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Valparaiso

$245+ Cheap flights from Madison to Valparaiso, FL (MSN - VPS)

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 10/23. Fares are subject to change and may not be available on all flights or dates of travel.
MSN — VPS
Oct 29 — Nov 51
Wed 10/29
Wed 11/5
1 adult, Economy
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Cheap flight deals from Madison to Valparaiso

Discover tips and strategies to find the most affordable flight options for your journey from Madison (MSN) to Valparaiso (VPS). 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 29, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$377
(American Airlines)

One-way from

$245
(Delta)

Popular in

December

Cheapest in

July

Average price

$474
Provider with most accurate pricing for Madison Truax Field-Valparaiso Destin-Ft Walton Beach flight deals.
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Provider most trusted by Cheapflights users for Madison Truax Field-Valparaiso Destin-Ft Walton Beach flights.
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From Madison Truax Field to Valparaiso Destin-Ft Walton Beach
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One-way flight from Madison Truax Field to Valparaiso Destin-Ft Walton Beach
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Highest demand for flights based on searches. 14% potential increase in price ($82 potential increase over avg. RT price).
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Cheapest flight prices on average. 5% potential price decrease ($27 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Find flight deals from Madison to Valparaiso

Cheapest flights from Madison to Valparaiso
Explore the most affordable flight options available from Madison to Valparaiso. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 29, 2025.

This Delta deal was found by Cheapflights users on 9/27. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/245:15 pmMSN - VPS
1 stop5h 50mDelta
Sun 11/23:45 pmVPS - MSN
1 stop7h 00mDelta
Deal found 9/27$405
This Delta deal was found by Cheapflights users on 9/29. 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.
Thu 10/235:15 pmMSN - VPS
1 stop5h 50mDelta
Mon 10/276:00 amVPS - MSN
1 stop4h 32mDelta
Deal found 9/29$420
This American Airlines deal was found by Cheapflights users on 9/28. 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.
Wed 10/228:09 amMSN - VPS
1 stop4h 45mAmerican Airlines
Tue 10/2811:20 amVPS - MSN
1 stop5h 24mAmerican Airlines
Deal found 9/28$427
This Delta deal was found by Cheapflights users on 9/29. 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.
Wed 10/85:30 amMSN - VPS
1 stop4h 24mDelta
Sun 10/126:00 amVPS - MSN
1 stop4h 32mDelta
Deal found 9/29$457
This American Airlines deal was found by Cheapflights users on 9/28. 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.
Wed 10/88:09 amMSN - VPS
1 stop4h 45mAmerican Airlines
Sun 10/127:07 amVPS - MSN
1 stop5h 21mAmerican Airlines
Deal found 9/28$492
This American Airlines deal was found by Cheapflights users on 9/29. 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.
Thu 10/237:20 amMSN - VPS
1 stop7h 54mAmerican Airlines
Mon 10/274:04 pmVPS - MSN
2 stops7h 32mAmerican Airlines
Deal found 9/29$552

Cheapflights Fare Finder

 
Customize your flight search to find flights from Madison to Valparaiso 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 29, 2025.
Use the filters below to find and compare flights from Madison to Valparaiso that are best for you.

Fly from

Madison

Fly to

Valparaiso

Route

Depart

Return

Price

MadisonValparaiso

MSN - VPS

MSNVPS

Madison Truax Field

Sat 2/21

11:22 am-6:34 pm

1 stop7h 12m

Valparaiso Destin-Ft Walton Beach

Sat 2/28

12:30 pm-5:30 pm

1 stop5h 00m

$377

MadisonValparaiso

MSN - VPS

MSNVPS

Madison Truax Field

Fri 10/24

5:15 pm-11:05 pm

1 stop5h 50m

Valparaiso Destin-Ft Walton Beach

Sun 11/2

3:45 pm-10:45 pm

1 stop7h 00m

$405

MadisonValparaiso

MSN - VPS

MSNVPS

Madison Truax Field

Tue 3/10

5:17 pm-11:08 pm

1 stop5h 51m

Valparaiso Destin-Ft Walton Beach

Wed 3/11

6:00 am-10:17 am

1 stop4h 17m

$407

MadisonValparaiso

MSN - VPS

MSNVPS

Madison Truax Field

Thu 10/23

5:15 pm-11:05 pm

1 stop5h 50m

$245

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/27

Compare providers for flights from Madison to Valparaiso

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 Valparaiso in September.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
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-Valparaiso, Florida flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Madison-Valparaiso, Florida flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Madison-Valparaiso, Florida flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Madison-Valparaiso, Florida 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-Valparaiso, Florida 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 Valparaiso

Have a flexible travel schedule? Discover the best time to fly to Valparaiso 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 Valparaiso

What is the cheapest month to book a flight from Madison to Valparaiso, Florida?

Currently, September is the cheapest month in which you can book a flight from Madison to Valparaiso, Florida (average of $267). Flying from Madison to Valparaiso, Florida in March is currently the most expensive (average of $386). 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 Valparaiso

Get insights into the airlines that provide service to Valparaiso. 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 Valparaiso. Reviews last updated September 29, 2025.
Get a feel of what it's like to fly with Delta and American Airlines from Madison to Valparaiso by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
7,964 reviews

Crew

8.5

Comfort

7.9

Entertainment

7.9

Boarding

8.2

Overall

8.0

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
7,964 reviews
Delta
8.0
Very good
7,964 reviews

Crew

8.5

Comfort

7.9

Entertainment

7.9

Boarding

8.2

Overall

8.0

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
7,964 reviews

Crew

8.5

Comfort

7.9

Entertainment

7.9

Boarding

8.2

Overall

8.0

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 Valparaiso. 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 Valparaiso, Florida?

    American Airlines and Delta can get you from Madison to Valparaiso, Florida in just under 5h 50m. Your travel time can differ by up to 1h 22m. Airlines will cover a distance of 887 mi. This flight may include one or multiple stops.

  • What are the cheapest airlines flying from Madison to Valparaiso, Florida round-trip?

    According to our current data, American Airlines ($327), and Delta ($327) offers the cheapest pricing from Madison to Valparaiso, Florida. American Airlines is currently priced 32% below the average price you’ll pay for this route.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Madison to Valparaiso 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 Valparaiso, Florida?

    Currently, September is the cheapest month in which you can book a flight from Madison to Valparaiso, Florida (average of $267). Flying from Madison to Valparaiso, Florida in March is currently the most expensive (average of $386). 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 Valparaiso?

Book flights to Valparaiso if you plan to visit one of these locations
Crestview
Andalusia
Niceville

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Top 2 airlines flying from Madison to Valparaiso

Discover the top 2 airlines that operate flights from Madison to Valparaiso. 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 29, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$327Average$487FlexibilityNo cancel feeOn-time71%
DeltaCheapest$327Average$461FlexibilityNo cancel feeOn-timeN/A

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