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Pensacola

$126+ Cheap flights from Madison to Pensacola (MSN - PNS)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 5/5. Fares are subject to change and may not be available on all flights or dates of travel.
MSN — PNS
Mar 28 — Apr 41
Sat 3/28
Sat 4/4
1 adult, Economy
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Cheap flight deals from Madison to Pensacola

Cheapest flights from Madison to Pensacola
Explore the most affordable flight options available from Madison to Pensacola. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 26, 2026.

This American Airlines deal was found by Cheapflights users on 2/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/2211:35 am
MSN
-
PNS
1 stop7h 57m
American Airlines
Sat 5/26:57 pm
PNS
-
MSN
1 stop4h 59m
American Airlines
Deal found 2/25$251
This United Airlines deal was found by Cheapflights users on 2/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/1812:13 pm
MSN
-
PNS
2 stops9h 44m
United Airlines
Wed 4/222:15 pm
PNS
-
MSN
1 stop7h 01m
United Airlines
Deal found 2/22$256
This Delta deal was found by Cheapflights users on 2/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/165:29 pm
MSN
-
PNS
1 stop5h 47m
Delta
Thu 5/286:00 am
PNS
-
MSN
1 stop4h 16m
Delta
Deal found 2/24$260
This American Airlines deal was found by Cheapflights users on 2/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/1111:24 am
MSN
-
PNS
1 stop5h 43m
American Airlines
Wed 3/185:23 am
PNS
-
MSN
1 stop4h 45m
American Airlines
Deal found 2/23$265
This Delta deal was found by Cheapflights users on 2/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/195:17 pm
MSN
-
PNS
1 stop4h 44m
Delta
Sat 9/266:00 am
PNS
-
MSN
1 stop4h 11m
Delta
Deal found 2/23$269
This United Airlines deal was found by Cheapflights users on 2/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/2210:05 am
MSN
-
PNS
2 stops11h 52m
United Airlines
Sat 5/22:11 pm
PNS
-
MSN
1 stop4h 56m
United Airlines
Deal found 2/24$270
This American Airlines deal was found by Cheapflights users on 2/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/197:15 am
MSN
-
PNS
1 stop6h 32m
American Airlines
Sat 9/262:41 pm
PNS
-
MSN
2 stops6h 46m
American Airlines
Deal found 2/25$274
This Delta deal was found by Cheapflights users on 2/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/175:15 pm
MSN
-
PNS
1 stop5h 58m
Delta
Tue 3/246:00 am
PNS
-
MSN
1 stop4h 31m
Delta
Deal found 2/23$285
This American Airlines deal was found by Cheapflights users on 2/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/129:18 am
MSN
-
PNS
2 stops7h 55m
American Airlines
Tue 5/195:53 pm
PNS
-
MSN
1 stop5h 03m
American Airlines
Deal found 2/25$290
This United Airlines deal was found by Cheapflights users on 2/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/112:50 pm
MSN
-
PNS
1 stop5h 38m
United Airlines
Wed 3/186:30 am
PNS
-
MSN
2 stops8h 28m
United Airlines
Deal found 2/23$291
This American Airlines deal was found by Cheapflights users on 2/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/1611:35 am
MSN
-
PNS
1 stop7h 58m
American Airlines
Thu 5/283:10 pm
PNS
-
MSN
1 stop7h 45m
American Airlines
Deal found 2/25$294

Find flight deals from Madison to Pensacola

Discover tips and strategies to find the most affordable flight options for your journey from Madison (MSN) to Pensacola (PNS). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated February 26, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$251
(American Airlines)

One-way from

$126
(American Airlines)

Popular in

June

Cheapest in

July

Average price

$346
Provider with most accurate pricing for Madison Truax Field-Pensacola flight deals.
Search Deals
Provider most trusted by Cheapflights users for Madison Truax Field-Pensacola flights.
Search Deals
From Madison Truax Field to Pensacola
Search Deals
One-way flight from Madison Truax Field to Pensacola
Search Deals
Highest demand for flights based on searches. 6% potential increase in price ($22 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($10 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in February 2026
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Madison 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, Cheapflights users made 2,558,603 searches. Data last updated February 26, 2026.
Use the filters below to find and compare flights from Madison to Pensacola that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

MadisonPensacola

MSN - PNS

MSNPNS

Madison Truax Field

Sun 4/12

5:15 pm-9:54 pm

1 stop4h 39m

Pensacola

Wed 4/15

6:00 am-10:32 am

1 stop4h 32m

$399

MadisonPensacola

MSN - PNS

MSNPNS

Madison Truax Field

Wed 3/18

2:50 pm-8:28 pm

1 stop5h 38m

Pensacola

Mon 3/23

2:18 pm-8:55 pm

1 stop6h 37m

$409

MadisonPensacola

MSN - PNS

MSNPNS

Madison Truax Field

Sun 5/24

5:43 am-10:39 am

1 stop4h 56m

Pensacola

Thu 5/28

6:00 am-12:41 pm

2 stops6h 41m

$492

MadisonPensacola

MSN - PNS

MSNPNS

Madison Truax Field

Thu 3/5

2:50 pm-8:28 pm

1 stop5h 38m

Pensacola

Sun 3/8

7:00 am-2:02 pm

1 stop7h 02m

$498

MadisonPensacola

MSN - PNS

MSNPNS

Madison Truax Field

Thu 4/9

2:44 pm-8:38 pm

1 stop5h 54m

Pensacola

Thu 4/16

2:15 pm-10:11 am

1 stop19h 56m

$508

MadisonPensacola

MSN - PNS

MSNPNS

Madison Truax Field

Sat 3/14

3:53 pm-8:28 pm

1 stop4h 35m

Pensacola

Fri 3/20

6:30 am-11:38 am

2 stops29h 08m

$528

MadisonPensacola

MSN - PNS

MSNPNS

Madison Truax Field

Fri 4/10

8:30 am-1:18 pm

1 stop4h 48m

Pensacola

Tue 4/14

6:15 am-3:10 pm

2 stops8h 55m

$550

MadisonPensacola

MSN - PNS

MSNPNS

Madison Truax Field

Tue 5/5

9:55 am-4:53 pm

1 stop6h 58m

$126

MadisonPensacola

MSN - PNS

MSNPNS

Madison Truax Field

Tue 5/19

5:29 pm-11:16 pm

1 stop5h 47m

$126

MadisonPensacola

MSN - PNS

MSNPNS

Madison Truax Field

Sat 5/9

11:35 am-6:12 pm

1 stop6h 37m

$126

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/25

Showing 1-10 of 15 resultsSorted by cheapest first
1
2

Compare providers for flights from Madison to Pensacola

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Madison to Pensacola in February.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Madison-Pensacola flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Madison-Pensacola flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Madison-Pensacola flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Madison-Pensacola flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Madison-Pensacola flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Best time to book a flight from Madison to Pensacola

Have a flexible travel schedule? Discover the best time to fly to Pensacola from Madison with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Madison to Pensacola

How far ahead should I book a flight from Madison to Pensacola?

Use this chart to determine the optimal time to book a round-trip flight from Madison to Pensacola. Price data was last updated on February 20, 2026.

To ensure you get the cheapest price possible for a flight from Madison to Pensacola, you should look to book at least 39 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.

What is the cheapest month to book a flight from Madison to Pensacola?

Currently, November is the cheapest month in which you can book a flight from Madison to Pensacola (average of $104). Flying from Madison to Pensacola in July is currently the most expensive (average of $200). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

Reviews of airlines servicing Pensacola

Get insights into the airlines that provide service to Pensacola. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Pensacola. Reviews last updated February 26, 2026.
Read through reviews of airlines operating flights from Madison to Pensacola, such as Delta, United Airlines, and American Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Delta
7.9
Good
8,237 reviews

Food

7.2

Boarding

8.1

Crew

8.5

Entertainment

7.8

Overall

7.9

Comfort

7.9

Reviews

1 / 20
2.0
Mediocre

Joseph,Aug 2023

MSP - MCO

Even if you have delta comfort plus, they will move your overhead bag. One of the perks for upgrading is that you have dedicated space for your carry on with comfort plus with delta. They moved my carry on luggage (3) compartments back and put in bags for other passengers that should have gone under their respective seats. When deboarding the plane, there was no help from anyone to retrieve my luggage back several rows. Delta is turning into pure garbage.
Delta
7.9
Good
8,237 reviews
Delta
7.9
Good
8,237 reviews

Food

7.2

Boarding

8.1

Crew

8.5

Entertainment

7.8

Overall

7.9

Comfort

7.9

Reviews

1 / 20
2.0
Mediocre

Joseph,Aug 2023

MSP - MCO

Even if you have delta comfort plus, they will move your overhead bag. One of the perks for upgrading is that you have dedicated space for your carry on with comfort plus with delta. They moved my carry on luggage (3) compartments back and put in bags for other passengers that should have gone under their respective seats. When deboarding the plane, there was no help from anyone to retrieve my luggage back several rows. Delta is turning into pure garbage.
United Airlines
7.4
Good
9,348 reviews
Delta
7.9
Good
8,237 reviews

Food

7.2

Boarding

8.1

Crew

8.5

Entertainment

7.8

Overall

7.9

Comfort

7.9

Reviews

1 / 20
2.0
Mediocre

Joseph,Aug 2023

MSP - MCO

Even if you have delta comfort plus, they will move your overhead bag. One of the perks for upgrading is that you have dedicated space for your carry on with comfort plus with delta. They moved my carry on luggage (3) compartments back and put in bags for other passengers that should have gone under their respective seats. When deboarding the plane, there was no help from anyone to retrieve my luggage back several rows. Delta is turning into pure garbage.
American Airlines
7.2
Good
11,352 reviews
Delta
7.9
Good
8,237 reviews

Food

7.2

Boarding

8.1

Crew

8.5

Entertainment

7.8

Overall

7.9

Comfort

7.9

Reviews

1 / 20
2.0
Mediocre

Joseph,Aug 2023

MSP - MCO

Even if you have delta comfort plus, they will move your overhead bag. One of the perks for upgrading is that you have dedicated space for your carry on with comfort plus with delta. They moved my carry on luggage (3) compartments back and put in bags for other passengers that should have gone under their respective seats. When deboarding the plane, there was no help from anyone to retrieve my luggage back several rows. Delta is turning into pure garbage.

Related info for your journey

Find useful and relevant information for your journey from Madison to Pensacola. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How long is the flight from Madison to Pensacola?

    Airlines like Delta and United Airlines fly from Madison to Pensacola in about 4h 39m. The time it takes to get you to your destination can typically vary by up to 59m. Madison and Pensacola are separated by a distance of 882 mi. This flight may include one or multiple stops.

  • What are the cheapest airlines flying from Madison to Pensacola round-trip?

    Cheapflights users have booked flights from Madison to Pensacola round-trip from $222. Other airlines that can offer you cheap pricing are American Airlines, from $248, and United Airlines, from $293. You may be able to fly from Madison to Pensacola for 33% less than the average price by searching for these airlines.

  • Can I find deals for flights from Madison to Pensacola that include hotel bookings?

    Yes. In addition to deals on Madison to Pensacola flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Madison to Pensacola?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Madison to Pensacola.

  • Can I find deals for business class flights from Madison to Pensacola?

    Yes. Cheapflights offers flight deals from Madison to Pensacola by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Madison to Pensacola?

    Currently, November is the cheapest month in which you can book a flight from Madison to Pensacola (average of $104). Flying from Madison to Pensacola in July is currently the most expensive (average of $200). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Traveling to a place near Pensacola?

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

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Top 3 airlines flying from Madison to Pensacola

Discover the top 3 airlines that operate flights from Madison to Pensacola. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated February 26, 2026.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$222Average$338FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$248Average$314FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$293Average$397FlexibilityNo cancel feeOn-time69%

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