MDW - PNS

$104 Find Cheap Flights from Chicago Midway Airport to Pensacola - Compare and Save

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Everything you should know

Cheapest round-trip
$325
Typical prices: $302-$460
Delta
Mon 12/17Thu 12/20
MDW - PNS • 1 stop
Cheapest non-stop
$627
Typical prices: $327-$486
Southwest
Mon 3/19Sun 3/25
MDW - PNS • Non-stop
Nonstop flights
Not available
There are currently no direct flights between Chicago Midway Airport and Pensacola. You'll need to take a connecting flight to reach the destination.
Insights
Insights
When to book
22 weeks
in advance
Our data shows that travelers who book at least 22 weeks in advance save around 46% compared to booking last minute.
Insights
Insights
When to travel
November
Cheapest • 25% price drop
March
Most popular
Good to know
+1
Good to know
+1
Top layover airports
Orlando (MCO)
Cheapest • Avg $171 (round-trip)
Atlanta Hartsfield-Jackson (ATL)
Shortest trip • 4h 25m (one-way)
Insights
Insights
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We hope you love your trip to Pensacola!
Flight Deals
Booking Insights
Flight Deals

Cheap Flights from Midway to Pensacola (MDW-PNS)

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

Recent round-trip flight deals from Midway to Pensacola

Thu, Dec 17 - Sun, Dec 20
Delta Logo
5:12 pm - 11:39 pmMDW  Chicago Midway-PNS Pensacola
6h 27m1 stop Atlanta Hartsfield-Jackson
Delta Logo
5:59 pm - 10:22 pmPNS  Pensacola-MDW Chicago Midway
4h 23m1 stop Atlanta Hartsfield-Jackson
$325Delta
Wed, Dec 2 - Sun, Dec 6
Delta Logo
1:02 pm - 5:57 pmMDW  Chicago Midway-PNS Pensacola
4h 55m1 stop Atlanta Hartsfield-Jackson
Delta Logo
7:00 am - 12:04 pmPNS  Pensacola-MDW Chicago Midway
5h 04m1 stop Atlanta Hartsfield-Jackson
$325Delta
Sat, Dec 12 - Sun, Dec 20
Delta Logo
6:00 am - 11:12 amMDW  Chicago Midway-PNS Pensacola
5h 12m1 stop Atlanta Hartsfield-Jackson
Delta Logo
5:59 pm - 10:22 pmPNS  Pensacola-MDW Chicago Midway
4h 23m1 stop Atlanta Hartsfield-Jackson
$325Delta
Wed, Dec 2 - Sun, Dec 6
Southwest Logo
8:50 am - 6:10 pmMDW  Chicago Midway-PNS Pensacola
9h 20m2 stops Baltimore/Washington Nashville Intl
Southwest Logo
5:55 pm - 12:10 amPNS  Pensacola-MDW Chicago Midway
6h 15m1 stop Nashville Intl
$330Southwest
Thu, Jan 21 - Sun, Jan 24
Delta Logo
5:45 pm - 11:41 pmMDW  Chicago Midway-PNS Pensacola
5h 56m1 stop Atlanta Hartsfield-Jackson
Delta Logo
5:25 pm - 11:55 pmPNS  Pensacola-MDW Chicago Midway
6h 30m1 stop Atlanta Hartsfield-Jackson
$338Delta
Wed, Nov 18 - Sat, Nov 21
Southwest Logo
8:50 am - 3:35 pmMDW  Chicago Midway-PNS Pensacola
6h 45m1 stop Dallas Love Field
Southwest Logo
6:25 pm - 12:25 amPNS  Pensacola-MDW Chicago Midway
6h 00m1 stop Nashville Intl
$345Southwest
Thu, Feb 4 - Mon, Feb 8
Multiple Airlines Logo
8:47 pm - 2:40 pmMDW  Chicago Midway-PNS Pensacola
17h 53m1 stop Orlando
Multiple Airlines Logo
8:38 am - 11:46 pmPNS  Pensacola-MDW Chicago Midway
15h 08m2 stops Tampa Atlanta Hartsfield-Jackson
$345Multiple Airlines
Tue, Nov 24 - Tue, Dec 1
Multiple Airlines Logo
8:42 pm - 5:35 pmMDW  Chicago Midway-PNS Pensacola
20h 53m1 stop Orlando
Multiple Airlines Logo
7:05 pm - 11:33 amPNS  Pensacola-MDW Chicago Midway
16h 28m2 stops Fort Lauderdale Atlanta Hartsfield-Jackson
$349Multiple Airlines
Wed, Nov 18 - Sat, Nov 21
Southwest Logo
10:55 am - 8:10 pmMDW  Chicago Midway-PNS Pensacola
9h 15m2 stops Dallas Love Field Houston Hobby
Southwest Logo
6:25 pm - 12:25 amPNS  Pensacola-MDW Chicago Midway
6h 00m1 stop Nashville Intl
$350Southwest
Wed, Nov 18 - Mon, Nov 23
Multiple Airlines Logo
6:08 am - 7:05 pmMDW  Chicago Midway-PNS Pensacola
12h 57m2 stops Atlanta Hartsfield-Jackson Fort Lauderdale
Multiple Airlines Logo
6:30 pm - 7:47 pmPNS  Pensacola-MDW Chicago Midway
25h 17m1 stop Orlando
$352Multiple Airlines
Booking Insights

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

Round-trip flights from Chicago Midway Airport to Pensacola typically range from $302 to $460. The lowest price found in the past 5 days was $325, on Delta.

