HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
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 12/3. Fares are subject to change and may not be available on all flights or dates of travel.
MSN — PNS
Oct 17 — Oct 241
Fri 10/17
Fri 10/24
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Madison to Pensacola with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

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

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 September 17, 2025.

Round-trip from

$199
(American Airlines)

One-way from

$126
(American Airlines)

Popular in

December

Cheapest in

July

Average price

$308
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. 7% potential increase in price ($27 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($13 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in September 2025
Search Deals

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 September 17, 2025.

This American Airlines deal was found by Cheapflights users on 9/15. 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 10/187:20 amMSN - PNS
1 stop6h 38mAmerican Airlines
Sat 10/256:53 pmPNS - MSN
1 stop4h 58mAmerican Airlines
Deal found 9/15$249
This Delta deal was found by Cheapflights users on 9/15. 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 10/45:40 amMSN - PNS
1 stop5h 10mDelta
Sat 10/1112:13 pmPNS - MSN
2 stops10h 32mDelta
Deal found 9/15$259
This United Airlines deal was found by Cheapflights users on 9/15. 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 9/3012:26 pmMSN - PNS
2 stops9h 33mUnited Airlines
Sat 10/42:17 pmPNS - MSN
1 stop4h 38mUnited Airlines
Deal found 9/15$264
This Booking.com deal was found by Cheapflights users on 9/16. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/247:59 pmMSN - PNS
1 stop19h 58mFrontier
Sun 11/24:30 pmPNS - MSN
1 stop26h 45mFrontier
Deal found 9/16$275
This Delta deal was found by Cheapflights users on 9/14. 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 10/115:30 amMSN - PNS
1 stop5h 09mDelta
Sun 10/126:00 amPNS - MSN
1 stop4h 32mDelta
Deal found 9/14$279
This American Airlines deal was found by Cheapflights users on 9/15. 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 10/176:45 amMSN - PNS
1 stop5h 52mAmerican Airlines
Tue 10/211:16 pmPNS - MSN
1 stop7h 13mAmerican Airlines
Deal found 9/15$294
This American Airlines deal was found by Cheapflights users on 9/15. 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 9/308:10 amMSN - PNS
2 stops8h 42mAmerican Airlines
Sat 10/46:40 amPNS - MSN
2 stops6h 50mAmerican Airlines
Deal found 9/15$309
This Delta deal was found by Cheapflights users on 9/15. 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 12/115:28 amMSN - PNS
1 stop5h 13mDelta
Sun 12/146:00 amPNS - MSN
1 stop4h 40mDelta
Deal found 9/15$314
This United Airlines deal was found by Cheapflights users on 9/16. 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 9/2012:19 pmMSN - PNS
2 stops9h 41mUnited Airlines
Wed 9/242:15 pmPNS - MSN
1 stop6h 25mUnited Airlines
Deal found 9/16$329

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 September 17, 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

