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San José

$260+ 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 1/8. Fares are subject to change and may not be available on all flights or dates of travel.
MSN — SJO
Oct 11 — Oct 181
Sat 10/11
Sat 10/18
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 January, booked 54 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 September 11, 2025.

Round-trip from

$426
(American Airlines)

One-way from

$260
(United Airlines)

Popular in

December

Cheapest in

September

Average price

$533
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. 8% potential increase in price ($64 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($30 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 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 September 11, 2025.

This American Airlines deal was found by Cheapflights users on 9/10. 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.
Tue 11/47:00 amMSN - SJO
1 stop15h 13mAmerican Airlines
Tue 11/116:00 amSJO - MSN
1 stop14h 19mAmerican Airlines
Deal found 9/10$426
This American Airlines deal was found by Cheapflights users on 9/11. 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.
Sat 11/153:10 pmMSN - SJO
1 stop23h 00mAmerican Airlines
Fri 11/211:35 pmSJO - MSN
1 stop10h 16mAmerican Airlines
Deal found 9/11$434
This American Airlines deal was found by Cheapflights users on 9/10. 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.
Sat 11/14:15 pmMSN - SJO
2 stops22h 24mAmerican Airlines
Sat 12/66:00 amSJO - MSN
1 stop10h 09mAmerican Airlines
Deal found 9/10$450
This American Airlines deal was found by Cheapflights users on 9/11. 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.
Tue 9/233:51 pmMSN - SJO
2 stops20h 21mAmerican Airlines
Fri 10/36:00 amSJO - MSN
2 stops16h 10mAmerican Airlines
Deal found 9/11$520
This American Airlines deal was found by Cheapflights users on 9/11. 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.
Fri 10/178:25 pmMSN - SJO
2 stops17h 55mAmerican Airlines
Tue 10/212:40 pmSJO - MSN
2 stops18h 55mAmerican Airlines
Deal found 9/11$538
This United Airlines deal was found by Cheapflights users on 9/11. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/158:25 amMSN - SJO
2 stops13h 35mUnited Airlines
Fri 11/2111:28 pmSJO - MSN
2 stops12h 16mUnited Airlines
Deal found 9/11$547
This Delta deal was found by Cheapflights users on 9/10. 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.
Tue 10/75:30 amMSN - SJO
1 stop7h 28mDelta
Tue 10/211:23 pmSJO - MSN
1 stop8h 22mDelta
Deal found 9/10$576
This Copa Airlines deal was found by Cheapflights users on 9/10. 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 Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/78:15 amMSN - SJO
2 stops25h 04mCopa Airlines
Tue 10/215:55 pmSJO - MSN
2 stops24h 00mCopa Airlines
Deal found 9/10$609

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 September 11, 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

