago Midway Airport to Pensacola?

Find which airlines fly direct from Midway to Pensacola, which days they fly and book direct flights.

Nonstop 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

Nonstop 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
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
DeltaOverall score based on 10838 reviews
8.6Crew
8.0Entertainment
8.2Boarding
7.9Comfort
7.4Food
Airline reviews

I would fly again the whole experience was great. The only feed back I can give that they don't do that American Airlines does is the crew there is more humorous with boarding and thank their passengers. It makes it more fun to fly with them. I would however fly Delta again.

10.0 ExcellentDonnel, Apr 2024ATL - EYW
Read more about Delta reviews

I would fly again the whole experience was great. The only feed back I can give that they don't do that American Airlines does is the crew there is more humorous with boarding and thank their passengers. It makes it more fun to fly with them. I would however fly Delta again.

Horrible. This was not first class. This was a connecting flight whi h was late. My original flight never came. I hated the fact that delta gave me a connecting flight from New York to Orlando Florida. No meals and the television screens were not working. There wasn't even any power to charge your phones. This is NOT FIRST CLASS DELTA!!! Do better next time!

They did a fine job. Can't wait to use Delta in the future.

Seat back monitors and outlets were dead and not working.

The experience was good and the flight departed on time and landed early

The flight was delayed but we got to our final destination.

public website still broken for years randomly blocking browsers with privacy options active after loading a page maybe once. check-in on laptop was almost impossible but eventually randomly worked. had to print pass at airport since couldn't get back in to load digital pass on mobile firefox or chrome. red eye flight so smooth onboarding, plenty of room to spread out, easy offboarding. onboard wifi instructions mention vpn can cause problems connecting but fails to also mention private dns. no printed or built in menu list, seems weird to require personal device to point at qr code link for menu which does not even allow direct ordering. people with health condition risk related dietary restrictions trying to avoid for example cholesterol and sugar are left guessing what they can order either way without nutritional info highlights (cranberry juice was minute maid cocktail with as much suger as typical can of soda). tap to pay wasn't working and always seems sketchy to manually enter card info. good movie variety, so limited tv was okay.

Horrible. Flight ORD to CGH was okay, but Paris was a nightmare. Old planes, delays, involuntary downgrades, broken planes, terrible communication. CGH to CPT was my worst flight ever.

Boarding super slow with people allowed to linger in aisles

There were choices for the snacks. Good choices and tasty lunch and breakfast as well.

Great! The plane was decently sized and comfortable. The staff was nice and there was great in flight entertainment

Last minute gate change nearly caused us to miss our flight. Change was not announced or displayed in the main board at the old gate. Terrible communication. When we landed we had to wait 20 minutes because there was another plane at the assigned gate. Not the crew’s fault, but adding 20 minutes to a 45 minute flight sucked.

delay several times and wait extra long to board. no entertainment service because there are problem for some rows. always encounter some delays for the last flight of the day.

The flight experience was very good! Especially the United Club!

I was not able to buy food in the flight. They refer to include your Credit card in the APP, and if you are not from USA (i have a credit card form Canada) it is not possible

The flight from Ottawa to Chicago took a lot longer due to DC in Ottawa. We got to Chicago and went to our gate to catch our flight. We only had nine minutes I found that very stressful.

Good boarding. Crew started quick with drinks and food. They came around several times for trash which I really liked. Other than turbulence due to storms in the area, flight was great.

The control panel for the seat back screen did not work at all after takeoff.

Plane was so old it had cigarette butt trays in the seat

Everything was good, hard to really comfortable on a flight that long.

Book cheap flights from Chicago to Pensacola

Recent one-way flight deals

 
Only flying one-way? Below are some of the best one-way flight deals from Chicago to Pensacola found on KAYAK in the last 72 hours.
5/11Sat
1 stopFrontier
10h 23mMDW-PNS
$81
5/10Fri
1 stopFrontier
11h 57mMDW-PNS
$85
5/17Fri
1 stopFrontier
15h 41mMDW-PNS
$88
5/10Fri
1 stopFrontier
11h 57mMDW-PNS
$90
5/30Thu
1 stopFrontier
10h 07mMDW-PNS
$98
5/31Fri
1 stopDelta
5h 39mMDW-PNS
$104
5/12Sun
1 stopDelta
4h 54mMDW-PNS
$139
5/9Thu
1 stopDelta
6h 44mMDW-PNS
$269
5/11Sat
2 stops
21h 45mMDW-PNS
$438
5/30Thu
2 stopsDelta
8h 49mMDW-PNS
$471

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Last minute flights from Midway to Pensacola

Last minute flight, train and bus deals

 
These last-minute flight deals are the cheapest flights found on KAYAK in the last 72 hours for flights from Chicago to Pensacola that are departing in the next 10 days.
5/8Wed
multi-stopFrontier
13h 16mMDW-PNS
5/11Sat
multi-stopFrontier
10h 38mPNS-MDW
$234
5/9Thu
multi-stopFrontier
18h 34mMDW-PNS
5/11Sat
multi-stopFrontier
10h 38mPNS-MDW
$237
5/9Thu
multi-stopFrontier
18h 34mMDW-PNS
5/11Sat
multi-stopFrontier
10h 38mPNS-MDW
$244
5/5Sun
multi-stopFrontier
21h 43mMDW-PNS
5/11Sat
multi-stopFrontier
10h 38mPNS-MDW
$274
5/6Mon
multi-stopDelta
5h 19mMDW-PNS
5/8Wed
multi-stopDelta
3h 51mPNS-MDW
$378
5/8Wed
multi-stopDelta
5h 45mMDW-PNS
5/10Fri
multi-stopDelta
5h 15mPNS-MDW
$438
5/7Tue
multi-stopDelta
4h 54mMDW-PNS
5/9Thu
multi-stopDelta
4h 04mPNS-MDW
$458
5/5Sun
multi-stopDelta
6h 46mMDW-PNS
5/11Sat
multi-stopDelta
11h 40mPNS-MDW
$791
5/8Wed
multi-stopDelta
8h 55mMDW-PNS
5/11Sat
multi-stopDelta
4h 04mPNS-MDW
$1,007
5/8Wed
multi-stopDelta
8h 55mMDW-PNS
5/11Sat
multi-stopDelta
4h 04mPNS-MDW
$1,082

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Chicago Midway Airport - Pensacola Flights

Departure:

Chicago Midway Airport (MDW)United States

Destination:

Pensacola (PNS)United States

Return flight deals:

Pensacola - Chicago Midway Airport

Cabin classes: