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San José

$292+ Cheap flights from Madison (MSN) to San José (SJO)

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 3/26. Fares are subject to change and may not be available on all flights or dates of travel.
MSN — SJO
Nov 27 — Dec 41
Thu 11/27
Thu 12/4
1 adult, Economy
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Cheapflights Tip: The best prices from Madison Truax Field to San José Juan Santamaria Intl are usually found in September or August, booked 47 days in advance, depart on a Tuesday or Friday and return on a Wednesday

Cheap flight deals from Madison to San José

Discover tips and strategies to find the most affordable flight options for your journey from Madison (MSN) to San José (SJO). 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 October 28, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$475
(American Airlines)

One-way from

$292
(Delta)

Popular in

December

Cheapest in

September

Average price

$611
Provider with most accurate pricing for Madison Truax Field-San José Juan Santamaria Intl flight deals.
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Provider most trusted by Cheapflights users for Madison Truax Field-San José Juan Santamaria Intl flights.
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From Madison Truax Field to San José Juan Santamaria Intl
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One-way flight from Madison Truax Field to San José Juan Santamaria Intl
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Highest demand for flights based on searches. 10% potential increase in price ($78 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($32 potential savings vs. average RT price).
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Average for round-trip flights in October 2025
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Find flight deals from Madison to San José

Cheapest flights from Madison to San José
Explore the most affordable flight options available from Madison to San José. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 28, 2025.

This American Airlines deal was found by Cheapflights users on 10/27. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/711:14 amMSN - SJO
1 stop11h 45mAmerican Airlines
Tue 12/1612:56 pmSJO - MSN
1 stop10h 44mAmerican Airlines
Deal found 10/27$475
This American Airlines deal was found by Cheapflights users on 10/26. 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 12/106:09 amMSN - SJO
1 stop16h 19mAmerican Airlines
Wed 12/176:00 amSJO - MSN
1 stop16h 42mAmerican Airlines
Deal found 10/26$482
This Delta deal was found by Cheapflights users on 10/27. 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.
Tue 11/45:30 amMSN - SJO
1 stop7h 20mDelta
Tue 11/112:31 pmSJO - MSN
1 stop8h 01mDelta
Deal found 10/27$516
This United Airlines deal was found by Cheapflights users on 10/27. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/46:30 amMSN - SJO
2 stops14h 09mUnited Airlines
Tue 11/1111:28 pmSJO - MSN
2 stops12h 17mUnited Airlines
Deal found 10/27$520
This American Airlines deal was found by Cheapflights users on 10/27. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/261:10 pmMSN - SJO
1 stop9h 03mAmerican Airlines
Wed 12/312:56 pmSJO - MSN
1 stop10h 44mAmerican Airlines
Deal found 10/27$527
This American Airlines deal was found by Cheapflights users on 10/27. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/95:00 amMSN - SJO
1 stop17h 28mAmerican Airlines
Mon 1/121:51 pmSJO - MSN
1 stop9h 50mAmerican Airlines
Deal found 10/27$528
This Kiwi.com deal was found by Cheapflights users on 10/27. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/106:08 pmMSN - SJO
1 stop17h 34mMultiple Airlines
Sat 1/102:58 pmSJO - MSN
2 stops46h 50mMultiple Airlines
Deal found 10/27$564
This American Airlines deal was found by Cheapflights users on 10/28. 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.
Sat 11/15:46 pmMSN - SJO
2 stops19h 26mAmerican Airlines
Sat 12/66:20 amSJO - MSN
2 stops14h 46mAmerican Airlines
Deal found 10/28$568

Cheapflights Fare Finder

 
Customize your flight search to find flights from Madison to San José 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 October 28, 2025.
Use the filters below to find and compare flights from Madison to San José that are best for you.

Fly from

Madison

Fly to

San José

Route

Depart

Return

Price

MadisonSan José

MSN - SJO

MSNSJO

Madison Truax Field

Sun 12/7

11:14 am-10:59 pm

1 stop11h 45m

San José Juan Santamaria Intl

Tue 12/16

12:56 pm-11:40 pm

1 stop10h 44m

$475

MadisonSan José

MSN - SJO

MSNSJO

Madison Truax Field

Tue 1/13

6:00 am-10:30 pm

1 stop16h 30m

San José Juan Santamaria Intl

Thu 1/22

1:51 pm-11:41 pm

1 stop9h 50m

$482

MadisonSan José

MSN - SJO

MSNSJO

Madison Truax Field

Sun 12/7

6:59 am-10:20 pm

2 stops15h 21m

San José Juan Santamaria Intl

Tue 12/16

7:00 am-8:30 pm

2 stops13h 30m

$486

MadisonSan José

MSN - SJO

MSNSJO

Madison Truax Field

Sun 1/11

7:00 am-11:43 pm

1 stop16h 43m

San José Juan Santamaria Intl

Wed 4/22

1:45 pm-10:51 pm

1 stop8h 06m

$499

MadisonSan José

MSN - SJO

MSNSJO

Madison Truax Field

Tue 1/6

7:00 am-10:30 pm

2 stops15h 30m

San José Juan Santamaria Intl

Tue 3/10

12:01 am-2:02 pm

2 stops13h 01m

$503

MadisonSan José

MSN - SJO

MSNSJO

Madison Truax Field

Sun 3/1

6:14 am-10:40 pm

1 stop16h 26m

San José Juan Santamaria Intl

Fri 3/6

12:23 am-10:37 am

1 stop10h 14m

$517

MadisonSan José

MSN - SJO

MSNSJO

Madison Truax Field

Thu 2/5

7:20 am-10:30 pm

1 stop15h 10m

San José Juan Santamaria Intl

Thu 2/12

7:00 am-11:29 pm

1 stop16h 29m

$517

MadisonSan José

MSN - SJO

MSNSJO

Madison Truax Field

Thu 3/26

11:11 am-9:15 pm

1 stop11h 04m

$292

MadisonSan José

MSN - SJO

MSNSJO

Madison Truax Field

Thu 3/26

6:30 am-7:39 pm

2 stops14h 09m

$318

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/26

Compare providers for flights from Madison to San José

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 San José in October.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star
eDreamsPrice Accuracy3 starsTrust Score*3 stars
AranGrantPrice Accuracy2 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-San José flights, users find the pricing of eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Madison-San José flight deals on Cheapflights vs. eDreams >95% of the time. Price accuracy is based on data collected from Madison-San José flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Madison-San José 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 Madison-San José 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 San José

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

How far ahead should I book a flight from Madison to San José?

Use this chart to determine the optimal time to book a round-trip flight from Madison to San José. Price data was last updated on October 24, 2025.

The price you pay for your flight from Madison to San José may vary depending on when you book. For the best chance of a lower fare, look to book 47 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.

What is the cheapest month to book a flight from Madison to San José?

Currently, August is the cheapest month in which you can book a flight from Madison to San José (average of $184). Flying from Madison to San José in April is currently the most expensive (average of $491). 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 SJO?

Find hourly flight availability from Madison to San José. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated October 28, 2025.

One of the essential ways to save on airfare from Madison to San José is to remain as flexible as possible. Flights that are in the afternoon tend to be the most expensive. A flight at noon could potentially save you up to 12% on airfare.

Reviews of airlines servicing San José

Get insights into the airlines that provide service to San José. 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 San José. Reviews last updated October 28, 2025.
Read through reviews of airlines operating flights from Madison to San José, such as Delta and American Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Delta
7.9
Good
7,994 reviews

Crew

8.5

Entertainment

7.9

Overall

7.9

Boarding

8.2

Comfort

7.9

Food

7.3

Reviews

1 / 20
8.0
Excellent

Matthew,Oct 2025

GSP - ATL

This is always a full flight since it is the connecting route to primary destinations through Atlanta. That said, the crew handles the full load well. Not much more to say, it is a short flight with no in-flight services due to the length.
Delta
7.9
Good
7,994 reviews
Delta
7.9
Good
7,994 reviews

Crew

8.5

Entertainment

7.9

Overall

7.9

Boarding

8.2

Comfort

7.9

Food

7.3

Reviews

1 / 20
8.0
Excellent

Matthew,Oct 2025

GSP - ATL

This is always a full flight since it is the connecting route to primary destinations through Atlanta. That said, the crew handles the full load well. Not much more to say, it is a short flight with no in-flight services due to the length.
American Airlines
7.2
Good
11,032 reviews
Delta
7.9
Good
7,994 reviews

Crew

8.5

Entertainment

7.9

Overall

7.9

Boarding

8.2

Comfort

7.9

Food

7.3

Reviews

1 / 20
8.0
Excellent

Matthew,Oct 2025

GSP - ATL

This is always a full flight since it is the connecting route to primary destinations through Atlanta. That said, the crew handles the full load well. Not much more to say, it is a short flight with no in-flight services due to the length.

Related info for your journey

Find useful and relevant information for your journey from Madison to San José. 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 San José?

    There are many flights that can get you from Madison to San José in 11h 45m. Fly via American Airlines to get the fastest option. Airlines will cover a distance of 2309 mi.

  • What are the cheapest airlines flying from Madison to San José round-trip?

    Cheapflights users have booked flights from Madison to San José round-trip from $495. Another airline that can offer you cheap pricing is American Airlines. Delta is currently priced 29% below the average price you’ll pay for this route.

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

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

  • How can I find direct flights from Madison to San José?

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

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

    Yes. Cheapflights offers flight deals from Madison to San José 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 San José?

    Currently, August is the cheapest month in which you can book a flight from Madison to San José (average of $184). Flying from Madison to San José in April is currently the most expensive (average of $491). 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 San José?

Book flights to San José if you plan to visit one of these locations
Heredia
Manuel Antonio
Alajuela
Monteverde
Jacó
Dominical

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Top 2 airlines flying from Madison to San José

Discover the top 2 airlines that operate flights from Madison to San José. 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 October 28, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$495Average$1,007FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$503Average$714FlexibilityNo cancel feeOn-time71%

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