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$377+ Cheap flights from Valparaiso, FL to Madison (VPS - MSN)

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 12/10. Fares are subject to change and may not be available on all flights or dates of travel.
VPS — MSN
Dec 3 — Dec 101
Wed 12/3
Wed 12/10
1 adult, Economy
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Cheap flight deals from Valparaiso to Madison

Discover tips and strategies to find the most affordable flight options for your journey from Valparaiso (VPS) to Madison (MSN). 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 November 3, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$377
(Delta)
Provider with most accurate pricing for Valparaiso Destin-Ft Walton Beach-Madison Truax Field flight deals.
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Provider most trusted by Cheapflights users for Valparaiso Destin-Ft Walton Beach-Madison Truax Field flights.
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From Valparaiso Destin-Ft Walton Beach to Madison Truax Field
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Find flight deals from Valparaiso to Madison

Cheapest flights from Valparaiso to Madison
Explore the most affordable flight options available from Valparaiso to Madison. Find the lowest fares from popular airlines and budget airlines, with prices last updated on November 3, 2025.

This Delta deal was found by Cheapflights users on 11/3. 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.
Wed 12/1012:00 pmVPS - MSN
1 stop4h 21mDelta
Sat 12/135:38 amMSN - VPS
1 stop5h 28mDelta
Deal found 11/3$377
This American Airlines deal was found by Cheapflights users on 11/3. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/113:35 pmVPS - MSN
1 stop6h 19mAmerican Airlines
Sun 12/145:00 amMSN - VPS
1 stop5h 59mAmerican Airlines
Deal found 11/3$405
This Delta deal was found by Cheapflights users on 11/3. 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.
Thu 12/116:00 amVPS - MSN
2 stops6h 50mDelta
Sun 12/146:00 amMSN - VPS
1 stop6h 12mDelta
Deal found 11/3$411

Cheapflights Fare Finder

 
Customize your flight search to find flights from Valparaiso to Madison 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 November 3, 2025.
Use the filters below to find and compare flights from Valparaiso to Madison that are best for you.

Fly from

Valparaiso

Fly to

Madison

Route

Depart

Return

Price

ValparaisoMadison

VPS - MSN

VPSMSN

Valparaiso Destin-Ft Walton Beach

Wed 12/10

12:00 pm-4:21 pm

1 stop4h 21m

Madison Truax Field

Sat 12/13

5:38 am-11:06 am

1 stop5h 28m

$377

ValparaisoMadison

VPS - MSN

VPSMSN

Valparaiso Destin-Ft Walton Beach

Thu 12/11

3:35 pm-9:54 pm

1 stop6h 19m

Madison Truax Field

Sun 12/14

5:00 am-10:59 am

1 stop5h 59m

$405

ValparaisoMadison

VPS - MSN

VPSMSN

Valparaiso Destin-Ft Walton Beach

Thu 12/11

6:00 am-12:50 pm

2 stops6h 50m

Madison Truax Field

Sun 12/14

6:00 am-12:12 pm

1 stop6h 12m

$411

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/3

Compare providers for flights from Valparaiso to Madison

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 Valparaiso to Madison in November.
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 Valparaiso, Florida-Madison flights, users find the pricing of eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Valparaiso, Florida-Madison flight deals on Cheapflights vs. eDreams >95% of the time. Price accuracy is based on data collected from Valparaiso, Florida-Madison flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Valparaiso, Florida-Madison 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 Valparaiso, Florida-Madison 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 Valparaiso to Madison

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

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

Currently, May is the cheapest month in which you can book a flight from Valparaiso, Florida to Madison (average of $114). Flying from Valparaiso, Florida to Madison in October is currently the most expensive (average of $256). 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 Madison

Get insights into the airlines that provide service to Madison. 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 Madison. Reviews last updated November 3, 2025.
Peruse reviews from past customers who have flown with American Airlines from Valparaiso to Madison to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
American Airlines
7.2
Good
11,037 reviews

Crew

8.0

Overall

7.2

Entertainment

6.9

Food

6.4

Comfort

7.2

Boarding

7.5

Reviews

1 / 20
2.0
Mediocre

Anonymous,Aug 2025

MIA - DCA

Flight delayed 5 hours and was told it was due to mechanical issues. Instead of providing lodging due to missed connecting flight, American changed the cause of delay to weather, which meant they were not able required to provide a hotel. To make matters worse, one of our checked bags was lost even though its status said it was “by the plane” but no one at the service desk seemed able to locate it.
American Airlines
7.2
Good
11,037 reviews
American Airlines
7.2
Good
11,037 reviews

Crew

8.0

Overall

7.2

Entertainment

6.9

Food

6.4

Comfort

7.2

Boarding

7.5

Reviews

1 / 20
2.0
Mediocre

Anonymous,Aug 2025

MIA - DCA

Flight delayed 5 hours and was told it was due to mechanical issues. Instead of providing lodging due to missed connecting flight, American changed the cause of delay to weather, which meant they were not able required to provide a hotel. To make matters worse, one of our checked bags was lost even though its status said it was “by the plane” but no one at the service desk seemed able to locate it.

Related info for your journey

Find useful and relevant information for your journey from Valparaiso to Madison. 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 Valparaiso, Florida to Madison?

    A quick flight from Valparaiso, Florida to Madison can take about 4h 21m. Delta provides one of the quickest options available for as low as $377. The distance from Valparaiso, Florida to Madison is about 887 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • What is the cheapest airline to fly from Valparaiso, Florida to Madison round-trip?

    American Airlines, at $357, was found to be the cheapest airline from Valparaiso, Florida to Madison..

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

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

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

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

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

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

    Currently, May is the cheapest month in which you can book a flight from Valparaiso, Florida to Madison (average of $114). Flying from Valparaiso, Florida to Madison in October is currently the most expensive (average of $256). 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 Madison?

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Baraboo
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Top airline flying from Valparaiso to Madison

Discover the top airline that operate flights from Valparaiso to Madison. 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 November 3, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$357Average$396FlexibilityNo cancel feeOn-time71%

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