MDW - PNS

$54 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 2/26. 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.
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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 47,946,175 times on KAYAK, and here is why:

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Cheap Flight Deals from Chicago Midway Airport to Pensacola (MDW-PNS)

 
These are the cheapest deals for flights from Midway to Pensacola currently on KAYAK along with options from the most popular airlines KAYAK users selected for this route. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.

Recent round-trip flight deals from Midway to Pensacola

Recommended round-trip deals departing in the coming months from the most popular airlines that fly from Midway to Pensacola.

Recent one-way flight deals from Midway to Pensacola

Only flying one-way? Below are some of the best one-way flight deals from Midway to Pensacola found on KAYAK recently.

Recent last minute flight deals from Midway to Pensacola

Leaving soon but still want a bargain? Check out these latest deals for last minute flights from Midway to Pensacola.

Recent direct flight deals from Midway to Pensacola

The latest deals for direct flights from Midway to Pensacola so you can sit back and relax without the need for a layover.

Cheap bus & train deals from Midway to Pensacola

Find recent round-trip train or bus tickets from Midway to Pensacola.

All round-trip flight deals to Pensacola

The cheapest plane tickets to Pensacola found on KAYAK recently.
Discover the best prices and deals for you by selecting your travel dates.
Choose your dates
7:15 am - 6:17 pmMDW-PNS
11h 02m1 stop
7:17 pm - 12:17 amPNS-MDW
29h 00m1 stop
$118Frontier
Find Deal
Do, Feb 6 - Mo, Feb 10
7:15 am - 6:35 pmMDW-PNS
11h 20m1 stop
7:17 pm - 12:13 amPNS-MDW
28h 56m1 stop
$128Frontier
Find Deal
Fr, Jan 10 - Mo, Jan 13
7:15 am - 6:22 pmMDW-PNS
11h 07m1 stop
7:17 pm - 12:13 amPNS-MDW
28h 56m1 stop
$138Frontier
Find Deal
Fr, Dez 6 - So, Dez 8
7:15 am - 6:22 pmMDW-PNS
11h 07m1 stop
7:17 pm - 12:13 amPNS-MDW
28h 56m1 stop
$148Frontier
Find Deal
Fr, Dez 6 - Mo, Dez 9
6:00 am - 11:02 amMDW-PNS
5h 02m1 stop
6:05 pm - 10:20 pmPNS-MDW
4h 15m1 stop
$228Delta
Find Deal
Fr, Jan 3 - Fr, Jan 10
6:00 am - 11:02 amMDW-PNS
5h 02m1 stop
5:42 pm - 10:06 pmPNS-MDW
4h 24m1 stop
$238Delta
Find Deal
Fr, Jan 3 - Fr, Jan 3
6:25 am - 11:00 amMDW-PNS
4h 35m1 stop
6:05 pm - 12:25 amPNS-MDW
6h 20m1 stop
$288Southwest
Find Deal
Mi, Feb 12 - So, Feb 16
6:10 am - 4:15 pmMDW-PNS
10h 05m2 stops
6:05 pm - 12:25 amPNS-MDW
6h 20m1 stop
$293Southwest
