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Cheap flights from Chicago Midway Airport to Pensacola from $144

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 9/30. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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
2:00 pm - 5:35 pm
MDW
-
PNS
3h 35m
1 stop
Southwest Logo
9:40 am - 2:20 pm
PNS
-
MDW
4h 40m
1 stop
$288Southwest
Wed, Aug 26 - Sat, Aug 29
Southwest Logo
2:00 pm - 5:35 pm
MDW
-
PNS
3h 35m
1 stop
Southwest Logo
3:00 pm - 8:45 pm
PNS
-
MDW
5h 45m
1 stop
$292Southwest
Wed, Sep 9 - Wed, Sep 16
Southwest Logo
6:45 am - 11:50 am
MDW
-
PNS
5h 05m
1 stop
Southwest Logo
9:40 am - 2:20 pm
PNS
-
MDW
4h 40m
1 stop
$292Southwest
Sat, Sep 12 - Sat, Sep 19
Southwest Logo
2:00 pm - 5:35 pm
MDW
-
PNS
3h 35m
1 stop
Southwest Logo
4:10 pm - 10:10 pm
PNS
-
MDW
6h 00m
1 stop
$292Southwest
Wed, Sep 30 - Wed, Oct 7
Southwest Logo
2:00 pm - 5:35 pm
MDW
-
PNS
3h 35m
1 stop
Southwest Logo
10:50 am - 3:55 pm
PNS
-
MDW
5h 05m
1 stop
$292Southwest
Wed, Aug 19 - Sat, Aug 22
Southwest Logo
2:00 pm - 5:35 pm
MDW
-
PNS
3h 35m
1 stop
Southwest Logo
7:00 am - 12:15 pm
PNS
-
MDW
5h 15m
1 stop
$292Southwest
Tue, Sep 8 - Tue, Sep 15
Delta Logo
4:19 pm - 8:20 pm
MDW
-
PNS
4h 01m
1 stop
Delta Logo
8:05 am - 11:50 am
PNS
-
MDW
3h 45m
1 stop
$297Delta
Sat, Oct 10 - Tue, Oct 13
Delta Logo
4:19 pm - 8:20 pm
MDW
-
PNS
4h 01m
1 stop
Delta Logo
11:58 am - 4:19 pm
PNS
-
MDW
4h 21m
1 stop
$297Delta
Sat, Oct 10 - Wed, Oct 14
Delta Logo
5:15 pm - 11:30 pm
MDW
-
PNS
6h 15m
1 stop
Delta Logo
5:40 pm - 10:33 pm
PNS
-
MDW
4h 53m
1 stop
$297Delta
Tue, Oct 27 - Tue, Nov 3
Delta Logo
6:04 am - 10:52 am
MDW
-
PNS
4h 48m
1 stop
Delta Logo
8:05 am - 11:50 am
PNS
-
MDW
3h 45m
1 stop
$297Delta
Wed, Oct 21 - Tue, Oct 27

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Delta flights from Chicago Midway Airport to Pensacola

Our best Delta deals on Chicago Midway Airport to Pensacola flight tickets
Delta
Oct 10
MDW4:19 pmChicago Midway
4h 01m
1 stop
PNS8:20 pmPensacola
Oct 17
PNS5:40 pmPensacola
4h 53m
1 stop
MDW10:33 pmChicago Midway
$297
Delta
Aug 14
MDW5:10 pmChicago Midway
6h 34m
1 stop
PNS11:44 pmPensacola
Aug 17
PNS6:08 pmPensacola
4h 28m
1 stop
MDW10:36 pmChicago Midway
$339
Delta
Sep 3
MDW6:05 amChicago Midway
6h 32m
1 stop
PNS12:37 pmPensacola
Sep 8
PNS9:26 amPensacola
5h 58m
1 stop
MDW3:24 pmChicago Midway
$341

Southwest flights from Chicago Midway Airport to Pensacola

Our best Southwest deals on Chicago Midway Airport to Pensacola flight tickets
Southwest
Aug 26
MDW2:00 pmChicago Midway
3h 35m
1 stop
PNS5:35 pmPensacola
Aug 29
PNS9:40 amPensacola
4h 40m
1 stop
MDW2:20 pmChicago Midway
$288
Southwest
Sep 9
MDW2:00 pmChicago Midway
3h 35m
1 stop
PNS5:35 pmPensacola
Sep 16
PNS3:00 pmPensacola
5h 45m
1 stop
MDW8:45 pmChicago Midway
$292
Southwest
Sep 1
MDW2:00 pmChicago Midway
3h 35m
1 stop
PNS5:35 pmPensacola
Sep 6
PNS5:55 pmPensacola
5h 00m
1 stop
MDW10:55 pmChicago Midway
$293

momondo Fare Finder

 
Customize your flight search to find flights from Chicago Midway Airport to Pensacola that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, momondo users made 832,500 searches. Data last updated July 31, 2026.
Use the filters below to find and compare flights from Chicago Midway Airport to Pensacola that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoPensacola

MDW - PNS

MDWPNS

Chicago Midway

Wed 8/26

2:00 pm-5:35 pm

1 stop3h 35m

Pensacola

Sat 8/29

9:40 am-2:20 pm

1 stop4h 40m

$288

ChicagoPensacola

MDW - PNS

MDWPNS

Chicago Midway

Wed 9/9

2:00 pm-5:35 pm

1 stop3h 35m

Pensacola

Wed 9/16

3:00 pm-8:45 pm

1 stop5h 45m

$292

ChicagoPensacola

MDW - PNS

MDWPNS

Chicago Midway

Sat 9/12

6:45 am-11:50 am

1 stop5h 05m

Pensacola

Sat 9/19

9:40 am-2:20 pm

1 stop4h 40m

$292

ChicagoPensacola

MDW - PNS

MDWPNS

Chicago Midway

Wed 9/30

2:00 pm-5:35 pm

1 stop3h 35m

Pensacola

Wed 10/7

4:10 pm-10:10 pm

1 stop6h 00m

$292

ChicagoPensacola

MDW - PNS

MDWPNS

Chicago Midway

Wed 8/19

2:00 pm-5:35 pm

1 stop3h 35m

Pensacola

Sat 8/22

10:50 am-3:55 pm

1 stop5h 05m

$292

ChicagoPensacola

MDW - PNS

MDWPNS

Chicago Midway

Tue 9/8

2:00 pm-5:35 pm

1 stop3h 35m

Pensacola

Tue 9/15

7:00 am-12:15 pm

1 stop5h 15m

$292
Quickest round-trip

ChicagoPensacola

MDW - PNS

MDWPNS

Chicago Midway

Sat 10/10

4:19 pm-8:20 pm

1 stop4h 01m

Pensacola

Tue 10/13

8:05 am-11:50 am

1 stop3h 45m

$297

ChicagoPensacola

MDW - PNS

MDWPNS

Chicago Midway

Sat 10/10

4:19 pm-8:20 pm

1 stop4h 01m

Pensacola

Wed 10/14

11:58 am-4:19 pm

1 stop4h 21m

$297

ChicagoPensacola

MDW - PNS

MDWPNS

Chicago Midway

Tue 10/27

5:15 pm-11:30 pm

1 stop6h 15m

Pensacola

Tue 11/3

5:40 pm-10:33 pm

1 stop4h 53m

$297

ChicagoPensacola

MDW - PNS

MDWPNS

Chicago Midway

Wed 10/21

6:04 am-10:52 am

1 stop4h 48m

Pensacola

Tue 10/27

8:05 am-11:50 am

1 stop3h 45m

$297

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 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 September instead. Flights to Pensacola in September, while not as cheap as those in November, still average around $259.

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 Wednesday. momondo users have found tickets for Wednesday departures for as low as $336. 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 $436.

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

$281

Fastest flight time

2h 10m

Direct flights

None
The best one-way flight to Pensacola from Chicago Midway Airport in the past 72 hours is $281. The best round-trip flight deal from Chicago Midway Airport to Pensacola found on momondo in the last 72 hours is $414.
The fastest flight from Chicago Midway Airport to Pensacola takes 2h 10m
There are no direct flights from Chicago Midway Airport to Pensacola. There are no popular flight routes from Chicago Midway Airport to Pensacola.
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 10m.

  • 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
SouthwestPriceFrom $207Free CancellationRating
8.0
4,226 reviews
Search Southwest flights
DeltaPriceFrom $227Free CancellationRating
7.8
8,494 reviews
Search Delta flights

  • Southwest Flights From Chicago Midway Airport to Pensacola

    Southwest is one of the most popular airlines flying from Chicago Midway Airport to Pensacola, operating 6 flights/week on average for this route. A good Southwest flight deal for Chicago Midway Airport to Pensacola starts from $207 round-trip, up to an average price of $376. Our users have rated Southwest at 8.0/10.

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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