MDW - PNS

$93 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 1/9. 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, 0 bags

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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Flight 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

Tue, Dec 9 - Tue, Dec 16
Southwest Logo
10:50 am - 3:35 pmMDW-PNS
4h 45m1 stop
Southwest Logo
4:15 pm - 8:15 pmPNS-MDW
4h 00m1 stop
$224Southwest
Find Deal
Thu, Nov 20 - Tue, Nov 25
Delta Logo
6:00 am - 10:41 amMDW-PNS
4h 41m1 stop
Delta Logo
5:00 pm - 11:40 pmPNS-MDW
6h 40m1 stop
$229Delta
Find Deal
Tue, Dec 9 - Tue, Dec 16
Southwest Logo
10:50 am - 3:35 pmMDW-PNS
4h 45m1 stop
Southwest Logo
7:20 am - 4:50 pmPNS-MDW
9h 30m2 stops
$230Southwest
Find Deal
Sat, Dec 6 - Mon, Dec 8
Southwest Logo
8:25 am - 5:00 pmMDW-PNS
8h 35m2 stops
Southwest Logo
4:15 pm - 10:35 pmPNS-MDW
6h 20m1 stop
$234Southwest
Find Deal
Tue, Nov 11 - Fri, Nov 14
Multiple Airlines Logo
1:56 pm - 7:11 pmMDW-PNS
29h 15m2 stops
Multiple Airlines Logo
11:17 am - 10:10 pmPNS-MDW
10h 53m1 stop
$236Multiple Airlines
Find Deal
Tue, Dec 9 - Tue, Dec 16
Southwest Logo
9:25 am - 6:35 pmMDW-PNS
9h 10m2 stops
Southwest Logo
9:55 am - 5:05 pmPNS-MDW
7h 10m2 stops
$239Southwest
Find Deal
Sat, Nov 15 - Tue, Nov 18
Southwest Logo
12:00 pm - 5:00 pmMDW-PNS
5h 00m1 stop
Southwest Logo
7:20 am - 12:45 pmPNS-MDW
5h 25m1 stop
$249Southwest
Find Deal
Fri, Nov 21 - Tue, Nov 25
Delta Logo
6:00 am - 10:41 amMDW-PNS
4h 41m1 stop
Delta Logo
7:10 pm - 11:40 pmPNS-MDW
4h 30m1 stop
$254Delta
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Fri, Feb 6 - Sat, Feb 14
Southwest Logo
5:25 am - 9:25 amMDW-PNS
4h 00m1 stop
Southwest Logo
7:45 am - 5:05 pmPNS-MDW
9h 20m1 stop
$255Southwest
Find Deal
Fri, Nov 14 - Mon, Nov 17
Frontier Logo
12:30 pm - 3:23 pmMDW-PNS
26h 53m1 stop
Frontier Logo
5:15 pm - 11:38 amPNS-MDW
18h 23m2 stops
$304Frontier
Find Deal

Everything you should know

Top airlines
Southwest
Cheapest • from $224 (round-trip)
Southwest
Best reviews • 8.0 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
When to travel
September
Cheapest • 38% price drop
March
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
Cheapest round-trip
$224
Overall average: $383
Southwest
Tue 12/9Tue 12/16
MDW - PNS • 1 stop
Cheapest one-way
$93
Typical prices: $258-$295
Multiple Airlines
Fri 1/9
MDW - PNS • 1 stop
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We hope you love your trip to Pensacola!
Booking Insights

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 Tuesday and more expensive on a Sunday. 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 September, where tickets cost $217 (return) on average. On the other hand, the most expensive months are November and March, where the average cost of round-trip tickets is $467 and $387 respectively.

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

The average round-trip 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.

Yes, flying with a layover may cost you more time, but you can also save money on the route, with a 1 stop layover the cheapest option at $323 on average.

Good to know

Low seasonNovember
Cheapest flight$93
Best time to beat the crowds but there is an average 33% increase in price.
Most popular time to fly with an average 10% 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 $93 for a one-way ticket and $224 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.

  • 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 $362 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 $263 and an overall rating of 7.9.

  • 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.

Reviews of the 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 4241 reviews
8.1Boarding
8.6Crew
7.0Food
8.0Comfort
7.5Entertainment
Airline reviews

All was good. I just had a hard time getting connected to the WiFi/internet during the flight

10.0 ExcellentAnonymous, Oct 2025MDW - BWI
Read more Southwest reviews

All was good. I just had a hard time getting connected to the WiFi/internet during the flight

Better and more food and drinks. Put msnbc and free speech tv on the news channel selection list.

The quality of Southwest Airlines continues to degrade each time I fly with them. If it were not for the free luggage, I would probably choose another airline. Their prices are a little bit competitive, but way too high for the quality of the service. Southwest is not unique in this way. Domestic flight in the United States of America has continued to be a lower and lower quality product. Very sad when you compare the quality of domestic airlines to that of many international airlines around the world.

after landing, we stay 2 hours on the taxi way before reaching the gate The airline and the crew were good though

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

Staff were friendly and happy. Delta could make sure passengers that don't have the app know of changes. Without Kayak I would not have known about the change of gate or the delay. Kayak was faster to notify me.

They ended up paying for the bag twice, but the counter wouldn't take my baggage receipt. Left it to me to resolve. Not sure how to resolve the issue.

The flight was an hour and a half late departing which was inconvenient

The flight was great. The gate location was way to far away!!!

The flight attendant in first class was beyond rude and didn't care at all about her job. AND the gate agent was even worse than the flight attendant for rudeness. She was awful.

Movie selection was meh. Food was great. Crew as always great. I paid for premium because that’s the only way not to feel like a sardine. That’s how economy should be imo. Sadly passengers have to pay an extra $1000 to get what they should at base price but that’s all airlines. The airline industry in general treats passengers as cargo.

Always good but we must do something about people in rows ahead of you that don't put their seats back up when they are suppose to. And It's rough to not be able to even lean over to get something out of my purse.

this crew didn't care much. bumping carts into seats more times than i care to remember

Everything was fine except the entertainment was not working for half of the flight.

Easy boarding with an extremely kind attendant. Seats were spacious and we had 3 seats for 2 people so we could stretch out. Comfortable air flow and very attentive and hospital attendants. Bathrooms and food were the only negative. Bathrooms were so small you could hardly get in and close the door. I don’t think an obese person would fit or a person with a movement disability. Food was the trending food for flights, nonexistent. We spent $40 getting sandwich and snack at airport for our 6 hour flught.

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

Information on your arrival and departure airports

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