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Cheap flights from Pensacola to Chicago Midway Airport from $53

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Pensacola to Chicago Midway Airport departing on 2/25. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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Find the cheapest flights from Pensacola to Chicago

Cheap round-trip flights

These are some of the best round-trip flight deals from Pensacola to Chicago that have been recently found on momondo from popular airlines, departing in the coming months.

Cheap one-way flights

Flying one-way? These are some of the best deals recently discovered on momondo for flights from Pensacola to Chicago.

Cheap last minute flights

Planning a quick getaway from Pensacola to Chicago? These are the last-minute flight deals available now.

Cheap direct flights

If you prefer a non-stop journey, check out our latest direct flight deals to Chicago, so you can enjoy a seamless trip without layovers.

Cheap bus & train deals from Pensacola to Chicago

Find recent round-trip train or bus tickets from Pensacola to Chicago.

All round-trip flight deals to Chicago

The cheapest plane tickets to Chicago found on KAYAK recently.
7:17 pm - 12:13 amPNS-MDW
28h 56m1 stop
7:15 am - 6:17 pmMDW-PNS
11h 02m1 stop
$140Frontier
Find Deal
Sun, Jan 12 - Sun, Jan 19
7:27 pm - 12:17 amPNS-MDW
28h 50m1 stop
6:40 am - 6:27 pmMDW-PNS
11h 47m1 stop
$196Frontier
Find Deal
Thu, Feb 13 - Mon, Feb 17
7:27 pm - 12:17 amPNS-MDW
28h 50m1 stop
6:40 am - 6:30 pmMDW-PNS
11h 50m1 stop
$197Frontier
Find Deal
Thu, Feb 20 - Sun, Feb 23
9:41 am - 2:53 pmPNS-MDW
5h 12m1 stop
12:44 pm - 4:58 pmMDW-PNS
4h 14m1 stop
$228Delta
Find Deal
Sat, Jan 11 - Tue, Jan 28
6:00 am - 10:12 amPNS-MDW
4h 12m1 stop
6:00 am - 11:27 amMDW-PNS
5h 27m1 stop
$238Delta
Find Deal
Tue, Jan 7 - Sun, Jan 12
12:32 pm - 4:21 pmPNS-MDW
3h 49m1 stop
12:44 pm - 4:58 pmMDW-PNS
4h 14m1 stop
$263Delta
Find Deal
Sun, Jan 12 - Tue, Jan 28
5:00 pm - 10:55 pmPNS-MDW
5h 55m1 stop
5:55 am - 9:40 amMDW-PNS
3h 45m1 stop
$293Southwest
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Fri, Feb 7 - Sat, Feb 8
3:40 pm - 10:55 pmPNS-MDW
7h 15m2 stops
9:10 am - 4:05 pmMDW-PNS
6h 55m1 stop
$298Southwest
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Fri, Feb 7 - Sat, Feb 8
10:35 am - 8:30 pmPNS-MDW
9h 55m2 stops
5:55 am - 1:20 pmMDW-PNS
7h 25m2 stops
$303Southwest
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Fri, Feb 7 - Sat, Feb 8
6:03 pm - 10:20 pmPNS-MDW
4h 17m1 stop
6:00 am - 11:25 amMDW-PNS
5h 25m1 stop
$322Delta
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Tue, Mar 4 - Sat, Mar 8
5:23 pm - 12:17 amPNS-MDW
6h 54m1 stop
$53Frontier
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Tue, Feb 25
5:23 pm - 12:17 amPNS-MDW
6h 54m1 stop
$54Frontier
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Tue, Feb 25
7:17 pm - 12:17 amPNS-MDW
29h 00m1 stop
$61Frontier
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Thu, Jan 30
7:17 pm - 12:17 amPNS-MDW
29h 00m1 stop
$62Frontier
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Mon, Jan 27
9:20 am - 7:29 pmPNS-MDW
10h 09m1 stop
Wed, Apr 9
5:40 pm - 10:20 pmPNS-MDW
4h 40m1 stop
$114Delta
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Sun, Jan 19
1:59 pm - 6:00 pmPNS-MDW
4h 01m1 stop
$124Delta
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Wed, Apr 23
6:05 pm - 12:15 amPNS-MDW
6h 10m1 stop
$144Southwest
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Sun, Mar 2
7:25 am - 3:21 pmPNS-MDW
7h 56m1 stop
Sun, Jan 26
11:40 am - 7:20 pmPNS-MDW
7h 40m2 stops
$154Southwest
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Tue, Feb 4
4:25 pm - 10:20 pmPNS-MDW
5h 55m1 stop
5:20 am - 11:10 amMDW-PNS
5h 50m1 stop
$413Southwest
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Tue, Dec 24 - Sun, Jan 5
6:00 am - 11:21 amPNS-MDW
5h 21m1 stop
10:08 am - 3:28 pmMDW-PNS
5h 20m1 stop
$418Delta
Find Deal
Mon, Dec 23 - Wed, Dec 25
6:30 pm - 12:20 amPNS-MDW
5h 50m1 stop
5:30 am - 9:15 amMDW-PNS
3h 45m1 stop
$443Southwest
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Thu, Dec 26 - Thu, Jan 2
10:35 am - 6:40 pmPNS-MDW
8h 05m2 stops
5:30 am - 9:15 amMDW-PNS
3h 45m1 stop
$448Southwest
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Tue, Dec 24 - Sun, Jan 5
5:40 pm - 10:06 pmPNS-MDW
4h 26m1 stop
12:10 pm - 4:37 pmMDW-PNS
4h 27m1 stop
$503Delta
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Fri, Dec 27 - Fri, Jan 3
6:30 pm - 12:20 amPNS-MDW
5h 50m1 stop
5:30 am - 9:15 amMDW-PNS
3h 45m1 stop
$513Southwest
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Fri, Dec 27 - Sun, Dec 29
5:25 pm - 1:00 amPNS-MDW
7h 35m2 stops
5:30 am - 9:15 amMDW-PNS
3h 45m1 stop
$518Southwest
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Thu, Dec 26 - Thu, Jan 2
8:45 am - 5:15 pmPNS-MDW
8h 30m2 stops
9:00 am - 5:50 pmMDW-PNS
8h 50m2 stops
$528Southwest
Find Deal
Wed, Dec 25 - Mon, Dec 30
10:13 am - 4:17 pmPNS-MDW
6h 04m1 stop
12:10 pm - 4:37 pmMDW-PNS
4h 27m1 stop
$548Delta
Find Deal
Thu, Dec 26 - Fri, Jan 3
4:25 pm - 10:20 pmPNS-MDW
5h 55m1 stop
5:20 am - 11:10 amMDW-PNS
5h 50m1 stop
$568Southwest
Find Deal
Tue, Dec 24 - Thu, Dec 26
1:30 pm - 3:45 pmPNS-MDW
2h 15mnonstop
8:05 am - 10:20 amMDW-PNS
2h 15mnonstop
$389Southwest
Find Deal
Mon, Mar 24 - Thu, Mar 27