Find Deal
Mo, Feb 10 - So, Feb 16
5:35 pm - 6:05 pmMDW-PNS
24h 30m3 stops
7:00 pm - 5:51 pmPNS-MDW
22h 51m2 stops
Mo, Dez 30 - Sa, Jan 4
5:35 pm - 6:05 pmMDW-PNS
24h 30m3 stops
5:04 pm - 5:51 pmPNS-MDW
24h 47m3 stops
Mo, Dez 30 - Sa, Jan 4
7:05 am - 4:23 pmMDW-PNS
9h 18m1 stop
$54Frontier
Find Deal
Mi, Feb 26
7:15 am - 6:13 pmMDW-PNS
10h 58m1 stop
$60Frontier
Find Deal
Mo, Jan 13
7:15 am - 6:13 pmMDW-PNS
10h 58m1 stop
$70Frontier
Find Deal
So, Jan 12
7:05 am - 4:23 pmMDW-PNS
9h 18m1 stop
$74Frontier
Find Deal
Di, Feb 25
11:33 am - 7:10 pmMDW-PNS
7h 37m1 stop
Mo, Jan 20
6:00 am - 10:06 amMDW-PNS
4h 06m1 stop
$114Delta
Find Deal
Di, Dez 17
6:00 am - 11:27 amMDW-PNS
5h 27m1 stop
$124Delta
Find Deal
Do, Feb 20
10:26 am - 7:10 pmMDW-PNS
8h 44m1 stop
Fr, Dez 20
8:05 am - 10:20 amMDW-PNS
2h 15mnonstop
$140Southwest
Find Deal
Mo, Mrz 10
10:05 am - 3:25 pmMDW-PNS
5h 20m1 stop
$144Southwest
Find Deal
Mi, Jan 15
9:48 pm - 7:58 pmMDW-PNS
22h 10m1 stop
8:58 pm - 1:40 pmPNS-MDW
16h 42m1 stop
$338Frontier
Find Deal
Fr, Nov 22 - So, Nov 24
11:50 am - 3:14 pmMDW-PNS
27h 24m2 stops
7:10 pm - 12:13 amPNS-MDW
53h 03m2 stops
Mo, Nov 25 - Mo, Dez 2
5:10 am - 7:58 pmMDW-PNS
14h 48m1 stop
5:38 pm - 1:10 pmPNS-MDW
19h 32m1 stop
$378Frontier
Find Deal
Sa, Nov 23 - Mo, Nov 25
9:37 pm - 3:14 pmMDW-PNS
17h 37m2 stops
7:10 pm - 12:13 amPNS-MDW
53h 03m2 stops
Mo, Nov 25 - Mo, Dez 2
7:00 am - 7:58 pmMDW-PNS
12h 58m1 stop
8:58 pm - 8:42 pmPNS-MDW
23h 44m1 stop
$388Frontier
Find Deal
Do, Nov 21 - So, Nov 24
9:48 pm - 7:58 pmMDW-PNS
22h 10m1 stop
8:58 pm - 8:42 pmPNS-MDW
23h 44m1 stop
$398Frontier
Find Deal
Fr, Nov 22 - So, Nov 24
8:35 am - 5:20 pmMDW-PNS
8h 45m1 stop
5:40 am - 2:25 pmPNS-MDW
8h 45m2 stops
$423Southwest
Find Deal
Fr, Nov 22 - So, Nov 24
8:50 am - 5:20 pmMDW-PNS
8h 30m2 stops
5:40 am - 2:25 pmPNS-MDW
8h 45m2 stops
$428Southwest
Find Deal
Fr, Nov 22 - So, Nov 24
3:19 pm - 8:22 pmMDW-PNS
5h 03m1 stop
3:12 pm - 9:46 pmPNS-MDW
6h 34m1 stop
$533Delta
Find Deal
Do, Nov 21 - So, Nov 24
6:00 am - 10:15 amMDW-PNS
4h 15m1 stop
5:37 pm - 9:46 pmPNS-MDW
4h 09m1 stop
$593Delta
Find Deal
Fr, Nov 22 - Mo, Dez 2
8:05 am - 10:20 amMDW-PNS
2h 15mnonstop
1:30 pm - 3:45 pmPNS-MDW
2h 15mnonstop
$414Southwest
Find Deal
Fr, Mrz 14 - Mo, Mrz 17
8:05 am - 10:20 amMDW-PNS
2h 15mnonstop
9:40 am - 11:55 amPNS-MDW
2h 15mnonstop
$438Southwest
Find Deal
Fr, Mrz 14 - So, Mrz 16
9:25 am - 11:40 amMDW-PNS
2h 15mnonstop
2:45 pm - 5:00 pmPNS-MDW
2h 15mnonstop
$448Southwest
Find Deal
So, Mrz 16 - Sa, Mrz 22
11:00 am - 1:10 pmMDW-PNS
2h 10mnonstop
4:15 pm - 6:25 pmPNS-MDW
2h 10mnonstop
$536Southwest
Find Deal
Sa, Apr 5 - Sa, Apr 12

