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$282+ Cheap flights from Valparaiso, FL to Madison (VPS - MSN)

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 2/18. Fares are subject to change and may not be available on all flights or dates of travel.
VPS — MSN
Mar 5 — Mar 121
Thu 3/5
Thu 3/12
1 adult, Economy
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Cheap 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 February 3, 2026.

This Delta deal was found by Cheapflights users on 2/2. 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 2/75:56 pm
VPS
-
MSN
1 stop4h 34m
Delta
Sat 2/141:20 pm
MSN
-
VPS
1 stop4h 59m
Delta
Deal found 2/2$479
This Delta deal was found by Cheapflights users on 2/2. 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.
Sun 3/15:12 pm
VPS
-
MSN
1 stop5h 12m
Delta
Wed 3/411:20 am
MSN
-
VPS
1 stop6h 59m
Delta
Deal found 2/2$504
This American Airlines deal was found by Cheapflights users on 2/1. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/171:00 pm
VPS
-
MSN
1 stop6h 36m
American Airlines
Sat 3/215:17 pm
MSN
-
VPS
1 stop5h 07m
American Airlines
Deal found 2/1$632
This Sun Country Air deal was found by Cheapflights users on 2/3. 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 Sun Country Air is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/1811:01 am
VPS
-
MSN
2 stops26h 48m
Sun Country Air
Sun 2/222:51 pm
MSN
-
VPS
2 stops26h 20m
Sun Country Air
Deal found 2/3$972

Find 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 February 3, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$504
(Delta)

One-way from

$282
(Delta)
Provider with most accurate pricing for Valparaiso Destin-Ft Walton Beach-Madison Truax Field flight deals.
Search Deals
Provider most trusted by Cheapflights users for Valparaiso Destin-Ft Walton Beach-Madison Truax Field flights.
Search Deals
From Valparaiso Destin-Ft Walton Beach to Madison Truax Field
Search Deals
One-way flight from Valparaiso Destin-Ft Walton Beach to Madison Truax Field
Search Deals

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 February 3, 2026.
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

Sun 3/1

5:12 pm-10:24 pm

1 stop5h 12m

Madison Truax Field

Wed 3/4

11:20 am-6:19 pm

1 stop6h 59m

$504

ValparaisoMadison

VPS - MSN

VPSMSN

Valparaiso Destin-Ft Walton Beach

Tue 3/17

1:00 pm-7:36 pm

1 stop6h 36m

Madison Truax Field

Sat 3/21

5:17 pm-10:24 pm

1 stop5h 07m

$632

ValparaisoMadison

VPS - MSN

VPSMSN

Valparaiso Destin-Ft Walton Beach

Wed 2/18

11:01 am-1:49 pm

2 stops26h 48m

Madison Truax Field

Sun 2/22

2:51 pm-5:11 pm

2 stops26h 20m

$972

ValparaisoMadison

VPS - MSN

VPSMSN

Valparaiso Destin-Ft Walton Beach

Wed 2/18

5:11 pm-10:24 pm

1 stop5h 13m

$282

ValparaisoMadison

VPS - MSN

VPSMSN

Valparaiso Destin-Ft Walton Beach

Wed 2/18

11:01 am-1:49 pm

3 stops26h 48m

$604

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/2

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 February.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice 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 FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Valparaiso, Florida-Madison flight deals on Cheapflights vs. FlightHub >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 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 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 December is currently the most expensive (average of $260). 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 February 3, 2026.
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
11,216 reviews

Overall

7.2

Boarding

7.5

Comfort

7.2

Entertainment

6.9

Crew

8.0

Food

6.4

Reviews

1 / 20
4.0
Okay

Susie,Jan 2026

TPA - CLT

I was sitting at the back of the plane and the flight attendants were so loud, talking to each other and laughing! I thought they were having a party back there.
American Airlines
7.2
Good
11,216 reviews
American Airlines
7.2
Good
11,216 reviews

Overall

7.2

Boarding

7.5

Comfort

7.2

Entertainment

6.9

Crew

8.0

Food

6.4

Reviews

1 / 20
4.0
Okay

Susie,Jan 2026

TPA - CLT

I was sitting at the back of the plane and the flight attendants were so loud, talking to each other and laughing! I thought they were having a party back there.

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 5h 12m. Delta provides one of the quickest options available for as low as $504. 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 December is currently the most expensive (average of $260). 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?

Book flights to Madison if you plan to visit one of these locations
Portage
Middleton
Baraboo
Fitchburg

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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 February 3, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$357Average$431FlexibilityNo cancel feeOn-time71%

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