Frontier flights from Pensacola to Chicago Midway Airport

Our best Frontier deals on Pensacola to Chicago Midway Airport flight tickets
Frontier
Jan 12
PNS7:17 pmPensacola
28h 56m
1 stop
MDW12:13 amChicago Midway
Jan 19
MDW7:15 amChicago Midway
11h 02m
1 stop
PNS6:17 pmPensacola
Frontier
Feb 13
PNS7:27 pmPensacola
28h 50m
1 stop
MDW12:17 amChicago Midway
Feb 17
MDW6:40 amChicago Midway
11h 47m
1 stop
PNS6:27 pmPensacola
Frontier
Feb 20
PNS7:27 pmPensacola
28h 50m
1 stop
MDW12:17 amChicago Midway
Feb 23
MDW6:40 amChicago Midway
11h 50m
1 stop
PNS6:30 pmPensacola

Southwest flights from Pensacola to Chicago Midway Airport

Our best Southwest deals on Pensacola to Chicago Midway Airport flight tickets
Southwest
Feb 7
PNS5:00 pmPensacola
5h 55m
1 stop
MDW10:55 pmChicago Midway
Feb 8
MDW5:55 amChicago Midway
3h 45m
1 stop
PNS9:40 amPensacola
Southwest
Feb 7
PNS3:40 pmPensacola
7h 15m
2 stops
MDW10:55 pmChicago Midway
Feb 8
MDW9:10 amChicago Midway
6h 55m
1 stop
PNS4:05 pmPensacola
Southwest
Feb 7
PNS10:35 amPensacola
9h 55m
2 stops
MDW8:30 pmChicago Midway
Feb 8
MDW5:55 amChicago Midway
7h 25m
2 stops
PNS1:20 pmPensacola

See travel insights to Chicago from

How to get the cheapest flight ticket from Pensacola to Chicago Midway Airport

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest month to fly to Chicago Midway Airport?

