$273+ Cheap flights from Madison to Pensacola (MSN - PNS)
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 10/25. Fares are subject to change and may not be available on all flights or dates of travel.
MSN — PNS
Oct 4 — Oct 111
Round-trip
1 adult, Economy
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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.Cheap flight deals from Madison to Pensacola
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Best
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One-way
Cheapest flights from Madison to PensacolaExplore 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 4, 2026.
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 4, 2026.
This Kiwi.com deal was found by Cheapflights users on 9/3. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/256:00 pm -
1 stop25h 59m
Tue 11/37:00 pm -
2 stops14h 53m
Deal found 9/3![Multiple Airlines logo]()
$273
This Kiwi.com deal was found by Cheapflights users on 9/3. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/186:00 pm -
1 stop25h 20m
Mon 10/268:54 pm -
1 stop12h 56m
Deal found 9/3![Multiple Airlines logo]()
$277
This Kiwi.com deal was found by Cheapflights users on 9/2. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/2010:30 am -
1 stop26h 15m
Mon 10/268:54 pm -
1 stop12h 56m
Deal found 9/2![Multiple Airlines logo]()
$281
This Delta deal was found by Cheapflights users on 9/2. 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 10/245:51 am -
1 stop6h 43m
Tue 11/105:50 pm -
1 stop5h 00m
Deal found 9/2![Delta logo]()
$285
This United Airlines deal was found by Cheapflights users on 9/2. 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 10/2412:39 pm -
2 stops9h 31m
Sat 11/72:22 pm -
1 stop6h 43m
Deal found 9/2![United Airlines logo]()
$290
This United Airlines deal was found by Cheapflights users on 9/3. 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 10/2412:39 pm -
2 stops9h 31m
Sat 10/316:30 am -
2 stops8h 37m
Deal found 9/3![United Airlines logo]()
$295
This Kiwi.com deal was found by Cheapflights users on 9/3. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/2810:33 am -
2 stops8h 22m
Mon 11/95:30 pm -
1 stop16h 20m
Deal found 9/3![Multiple Airlines logo]()
$296
This Kiwi.com deal was found by Cheapflights users on 9/3. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/2110:33 am -
2 stops8h 32m
Tue 11/31:20 pm -
1 stop20h 33m
Deal found 9/3![Breeze Airways logo]()
$300
Best flights from Madison to PensacolaDiscover carefully curated flight deals from Madison to Pensacola that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 4, 2026.
Discover carefully curated flight deals from Madison to Pensacola that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 4, 2026.
This Delta deal was found by Cheapflights users on 9/3. 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.
Fri 9/185:05 pm -
1 stop6h 16m
Tue 9/225:30 pm -
1 stop5h 11m
Deal found 9/3![Delta logo]()
$349
This United Airlines deal was found by Cheapflights users on 9/3. 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 10/208:17 am -
1 stop5h 17m
Sat 10/244:18 pm -
1 stop6h 17m
Deal found 9/3![United Airlines logo]()
$365
This Delta deal was found by Cheapflights users on 9/4. 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 2/185:17 pm -
1 stop6h 10m
Mon 2/225:45 pm -
1 stop4h 49m
Deal found 9/4![Delta logo]()
$351
This United Airlines deal was found by Cheapflights users on 9/2. 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 10/176:42 am -
2 stops9h 35m
Sat 10/247:00 am -
2 stops8h 04m
Deal found 9/2![United Airlines logo]()
$393
This Delta deal was found by Cheapflights users on 8/30. 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 10/15:50 am -
1 stop4h 49m
Tue 10/66:00 am -
1 stop4h 19m
Deal found 8/30![Delta logo]()
$411
This United Airlines deal was found by Cheapflights users on 8/31. 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.
Sun 1/246:40 am -
1 stop6h 36m
Sun 1/312:18 pm -
1 stop6h 45m
Deal found 8/31![United Airlines logo]()
$434
This United Airlines deal was found by Cheapflights users on 8/30. 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.
Fri 10/166:49 am -
1 stop6h 25m
Fri 10/234:18 pm -
1 stop6h 17m
Deal found 8/30![United Airlines logo]()
$448
This Delta deal was found by Cheapflights users on 9/2. 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.
Fri 2/125:17 pm -
1 stop6h 10m
Mon 2/1511:59 am -
1 stop4h 35m
Deal found 9/2![Delta logo]()
$458
This United Airlines deal was found by Cheapflights users on 8/30. 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 10/2111:15 am -
2 stops10h 55m
Thu 10/2910:30 am -
2 stops13h 07m
Deal found 8/30![United Airlines logo]()
$469
This Delta deal was found by Cheapflights users on 8/30. 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.
Fri 10/165:20 pm -
1 stop6h 10m
Sun 10/186:00 am -
1 stop4h 19m
Deal found 8/30![Delta logo]()
$491
This United Airlines deal was found by Cheapflights users on 9/1. 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 10/2412:39 pm -
2 stops9h 31m
Sat 10/316:30 am -
3 stops16h 37m
Deal found 9/1![United Airlines logo]()
$502
Last-minute flights from Madison to PensacolaDiscover last-minute flight deals from Madison to Pensacola. Data last updated September 4, 2026 and is based on user searches.
Discover last-minute flight deals from Madison to Pensacola. Data last updated September 4, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 9/3. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/186:00 pm -
1 stop25h 20m
Mon 10/268:54 pm -
1 stop12h 56m
Deal found 9/3![Multiple Airlines logo]()
$277
This Kiwi.com deal was found by Cheapflights users on 9/2. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/2010:30 am -
1 stop26h 15m
Mon 10/268:54 pm -
1 stop12h 56m
Deal found 9/2![Multiple Airlines logo]()
$281
This Kiwi.com deal was found by Cheapflights users on 9/3. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/2110:33 am -
2 stops8h 32m
Tue 11/31:20 pm -
1 stop20h 33m
Deal found 9/3![Breeze Airways logo]()
$300
This Delta deal was found by Cheapflights users on 9/2. 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 10/245:51 am -
1 stop6h 43m
Tue 11/105:50 pm -
1 stop5h 00m
Deal found 9/2![Delta logo]()
$285
This United Airlines deal was found by Cheapflights users on 9/2. 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 10/2412:39 pm -
2 stops9h 31m
Sat 11/72:22 pm -
1 stop6h 43m
Deal found 9/2![United Airlines logo]()
$290
This United Airlines deal was found by Cheapflights users on 9/3. 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 10/2412:39 pm -
2 stops9h 31m
Sat 10/316:30 am -
2 stops8h 37m
Deal found 9/3![United Airlines logo]()
$295
This Kiwi.com deal was found by Cheapflights users on 9/3. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/256:00 pm -
1 stop25h 59m
Tue 11/37:00 pm -
2 stops14h 53m
Deal found 9/3![Multiple Airlines logo]()
$273
This Kiwi.com deal was found by Cheapflights users on 9/3. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/2810:33 am -
2 stops8h 22m
Mon 11/95:30 pm -
1 stop16h 20m
Deal found 9/3![Multiple Airlines logo]()
$296
One-way flights from Madison to PensacolaSearch for one-way flight options from Madison to Pensacola. Find affordable one-way fares based on user searches. Data last updated September 4, 2026.
Search for one-way flight options from Madison to Pensacola. Find affordable one-way fares based on user searches. Data last updated September 4, 2026.
