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Cheap flights from Chicago Midway Airport to Pensacola from $142

1 adult
1 adult, Economy, 0 bags

Discover deals from 900+ travel sites with momondo.

Find the cheapest flights from Chicago Midway Airport to Pensacola

Cheap round-trip flights

Enter your travel dates to find the best prices.
Southwest Logo
12:25 pm - 8:15 pmMDW  Chicago Midway-PNS Pensacola
7h 50m1 stop Houston Hobby
Southwest Logo
10:30 am - 3:05 pmPNS  Pensacola-MDW Chicago Midway
4h 35m1 stop Lambert-St Louis
$339Southwest
Tue, Oct 20 - Fri, Oct 23
Southwest Logo
9:30 am - 3:25 pmMDW  Chicago Midway-PNS Pensacola
5h 55m1 stop Nashville Intl
Southwest Logo
4:10 pm - 10:15 pmPNS  Pensacola-MDW Chicago Midway
6h 05m1 stop Nashville Intl
$339Southwest
Wed, Oct 21 - Wed, Oct 28
Delta Logo
6:04 am - 10:54 amMDW  Chicago Midway-PNS Pensacola
4h 50m1 stop Atlanta Hartsfield-Jackson
Delta Logo
5:50 pm - 10:54 pmPNS  Pensacola-MDW Chicago Midway
5h 04m1 stop Atlanta Hartsfield-Jackson
$339Delta
Sat, Nov 7 - Wed, Nov 11
Delta Logo
5:13 pm - 11:41 pmMDW  Chicago Midway-PNS Pensacola
6h 28m1 stop Atlanta Hartsfield-Jackson
Delta Logo
6:13 pm - 10:54 pmPNS  Pensacola-MDW Chicago Midway
4h 41m1 stop Atlanta Hartsfield-Jackson
$339Delta
Wed, Nov 11 - Sun, Nov 15
Southwest Logo
7:10 am - 12:00 pmMDW  Chicago Midway-PNS Pensacola
4h 50m1 stop Houston Hobby
Southwest Logo
4:05 pm - 11:00 pmPNS  Pensacola-MDW Chicago Midway
6h 55m1 stop Nashville Intl
$339Southwest
Fri, Feb 5 - Mon, Feb 8
Southwest Logo
10:15 am - 4:10 pmMDW  Chicago Midway-PNS Pensacola
5h 55m1 stop Lambert-St Louis
Southwest Logo
5:40 am - 11:50 amPNS  Pensacola-MDW Chicago Midway
6h 10m1 stop Houston Hobby
$339Southwest
Wed, Mar 24 - Wed, Mar 31
Delta Logo
1:05 pm - 7:42 pmMDW  Chicago Midway-PNS Pensacola
6h 37m1 stop Atlanta Hartsfield-Jackson
Delta Logo
5:45 pm - 10:10 pmPNS  Pensacola-MDW Chicago Midway
4h 25m1 stop Atlanta Hartsfield-Jackson
$339Delta
Thu, Mar 11 - Tue, Mar 16
Frontier Logo
6:16 am - 7:11 pmMDW  Chicago Midway-PNS Pensacola
12h 55m2 stops Atlanta Hartsfield-Jackson Orlando
Frontier Logo
8:06 pm - 11:22 amPNS  Pensacola-MDW Chicago Midway
15h 16m2 stops Orlando Dallas/Fort Worth
$386Frontier
Fri, Oct 30 - Mon, Nov 2
Frontier Logo
6:15 am - 7:59 pmMDW  Chicago Midway-PNS Pensacola
13h 44m2 stops Atlanta Hartsfield-Jackson Orlando
Frontier Logo
8:06 pm - 11:22 amPNS  Pensacola-MDW Chicago Midway
15h 16m2 stops Orlando Dallas/Fort Worth
$394Frontier
Mon, Oct 26 - Mon, Nov 2
Frontier Logo
6:16 am - 7:11 pmMDW  Chicago Midway-PNS Pensacola
12h 55m2 stops Atlanta Hartsfield-Jackson Orlando
Frontier Logo
8:06 pm - 11:22 amPNS  Pensacola-MDW Chicago Midway
15h 16m2 stops Orlando Dallas/Fort Worth
$394Frontier
Thu, Nov 5 - Mon, Nov 9

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Southwest flights from Chicago Midway Airport to Pensacola

Our best Southwest deals on Chicago Midway Airport to Pensacola flight tickets
Southwest
Oct 24
MDW8:40 amChicago Midway
4h 55m
1 stop
PNS1:35 pmPensacola
Oct 31
PNS7:40 amPensacola
7h 50m
2 stops
MDW3:30 pmChicago Midway
$344
Southwest
Oct 24
MDW10:25 amChicago Midway
6h 55m
2 stops
PNS5:20 pmPensacola
Oct 31
PNS7:40 amPensacola
7h 35m
2 stops
MDW3:15 pmChicago Midway
$349
Southwest
Dec 7
MDW7:05 amChicago Midway
8h 30m
1 stop
PNS3:35 pmPensacola
Dec 10
PNS7:55 amPensacola
9h 10m
2 stops
MDW5:05 pmChicago Midway
$350

Delta flights from Chicago Midway Airport to Pensacola

Our best Delta deals on Chicago Midway Airport to Pensacola flight tickets
Delta
Oct 24
MDW4:19 pmChicago Midway
4h 01m
1 stop
PNS8:20 pmPensacola
Nov 7
PNS5:40 pmPensacola
4h 53m
1 stop
MDW10:33 pmChicago Midway
$339
Delta
Jan 8
MDW6:00 amChicago Midway
4h 47m
1 stop
PNS10:47 amPensacola
Jan 10
PNS5:45 pmPensacola
4h 25m
1 stop
MDW10:10 pmChicago Midway
$359
Delta
Dec 22
MDW12:55 pmChicago Midway
3h 59m
1 stop
PNS4:54 pmPensacola
Jan 1
PNS8:05 amPensacola
6h 36m
1 stop
MDW2:41 pmChicago Midway
$379

momondo Fare Finder

 
Use the filters below to find and compare flights from Chicago Midway Airport to Pensacola that are best for you.