The month of March is, on average, the cheapest month to fly to Chicago Midway Airport from Pensacola, with most prices found around $207. If you are unable to visit Chicago Midway Airport during the month of March, then departing from Pensacola during the month April is also very affordable. Most momondo users find prices during this month for around $218.

What is the cheapest day to depart on your flight to Chicago Midway Airport?

According to our data, Tuesday is the cheapest day to fly to Chicago Midway Airport from Pensacola. The lowest ticket price found for a Tuesday departure recently was $289. Keep in mind that prices can always vary depending on your route and whether or not you are flying domestic or international. On the other hand, Wednesday is the most expensive day to depart from Pensacola because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $488.

What is the cheapest time of day to depart on your flight to Chicago Midway Airport?

Flying to Chicago Midway Airport from Pensacola in the afternoon is the least expensive time of day to depart. momondo users have found prices as low as $319 when looking at flights departing in the afternoon. Try not to purchase tickets at noon because they tend to be around $430. Of course, these prices can vary depending on the time of year and what airport you fly to.

What is the cheapest Pensacola to Chicago Midway flight route?

Fly from Pensacola to Chicago Midway for the best Pensacola - Chicago Midway flight prices

What cabin class options are available on Pensacola to Chicago Midway flights?

There are 1 cabin classes available to choose from on Pensacola to Chicago Midway flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Can stopping save me money on Pensacola to Chicago Midway Airport flights?

You could potentially save up to 67% on your flight if you consider stops on a Pensacola to Chicago Midway Airport flight.

When to book flights from Pensacola to Chicago Midway Airport

Are you open to changing your travel dates? Check out the ideal times to fly from Pensacola to Chicago Midway Airport according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Pensacola to Chicago Midway Airport (PNS to MDW) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Pensacola to Chicago Midway Airport

Best Price Found

$53

Fastest flight time

2h 10m

Direct flights

Mon, Tue, Fri, Sat and Sun
The best one-way flight to Chicago Midway Airport from Pensacola in the past 72 hours is $53. The best round-trip flight deal from Pensacola to Chicago Midway Airport found on momondo in the last 72 hours is $140.
The fastest flight from Pensacola to Chicago Midway Airport takes 2h 10m
Direct flights go from Pensacola to Chicago Midway Airport on Monday, Tuesday, Friday, Saturday and Sunday. The only airline offering direct flights is Southwest.

  • How far is Pensacola to Chicago Midway by plane?

    The distance between Pensacola and Chicago Midway is about 785.3 mi. Flights usually cover this in 2h 15m, depending on flying conditions and air traffic around both airports.

  • When did momondo last update prices for flights from Pensacola Airport to Chicago Midway Airport?

    Prices for flights from Pensacola Airport to Chicago Midway Airport refresh daily.

  • How many operators does momondo search for flights from Pensacola Airport to Chicago Midway Airport?

  • How old do you have to be to fly from Pensacola Airport to Chicago Midway Airport?

    The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Pensacola Airport to Chicago Midway Airport.

  • What documentation or ID do you need to fly to Chicago Midway Airport?

    The required travel and health documents for your Chicago Midway Airport trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Chicago Midway Airport. We recommend that you seek guidance from your airline or a reliable third party such as IATA.

  • What is the most popular plane model from Pensacola to Chicago Midway Airport?

  • What is the most popular airline from Pensacola to Chicago Midway Airport?


Best airlines flying from Pensacola to Chicago Midway Airport

Compare and see reviews for airlines that fly from Pensacola to Chicago Midway Airport with momondo
Airline
Rating
Free Cancellation
Price
DeltaPriceFrom $207Free CancellationRating
8.0
8,594 reviews
Search Delta flights
SouthwestPriceFrom $263Free CancellationRating
8.1
4,804 reviews
Search Southwest flights

Why use momondo?

Why should I use momondo to find a flight deal from Pensacola to Chicago?

To find the flight that best suits your needs, momondo gathers a range of flights from a large pool of different airlines and agents; you can then use our insights and filters to find and book the right flight to Chicago from Pensacola.

Can I find flights from Pensacola to Chicago with flexible booking policies on momondo?

Yes. momondo enables you to select and highlight flights to Chicago from Pensacola with this policy.

How can momondo help me find flights from Pensacola to Chicago?

momondo provides multiple filters to help you find the best flight to Chicago from Pensacola. Filter by price, airline, airports, cabin, aircraft, payment method, number of stops and more.

I’m not ready to book a flight from Pensacola to Chicago right now. Can momondo alert me if prices change?

Yes. momondo can track prices for Pensacola to Chicago flights and alert you when they change. Perform a search to set up the price alert. All that is required is a valid email address.


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