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, Tuesday 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 Wednesday 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 $268 on average. On the other hand, the most expensive months are March and December, where the average cost of tickets is $436 and $426 respectively.

Can I save money by flying with a layover from Chicago Midway Airport to Pensacola?

The average 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 $235, prices are generally cheapest when you fly direct.

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 3 days before departure. For the absolute cheapest price, our data suggests you should book 155 days before departure.

Good to know

Low season

June

High season

March

Cheapest flight

$54
Best time to beat the crowds with an average 2% drop in price.
Most popular time to fly with an average 63% 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 $54 for a one-way ticket and $118 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?

    The Boeing 737-700 is the aircraft model that flies most regularly on the Chicago Midway Airport to Pensacola flight route.

  • Which airline alliances offer flights from Chicago Midway Airport to Pensacola?

    SkyTeam is the only airline alliance operating flights between Chicago Midway Airport and Pensacola.

  • 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 $413 and an overall rating of 8.1, Southwest is the most popular choice. Delta is also a great choice for the route, with an average price of $363 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.

See more FAQs

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.
8.1
SouthwestOverall score based on 5015 reviews
8.2Boarding
7.2Food
8.1Comfort
7.7Entertainment
8.7Crew
Airline reviews

Excellent experience. WiFi worked on this leg of My trip

10.0 ExcellentDONALD, Nov 2024MDW - MCO
Read more Southwest reviews

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 attendant was proactive in helping with placing carry on in overhead bins. This was the first time I had ever been offered help without asking or obviously struggling. Many on the flight were older people like myself and vertically challenged. I would hope this would be the norm on all flights.

wifi wasn't working correctly so couldn't watch live tv

Flight was delayed by 12 minutes. Boarding wasn’t fun. The crew was nice though.

The flight was promptly on schedule and Southwest delivered everything they promised. No excuses for any shortfalls just 100% ownership of their responsibilities and business. The boarding and seating policy is a complete shambles. What started out as a great idea when Southwest first hit the market has been turned into a disaster due to the lack of integrity in many of the people who fly Southwest and take advantage of Southwest generosity at the expense of their fellow passengers.

Flight was delayed more than 2 hour do the scheduling issues and then some confusing weight and balance matters, followed by a miscommunication with the tower on which runway was going to be used based on the airplane weight. All these things should have been figured out in advance. Instead of arriving at 12:30 a.m. we arrived at 2:30 a.m. very difficult to find a taxi or other transport at SFO. Luggage was delayed. An extension of an unpleasant flight day

It good. Just not that plane didn’t have power outlets to charge devices etc.

Although the flight was delayed, but the crew was amazing. They did the best they could to make the time enjoyable.

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.

Loyal Delta traveler, but last nights flight was a train wreck. Seated in 1B after multiple delays. Then we couldn’t takeoff because of an issue with the passenger that was ‘not in compliance’ and had to deplane along with the threat if they did not deplane, all the passengers would be required to do so. Finally they were escorted off, but the experience threw off the crew. Disruptive for everyone. Service was a mess, televisions didn’t work, bathroom door kept swinging open during the entire flight whenever empty …

My flight was cancelled twice and the third time I tried to rebook it online I cancelled the flight because it looked like I would get a refund to my credit card. Instead I now have a credit. I was also on hold for three hours waiting for a representative and then disconnected. I will never fly delta again.

It was very cold because the air conditioner was on high power, and my son got sick.

Awful. Flight was continuously getting delayed and gates kept changing without any reason. Flight was delayed for more then 3 hours

5-hour delay due to storms in Tanoa and airspace restricted by Miami traffic controllers.

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.

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.
2/26Mi
1 stopFrontier
9h 18mMDW-PNS
$54
1/13Mo
1 stopFrontier
10h 58mMDW-PNS
$60
1/12So
1 stopFrontier
10h 58mMDW-PNS
$70
2/25Di
1 stopFrontier
9h 18mMDW-PNS
$74
1/20Mo
1 stop
7h 37mMDW-PNS
$107
12/17Di
1 stopDelta
4h 06mMDW-PNS
$114
2/20Do
1 stopDelta
5h 27mMDW-PNS
$124
12/20Fr
1 stop
8h 44mMDW-PNS
$133
3/10Mo
nonstopSouthwest
2h 15mMDW-PNS
$140
1/15Mi
1 stopSouthwest
5h 20mMDW-PNS
$144

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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.
11/22Fr
multi-stopFrontier
22h 10mMDW-PNS
11/24So
multi-stopFrontier
16h 42mPNS-MDW
$338
11/25Mo
multi-stop
27h 24mMDW-PNS
12/2Mo
multi-stop
53h 03mPNS-MDW
$373
11/23Sa
multi-stopFrontier
14h 48mMDW-PNS
11/25Mo
multi-stopFrontier
19h 32mPNS-MDW
$378
11/25Mo
multi-stop
17h 37mMDW-PNS
12/2Mo
multi-stop
53h 03mPNS-MDW
$387
11/21Do
multi-stopFrontier
12h 58mMDW-PNS
11/24So
multi-stopFrontier
23h 44mPNS-MDW
$388
11/22Fr
multi-stopFrontier
22h 10mMDW-PNS
11/24So
multi-stopFrontier
23h 44mPNS-MDW
$398
11/22Fr
multi-stopSouthwest
8h 45mMDW-PNS
11/24So
multi-stopSouthwest
8h 45mPNS-MDW
$423
11/22Fr
multi-stopSouthwest
8h 30mMDW-PNS
11/24So
multi-stopSouthwest
8h 45mPNS-MDW
$428
11/21Do
multi-stopDelta
5h 03mMDW-PNS
11/24So
multi-stopDelta
6h 34mPNS-MDW
$533
11/22Fr
multi-stopDelta
4h 15mMDW-PNS
12/2Mo
multi-stopDelta
4h 09mPNS-MDW
$593

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

Information on your arrival and departure airports

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