Tue 11/4

7:00 am-10:13 pm

1 stop15h 13m

San José Juan Santamaria Intl

Tue 11/11

6:00 am-8:19 pm

1 stop14h 19m

$426

MadisonSan José

MSN - SJO

MSNSJO

Madison Truax Field

Sat 11/1

4:15 pm-12:12 pm

2 stops20h 57m

San José Juan Santamaria Intl

Sat 12/6

1:21 pm-11:50 pm

2 stops10h 29m

$450

MadisonSan José

MSN - SJO

MSNSJO

Madison Truax Field

Fri 1/9

10:38 am-11:00 pm

2 stops12h 22m

San José Juan Santamaria Intl

Tue 1/20

8:05 am-9:16 pm

2 stops13h 11m

$538

MadisonSan José

MSN - SJO

MSNSJO

Madison Truax Field

Sat 1/24

7:00 am-9:30 pm

1 stop14h 30m

San José Juan Santamaria Intl

Sat 1/31

6:29 am-4:37 pm

1 stop10h 08m

$552

MadisonSan José

MSN - SJO

MSNSJO

Madison Truax Field

Tue 10/7

5:30 am-11:58 am

1 stop7h 28m

San José Juan Santamaria Intl

Tue 10/21

1:23 pm-10:45 pm

1 stop8h 22m

$576

MadisonSan José

MSN - SJO

MSNSJO

Madison Truax Field

Thu 1/8

8:15 am-7:53 pm

2 stops11h 38m

San José Juan Santamaria Intl

Sun 1/18

6:30 am-9:05 pm

2 stops14h 35m

$587

MadisonSan José

MSN - SJO

MSNSJO

Madison Truax Field

Sat 1/24

8:15 am-8:21 am

2 stops24h 06m

San José Juan Santamaria Intl

Fri 1/30

4:09 am-7:07 pm

2 stops14h 58m

$609

MadisonSan José

MSN - SJO

MSNSJO

Madison Truax Field

Tue 1/13

8:15 am-7:06 am

2 stops22h 51m

San José Juan Santamaria Intl

Wed 1/21

4:09 am-7:07 pm

2 stops14h 58m

$609

MadisonSan José

MSN - SJO

MSNSJO

Madison Truax Field

Tue 11/4

8:25 am-8:19 am

2 stops23h 54m

San José Juan Santamaria Intl

Mon 11/10

4:08 am-7:21 pm

2 stops15h 13m

$609

MadisonSan José

MSN - SJO

MSNSJO

Madison Truax Field

Tue 10/7

8:15 am-8:19 am

2 stops25h 04m

San José Juan Santamaria Intl

Tue 10/21

5:55 pm-6:55 pm

2 stops24h 00m

$609

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/11

Showing 1-10 of 12 results
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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, San José Province?

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 August 29, 2025.

To ensure you get the cheapest price possible for a flight from Madison to San José, San José Province, you should look to book at least 54 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.

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

Currently, September is the cheapest month in which you can book a flight from Madison to San José, San José Province (average of $398). Flying from Madison to San José, San José Province in March is currently the most expensive (average of $555). 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 September 11, 2025.

One of the essential ways to save on airfare from Madison to San José, San José Province 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 13% 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 September 11, 2025.
Read through reviews of airlines operating flights from Madison to San José, such as Delta, United Airlines, and American Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
7,960 reviews

Boarding

8.2

Entertainment

7.9

Crew

8.5

Overall

8.0

Comfort

7.9

Food

7.3

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Delta
8.0
Very good
7,960 reviews
Delta
8.0
Very good
7,960 reviews

Boarding

8.2

Entertainment

7.9

Crew

8.5

Overall

8.0

Comfort

7.9

Food

7.3

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
United Airlines
7.4
Good
8,937 reviews
Delta
8.0
Very good
7,960 reviews

Boarding

8.2

Entertainment

7.9

Crew

8.5

Overall

8.0

Comfort

7.9

Food

7.3

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
American Airlines
7.2
Good
10,000 reviews
Delta
8.0
Very good
7,960 reviews

Boarding

8.2

Entertainment

7.9

Crew

8.5

Overall

8.0

Comfort

7.9

Food

7.3

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!

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, San José Province?

    A quick flight from Madison to San José, San José Province can take about 15h 13m. American Airlines provides one of the quickest options available for as low as $426. Madison and San José, San José Province are separated by a distance of 2309 mi.

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

    Flying on Delta is currently your cheapest option to San José, San José Province, with prices starting at $495. Additional round-trip tickets that might be worth considering are offered by American Airlines and United Airlines, with the lowest prices starting at $505 and $557, respectively. Delta is priced at 30% lower than the current average price of a flight leaving 3 months from now.

  • 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, San José Province?

    Currently, September is the cheapest month in which you can book a flight from Madison to San José, San José Province (average of $398). Flying from Madison to San José, San José Province in March is currently the most expensive (average of $555). 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

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Top 3 airlines flying from Madison to San José

Discover the top 3 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 September 11, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$495Average$1,017FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$505Average$717FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$557Average$852FlexibilityNo cancel feeOn-time69%

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