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

Based on deals KAYAK users found in the last 12 months, Wednesday is the cheapest day of the week to fly from Chicago Midway Airport to Pensacola. It’s 25% cheaper than the average day, while Friday is the most expensive, with prices 12% higher.

What’s the cheapest month to fly from Chicago Midway Airport to Pensacola?

•November is the cheapest month to fly from Chicago Midway Airport to Pensacola at $283 round-trip.
•December ($446) and March ($434) are the most expensive months.
•The price difference between flying in the cheapest and most expensive months is 57% on average.
This is based on KAYAK aggregated and averaged internal data over the past 12 months.

When are flights from Chicago Midway Airport to Pensacola the cheapest?

Flights from Chicago Midway Airport to Pensacola are cheapest 22 weeks before departure. Booking in this window typically costs about 46% less than the average last-minute fare (within 2 weeks of the flight), based on KAYAK data.

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Key details for Chicago Midway Airport to Pensacola flights

Low season

December

Cheapest flight

$104
Beat the crowds with an average 59% drop in travelers.
The most popular month to fly with an average 113% increase in travelers.
One-way 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

Your Chicago Midway Airport to Pensacola 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 Chicago Midway Airport to Pensacola?

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

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

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

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

    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 Chicago Midway Airport to Pensacola flight?

    Round-trip flights from Chicago Midway Airport to Pensacola range from $302 to $460, with an average of $375 over the past 12 months. Anything below $302 counts as a good deal.

  • How expensive are last-minute Chicago Midway Airport to Pensacola flights?

    Last-minute fares on this route (booked within two weeks of departure) run 17% above the $375 route average. Book 22 weeks before departure for the lowest fares.

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

    On this route, layover flights are cheaper than nonstop options on average. Layover fares average $171 round-trip via Orlando (MCO), compared to $414 for nonstop.

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

    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 Chicago Midway Airport to Pensacola?

    The Embraer 175 family is used most often on this route, operated mainly by American Airlines. Other aircraft seen on the route include Boeing 737-800 variants.

  • Have flight prices from Chicago Midway Airport to Pensacola 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 $325 to $1,604. That means the highest observed fare was about 5x higher than the lowest one.

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

    One-way fares from Chicago Midway Airport to Pensacola are currently lower than usual. Average one-way flight prices are about $156, which is 27% below the typical average for this route.

  • What car rental options are available at Pensacola Airport (PNS)?

    Pensacola Airport (PNS) hosts 5 major car rental companies, with daily rates averaging $63 for economy cars. Top options include:

    • Dollar
    • Hertz
    • Budget
    • Ace
    • Alamo

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

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

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

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

    • Atlanta Hartsfield-Jackson (ATL) - 63% of one-stop connections
    • Nashville Intl (BNA) - 28% of one-stop connections
    • Orlando (MCO) - 3% of one-stop connections
    • Lambert-St Louis (STL) - 3% of one-stop connections

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

    Yes. Flexible dates can save you up to 34% on flights from Chicago Midway Airport to Pensacola. Wednesday is the cheapest departure day at $282 round-trip on average, while Friday is the most expensive at $422, a difference of $140.

    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 Chicago Midway Airport to Pensacola?

    Flying via Atlanta Hartsfield-Jackson (ATL) gives the shortest average 1-stop total travel time at 4h 25m, compared with 4h 28m via Nashville Intl (BNA) and 4h 32m via Lambert-St Louis (STL).

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

    Among airlines operating Chicago Midway Airport to Pensacola 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 Chicago Midway Airport to Pensacola 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 Chicago Midway Airport to Pensacola 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 Friday. On this route, Wednesday flights average $282, about $140 less than Friday fares (33% savings) based on the last 12 months.
  • For the best chance at a low fare, aim to book around 22 weeks before you fly. On this route, that window historically saves about 46% versus last-minute pricing (KAYAK booking data, last 12 months).
  • If you can choose when to travel, plan your Chicago Midway Airport to Pensacola trip for November. Fares historically average $283 round-trip in that month - typically $163 less than the most expensive month, which is December (based on the last 12 months).
  • If you have the time, taking a 1-stop flight through Orlando Airport (MCO) can be cheaper than flying direct. The cheapest layover option averages $171 round-trip on this route - about $243 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 Pensacola Airport.

    • Hilton Garden Inn Pensacola Airport - Medical Center
    • Hyatt Place Pensacola Airport
    • Tru by Hilton Pensacola Airport Medical Center

More options for your flight from Midway to Pensacola

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

Car rentals in Pensacola
Hotels in Pensacola
Vacations in Pensacola