Sat 12/6

3:55 pm-9:18 pm

1 stop5h 23m

Pensacola

Sat 12/13

3:25 pm-10:04 pm

1 stop6h 39m

$249

MadisonPensacola

MSN - PNS

MSNPNS

Madison Truax Field

Sat 10/18

7:20 am-1:58 pm

1 stop6h 38m

Pensacola

Sat 10/25

6:53 pm-11:51 pm

1 stop4h 58m

$249

MadisonPensacola

MSN - PNS

MSNPNS

Madison Truax Field

Sat 10/4

5:40 am-10:50 am

1 stop5h 10m

Pensacola

Sat 10/11

6:00 am-12:26 pm

1 stop6h 26m

$254

MadisonPensacola

MSN - PNS

MSNPNS

Madison Truax Field

Tue 10/14

6:29 am-3:00 pm

2 stops8h 31m

Pensacola

Tue 10/21

5:23 pm-10:56 pm

1 stop5h 33m

$254

MadisonPensacola

MSN - PNS

MSNPNS

Madison Truax Field

Thu 12/4

3:12 pm-10:50 pm

1 stop7h 38m

Pensacola

Mon 12/8

11:32 am-4:55 pm

1 stop5h 23m

$254

MadisonPensacola

MSN - PNS

MSNPNS

Madison Truax Field

Tue 9/30

8:15 am-1:15 pm

1 stop5h 00m

Pensacola

Sat 10/4

2:17 pm-6:55 pm

1 stop4h 38m

$259

MadisonPensacola

MSN - PNS

MSNPNS

Madison Truax Field

Sat 12/6

6:00 am-2:46 pm

2 stops8h 46m

Pensacola

Sat 12/13

7:00 am-2:20 pm

2 stops7h 20m

$259

MadisonPensacola

MSN - PNS

MSNPNS

Madison Truax Field

Fri 10/24

7:59 pm-3:57 pm

1 stop19h 58m

Pensacola

Sun 11/2

4:30 pm-7:15 pm

1 stop26h 45m

$275

MadisonPensacola

MSN - PNS

MSNPNS

Madison Truax Field

Wed 12/3

12:18 pm-8:31 pm

1 stop8h 13m

$126

MadisonPensacola

MSN - PNS

MSNPNS

Madison Truax Field

Wed 12/3

6:08 pm-3:36 pm

3 stops45h 28m

$229

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/15

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 September 12, 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, September is the cheapest month in which you can book a flight from Madison to Pensacola (average of $302). Flying from Madison to Pensacola in March is currently the most expensive (average of $415). 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 September 17, 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 12% versus a flight in the morning.

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 September 17, 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
8.0
Very good
7,961 reviews

Entertainment

7.9

Overall

8.0

Boarding

8.2

Comfort

7.9

Crew

8.5

Food

7.3

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
8.0
Very good
7,961 reviews
Delta
8.0
Very good
7,961 reviews

Entertainment

7.9

Overall

8.0

Boarding

8.2

Comfort

7.9

Crew

8.5

Food

7.3

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
8,926 reviews
Delta
8.0
Very good
7,961 reviews

Entertainment

7.9

Overall

8.0

Boarding

8.2

Comfort

7.9

Crew

8.5

Food

7.3

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
10,000 reviews
Delta
8.0
Very good
7,961 reviews

Entertainment

7.9

Overall

8.0

Boarding

8.2

Comfort

7.9

Crew

8.5

Food

7.3

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 fly from Madison to Pensacola in about 5h 23m. The time it takes to get you to your destination can typically vary by up to . Madison and Pensacola are separated by a distance of 882 mi.

  • 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 30% 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, September is the cheapest month in which you can book a flight from Madison to Pensacola (average of $302). Flying from Madison to Pensacola in March is currently the most expensive (average of $415). 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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Madison to Pensacola

See prices for flight routes from nearby airports that may be better suited for you.
O'Hare Intl to Orlando flights
O'Hare Intl to Miami flights
O'Hare Intl to Fort Lauderdale flights
Minneapolis to Orlando flights
Minneapolis to Miami flights
O'Hare Intl to Tampa flights
O'Hare Intl to Fort Myers flights
Minneapolis to Fort Lauderdale flights
Minneapolis to Tampa flights
Minneapolis to Fort Myers flights
O'Hare Intl to Sarasota flights
O'Hare Intl to Jacksonville flights
O'Hare Intl to West Palm Beach flights
Milwaukee to Orlando flights
O'Hare Intl to Key West flights
Milwaukee to Fort Myers flights
Minneapolis to Jacksonville flights
Milwaukee to Fort Lauderdale flights
Milwaukee to Miami flights
O'Hare Intl to Pensacola flights
Minneapolis to Sarasota flights
Appleton to Orlando flights
Milwaukee to Tampa flights
Minneapolis to Pensacola flights
O'Hare Intl to Panama City flights
Minneapolis to Valparaiso flights
Madison to Miami flights
Appleton to Fort Myers flights
Minneapolis to West Palm Beach flights
Appleton to Pensacola flights
Madison to Orlando flights
Green Bay to Pensacola flights
Appleton to Orlando Sanford Intl flights
Appleton to Tampa flights
Minneapolis to Key West flights
Madison to Fort Lauderdale flights
Appleton to Fort Lauderdale flights
Madison to Fort Myers flights
Madison to Sarasota flights
Milwaukee to Sarasota flights
Green Bay to Orlando flights
Appleton to Jacksonville flights
Appleton to Sarasota flights
Minneapolis to Daytona Beach flights
Milwaukee to Pensacola flights
Milwaukee to Jacksonville flights
Green Bay to Fort Myers flights
Appleton to Miami flights
Minneapolis to St Petersburg flights
Milwaukee to West Palm Beach flights

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 September 17, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$248Average$319FlexibilityNo cancel feeOn-time71%
DeltaCheapest$248Average$374FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$318Average$742FlexibilityNo cancel feeOn-time69%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.