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Cheap flights from Chicago Midway Airport to Pensacola from $74

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 12/9. 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

Enter your travel dates to find the best prices.
Southwest Logo
5:25 am - 9:25 amMDW-PNS
4h 00m1 stop
Southwest Logo
10:25 am - 5:25 pmPNS-MDW
7h 00m2 stops
$207Southwest
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Sun, Feb 1 - Sat, Feb 7
Multiple Airlines Logo
11:36 am - 11:22 amMDW-PNS
23h 46m1 stop
Multiple Airlines Logo
4:30 pm - 11:30 amPNS-MDW
19h 00m1 stop
$218Multiple Airlines
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Sat, Nov 1 - Sat, Nov 8
Southwest Logo
10:50 am - 3:35 pmMDW-PNS
4h 45m1 stop
Southwest Logo
3:30 pm - 8:20 pmPNS-MDW
4h 50m1 stop
$224Southwest
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Tue, Nov 18 - Sat, Nov 22
Delta Logo
10:47 am - 2:49 pmMDW-PNS
4h 02m1 stop
Delta Logo
5:00 pm - 11:40 pmPNS-MDW
6h 40m1 stop
$229Delta
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Wed, Nov 19 - Sat, Nov 22
Multiple Airlines Logo
11:36 am - 11:22 amMDW-PNS
23h 46m1 stop
Multiple Airlines Logo
4:30 pm - 12:37 pmPNS-MDW
20h 07m2 stops
$233Multiple Airlines
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Sat, Nov 1 - Sat, Nov 8
Southwest Logo
5:25 am - 9:25 amMDW-PNS
4h 00m1 stop
Southwest Logo
7:05 am - 6:10 pmPNS-MDW
11h 05m1 stop
$235Southwest
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Fri, Feb 6 - Mon, Feb 9
Delta Logo
10:40 am - 5:08 pmMDW-PNS
6h 28m1 stop
Delta Logo
6:00 am - 9:52 amPNS-MDW
3h 52m1 stop
$239Delta
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Wed, Nov 5 - Tue, Nov 11
Delta Logo
5:09 pm - 9:17 pmMDW-PNS
4h 08m1 stop
Delta Logo
4:27 pm - 10:14 pmPNS-MDW
5h 47m1 stop
$249Delta
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Mon, Nov 3 - Fri, Nov 7
Southwest Logo
12:30 pm - 6:50 pmMDW-PNS
6h 20m2 stops
Southwest Logo
7:05 am - 6:10 pmPNS-MDW
11h 05m1 stop
$253Southwest
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Fri, Feb 6 - Mon, Feb 9
Frontier Logo
12:30 pm - 3:23 pmMDW-PNS
26h 53m1 stop
Frontier Logo
4:30 pm - 10:26 amPNS-MDW
17h 56m2 stops
$263Frontier
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Fri, Oct 31 - Fri, Nov 7

Southwest flights from Chicago Midway Airport to Pensacola

Our best Southwest deals on Chicago Midway Airport to Pensacola flight tickets
Southwest
Feb 1
MDW5:25 amChicago Midway
4h 00m
1 stop
PNS9:25 amPensacola
Feb 7
PNS10:25 amPensacola
7h 00m
2 stops
MDW5:25 pmChicago Midway
$207
Find similar
Southwest
Nov 18
MDW10:50 amChicago Midway
4h 45m
1 stop
PNS3:35 pmPensacola
Nov 22
PNS3:30 pmPensacola
4h 50m
1 stop
MDW8:20 pmChicago Midway
$224
Find similar
Southwest
Feb 6
MDW5:25 amChicago Midway
4h 00m
1 stop
PNS9:25 amPensacola
Feb 9
PNS7:05 amPensacola
11h 05m
1 stop
MDW6:10 pmChicago Midway
$235
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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
Nov 19
MDW10:47 amChicago Midway
4h 02m
1 stop
PNS2:49 pmPensacola
Nov 22
PNS5:00 pmPensacola
6h 40m
1 stop
MDW11:40 pmChicago Midway
$229
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Delta
Nov 5
MDW10:40 amChicago Midway
6h 28m
1 stop
PNS5:08 pmPensacola
Nov 11
PNS6:00 amPensacola
3h 52m
1 stop
MDW9:52 amChicago Midway
$239
Find similar
Delta
Nov 3
MDW5:09 pmChicago Midway
4h 08m
1 stop
PNS9:17 pmPensacola
Nov 7
PNS4:27 pmPensacola
5h 47m
1 stop
MDW10:14 pmChicago Midway
$249
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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 October 21, 2025.
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

ChicagoPensacola

MDW - PNS

MDWPNS

Chicago Midway

Sun 2/1

5:25 am-9:25 am

1 stop4h 00m

Pensacola

Sat 2/7

10:25 am-5:25 pm

2 stops7h 00m

$207

ChicagoPensacola

MDW - PNS

MDWPNS

Chicago Midway

Sat 11/1

11:36 am-11:22 am

1 stop23h 46m

Pensacola

Sat 11/8

4:30 pm-11:30 am

1 stop19h 00m

$218

ChicagoPensacola

MDW - PNS

MDWPNS

Chicago Midway

Tue 11/18

10:50 am-3:35 pm

1 stop4h 45m

Pensacola

Sat 11/22

3:30 pm-8:20 pm

1 stop4h 50m

$224

ChicagoPensacola

MDW - PNS

MDWPNS

Chicago Midway

Wed 11/19

10:47 am-2:49 pm

1 stop4h 02m

Pensacola

Sat 11/22

5:00 pm-11:40 pm

1 stop6h 40m

$229

ChicagoPensacola

MDW - PNS

MDWPNS

Chicago Midway

Sat 11/1

11:36 am-11:22 am

1 stop23h 46m

Pensacola

Sat 11/8

4:30 pm-12:37 pm

2 stops20h 07m

$233

ChicagoPensacola

MDW - PNS

MDWPNS

Chicago Midway

Fri 2/6

5:25 am-9:25 am

1 stop4h 00m

Pensacola

Mon 2/9

7:05 am-6:10 pm

1 stop11h 05m

$235

ChicagoPensacola

MDW - PNS

MDWPNS

Chicago Midway

Wed 11/5

10:40 am-5:08 pm

1 stop6h 28m

Pensacola

Tue 11/11

6:00 am-9:52 am

1 stop3h 52m

$239

ChicagoPensacola

MDW - PNS

MDWPNS

Chicago Midway

Mon 11/3

5:09 pm-9:17 pm

1 stop4h 08m

Pensacola

Fri 11/7

4:27 pm-10:14 pm

1 stop5h 47m

$249

ChicagoPensacola

MDW - PNS

MDWPNS

Chicago Midway

Fri 2/6

12:30 pm-6:50 pm

2 stops6h 20m

Pensacola

Mon 2/9

7:05 am-6:10 pm

1 stop11h 05m

$253

ChicagoPensacola

MDW - PNS

MDWPNS

Chicago Midway

Fri 10/31

12:30 pm-3:23 pm

1 stop26h 53m

Pensacola

Fri 11/7

4:30 pm-10:26 am

2 stops17h 56m

$263

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 September. Flight prices, which tend to average around $217, are often lower during this time because this is during the off-season. If you aren’t able to travel during the month of September, then book flights to Pensacola from Chicago Midway Airport during January instead. Flights to Pensacola in January, while not as cheap as those in September, still average around $228.

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 $314. However, this price may fluctuate depending on the airline, the season, and holidays. On the other hand, Friday 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 $394.

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 afternoon when flights can be purchased for as low as $293. Flights to Pensacola are more costly in the evening, with an average ticket price of $379. Departure times in the evening 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 to Pensacola flights?

There is only 1 cabin class 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?

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

Fastest flight time

2h 10m

Direct flights

Every day

Airports in Pensacola

1 airport
The fastest flight from Chicago Midway Airport to Pensacola takes 2h 10m
Direct flights go from Chicago Midway Airport to Pensacola every day.
There is 1 airport near Pensacola: Pensacola (PNS)
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  • 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 $196Free CancellationRating
7.9
7,978 reviews
Search Delta flights
SouthwestPriceFrom $214Free CancellationRating
8.0
4,235 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
Perdido Key
Navarre Beach
Navarre
Milton
Atmore
Gulf Breeze
Warrington
Evergreen

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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