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Cheap flights from Chicago Midway Airport to Pensacola from $54

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago Midway Airport to Pensacola departing on 2/26. 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 Chicago Midway Airport to Pensacola

Cheap round-trip flights

These are some of the best round-trip flight deals from Chicago Midway Airport to Pensacola 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 Chicago Midway Airport to Pensacola.

Cheap last minute flights

Planning a quick getaway from Chicago Midway Airport to Pensacola? 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 Pensacola, so you can enjoy a seamless trip without layovers.

Cheap bus & train deals from Chicago Midway Airport to Pensacola

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

All round-trip flight deals to Pensacola

The cheapest plane tickets to Pensacola found on KAYAK recently.
7:15 am - 6:17 pmMDW-PNS
11h 02m1 stop
7:17 pm - 12:17 amPNS-MDW
29h 00m1 stop
$118Frontier
Find Deal
Thu, Feb 6 - Mon, Feb 10
6:40 am - 4:36 pmMDW-PNS
9h 56m1 stop
5:23 pm - 12:17 amPNS-MDW
6h 54m1 stop
$128Frontier
Find Deal
Sat, Feb 22 - Wed, Feb 26
7:15 am - 6:13 pmMDW-PNS
10h 58m1 stop
8:17 pm - 9:32 pmPNS-MDW
25h 15m1 stop
$158Frontier
Find Deal
Thu, Dec 12 - Tue, Dec 17
7:15 am - 6:22 pmMDW-PNS
11h 07m1 stop
7:17 pm - 12:13 amPNS-MDW
28h 56m1 stop
$208Frontier
Find Deal
Fri, Dec 6 - Sun, Dec 8
10:57 am - 5:00 pmMDW-PNS
6h 03m1 stop
6:00 am - 11:59 amPNS-MDW
5h 59m1 stop
$228Delta
Find Deal
Tue, Jan 7 - Tue, Feb 4
10:57 am - 5:00 pmMDW-PNS
6h 03m1 stop
9:38 am - 2:53 pmPNS-MDW
5h 15m1 stop
$238Delta
Find Deal
Wed, Feb 12 - Sun, Feb 16
9:05 am - 3:25 pmMDW-PNS
6h 20m2 stops
11:40 am - 4:55 pmPNS-MDW
5h 15m1 stop
$293Southwest
Find Deal
Tue, Jan 7 - Tue, Feb 4
6:25 am - 3:25 pmMDW-PNS
9h 00m2 stops
8:20 am - 6:35 pmPNS-MDW
10h 15m2 stops
$298Southwest
Find Deal
Tue, Jan 7 - Tue, Feb 4
5:35 pm - 6:05 pmMDW-PNS
24h 30m3 stops
5:04 pm - 5:51 pmPNS-MDW
24h 47m3 stops
Mon, Dec 30 - Sat, Jan 4
12:05 pm - 4:09 pmMDW-PNS
28h 04m3 stops
5:15 pm - 11:10 amPNS-MDW
17h 55m3 stops
Wed, Dec 4 - Tue, Dec 10
7:05 am - 4:23 pmMDW-PNS
9h 18m1 stop
$54Frontier
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Wed, Feb 26
7:15 am - 6:17 pmMDW-PNS
11h 02m1 stop
$60Frontier
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Thu, Jan 23
7:15 am - 6:17 pmMDW-PNS
11h 02m1 stop
$70Frontier
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Sun, Jan 19
7:05 am - 4:23 pmMDW-PNS
9h 18m1 stop