This deal was found by Cheapflights users on 8/31. 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/136:30 am -
1 stop6h 39m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 8/31![United Airlines logo]()
$424
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 September 4, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $273 (Kiwi.com) |
Popular in | May |
Cheapest in | February |
Average price | $284 |
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 7,457,451 searches. Data last updated September 4, 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
Cheapest round-trip
MadisonPensacola
MSN Madison Truax Field - PNS Pensacola
MSNPNS
Madison Truax Field
Fri 9/18
5:05 pm-11:21 pm
1 stop6h 16m
Pensacola
Tue 9/22
5:30 pm-10:41 pm
1 stop5h 11m
$349
MadisonPensacola
MSN Madison Truax Field - PNS Pensacola
MSNPNS
Madison Truax Field
Thu 2/18
5:17 pm-11:27 pm
1 stop6h 10m
Pensacola
Mon 2/22
5:45 pm-10:34 pm
1 stop4h 49m
$351
MadisonPensacola
MSN Madison Truax Field - PNS Pensacola
MSNPNS
Madison Truax Field
Tue 10/20
8:17 am-1:34 pm
1 stop5h 17m
Pensacola
Sat 10/24
4:18 pm-10:35 pm
1 stop6h 17m
$365
MadisonPensacola
MSN Madison Truax Field - PNS Pensacola
MSNPNS
Madison Truax Field
Sat 10/17
6:42 am-4:17 pm
2 stops9h 35m
Pensacola
Sat 10/24
7:00 am-3:04 pm
2 stops8h 04m
$393
MadisonPensacola
MSN Madison Truax Field - PNS Pensacola
MSNPNS
Madison Truax Field
Thu 10/1
5:50 am-10:39 am
1 stop4h 49m
Pensacola
Tue 10/6
6:00 am-10:19 am
1 stop4h 19m
$411
Quickest round-trip
MadisonPensacola
MSN Madison Truax Field - PNS Pensacola
MSNPNS
Madison Truax Field
Sun 9/13
6:30 am-1:09 pm
1 stop6h 39m
Pensacola
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$424
MadisonPensacola
MSN Madison Truax Field - PNS Pensacola
MSNPNS
Madison Truax Field
Sun 1/24
6:40 am-1:16 pm
1 stop6h 36m
Pensacola
Sun 1/31
2:18 pm-9:03 pm
1 stop6h 45m
$434
MadisonPensacola
MSN Madison Truax Field - PNS Pensacola
MSNPNS
Madison Truax Field
Fri 10/16
6:49 am-1:14 pm
1 stop6h 25m
Pensacola
Fri 10/23
4:18 pm-10:35 pm
1 stop6h 17m
$448
MadisonPensacola
MSN Madison Truax Field - PNS Pensacola
MSNPNS
Madison Truax Field
Fri 2/12
5:17 pm-11:27 pm
1 stop6h 10m
Pensacola
Mon 2/15
11:59 am-4:34 pm
1 stop4h 35m
$458
MadisonPensacola
MSN Madison Truax Field - PNS Pensacola
MSNPNS
Madison Truax Field
Wed 10/21
11:15 am-10:10 pm
2 stops10h 55m
Pensacola
Thu 10/29
10:30 am-11:37 pm
2 stops13h 07m
$469
Showing 1-10 of 12 resultsSorted by cheapest first
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 September.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars |
- 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.
MSN-PNS
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?
To ensure you get the cheapest price possible for a flight from Madison to Pensacola, you should look to book at least 22 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, February is the cheapest month in which you can book a flight from Madison to Pensacola (average of $283). Flying from Madison to Pensacola in May is currently the most expensive (average of $434). 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.
How much does it cost to fly round-trip from Madison to Pensacola?
Airfare is below average for this route at the moment.
Madison to Pensacola flights typically cost between $274 and $346 in October.The cheapest round-trip price found within the last 5 days was $273 on Multiple Airlines (Oct 25-Nov 3).
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 4, 2026.
Read through reviews of airlines operating flights from Madison to Pensacola, such as Delta,United Airlines, andAmerican Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Comfort
7.8
Food
7.2
Crew
8.5
Entertainment
7.8
Overall
7.8
Boarding
8.1
Reviews
1 / 20
4.0
OkayJoel,May 2026
ATL - JAX
Comfort
7.8
Food
7.2
Crew
8.5
Entertainment
7.8
Overall
7.8
Boarding
8.1
Reviews
1 / 20
4.0
OkayJoel,May 2026
ATL - JAX
Comfort
7.8
Food
7.2
Crew
8.5
Entertainment
7.8
Overall
7.8
Boarding
8.1
Reviews
1 / 20
4.0
OkayJoel,May 2026
ATL - JAX
Comfort
7.8
Food
7.2
Crew
8.5
Entertainment
7.8
Overall
7.8
Boarding
8.1
Reviews
1 / 20
4.0
OkayJoel,May 2026
ATL - JAX
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.
Traveling to a place near Pensacola?
Book flights to Pensacola if you plan to visit one of these locationsNavarre
Gulf Breeze
Foley
Navarre Beach
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Madison and Pensacola flights
Browse other Madison and Pensacola flight options. Last updated on September 4, 2026.
Other flights from Madison
Browse through other flights departing from Madison. Flights are based on user searches made on Cheapflights and were last updated on September 4, 2026.
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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 7,457,451 searches. Data last updated September 4, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$248 | Average$341 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$248 | Average$306 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$290 | Average$364 | FlexibilityNo cancel fee | On-time69% |