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Route

Depart

Return

Price

Cheapest round-trip

ChicagoPensacola

MDW Chicago Midway - PNS Pensacola

MDWPNS

Chicago Midway

Tue 10/20

12:25 pm-8:15 pm

1 stop7h 50m

Pensacola

Fri 10/23

10:30 am-3:05 pm

1 stop4h 35m

$339

ChicagoPensacola

MDW Chicago Midway - PNS Pensacola

MDWPNS

Chicago Midway

Wed 10/21

9:30 am-3:25 pm

1 stop5h 55m

Pensacola

Wed 10/28

4:10 pm-10:15 pm

1 stop6h 05m

$339
Quickest round-trip

ChicagoPensacola

MDW Chicago Midway - PNS Pensacola

MDWPNS

Chicago Midway

Sat 11/7

6:04 am-10:54 am

1 stop4h 50m

Pensacola

Wed 11/11

5:50 pm-10:54 pm

1 stop5h 04m

$339

ChicagoPensacola

MDW Chicago Midway - PNS Pensacola

MDWPNS

Chicago Midway

Wed 11/11

5:13 pm-11:41 pm

1 stop6h 28m

Pensacola

Sun 11/15

6:13 pm-10:54 pm

1 stop4h 41m

$339

ChicagoPensacola

MDW Chicago Midway - PNS Pensacola

MDWPNS

Chicago Midway

Fri 2/5

7:10 am-12:00 pm

1 stop4h 50m

Pensacola

Mon 2/8

4:05 pm-11:00 pm

1 stop6h 55m

$339

ChicagoPensacola

MDW Chicago Midway - PNS Pensacola

MDWPNS

Chicago Midway

Wed 3/24

10:15 am-4:10 pm

1 stop5h 55m

Pensacola

Wed 3/31

5:40 am-11:50 am

1 stop6h 10m

$339

ChicagoPensacola

MDW Chicago Midway - PNS Pensacola

MDWPNS

Chicago Midway

Thu 3/11

1:05 pm-7:42 pm

1 stop6h 37m

Pensacola

Tue 3/16

5:45 pm-10:10 pm

1 stop4h 25m

$339

ChicagoPensacola

MDW Chicago Midway - PNS Pensacola

MDWPNS

Chicago Midway

Fri 10/30

6:16 am-7:11 pm

2 stops12h 55m

Pensacola

Mon 11/2

8:06 pm-11:22 am

2 stops15h 16m

$386

ChicagoPensacola

MDW Chicago Midway - PNS Pensacola

MDWPNS

Chicago Midway

Mon 10/26

6:15 am-7:59 pm

2 stops13h 44m

Pensacola

Mon 11/2

8:06 pm-11:22 am

2 stops15h 16m

$394

ChicagoPensacola

MDW Chicago Midway - PNS Pensacola

MDWPNS

Chicago Midway

Thu 11/5

6:16 am-7:11 pm

2 stops12h 55m

Pensacola

Mon 11/9

8:06 pm-11:22 am

2 stops15h 16m

$394

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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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 typical price of a round-trip flight between Chicago Midway Airport and Pensacola?

Prices are currently low for flights on this route.

Typical prices usually range from $353 to $410.
The lowest price recently found on this route was $339.

What is the cheapest month to fly to Pensacola?

The cheapest month to fly to Pensacola from Chicago Midway Airport is in November. Flight prices, which tend to average around $132, are often lower during this time because this is during the off-season. If you aren’t able to travel during the month of November, then book flights to Pensacola from Chicago Midway Airport during February instead. Flights to Pensacola in February, while not as cheap as those in November, still average around $311.

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 $356. However, this price may fluctuate depending on the airline, the season, and holidays. On the other hand, Sunday 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 $440.

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

The cheapest time of day to fly to Pensacola is at noon when flights can be purchased for as low as $352. Flights to Pensacola are more costly in the afternoon, with an average ticket price of $403. Departure times in the afternoon 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

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

There is only 1 cabin class available to choose from on Chicago Midway Airport 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?

No. A direct flight is the cheapest option for a flight between Chicago Midway Airport to Pensacola.

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

$142

Fastest flight time

2h 15m

Direct flights

Tue, Wed, Thu, 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 $142. The best round-trip flight deal from Chicago Midway Airport to Pensacola found on momondo in the last 72 hours is $339.
The fastest flight from Chicago Midway Airport to Pensacola takes 2h 15m
Direct flights go from Chicago Midway Airport to Pensacola on Tuesday, Wednesday, Thursday, Friday, Saturday and Sunday. The only airline offering direct flights is Southwest.
There is 1 airport in Pensacola. From Chicago Midway Airport there are direct flights to Pensacola (PNS).
Search flight deals

Frequently asked questions about flying from Chicago Midway Airport to Pensacola

  • 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 15m.

  • 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 $227Free CancellationRating
7.8
8,605 reviews
Search Delta flights
SouthwestPriceFrom $282Free CancellationRating
8.0
4,202 reviews
Search Southwest flights

Traveling to a place near Pensacola?

Book flights to Pensacola if you plan to visit one of these locations
Orange Beach
Pensacola Beach
Foley
Navarre Beach
Navarre
Atmore
Gulf Breeze
Perdido Key
Milton
Evergreen
Warrington

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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