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PNS - MDW

$82 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 6/5. 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
Sat 6/29
Sat 7/6

Search 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
In the last 7 days travelers have searched 42,686,544 times on KAYAK, and here is why:

Save 21% or moreCompare multiple travel sites with one search.

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Cheap flight deals 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 and deals for you by selecting your travel dates.
Choose your dates
8:10 pm - 11:52 amPNS-MDW
15h 42m1 stop
6:00 am - 7:13 pmMDW-PNS
13h 13m1 stop
$170Frontier
Find Deal
Fri, Sep 6 - Tue, Sep 10
8:10 pm - 11:52 amPNS-MDW
15h 42m1 stop
7:59 pm - 6:48 amMDW-PNS
10h 49m1 stop
$171Frontier
Find Deal
Fri, Aug 30 - Tue, Sep 3
8:10 pm - 11:52 amPNS-MDW
15h 42m1 stop
6:00 am - 7:13 pmMDW-PNS
13h 13m1 stop
$184Frontier
Find Deal
Fri, Aug 30 - Sun, Sep 1
9:27 pm - 10:00 pmPNS-MDW
24h 33m1 stop
6:00 am - 7:13 pmMDW-PNS
13h 13m1 stop
$194Frontier
Find Deal
Wed, Aug 7 - Fri, Aug 23
7:48 am - 1:32 pmPNS-MDW
5h 44m1 stop
5:55 am - 8:24 pmMDW-PNS
14h 29m1 stop
$230Frontier
Find Deal
Wed, Jun 26 - Wed, Jul 3
3:24 pm - 9:46 pmPNS-MDW
6h 22m1 stop
6:00 am - 10:22 amMDW-PNS
4h 22m1 stop
$243Delta
Find Deal
Thu, Jul 4 - Fri, Jul 5
3:20 pm - 9:46 pmPNS-MDW
6h 26m1 stop
10:28 am - 4:37 pmMDW-PNS
6h 09m1 stop
$302Delta
Find Deal
Fri, Aug 2 - Mon, Aug 5
5:40 pm - 9:46 pmPNS-MDW
4h 06m1 stop
3:45 pm - 8:57 pmMDW-PNS
5h 12m1 stop
$312Delta
Find Deal
Mon, Jun 24 - Tue, Jun 25
8:05 am - 2:57 pmPNS-MDW
6h 52m1 stop
12:35 pm - 6:24 pmMDW-PNS
5h 49m1 stop
$313Delta
Find Deal
Sat, Aug 31 - Tue, Sep 3
7:36 pm - 9:37 pmPNS-MDW
26h 01m3 stops
9:07 pm - 5:30 pmMDW-PNS
20h 23m2 stops
Mon, Jul 15 - Fri, Jul 19

Flights from Pensacola to Midway - Travel Insights & Trends

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 flights from Pensacola to Chicago Midway Airport clicked on KAYAK for each day over the last 12 months.
When flying from Pensacola to Chicago Midway Airport, you should consider leaving on a Monday and avoid Wednesdays if you are looking for the best rates. For your return to Pensacola, you’ll find the best rates on Tuesdays and the most expensive ones on Fridays.

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 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 November, where tickets cost $206 on average. On the other hand, the most expensive months are September and July, where the average cost of tickets is $550 and $481 respectively.

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

The cheapest price for the route for each airline clicked by KAYAK users in the last 72 hours.
The best deals for a one-way ticket found by KAYAK users over the last 3 days were on Frontier ($82) and Delta ($104). The cheapest round-trip tickets were found on Frontier ($170) and Delta ($243).

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

There is a maximum of 1 nonstop flight a day that takes off from Pensacola and lands in Chicago Midway Airport, with an average flight time of 2h 15m. The most common departure time is 10:00 am and most flights take off in the morning. Each week, there are 7 flights.

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

Early birds can take the earliest flight from Pensacola at 10:40 am and will be landing in Chicago Midway Airport at 12:55 pm.

