PNS - MDW

$100 Find Cheap Flights from Pensacola to Chicago Midway Airport - 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 Pensacola to Midway departing on 11/12. 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
$195
Typical prices: $248-$553
Southwest
Tue 9/15Wed 9/16
PNS - MDW • 1 stop
Cheapest one-way
$100
Delta
Thu 11/12
PNS - MDW • 1 stop
When to travel
February
Cheapest • 100% price drop
July
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
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We hope you love your trip to Midway!
Flight Deals
Booking Insights
Flight Deals

Cheap Flights 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 for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Pensacola to Midway

Tue, Sep 15 - Wed, Sep 16
Southwest Logo
4:20 pm - 10:25 pmPNS  Pensacola-MDW Chicago Midway
6h 05m1 stop Nashville Intl
Southwest Logo
2:00 pm - 5:35 pmMDW  Chicago Midway-PNS Pensacola
3h 35m1 stop Lambert-St Louis
$195Southwest
Wed, Sep 23 - Tue, Sep 29
Southwest Logo
4:20 pm - 10:25 pmPNS  Pensacola-MDW Chicago Midway
6h 05m1 stop Nashville Intl
Southwest Logo
2:00 pm - 5:35 pmMDW  Chicago Midway-PNS Pensacola
3h 35m1 stop Lambert-St Louis
$195Southwest
Sat, Feb 6 - Mon, Feb 8
Delta Logo
3:35 pm - 10:10 pmPNS  Pensacola-MDW Chicago Midway
6h 35m1 stop Atlanta Hartsfield-Jackson
Delta Logo
1:05 pm - 7:42 pmMDW  Chicago Midway-PNS Pensacola
6h 37m1 stop Atlanta Hartsfield-Jackson
$199Delta
Tue, Oct 20 - Wed, Oct 21
Delta Logo
7:02 am - 11:50 amPNS  Pensacola-MDW Chicago Midway
4h 48m1 stop Atlanta Hartsfield-Jackson
Delta Logo
6:04 am - 12:34 pmMDW  Chicago Midway-PNS Pensacola
6h 30m1 stop Atlanta Hartsfield-Jackson
$199Delta
Sat, Sep 19 - Sat, Sep 26
Delta Logo
5:30 pm - 10:44 pmPNS  Pensacola-MDW Chicago Midway
5h 14m1 stop Atlanta Hartsfield-Jackson
Delta Logo
6:05 am - 12:39 pmMDW  Chicago Midway-PNS Pensacola
6h 34m1 stop Atlanta Hartsfield-Jackson
$199Delta
Mon, Oct 19 - Tue, Oct 20
Southwest Logo
6:05 pm - 11:55 pmPNS  Pensacola-MDW Chicago Midway
5h 50m1 stop Nashville Intl
Southwest Logo
9:30 am - 3:25 pmMDW  Chicago Midway-PNS Pensacola
5h 55m1 stop Nashville Intl
$200Southwest
Wed, Sep 23 - Tue, Sep 29
Southwest Logo
7:55 am - 3:50 pmPNS  Pensacola-MDW Chicago Midway
7h 55m2 stops Nashville Intl Baltimore/Washington
Southwest Logo
2:00 pm - 5:35 pmMDW  Chicago Midway-PNS Pensacola
3h 35m1 stop Lambert-St Louis
$200Southwest
Sat, Sep 19 - Sat, Sep 26
Southwest Logo
10:50 am - 4:00 pmPNS  Pensacola-MDW Chicago Midway
5h 10m1 stop Kansas City
Southwest Logo
6:45 am - 11:50 amMDW  Chicago Midway-PNS Pensacola
5h 05m1 stop Dallas Love Field
$200Southwest
Tue, Sep 15 - Wed, Sep 16
Southwest Logo
7:55 am - 3:25 pmPNS  Pensacola-MDW Chicago Midway
7h 30m2 stops Nashville Intl Atlanta Hartsfield-Jackson
Southwest Logo
2:00 pm - 5:35 pmMDW  Chicago Midway-PNS Pensacola
3h 35m1 stop Lambert-St Louis
$200Southwest
Sat, Sep 19 - Sat, Sep 26
Southwest Logo
10:50 am - 4:00 pmPNS  Pensacola-MDW Chicago Midway
5h 10m1 stop Kansas City
Southwest Logo
9:05 am - 6:05 pmMDW  Chicago Midway-PNS Pensacola
9h 00m2 stops Baltimore/Washington Lambert-St Louis
$205Southwest
Booking Insights

KAYAK's insights & trends for Pensacola to Midway flights

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 round-trip flights from Pensacola to Chicago Midway Airport clicked on KAYAK for each day over the last 12 months.

If you are looking for a flight deal from Pensacola to Chicago Midway Airport, look for departures on Saturdays and avoid leaving on a Monday, as it's usually the priciest day. When flying back from Chicago Midway Airport, Wednesday is the cheapest day to fly and Sunday is the most expensive.

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 round-trip 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 February, where tickets cost $0 (return) on average. On the other hand, the most expensive months are March and October, where the average cost of round-trip tickets is $502 and $448 respectively.

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

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 $423, prices are generally cheapest when you fly direct.

Find deals

Good to know

Low season

June

Cheapest flight

$100
Best time to beat the crowds with an average 36% drop in price.
Most popular time to fly with an average 4% increase in price.
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 5 days, the lowest price for a flight from Pensacola to Chicago Midway Airport was $100 for a one-way ticket and $195 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 airlines offer Wi-Fi service onboard planes from Pensacola to Chicago Midway Airport?

    Only American Airlines offers inflight Wi-Fi service on the Pensacola to Chicago Midway Airport flight route.

  • Which aircraft models fly most regularly from Pensacola to Chicago Midway Airport?

    The Embraer 175 is the aircraft model that flies most regularly on the Pensacola to Chicago Midway Airport flight route.

  • Which airline alliances offer flights from Pensacola to Chicago Midway Airport?

    SkyTeam is the only airline alliance operating flights between Pensacola and Chicago Midway Airport.

  • Which is the best airline for flights from Pensacola to Chicago, Southwest or Delta?

    The two airlines most popular with KAYAK users for flights from Pensacola to Chicago are Southwest and Delta. With an average price for the route of $397 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 $429 and an overall rating of 7.8.

  • 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.

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

  • Looking for a cheap flight? 25% of our users found flights on this route for $246 or less one-way and $636 or less round-trip.

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

Information on your arrival and departure airports

Pensacola (PNS)
Midway (MDW)