MDW - PNS

$144 Find Cheap Flights from Chicago Midway Airport to Pensacola - Compare and Save

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 9/30. 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

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Everything you should know

Cheapest round-trip
$288
Typical prices: $376-$386
Southwest
Wed 8/26Sat 8/29
MDW - PNS • 1 stop
Cheapest one-way
$144
Southwest
Wed 9/30
MDW - PNS • 1 stop
Nonstop flights
3 days a week
Mon, Fri, Sun
You can fly direct with Southwest. Average duration is 0
Direct flights
Direct flights
+1
+1
Direct flights
Direct flights
+1
When to travel
November
Cheapest • 62% price drop
March
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
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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

Wed, Aug 26 - Sat, Aug 29
Southwest Logo
2:00 pm - 5:35 pm
MDW
-
PNS
3h 35m
1 stop
Southwest Logo
9:40 am - 2:20 pm
PNS
-
MDW
4h 40m
1 stop
$288Southwest
Sat, Sep 12 - Sat, Sep 19
Southwest Logo
6:45 am - 11:50 am
MDW
-
PNS
5h 05m
1 stop
Southwest Logo
9:40 am - 2:20 pm
PNS
-
MDW
4h 40m
1 stop
$292Southwest
Wed, Sep 30 - Wed, Oct 7
Southwest Logo
2:00 pm - 5:35 pm
MDW
-
PNS
3h 35m
1 stop
Southwest Logo
4:10 pm - 10:10 pm
PNS
-
MDW
6h 00m
1 stop
$292Southwest
Wed, Aug 19 - Sat, Aug 22
Southwest Logo
2:00 pm - 5:35 pm
MDW
-
PNS
3h 35m
1 stop
Southwest Logo
10:50 am - 3:55 pm
PNS
-
MDW
5h 05m
1 stop
$292Southwest
Wed, Sep 9 - Wed, Sep 16
Southwest Logo
2:00 pm - 5:35 pm
MDW
-
PNS
3h 35m
1 stop
Southwest Logo
3:00 pm - 8:45 pm
PNS
-
MDW
5h 45m
1 stop
$292Southwest
Tue, Aug 25 - Thu, Aug 27
Southwest Logo
2:00 pm - 5:35 pm
MDW
-
PNS
3h 35m
1 stop
Southwest Logo
2:40 pm - 8:05 pm
PNS
-
MDW
5h 25m
1 stop
$292Southwest
Mon, Nov 16 - Wed, Nov 18
Delta Logo
1:00 pm - 7:45 pm
MDW
-
PNS
6h 45m
1 stop
Delta Logo
6:00 am - 12:05 pm
PNS
-
MDW
6h 05m
1 stop
$297Delta
Thu, Aug 20 - Sat, Aug 22
Delta Logo
12:46 pm - 5:03 pm
MDW
-
PNS
4h 17m
1 stop
Delta Logo
6:00 am - 10:10 am
PNS
-
MDW
4h 10m
1 stop
$297Delta
Wed, Oct 21 - Tue, Oct 27
Delta Logo
6:04 am - 10:52 am
MDW
-
PNS
4h 48m
1 stop
Delta Logo
8:05 am - 11:50 am
PNS
-
MDW
3h 45m
1 stop
$297Delta
Tue, Oct 27 - Tue, Nov 3
Delta Logo
5:15 pm - 11:30 pm
MDW
-
PNS
6h 15m
1 stop
Delta Logo
5:40 pm - 10:33 pm
PNS
-
MDW
4h 53m
1 stop
$297Delta
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 Wednesday and more expensive on a Sunday. On your return trip to Chicago Midway Airport, you should consider flying back on a Thursday, and avoid Mondays 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 $132 (return) on average. On the other hand, the most expensive months are March and December, where the average cost of round-trip tickets is $493 and $433 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.

Find deals

Good to know

Low season

August

Cheapest flight

$144
Best time to beat the crowds but there is an average 10% increase in price.
Most popular time to fly with an average 40% 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 5 days, the lowest price for a flight from Chicago Midway Airport to Pensacola was $144 for a one-way ticket and $288 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?

    American Airlines, and JetBlue offer 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 Boeing 737-800 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 $387 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 $311 and an overall rating of 7.8.

  • 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 $303 or less one-way and $477 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

Friday

Southwest

Southwest

Sunday

Southwest

Southwest

See more direct flights

Direct returns

Pensacola to Chicago Midway

Monday

Southwest

Southwest

Friday

Southwest

Southwest

Sunday

Southwest

Southwest

See more direct flights

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

Information on your arrival and departure airports

Chicago Midway Airport (MDW)
Pensacola (PNS)