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

If you prefer to fly at night, the latest flight from Pensacola to Chicago Midway Airport jets off at 2:50 pm and lands at 5:00 pm.

Good to know

Low season

March

High season

June

Cheapest flight

$82
Best time to beat the crowds with an average 37% drop in price.
Most popular time to fly and prices are also 24% 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 $82 for a one-way ticket and $170 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 aircraft models fly most regularly from Pensacola to Chicago Midway Airport?

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

  • 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.

  • 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.

See more FAQs

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

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

Nonstop 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

Nonstop 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
See more direct flights

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
DeltaOverall score based on 10457 reviews
7.9Comfort
8.6Crew
8.2Boarding
8.0Entertainment
7.4Food
Airline reviews

Rated entertainment as Mediocre as there were major problems with the Infotainment system that took probably a half hour for them to fix.

8.0 Excellentrghinftl, May 2024FLL - BOS
Read more about Delta reviews

Rated entertainment as Mediocre as there were major problems with the Infotainment system that took probably a half hour for them to fix.

Delta crushed it. Flight attendant in first was attentive and just never stopped. Honestly one of the best domestic flights I’ve been on.

The 1st class male crew member was very pleasant - the short female with round glasses , maybe in 50’s had no personality- never spoke when delivering my food, drink, & never smiled the whole trip! In fact looked annoyed when the boarding proses was happening- I would never hire this woman - unfriendly . Have never dealt with a crew member like her-

Best airline! Always friendly and welcoming. Skyclub was great and loved the fast free wifi on board. I also love that you can pre-order your meal on the app!

Delayed due to an ill passenger after loading. Not preventable on Delta's part. Was in first class. The seats are becoming worn and detaching from their velcro attachments. Only got snacks on flight. The attendant was not the friendliest.

I liked the ease of checking in, luggage check in, wheel chair assistance, boarding and flight.

I usually have a positive experience with Delta. Complimentary upgrades are always nice!

The main person that was coordinating everything was a short white/light skin Spanish man and he was very rude. It honestly made me feel like it was everyone’s First day at work. His announcements were very not reasonable and they did not make sense. The stewardess on the flight that made the announcements she didn’t even know what she was talking about she sounded inebriated. There were no snacks or drinks on our flight there wasn’t even much turbulence. This flight was not enjoyable nor was it what a Delta flight should be and just this past week I flew with Delta 3 times.

nothing Delta could do... the person sitting next to me was huge and overflowing into my seat

Crew was great! I need wheelchair assistance and they knew who I was and updated me that my chair was on its way and to just hang tight. There was some turbulence but the captain announced we would be going thru it and he handled the plane well. Landing was soft and his.

Flight was good, boarding was a breeze, flight attendants were friendly and professional. There was a medical issue with another passenger and the crew handled it in a calm and professional way.

The net issue I had was with the gate agent. We had added a carryon to our boarding pass when we checked bags. When I got to the boarding gate the agent was rude asking why I had a backpack - I said I added it - even had an orange tag on it. She ripped my tag off and swung her monitor around to show me how she was right- saying it isn’t wasn’t listed - only a checked bag. I explained again that I wasn’t sure what the issue was but I wouldn’t have an orange tag if I hadn’t added it. Then she finally checked my husband’s boarding pass and found that the agent at checkin had added my carryon to his boarding pass instead of mine. She sent me on my way without my orange tag. Was a bit embarrassing for me the tone she used with me assuming I was trying to get away with something.

Gate agent asked if I could switch seats so a family could sit together. Agent moved me to a seat in the front of the plane, no charge. It was easy. The agent did a great job.

Great seat space. However food and drink prices outrageous. Jabbing to pay for a carry on bag or stuck paying at the gate too much.