$74Frontier
Find Deal
Wed, Feb 12
11:33 am - 7:10 pmMDW-PNS
7h 37m1 stop
Mon, Jan 20
6:00 am - 11:02 amMDW-PNS
5h 02m1 stop
$114Delta
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Fri, Jan 3
6:00 am - 12:47 pmMDW-PNS
6h 47m1 stop
$124Delta
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Wed, Jan 1
10:26 am - 7:10 pmMDW-PNS
8h 44m1 stop
Fri, Dec 20
8:05 am - 10:20 amMDW-PNS
2h 15mnonstop
$140Southwest
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Mon, Mar 17
10:05 am - 3:25 pmMDW-PNS
5h 20m1 stop
$144Southwest
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Wed, Jan 15
11:50 am - 3:14 pmMDW-PNS
27h 24m2 stops
7:10 pm - 12:13 amPNS-MDW
53h 03m2 stops
Mon, Nov 25 - Mon, Dec 2
5:10 am - 7:58 pmMDW-PNS
14h 48m1 stop
5:38 pm - 1:10 pmPNS-MDW
19h 32m1 stop
$378Frontier
Find Deal
Sat, Nov 23 - Mon, Nov 25
9:48 pm - 7:58 pmMDW-PNS
22h 10m1 stop
8:58 pm - 8:42 pmPNS-MDW
23h 44m1 stop
$398Frontier
Find Deal
Fri, Nov 22 - Sun, Nov 24
7:32 pm - 6:05 pmMDW-PNS
22h 33m1 stop
7:10 pm - 11:42 amPNS-MDW
16h 32m2 stops
Tue, Nov 26 - Tue, Dec 3
1:35 pm - 9:35 pmMDW-PNS
8h 00m1 stop
11:55 am - 4:40 pmPNS-MDW
4h 45m1 stop
$413Southwest
Find Deal
Mon, Nov 25 - Thu, Nov 28
1:35 pm - 9:35 pmMDW-PNS
8h 00m1 stop
7:15 am - 4:00 pmPNS-MDW
8h 45m2 stops
$418Southwest
Find Deal
Mon, Nov 25 - Thu, Nov 28
11:50 am - 3:14 pmMDW-PNS
27h 24m2 stops
7:10 pm - 12:13 amPNS-MDW
29h 03m2 stops
Mon, Nov 25 - Mon, Dec 2
8:35 am - 5:20 pmMDW-PNS
8h 45m1 stop
5:40 am - 2:25 pmPNS-MDW
8h 45m2 stops
$423Southwest
Find Deal
Fri, Nov 22 - Sun, Nov 24
6:00 am - 12:44 pmMDW-PNS
6h 44m1 stop
6:00 am - 9:50 amPNS-MDW
3h 50m1 stop
$768Delta
Find Deal
Tue, Nov 26 - Tue, Dec 3
6:00 am - 10:15 amMDW-PNS
4h 15m1 stop
5:37 pm - 9:46 pmPNS-MDW
4h 09m1 stop
$773Delta
Find Deal
Fri, Nov 22 - Mon, Dec 2
8:05 am - 10:20 amMDW-PNS
2h 15mnonstop
1:30 pm - 3:45 pmPNS-MDW
2h 15mnonstop
$414Southwest
Find Deal
Fri, Mar 14 - Mon, Mar 17
8:05 am - 10:20 amMDW-PNS
2h 15mnonstop
9:40 am - 11:55 amPNS-MDW
2h 15mnonstop
$438Southwest
Find Deal
Fri, Mar 14 - Sun, Mar 16
9:25 am - 11:40 amMDW-PNS
2h 15mnonstop
2:45 pm - 5:00 pmPNS-MDW
2h 15mnonstop
$448Southwest
Find Deal
Sun, Mar 16 - Sat, Mar 22
11:00 am - 1:10 pmMDW-PNS
2h 10mnonstop
2:45 pm - 5:00 pmPNS-MDW
2h 15mnonstop
$456Southwest
Find Deal
Sat, Mar 15 - Sat, Mar 22
11:00 am - 1:10 pmMDW-PNS
2h 10mnonstop
4:15 pm - 6:25 pmPNS-MDW
2h 10mnonstop
$536Southwest
Find Deal
Sat, Apr 5 - Sat, Apr 12
8:05 am - 10:20 amMDW-PNS
2h 15mnonstop
9:40 am - 11:55 amPNS-MDW
2h 15mnonstop
$569Southwest
Find Deal
Thu, Apr 3 - Sun, Apr 6

