MDW - PNS

$129 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 5/27. 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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Everything you should know

Cheapest round-trip
$335
Typical prices: $401-$311
Southwest
Sat 6/27Sat 7/4
MDW - PNS • Non-stop
Cheapest one-way
$129
Typical prices: $175-$221
Multiple Airlines
Wed 5/27
MDW - PNS • 2 stops
Top airlines
Cheapest • from $335 (round-trip)
Best reviews • 7.9 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Nonstop flights
You can fly direct with Southwest. Average duration is 2h 15m
Direct flights
Direct flights
+1
+1
Direct flights
Direct flights
+1
When to travel
Cheapest • 100% price drop
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
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KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Pensacola!
Flight Deals
Booking Insights
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

Sat, Jun 27 - Sat, Jul 4
Southwest Logo
9:00 am - 11:10 am
MDW
-
PNS
2h 10mnonstop
Southwest Logo
12:50 pm - 3:05 pm
PNS
-
MDW
2h 15mnonstop
$335Southwest
Sat, Jun 27 - Sat, Jul 4
Southwest Logo
9:00 am - 11:10 am
MDW
-
PNS
2h 10mnonstop
Southwest Logo
10:00 am - 2:55 pm
PNS
-
MDW
4h 55m
1 stop
$341Southwest
Sat, Jun 27 - Fri, Jul 3
Southwest Logo
9:00 am - 11:10 am
MDW
-
PNS
2h 10mnonstop
Southwest Logo
10:40 am - 12:55 pm
PNS
-
MDW
2h 15mnonstop
$345Southwest
Wed, Jun 3 - Wed, Jun 10
Southwest Logo
11:35 am - 8:20 pm
MDW
-
PNS
8h 45m
2 stops
Southwest Logo
3:45 pm - 6:00 pm
PNS
-
MDW
2h 15mnonstop
$350Southwest
Sat, May 23 - Wed, May 27
Southwest Logo
8:10 am - 10:25 am
MDW
-
PNS
2h 15mnonstop
Southwest Logo
2:45 pm - 8:10 pm
PNS
-
MDW
5h 25m
1 stop
$354Southwest
Tue, Sep 22 - Tue, Sep 29
Delta Logo
10:35 am - 2:22 pm
MDW
-
PNS
3h 47m
1 stop
Delta Logo
8:00 am - 11:54 am
PNS
-
MDW
3h 54m
1 stop
$355Delta
Sat, Jun 27 - Sat, Jul 4
Southwest Logo
5:00 am - 2:15 pm
MDW
-
PNS
9h 15m
2 stops
Southwest Logo
10:00 am - 2:55 pm
PNS
-
MDW
4h 55m
1 stop
$356Southwest
Sat, May 23 - Wed, May 27
Southwest Logo
8:10 am - 10:25 am
MDW
-
PNS
2h 15mnonstop
Southwest Logo
10:10 am - 3:45 pm
PNS
-
MDW
5h 35m
2 stops
$359Southwest
Sat, Jun 27 - Fri, Jul 3
Southwest Logo
9:00 am - 11:10 am
MDW
-
PNS
2h 10mnonstop
Southwest Logo
11:05 am - 7:15 pm
PNS
-
MDW
8h 10m
2 stops
$360Southwest
Mon, Jun 1 - Mon, Jun 8
Southwest Logo
12:00 pm - 3:40 pm
MDW
-
PNS
3h 40m
1 stop
Southwest Logo
10:40 am - 12:55 pm
PNS
-
MDW
2h 15mnonstop
$363Southwest
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.

How much is a round-trip flight from Chicago Midway Airport to Pensacola?

This analysis is based on the cheapest round-trip price found on KAYAK in the last 12 months by searching for a flight from Chicago Midway Airport to Pensacola departing in June.

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 Thursday. On your return trip to Chicago Midway Airport, you should consider flying back on a Friday, 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 November, where tickets cost $0 (return) on average. On the other hand, the most expensive months are March and December, where the average cost of round-trip tickets is $469 and $400 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.

No, with an average price for the route of $335, prices are generally cheapest when you fly direct.

Good to know

Low seasonSeptember
Cheapest flight$129
Best time to beat the crowds with an average 37% drop in price.
Most popular time to fly with an average 5% 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 $129 for a one-way ticket and $335 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 Embraer 175 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.

  • 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.

  • 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 $370 and an overall rating of 7.9, Southwest is the most popular choice. Delta is also a great choice for the route, with an average price of $297 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.

KAYAK’s top tips for finding a cheap flight from Chicago Midway Airport to Pensacola

  • Looking for a cheap flight? 25% of our users found flights on this route for $447 or less round-trip.

Prefer to fly direct from Chicago Midway Airport to Pensacola?

 
Direct data is based off flight results for the next 60 days. Find direct flights from all airlines flying direct from Chicago Midway to Pensacola.
Find which airlines fly direct from Chicago Midway Airport to Pensacola Airport, which days they fly and book direct flights.

Direct 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

Direct 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

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.
7.9
SouthwestOverall score based on 4307 reviews
8.1Boarding
8.6Crew
7.5Entertainment
8.0Comfort
7.0Food
Airline reviews

The flight was okay. The pilots did an amazing job and kept us updated on the flight. The flight attendants were okay. They found time to be chatty with each other rather than focus on the guests. One of the attendants was a little less warm when asking about my bag I had on my lap that I was using during latter part of the mid- flight. Mind you, it was not the departure descent. I’m respectful to each and every attendant, it was the tone in her voice reminding me to place my carryon bag on the floor. I hope to have a better experience next time.

10.0 ExcellentMechelle, Apr 2026
MCI - PNS
Read more Southwest reviews

The flight was okay. The pilots did an amazing job and kept us updated on the flight. The flight attendants were okay. They found time to be chatty with each other rather than focus on the guests. One of the attendants was a little less warm when asking about my bag I had on my lap that I was using during latter part of the mid- flight. Mind you, it was not the departure descent. I’m respectful to each and every attendant, it was the tone in her voice reminding me to place my carryon bag on the floor. I hope to have a better experience next time.

Terrible. Even though there’s assigned seating now, they are still the slowest boarding airline of anyone.

I flew twice this week on Southwest, was delayed over 2 hours both ways. From Pittsburgh to Chicago it was due to weather but the gate agents, pilot etc were great at updating everyone. Today from Midway to Pittsburgh the plane had come from an international location, kept getting delayed, no information was given until we were delayed for the third time. It was ridiculous, whoever scheduled that plane to fly to Pittsburgh after didn’t consider a lot of things.

It was canceled. Supposedly weather. But there was no snow in Baltimore. At least we found out before driving to airport

The staff was very friendly, professional, and courteous. The overall flight was a great experience.

Okay, not wonderful. Short flight. Wi-fi didn't work properly. Stuck waiting for a gate to open upon arrival for 20 or so minutes.

They sent a notice that they were boarding an hour early. We had to leave the club and run to the gate. They said sorry, that came from corporate and was a mistake. They did not have enough seating because the flight before it had not taken off on time. They moved our gate and delayed it for an hour.

Plane crashed into a bus or some other vehicle on the ground while pulling out of the gate. No injuries, but wing tip was damaged and returned to gate for “maintenance issues” and we departed 5 hours later because the plane went out of service and new plane was flown in from a nearby airport, Midway.

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.

Very easy to use and convenient, you can perform any action within the same portal

Overall Good! The weather delayed our takeoff from Atlanta and our arrival in Miami! If Mother Nature can mess up a flight she will do it every time!

Okay considering we had weather delays which the Pilot notified us of immediately!

N Everything was perfect from boarding to assistance to baggage in Tampa

The boarding was organized and informative but the plane was tight meaning that you were sitting on one another and extremely uncomfortable. It’s disappointing that can’t have common seating comfort on the plane.

Everything could have benn better. Short fly, no food, no entertainment and no wifi.

Snacks and included beverages were appreciated. Boarding went smoothly. Plenty of overhead bin space. Seats get very uncomfortable after a couple of hours. After waiting 10 painful minutes for my walker, a very nice Delta guest agent pushed me in a wheelchair to the gate. It was finally delivered to me after another 15 minutes . Our checked bag was on the carousel long b4 I was able to retrieve it. Fortunately it was still there but somewhere along the way the straps we used to secure it were removed and and were not reattached. Wish I had made note of the agents name.

Stop changing gates. Stop cancelling flights Stop moving my seat.

The whole experience was excellent. As it most often is with Delta

We waited an hour on the runway to get a gate in Orlando

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

Information on your arrival and departure airports