MDW - PNS

$82 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 4/18. 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
$257
Multiple Airlines
Sat 4/4Mon 4/13
MDW - PNS • 1 stop
Cheapest non-stop
$325
Southwest
Sat 4/11Sat 4/18
MDW - PNS • Non-stop
Nonstop flights
Mon, Thu, Fri, Sat, Sun
You can fly direct with Southwest. Average duration is 2h 15m
Direct flights
Direct flights
+1
+1
Direct flights
Direct flights
+1
Top airlines
Cheapest • from $267 (round-trip)
Best reviews • 8.0 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Top layover airports
Cheapest • Avg $340 (round-trip)
Shortest trip • 4h 19m (one-way)
Insights
Insights
Insights
Insights
Start a new search
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, Apr 4 - Mon, Apr 13
Multiple Airlines Logo
6:00 am - 8:55 am
MDW
-
PNS
26h 55m
1 stop
Multiple Airlines Logo
7:00 am - 7:31 pm
PNS
-
MDW
36h 31m
2 stops
$257Multiple Airlines
Mon, Apr 27 - Thu, Apr 30
Multiple Airlines Logo
9:14 am - 3:36 pm
MDW
-
PNS
6h 22m
1 stop
Multiple Airlines Logo
4:31 pm - 10:28 am
PNS
-
MDW
17h 57m
1 stop
$259Multiple Airlines
Thu, Apr 2 - Sun, Apr 5
Multiple Airlines Logo
5:01 am - 9:14 pm
MDW
-
PNS
16h 13m
1 stop
Multiple Airlines Logo
3:36 pm - 10:19 pm
PNS
-
MDW
30h 43m
2 stops
$261Multiple Airlines
Tue, Apr 7 - Wed, Apr 8
Southwest Logo
8:00 am - 2:05 pm
MDW
-
PNS
6h 05m
1 stop
Southwest Logo
2:45 pm - 8:10 pm
PNS
-
MDW
5h 25m
1 stop
$267Southwest
Fri, Apr 17 - Wed, Apr 22
Multiple Airlines Logo
3:29 pm - 9:38 pm
MDW
-
PNS
30h 09m
2 stops
Multiple Airlines Logo
6:36 am - 7:26 am
PNS
-
MDW
24h 50m
1 stop
$269Multiple Airlines
Thu, Apr 23 - Sun, Apr 26
Multiple Airlines Logo
2:15 pm - 3:36 pm
MDW
-
PNS
25h 21m
2 stops
Multiple Airlines Logo
4:31 pm - 8:04 am
PNS
-
MDW
15h 33m
1 stop
$271Multiple Airlines
Tue, Apr 7 - Wed, Apr 8
Southwest Logo
3:00 pm - 7:00 pm
MDW
-
PNS
4h 00m
1 stop
Southwest Logo
10:10 am - 3:45 pm
PNS
-
MDW
5h 35m
2 stops
$272Southwest
Fri, Apr 17 - Wed, Apr 22
Southwest Logo
8:00 am - 3:40 pm
MDW
-
PNS
7h 40m
1 stop
Southwest Logo
2:45 pm - 8:10 pm
PNS
-
MDW
5h 25m
1 stop
$273Southwest
Sat, Apr 11 - Tue, Apr 14
Southwest Logo
8:10 am - 10:25 am
MDW
-
PNS
2h 15mnonstop
Southwest Logo
4:25 pm - 10:15 pm
PNS
-
MDW
5h 50m
1 stop
$277Southwest
Tue, Apr 7 - Wed, Apr 8
Southwest Logo
5:40 am - 2:05 pm
MDW
-
PNS
8h 25m
2 stops
Southwest Logo
7:40 am - 3:45 pm
PNS
-
MDW
8h 05m
2 stops
$278Southwest
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 Friday, and avoid Sundays for better deals.

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 $337, prices are generally cheapest when you fly direct.

Good to know

Low seasonSeptember
Cheapest flight$84
Best time to beat the crowds with an average 36% drop in price.
Most popular time to fly with an average 31% 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 $84 for a one-way ticket and $257 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 $363 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 $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 $311 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

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

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.
8.0
SouthwestOverall score based on 4320 reviews
8.0Comfort
7.0Food
8.6Crew
7.5Entertainment
8.1Boarding
Airline reviews

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

2.0 MediocreAnonymous, Feb 2026
BWI - PBI
Read more Southwest reviews

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.

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.

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

Flight was delayed by 3-hours and their fix was… complimentary pretzels.

The staff on board and gate was nice - a welcome change from the usual. We also arrived early, which was a great benefit, given that it takes 30 minutes plus to get bags at SRQ.

The staff was frielndly. The plane was terrible, it was too small and should be decommissioned. There were no back seat screens at all. The only beverages we had a choice from was coffee, tea or water. The only bathroom in the back was behind the flight attendant's jump seat and wasn't working. And I literally felt like I was sitting on top of the guy next to me. It was terribly hot in the plane and we had to sit on the tarmac in Chicago for 1/2 hour due to congestion in Mpls. Wouldn't they have know that before they even boarded us so that we could have sat in comfort in the terminal?

They took all carry-on luggage from Groups 6 -9 - I was group 5 and waiting in line to board - they made me check my luggage too. That then went to baggage claim and delayed departure from the airport. There was overhead room in my seating area - Delta over reacted. Also, had a gentleman next to me that took up 1/2 my seat.

Sorry I didn't realize I was writing a review for each leg. Please see my previous review - it applies to the entire flight, not just a single leg.

boarded at 5:30 pm, pushed away from gate at 6pm ... takeoff was not until ~6:45pm; disappointing

Paid for wifi that didn't work. No plug in seat to work. No entertainment.

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

Information on your arrival and departure airports