Every Allegiant Air flight I've ever taken has been delayed. This flight was delayed a full 2 hours. It was excuse after excuse after excuse. It was a flight from southern Florida. They made us board the plane on time, but made us wait for 2 hours on the tarmac. Because the engines were kept shut off, so was the air conditioning. One can only imagine how hot the air was in the cabin over those 2 hours on the tarmac, while in the hot Florida sun. Just terrible.

Actually, for the price, I'm willing to put up with a little discomfort (upright chairs) and at times inconveniences (like any airline), lack of entertainment (I can bring my own). My flight was non stop and smooth. I would fly this route again.

The flight was delayed 6 hours and we were only offered an $8 food credit. My husband stood in line to get the credit for 45 minutes and when he got close to the end of the line the computers went down.

Worst ever! Flight cancelled supposedly for weather even though we k ow of many others who flew into Bangor same time no problem. At the airport there was no customer service at all just refund and no possibility of rebook for 3-4 days. Aweful won’t fly with them again!!

It’s a budget airline so adjust expectations accordingly. Nothing is without a fee but such is necessary for tickets to remain so affordable.

No complaints. It’s a budget airline so can’t expect any frills.

Book cheap flights from Pensacola to Chicago

Recent one-way flight deals

 
Only flying one-way? Below are some of the best one-way flight deals from Pensacola to Chicago found on KAYAK in the last 72 hours.
6/5Wed
1 stopFrontier
5h 44mPNS-MDW
$82
6/8Sat
1 stopFrontier
16h 48mPNS-MDW
$88
6/8Sat
1 stopFrontier
16h 48mPNS-MDW
$89
6/26Wed
1 stopFrontier
5h 44mPNS-MDW
$100
9/21Sat
1 stopDelta
6h 09mPNS-MDW
$104
6/7Fri
1 stopFrontier
23h 39mPNS-MDW
$108
6/11Tue
1 stopDelta
6h 22mPNS-MDW
$139
6/25Tue
1 stopDelta
3h 54mPNS-MDW
$179
6/9Sun
1 stopDelta
6h 22mPNS-MDW
$189
6/10Mon
3 stops
20h 51mPNS-MDW
$314

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Last minute flights from Pensacola to Midway

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 Pensacola to Chicago that are departing in the next 10 days.
6/4Tue
multi-stopFrontier
18h 05mPNS-MDW
6/6Thu
multi-stopFrontier
22h 08mMDW-PNS
$213
6/4Tue
multi-stopFrontier
18h 05mPNS-MDW
6/7Fri
multi-stopFrontier
14h 54mMDW-PNS
$233
6/3Mon
multi-stopFrontier
16h 05mPNS-MDW
6/6Thu
multi-stopFrontier
22h 08mMDW-PNS
$241
6/3Mon
multi-stopFrontier
16h 05mPNS-MDW
6/5Wed
multi-stopFrontier
14h 40mMDW-PNS
$245
6/3Mon
multi-stopFrontier
16h 05mPNS-MDW
6/7Fri
multi-stopFrontier
14h 54mMDW-PNS
$273
6/4Tue
multi-stopFrontier
18h 05mPNS-MDW
6/7Fri
multi-stopFrontier
25h 06mMDW-PNS
$301
5/31Fri
multi-stopDelta
6h 56mPNS-MDW
6/5Wed
multi-stopDelta
3h 59mMDW-PNS
$328
6/3Mon
multi-stopFrontier
16h 05mPNS-MDW
6/7Fri
multi-stopFrontier
25h 06mMDW-PNS
$340
5/31Fri
multi-stopFrontier
23h 22mPNS-MDW
6/2Sun
multi-stopFrontier
21h 53mMDW-PNS
$342
6/2Sun
multi-stopDelta
4h 04mPNS-MDW
6/4Tue
multi-stopDelta
3h 59mMDW-PNS
$378

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Pensacola - Chicago Midway Airport Flights

Departure:

Pensacola (PNS)United States

Destination:

Chicago Midway Airport (MDW)United States

Return flight deals:

Chicago Midway Airport - Pensacola

Cabin classes: