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PNS - MDW

$112 Find Cheap Flights from Pensacola to Chicago Midway Airport - Compare and Save

1 adult
1 adult, Economy, 0 bags

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Everything you should know

Cheapest round-trip
$224
Typical prices: $341-$485
Southwest
Mon 12/10Fri 12/14
PNS - MDW • 1 stop
Cheapest non-stop
$650
Typical prices: $353-$477
Southwest
Mon 4/2Thu 4/5
PNS - MDW • Non-stop
Nonstop flights
Not available
There are currently no direct flights between Pensacola and Chicago Midway Airport. You'll need to take a connecting flight to reach the destination.
Insights
Insights
When to travel
April
Cheapest • 28% price drop
June
Most popular
Good to know
+1
Good to know
+1
Top layover airports
Dallas Love Field (DAL)
Cheapest • Avg $369 (round-trip)
Nashville Intl (BNA)
Shortest trip • 4h 29m (one-way)
Insights
Insights
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We hope you love your trip to Chicago Midway Airport!
Flight Deals
Booking Insights
Flight Deals

Cheap Flights from Pensacola to Midway (PNS-MDW)

 
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Pensacola to Midway

Thu, Dec 10 - Mon, Dec 14
Southwest Logo
4:10 pm - 10:40 pmPNS  Pensacola-MDW Chicago Midway
6h 30m1 stop Nashville Intl
Southwest Logo
12:45 pm - 6:05 pmMDW  Chicago Midway-PNS Pensacola
5h 20m1 stop Nashville Intl
$224Southwest
Wed, Nov 11 - Tue, Nov 17
Southwest Logo
4:10 pm - 10:45 pmPNS  Pensacola-MDW Chicago Midway
6h 35m1 stop Nashville Intl
Southwest Logo
12:45 pm - 6:10 pmMDW  Chicago Midway-PNS Pensacola
5h 25m1 stop Nashville Intl
$224Southwest
Wed, Nov 11 - Tue, Nov 17
Southwest Logo
7:55 am - 12:55 pmPNS  Pensacola-MDW Chicago Midway
5h 00m1 stop Nashville Intl
Southwest Logo
8:50 am - 6:10 pmMDW  Chicago Midway-PNS Pensacola
9h 20m2 stops Baltimore/Washington Nashville Intl
$229Southwest
Tue, Nov 3 - Tue, Nov 10
Southwest Logo
7:55 am - 12:55 pmPNS  Pensacola-MDW Chicago Midway
5h 00m1 stop Nashville Intl
Southwest Logo
8:50 am - 3:35 pmMDW  Chicago Midway-PNS Pensacola
6h 45m1 stop Dallas Love Field
$281Southwest
Sat, Nov 21 - Thu, Nov 26
Southwest Logo
5:25 pm - 12:50 amPNS  Pensacola-MDW Chicago Midway
7h 25m1 stop Houston Hobby
Southwest Logo
8:40 am - 3:00 pmMDW  Chicago Midway-PNS Pensacola
6h 20m1 stop Nashville Intl
$281Southwest
Mon, Nov 2 - Mon, Nov 9
Southwest Logo
5:55 pm - 12:05 amPNS  Pensacola-MDW Chicago Midway
6h 10m1 stop Nashville Intl
Southwest Logo
4:00 pm - 8:35 pmMDW  Chicago Midway-PNS Pensacola
4h 35m1 stop Nashville Intl
$281Southwest
Wed, Oct 28 - Mon, Nov 2
Southwest Logo
6:20 am - 11:25 amPNS  Pensacola-MDW Chicago Midway
5h 05m1 stop Houston Hobby
Southwest Logo
4:00 pm - 8:30 pmMDW  Chicago Midway-PNS Pensacola
4h 30m1 stop Nashville Intl
$281Southwest
Thu, Dec 10 - Sun, Dec 13
Southwest Logo
4:10 pm - 10:40 pmPNS  Pensacola-MDW Chicago Midway
6h 30m1 stop Nashville Intl
Southwest Logo
8:00 am - 1:40 pmMDW  Chicago Midway-PNS Pensacola
5h 40m1 stop Nashville Intl
$281Southwest
Sat, Nov 21 - Fri, Nov 27
Frontier Logo
6:35 pm - 7:47 pmPNS  Pensacola-MDW Chicago Midway
25h 12m1 stop Orlando
Frontier Logo
8:42 pm - 5:40 pmMDW  Chicago Midway-PNS Pensacola
20h 58m1 stop Orlando
$295Frontier
Thu, Nov 12 - Sun, Nov 15
Delta Logo
6:00 am - 10:24 amPNS  Pensacola-MDW Chicago Midway
4h 24m1 stop Atlanta Hartsfield-Jackson
Delta Logo
6:00 am - 11:09 amMDW  Chicago Midway-PNS Pensacola
5h 09m1 stop Atlanta Hartsfield-Jackson
$301Delta
Booking Insights

Price, demand and travel trends for Pensacola to Chicago Midway Airport flights

Use KAYAK data on prices, travel dates, airlines and seasonal trends to compare options and book flights with more confidence.

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

Round-trip flights from Pensacola to Chicago Midway Airport typically range from $341 to $485. The lowest price found in the past 5 days was $224, on Southwest.

What's the cheapest day of the week to fly from Pensacola to Chicago Midway Airport?

Based on deals KAYAK users found in the last 12 months, Wednesday is the cheapest day of the week to fly from Pensacola to Chicago Midway Airport. It’s 18% cheaper than the average day, while Sunday is the most expensive, with prices 34% higher.

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Key details for Pensacola to Chicago Midway Airport flights

Low season

March

Cheapest flight

$112
Beat the crowds with an average 27% drop in travelers.
The most popular month to fly with an average 162% increase in travelers.
One-way 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

Your Pensacola to Chicago Midway Airport flight questions, answered

Find helpful answers about this route, including flight times, airports, airlines and booking tips.

  • What cabin classes can I book on flights from Pensacola to Chicago Midway Airport?

    Only Economy Class is available on flights from Pensacola to Chicago Midway Airport.

  • How long is a flight from Pensacola to Chicago Midway Airport?

    A nonstop flight from Pensacola to Chicago Midway Airport takes 00m, covering 782 miles.

  • Do I need a passport to fly from Pensacola to Chicago Midway Airport?

    No, a passport is not required for this domestic route, but you will need a real ID-compliant driver's license, a state ID or another TSA-accepted form of identification.

  • How much should I expect to pay for a Pensacola to Chicago Midway Airport flight?

    Round-trip flights from Pensacola to Chicago Midway Airport range from $341 to $485, with an average of $409 over the past 12 months. Anything below $341 counts as a good deal.

  • How much can I save by taking a layover when flying from Pensacola to Chicago Midway Airport?

    On this route, layover flights are cheaper than nonstop options on average. Layover fares average $369 round-trip via Dallas Love Field (DAL), compared to $398 for nonstop.

  • What is the standard checked-bag allowance on flights from Pensacola to Chicago Midway Airport?

    There is no standard. Checked-bag policies vary by airline on this route. Most carriers charge $45–$90 for the first checked bag in economy. Premium fares and elite-status bookings typically include a free checked bag.

  • Which aircraft model is used most often on flights from Pensacola to Chicago Midway Airport?

    The Boeing 737 family is used most often on this route, operated mainly by Southwest and United Airlines. Other aircraft seen on the route include Embraer 175 variants.

  • Have flight prices from Pensacola to Chicago Midway Airport changed much recently?

    Yes. Based on fares seen in the past 5 days, round-trip prices on this route showed a wide range, from about $224 to $1,903. That means the highest observed fare was about 8x higher than the lowest one.

  • How are flight prices from Pensacola to Chicago Midway Airport looking right now?

    One-way fares from Pensacola to Chicago Midway Airport are currently lower than usual. Average one-way flight prices are about $115, which is 50% below the typical average for this route.

  • What car rental options are available at Chicago Midway Airport (MDW)?

    Chicago Midway Airport (MDW) hosts 5 major car rental companies, with daily rates starting from around $32 for economy cars. Top options include:

    • Hertz
    • Dollar
    • Budget
    • Alamo
    • Rent-A-Wreck

  • Which airports can I use when flying from Pensacola to Chicago Midway Airport?

    Flights from Pensacola to Chicago Midway Airport usually depart from Pensacola (PNS) and arrive at Chicago Midway (MDW).

  • Which airports do connecting flights from Pensacola to Chicago Midway Airport pass through?

    One-stop flights from Pensacola to Chicago Midway Airport most commonly connect through:

    • Atlanta Hartsfield-Jackson (ATL) - 53% of one-stop connections
    • Nashville Intl (BNA) - 44% of one-stop connections
    • Dallas Love Field (DAL) - 2% of one-stop connections

  • Can I save money by using flexible dates for flights from Pensacola to Chicago Midway Airport?

    Yes. Flexible dates can save you up to 39% on flights from Pensacola to Chicago Midway Airport. Wednesday is the cheapest departure day at $339 round-trip on average, while Sunday is the most expensive at $550, a difference of $211.

    KAYAK's flexible dates feature shows options up to 3 days before and after your selected dates, making it easier to compare nearby fares.

  • How much time can I save by choosing a different layover airport from Pensacola to Chicago Midway Airport?

    Flying via Nashville Intl (BNA) gives the shortest average 1-stop total travel time at 4h 29m, compared with 4h 33m via Atlanta Hartsfield-Jackson (ATL) and 6h 39m via Dallas Love Field (DAL).

  • What popular places can I visit in Chicago Midway Airport?

    Some of the most popular sights in Chicago Midway Airport are Magnificent Mile, Grant Park and Soldier Field. These are among the most viewed places in Chicago Midway Airport on KAYAK.

  • Which airlines offer extra legroom and free seat selection on Pensacola to Chicago Midway Airport flights?

    Among airlines operating Pensacola to Chicago Midway Airport flights:

    • Southwest: offers free seat selection

    Extra legroom and free seat selection availability depends on fare class and route.

  • Which airlines include bags at no extra cost on Pensacola to Chicago Midway Airport flights?

    Here are some options for this route, based on selected ticket types and cabin classes:

    • Southwest: a cabin bag in Economy Class class

    Bag allowance can vary by ticket type, cabin class, route and airline, so always check the fare details before booking.

Your guide to booking Pensacola to Chicago Midway Airport flights

Get tips on when to book, when to fly and what to know before your trip.
  • If your dates are flexible, aim for a Wednesday departure and avoid flying on Sunday. On this route, Wednesday flights average $339, about $211 less than Sunday fares (38% savings) based on the last 12 months.
  • If you can choose when to travel, plan your Pensacola to Chicago Midway Airport trip for April. Fares historically average $296 round-trip in that month - typically $206 less than the most expensive month, which is March (based on the last 12 months).
  • If you have the time, taking a 1-stop flight through Dallas Love Field Airport (DAL) can be cheaper than flying direct. The cheapest layover option averages $369 round-trip on this route - about $28 less than direct flights (based on the last 12 months).
  • If you're arriving late at night and need somewhere to stay, check out these hotels close to Chicago Midway Airport.

    • DoubleTree by Hilton Chicago Midway Airport
    • Holiday Inn Chicago - Midway Airport S by IHG
    • Skylark Motel

More options for your flight from Pensacola to Midway

Complete your trip to Chicago with a hotel stay or car rental

Car rentals in Chicago
Hotels in Chicago
Vacations in Chicago