Find flights
Deals
Insights
When to book
FAQs & Tips
Direct Flights
Airlines

PNS - MDW

$75 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
Wed 6/12
Wed 6/19

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 41,771,603 times on KAYAK, and here is why:

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

Track pricesNot ready to book? Create a price alert for when prices drop.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Bundle and saveSave money when you bundle your flight + hotel.

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
9:44 pm - 11:13 amPNS-MDW
13h 29m1 stop
6:00 am - 4:55 pmMDW-PNS
10h 55m1 stop
$149Frontier
Find Deal
Fri, May 31 - Tue, Jun 4
4:08 pm - 11:09 amPNS-MDW
19h 01m1 stop
5:01 am - 8:42 pmMDW-PNS
15h 41m1 stop
$153Frontier
Find Deal
Thu, May 30 - Mon, Jun 3
8:10 pm - 11:52 amPNS-MDW
15h 42m1 stop
6:00 am - 7:13 pmMDW-PNS
13h 13m1 stop
$156Frontier
Find Deal
Fri, Aug 23 - Sun, Aug 25
9:44 pm - 11:13 amPNS-MDW
13h 29m1 stop
5:01 am - 8:42 pmMDW-PNS
15h 41m1 stop
$157Frontier
Find Deal
Fri, May 31 - Mon, Jun 3
8:12 am - 2:09 pmPNS-MDW
5h 57m1 stop
5:01 am - 8:51 pmMDW-PNS
15h 50m1 stop
$159Frontier
Find Deal
Wed, May 22 - Wed, May 29
5:45 pm - 9:47 pmPNS-MDW
4h 02m1 stop
10:11 am - 2:26 pmMDW-PNS
4h 15m1 stop
$198Delta
Find Deal
Sat, Aug 24 - Wed, Aug 28
3:24 pm - 9:46 pmPNS-MDW
6h 22m1 stop
10:41 am - 4:34 pmMDW-PNS
5h 53m1 stop
$243Delta
Find Deal
Tue, Jun 25 - Tue, Jul 2
6:00 am - 9:51 amPNS-MDW
3h 51m1 stop
6:49 pm - 11:45 pmMDW-PNS
4h 56m1 stop
$293Delta
Find Deal
Fri, Jun 14 - Mon, Jun 17
5:57 pm - 10:01 pmPNS-MDW
4h 04m1 stop
6:00 am - 1:00 pmMDW-PNS
7h 00m1 stop
$318Delta
Find Deal
Thu, Jun 6 - Sun, Jun 9
7:26 pm - 7:43 pmPNS-MDW
24h 17m3 stops
8:33 pm - 5:31 pmMDW-PNS
20h 58m2 stops
Thu, May 30 - Mon, Jun 3

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 Sundays if you are looking for the best rates. For your return to Pensacola, you’ll find the best rates on Mondays 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 ($75) and Delta ($278). The cheapest round-trip tickets were found on Frontier ($149) and Delta ($198).

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

Each day, there are between 1 and 3 nonstop flights that take off from Pensacola and land in Chicago Midway Airport, with an average flight time of 2h 13m. The most common departure time is 12:00 pm and most flights take off in the morning. Each week, there are 10 flights. The most frequent day of departure is Sunday, when 30% of all weekly flights depart. The fewest flights depart on a Thursday.

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

$75
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 $75 for a one-way ticket and $149 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 10736 reviews
8.2Boarding
7.4Food
7.9Comfort
8.6Crew
8.0Entertainment
Airline reviews

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!

10.0 ExcellentGregory, May 2024MCO - JFK
Read more about Delta reviews

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.

Aircraft very cramped. Check-in was great with an agent helping us. Food was almost non-existent. Pre-flight went well once I got the app reloaded on my phone since we don’t fly much anymore.

I like that it got us where we were going. Everything else needed work. It was 1/2 hour late and we took off an hour late. The plane had to be cleaned and the disabled loaded on board before we could take off which took forever and then we sat at the terminal FOREVER before we took off. The ride was so bumpy that they couldn’t serve drinks and snack but to about 1/2 the plane. Seriously we should have flown out of Fort Lauderdale. We probably would’ve gotten home several hours earlier.

Flight was on time, the staff was personable & professional, & the plane arrived on time.

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.

My daughter dropped her cell phone right through the crack between walkway and plane. Right in front of myself, the lead flight attendant and crew below. In slow motion we all watched. The crew was on it as they got her phone back to her. Surprisingly, not damaged! This same head flight attendant was hilarious on the speaker! Loved his humor! Pilots were very clear to hear. Sometimes there’s a lot of noise interference or they sound muffled, but this time I could understand everything that was spoken. One more positive experience was renting a car through Allegiant which was my first time. We got a great car deal through Alamo and the car was really nice too, 2024 Blazer.

We waited for our captain to arrive and she made our flight take off 20 minutes late.

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
$75
6/1Sat
1 stopFrontier
13h 28mPNS-MDW
$86
7/5Fri
1 stopFrontier
10h 16mPNS-MDW
$120
7/6Sat
1 stopFrontier
11h 59mPNS-MDW
$160
7/21Sun
1 stopFrontier
15h 10mPNS-MDW
$179
7/7Sun
1 stopFrontier
15h 10mPNS-MDW
$180
11/3Sun
1 stopDelta
3h 59mPNS-MDW
$278
5/23Thu
1 stopFrontier
19h 01mPNS-MDW
$340
5/20Mon
1 stopFrontier
19h 28mPNS-MDW
$403
6/5Wed
2 stopsDelta
7h 25mPNS-MDW
$471

Search by stops

Search by airline

Search by price

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.
5/17Fri
multi-stopFrontier
23h 22mPNS-MDW
5/19Sun
multi-stopFrontier
10h 39mMDW-PNS
$226
5/15Wed
multi-stopDelta
6h 36mPNS-MDW
5/18Sat
multi-stopDelta
5h 51mMDW-PNS
$458
5/15Wed
multi-stopDelta
6h 36mPNS-MDW
5/18Sat
multi-stopDelta
13h 30mMDW-PNS
$781
5/17Fri
multi-stopDelta
4h 04mPNS-MDW
5/19Sun
multi-stopDelta
9h 41mMDW-PNS
$887
5/15Wed
multi-stopDelta
10h 29mPNS-MDW
5/18Sat
multi-stopDelta
11h 03mMDW-PNS
$1,109
5/17Fri
multi-stopDelta
7h 25mPNS-MDW
5/19Sun
multi-stopDelta
9h 41mMDW-PNS
$1,585

Search by stops

Search by airline

Search by price

Pensacola - Chicago Midway Airport Flights

Departure:

Pensacola (undefined)United States

Destination:

Chicago Midway Airport (MDW)United States

Return flight deals:

Chicago Midway Airport - Pensacola

Cabin classes: