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Pensacola

$239+ 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 2/27. Fares are subject to change and may not be available on all flights or dates of travel.
MSN — PNS
Nov 29 — Dec 61
Sat 11/29
Sat 12/6
1 adult, Economy
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Cheapflights Tip: The best prices from Madison Truax Field to Pensacola are usually found in July or September, booked 39 days in advance, depart on a Tuesday or Wednesday and return on a Friday

Find 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 October 30, 2025.

This American Airlines deal was found by Cheapflights users on 10/27. 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.
Thu 12/43:12 pmMSN - PNS
1 stop7h 38mAmerican Airlines
Mon 12/83:24 pmPNS - MSN
1 stop6h 31mAmerican Airlines
Deal found 10/27$249
This American Airlines deal was found by Cheapflights users on 10/29. 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 12/69:59 amMSN - PNS
2 stops8h 51mAmerican Airlines
Mon 12/83:24 pmPNS - MSN
1 stop6h 31mAmerican Airlines
Deal found 10/29$254
This Delta deal was found by Cheapflights users on 10/29. 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 12/96:00 amMSN - PNS
2 stops8h 45mDelta
Tue 12/1611:42 amPNS - MSN
2 stops11h 15mDelta
Deal found 10/29$259
This Delta deal was found by Cheapflights users on 10/28. 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 11/155:29 amMSN - PNS
1 stop5h 12mDelta
Thu 11/206:00 amPNS - MSN
1 stop4h 38mDelta
Deal found 10/28$264
This Delta deal was found by Cheapflights users on 10/28. 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.
Thu 11/1311:28 amMSN - PNS
1 stop6h 36mDelta
Mon 11/176:00 amPNS - MSN
1 stop4h 38mDelta
Deal found 10/28$279
This American Airlines deal was found by Cheapflights users on 10/28. 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.
Thu 11/135:00 amMSN - PNS
2 stops7h 26mAmerican Airlines
Mon 11/175:24 pmPNS - MSN
1 stop6h 06mAmerican Airlines
Deal found 10/28$284
This American Airlines deal was found by Cheapflights users on 10/27. 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.
Fri 11/217:07 amMSN - PNS
1 stop5h 19mAmerican Airlines
Mon 11/2411:56 amPNS - MSN
2 stops10h 09mAmerican Airlines
Deal found 10/27$289
This United Airlines deal was found by Cheapflights users on 10/29. 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.
Tue 11/116:30 amMSN - PNS
1 stop6h 45mUnited Airlines
Tue 11/182:17 pmPNS - MSN
1 stop6h 18mUnited Airlines
Deal found 10/29$309

Cheap 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 October 30, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$249
(American Airlines)

One-way from

$239
(Delta)

Popular in

March

Cheapest in

July

Average price

$318
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. 5% potential increase in price ($20 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 October 2025
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 October 30, 2025.
Use the filters below to find and compare flights from Madison to Pensacola that are best for you.

Fly from

Madison

Fly to

Pensacola

Route

Depart

Return

Price

MadisonPensacola

MSN - PNS

MSNPNS

Madison Truax Field

Wed 1/14

3:57 pm-9:43 pm

1 stop5h 46m

Pensacola

Sat 1/24

5:24 pm-11:40 pm

1 stop6h 16m

$249

MadisonPensacola

MSN - PNS

MSNPNS

Madison Truax Field

Tue 12/9

6:00 am-2:45 pm

2 stops8h 45m

Pensacola

Tue 12/16

6:00 am-10:59 am

1 stop4h 59m

$254

MadisonPensacola

MSN - PNS

MSNPNS

Madison Truax Field

Sat 11/15

5:29 am-12:41 pm

1 stop7h 12m

Pensacola

Thu 11/20

6:00 am-10:38 am

1 stop4h 38m

$264

MadisonPensacola

MSN - PNS

MSNPNS

Madison Truax Field

Thu 11/13

11:28 am-6:04 pm

1 stop6h 36m

Pensacola

Mon 11/17

6:00 am-10:38 am

1 stop4h 38m

$279

MadisonPensacola

MSN - PNS

MSNPNS

Madison Truax Field

Fri 11/21

7:07 am-12:26 pm

1 stop5h 19m

Pensacola

Mon 11/24

5:24 am-11:49 am

1 stop6h 25m

$284

MadisonPensacola

MSN - PNS

MSNPNS

Madison Truax Field

Thu 11/13

5:00 am-12:26 pm

2 stops7h 26m

Pensacola

Mon 11/17

5:24 pm-11:30 pm

1 stop6h 06m

$284

MadisonPensacola

MSN - PNS

MSNPNS

Madison Truax Field

Thu 11/20

5:29 am-10:41 am

1 stop5h 12m

Pensacola

Mon 11/24

6:00 am-10:38 am

1 stop4h 38m

$284

MadisonPensacola

MSN - PNS

MSNPNS

Madison Truax Field

Thu 12/4

6:13 am-2:05 pm

2 stops7h 52m

Pensacola

Mon 12/8

3:24 pm-9:55 pm

1 stop6h 31m

$299

MadisonPensacola

MSN - PNS

MSNPNS

Madison Truax Field

Tue 11/11

6:30 am-1:15 pm

1 stop6h 45m

Pensacola

Tue 11/18

2:17 pm-8:35 pm

1 stop6h 18m

$309

MadisonPensacola

MSN - PNS

MSNPNS

Madison Truax Field

Fri 2/27

5:45 am-12:53 pm

1 stop7h 08m

$239

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/27

Showing 1-10 of 12 results
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 October.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star
eDreamsPrice 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 eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Madison-Pensacola flight deals on Cheapflights vs. eDreams >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 eDreams the most. eDreams 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 October 24, 2025.

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 March is currently the most expensive (average of $240). 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.

What is the cheapest time of day to fly from MSN to PNS?

Find hourly flight availability from Madison to Pensacola. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated October 30, 2025.

When flying from Madison to Pensacola, the time of day you fly usually plays a role in the price. Save by searching for a flight at noon, which can drop the price by up to 50% versus a flight in the evening.

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 October 30, 2025.
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
7,998 reviews

Food

7.3

Crew

8.5

Comfort

7.9

Overall

7.9

Boarding

8.2

Entertainment

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
7,998 reviews
Delta
7.9
Good
7,998 reviews

Food

7.3

Crew

8.5

Comfort

7.9

Overall

7.9

Boarding

8.2

Entertainment

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
8,998 reviews
Delta
7.9
Good
7,998 reviews

Food

7.3

Crew

8.5

Comfort

7.9

Overall

7.9

Boarding

8.2

Entertainment

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
11,035 reviews
Delta
7.9
Good
7,998 reviews

Food

7.3

Crew

8.5

Comfort

7.9

Overall

7.9

Boarding

8.2

Entertainment

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 American Airlines and Delta fly from Madison to Pensacola in about 5h 46m. The time it takes to get you to your destination can typically vary by up to 2h 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 $248. Other airlines that can offer you cheap pricing are Delta, from $248, and United Airlines, from $318. You may be able to fly from Madison to Pensacola for 29% less than the average price by searching for these airlines.

  • What are the cheapest airlines to fly from Madison to Pensacola one-way?

    To fly one-way, consider booking your trip with Delta, which is currently one of the cheapest options available, starting at $239. United Airlines flights start at $277 while deals on Alaska Airlines start at $560 one-way.

  • 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 March is currently the most expensive (average of $240). 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
Perdido Key
Navarre Beach
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 October 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$248Average$324FlexibilityNo cancel feeOn-time71%
DeltaCheapest$248Average$373FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$318Average$618FlexibilityNo cancel feeOn-time69%

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