Frontier flights from Chicago Midway Airport to Pensacola

Our best Frontier deals on Chicago Midway Airport to Pensacola flight tickets
Frontier
Feb 6
MDW7:15 amChicago Midway
11h 02m
1 stop
PNS6:17 pmPensacola
Feb 10
PNS7:17 pmPensacola
29h 00m
1 stop
MDW12:17 amChicago Midway
Frontier
Feb 22
MDW6:40 amChicago Midway
9h 56m
1 stop
PNS4:36 pmPensacola
Feb 26
PNS5:23 pmPensacola
6h 54m
1 stop
MDW12:17 amChicago Midway
Frontier
Dec 12
MDW7:15 amChicago Midway
10h 58m
1 stop
PNS6:13 pmPensacola
Dec 17
PNS8:17 pmPensacola
25h 15m
1 stop
MDW9:32 pmChicago Midway

Delta flights from Chicago Midway Airport to Pensacola

Our best Delta deals on Chicago Midway Airport to Pensacola flight tickets
Delta
Jan 7
MDW10:57 amChicago Midway
6h 03m
1 stop
PNS5:00 pmPensacola
Feb 4
PNS6:00 amPensacola
5h 59m
1 stop
MDW11:59 amChicago Midway
Delta
Feb 12
MDW10:57 amChicago Midway
6h 03m
1 stop
PNS5:00 pmPensacola
Feb 16
PNS9:38 amPensacola
5h 15m
1 stop
MDW2:53 pmChicago Midway
Delta
Feb 13
MDW6:00 amChicago Midway
5h 27m
1 stop
PNS11:27 amPensacola
Feb 16
PNS9:38 amPensacola
5h 15m
1 stop
MDW2:53 pmChicago Midway

See travel insights to Pensacola from

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

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 Pensacola?

The cheapest month to fly to Pensacola from Chicago Midway Airport is in January. Flight prices, which tend to average around $268, are often lower during this time because this is during the off-season. If you aren’t able to travel during the month of January, then book flights to Pensacola from Chicago Midway Airport during April instead. Flights to Pensacola in April, while not as cheap as those in January, still average around $303.

What is the cheapest day to depart on your flight to Pensacola?

On average, the least expensive day to fly to Pensacola from Chicago Midway Airport is on a Tuesday. momondo users have found tickets for Tuesday departures for as low as $322. However, this price may fluctuate depending on the airline, the season, and holidays. On the other hand, Monday is the most expensive day to depart from Chicago Midway Airport because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $422.

What is the cheapest time of day to depart on your flight to Pensacola?

The cheapest time of day to fly to Pensacola is in the evening when flights can be purchased for as low as $207. Flights to Pensacola are more costly in the morning, with an average ticket price of $375. Departure times in the morning fall within the peak daily travel times, which is why tickets can be more expensive.

What is the cheapest Chicago Midway to Pensacola flight route?

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

How far in advance should I book a flight to Pensacola?

Most flyers found that booking tickets 53 days in advance of their planned departure date is the best time to get cheap flights to Pensacola. During this timeframe, flight prices are around $362. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Pensacola from Chicago Midway Airport for as low as $253 on momondo.

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

There are 1 cabin classes available to choose from on Chicago Midway to Pensacola 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 Chicago Midway Airport to Pensacola flights?

You could potentially save up to 61% on your flight if you consider stops on a Chicago Midway Airport to Pensacola flight.

When to book flights from Chicago Midway Airport to Pensacola

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

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

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

Best Price Found

$54

Fastest flight time

2h 05m

Direct flights

Mon, Tue, Fri, Sat and Sun

Airports in Pensacola

1 airport
The best one-way flight to Pensacola from Chicago Midway Airport in the past 72 hours is $54. The best round-trip flight deal from Chicago Midway Airport to Pensacola found on momondo in the last 72 hours is $118.
The fastest flight from Chicago Midway Airport to Pensacola takes 2h 05m
Direct flights go from Chicago Midway Airport to Pensacola on Monday, Tuesday, Friday, Saturday and Sunday. The only airline offering direct flights is Southwest.
There is 1 airport near Pensacola: Pensacola (PNS)

  • How far is Chicago Midway to Pensacola by plane?

    Chicago Midway and Pensacola are 785.3 mi apart from one another. A reasonable flight in good conditions will take 2h 05m.

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

    Prices for flights from Chicago Midway Airport to Pensacola Airport are refreshed on a daily basis.

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

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

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

    The necessary travel and health documents for your Pensacola Airport trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

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

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


Best airlines flying from Chicago Midway Airport to Pensacola

Compare and see reviews for airlines that fly from Chicago Midway Airport to Pensacola with momondo
Airline
Rating
Free Cancellation
Price
DeltaPriceFrom $206Free CancellationRating
8.0
8,755 reviews
Search Delta flights
SouthwestPriceFrom $258Free CancellationRating
8.1
5,005 reviews
Search Southwest flights

Why use momondo?

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

We help find the flight that best suits your needs, momondo compares prices from hundreds of airlines and travel agents and helps you filter them to find the best flight from Chicago to Pensacola for you.

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

All flight searches from Chicago to Pensacola on momondo can be filtered to show those which offer flexible booking policies.

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

Once all potential Chicago to Pensacola flight options are in front of you, momondo lets you sort and filter flights based on preferences such as airline, price and flight times amongst many other options.

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

Of course. momondo tracks the price of Chicago to Pensacola flights. All you need is a valid email address and we will do the rest; it is that quick and easy.


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