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San José

$188+ 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 3/1. Fares are subject to change and may not be available on all flights or dates of travel.
MSN — SJO
Jan 11 — Jan 181
Sun 1/11
Sun 1/18
1 adult, Economy
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1. Tell us where you want to go

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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 October, booked 42 days in advance, depart on a Tuesday or Friday and return on a Wednesday

Cheap 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 December 12, 2025.

This American Airlines deal was found by Cheapflights users on 12/11. 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 12/172:03 pmMSN - SJO
1 stop8h 25mAmerican Airlines
Fri 1/97:30 amSJO - MSN
2 stops16h 11mAmerican Airlines
Deal found 12/11$660
This American Airlines deal was found by Cheapflights users on 12/10. 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 12/218:10 pmMSN - SJO
1 stop24h 04mAmerican Airlines
Sun 12/2812:34 amSJO - MSN
1 stop16h 26mAmerican Airlines
Deal found 12/10$671
This American Airlines deal was found by Cheapflights users on 12/10. 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 12/218:10 pmMSN - SJO
1 stop24h 04mAmerican Airlines
Sun 12/287:00 amSJO - MSN
1 stop12h 40mAmerican Airlines
Deal found 12/10$676
This American Airlines deal was found by Cheapflights users on 12/11. 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.
Mon 12/228:10 pmMSN - SJO
1 stop24h 04mAmerican Airlines
Sun 12/287:00 amSJO - MSN
1 stop16h 28mAmerican Airlines
Deal found 12/11$685
This United Airlines deal was found by Cheapflights users on 12/10. 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.
Thu 12/1812:23 pmMSN - SJO
2 stops24h 52mUnited Airlines
Tue 12/306:30 amSJO - MSN
2 stops29h 18mUnited Airlines
Deal found 12/10$711
This United Airlines deal was found by Cheapflights users on 12/10. 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.
Thu 12/188:15 amMSN - SJO
2 stops29h 00mUnited Airlines
Sat 12/276:30 amSJO - MSN
2 stops16h 00mUnited Airlines
Deal found 12/10$729
This United Airlines deal was found by Cheapflights users on 12/10. 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.
Thu 12/188:15 amMSN - SJO
2 stops29h 00mUnited Airlines
Sun 12/286:30 amSJO - MSN
2 stops29h 18mUnited Airlines
Deal found 12/10$748
This Delta deal was found by Cheapflights users on 12/10. 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 12/185:38 amMSN - SJO
1 stop16h 42mDelta
Fri 12/267:00 amSJO - MSN
1 stop14h 21mDelta
Deal found 12/10$751

Find 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 December 12, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$398
(American Airlines)

One-way from

$188
(Delta)

Popular in

December

Cheapest in

September

Average price

$1,059
Provider with most accurate pricing for Madison Truax Field-San José Juan Santamaria Intl flight deals.
Search Deals
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
Search Deals
One-way flight from Madison Truax Field to San José Juan Santamaria Intl
Search Deals
Highest demand for flights based on searches. 10% potential increase in price ($86 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($32 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
Search Deals

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 December 12, 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

Wed 1/21

6:00 am-10:30 pm

1 stop16h 30m

San José Juan Santamaria Intl

Wed 1/28

7:09 am-6:44 pm

1 stop11h 35m

$398

MadisonSan José

MSN - SJO

MSNSJO

Madison Truax Field

Wed 1/21

7:30 am-8:39 pm

2 stops13h 09m

San José Juan Santamaria Intl

Wed 1/28

6:30 am-4:50 pm

2 stops10h 20m

$402

MadisonSan José

MSN - SJO

MSNSJO

Madison Truax Field

Sun 2/1

3:09 pm-11:43 pm

1 stop8h 34m

San José Juan Santamaria Intl

Tue 2/10

7:09 am-9:11 pm

2 stops14h 02m

$402

MadisonSan José

MSN - SJO

MSNSJO

Madison Truax Field

Mon 1/12

4:30 pm-12:38 pm

1 stop20h 08m

San José Juan Santamaria Intl

Thu 1/29

8:00 am-11:41 pm

2 stops15h 41m

$410

MadisonSan José

MSN - SJO

MSNSJO

Madison Truax Field

Wed 1/28

6:16 pm-11:37 am

1 stop17h 21m

San José Juan Santamaria Intl

Mon 2/2

1:30 pm-9:08 am

2 stops43h 38m

$471

MadisonSan José

MSN - SJO

MSNSJO

Madison Truax Field

Sun 2/1

7:00 am-10:15 pm

2 stops15h 15m

San José Juan Santamaria Intl

Tue 2/10

7:00 am-8:54 pm

2 stops13h 54m

$489

MadisonSan José

MSN - SJO

MSNSJO

Madison Truax Field

Wed 1/28

7:30 am-6:16 pm

2 stops10h 46m

San José Juan Santamaria Intl

Mon 2/2

6:30 am-7:07 pm

2 stops12h 37m

$502

MadisonSan José

MSN - SJO

MSNSJO

Madison Truax Field

Sat 1/24

6:30 am-6:16 pm

2 stops11h 46m

San José Juan Santamaria Intl

Sat 1/31

1:00 pm-11:44 pm

1 stop10h 44m

$514

MadisonSan José

MSN - SJO

MSNSJO

Madison Truax Field

Tue 1/13

3:48 pm-6:16 pm

2 stops26h 28m

San José Juan Santamaria Intl

Thu 1/22

6:30 am-11:51 am

2 stops29h 21m

$528

MadisonSan José

MSN - SJO

MSNSJO

Madison Truax Field

Sun 3/1

11:20 am-10:02 pm

1 stop10h 42m

$188

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/11

Showing 1-10 of 16 results
1
2

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 December.
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 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 December 5, 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 42 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 $492). 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 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 December 12, 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
8,007 reviews

Entertainment

7.9

Crew

8.5

Boarding

8.1

Overall

7.9

Food

7.3

Comfort

7.9

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
Delta
7.9
Good
8,007 reviews
Delta
7.9
Good
8,007 reviews

Entertainment

7.9

Crew

8.5

Boarding

8.1

Overall

7.9

Food

7.3

Comfort

7.9

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
American Airlines
7.2
Good
11,050 reviews
Delta
7.9
Good
8,007 reviews

Entertainment

7.9

Crew

8.5

Boarding

8.1

Overall

7.9

Food

7.3

Comfort

7.9

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.

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 13h 09m. Fly via American Airlines or United Airlines to get the fastest option. Airlines will cover a distance of 2309 mi. Both multi-stop and nonstop flights can be found to your destination and back.

  • 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 30% 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 $492). 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
Manuel Antonio
Alajuela
Monteverde
Jacó
Heredia
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 December 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$498Average$719FlexibilityNo cancel feeOn-time71%
DeltaCheapest$505Average$1,007FlexibilityNo cancel feeOn-timeN/A

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