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San José

$521+ Cheap flights from Madison (MSN) to San José (SJO)

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 8/22. Fares are subject to change and may not be available on all flights or dates of travel.
MSN — SJO
Aug 29 — Sep 51
Sat 8/29
Sat 9/5
1 adult, Economy
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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 July 30, 2026.

This American Airlines deal was found by Cheapflights users on 7/26. 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.
Thu 9/107:17 am
MSN
-
SJO
1 stop7h 40m
American Airlines
Thu 9/171:00 pm
SJO
-
MSN
2 stops18h 14m
American Airlines
Deal found 7/26$521
This American Airlines deal was found by Cheapflights users on 7/29. 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 8/225:46 pm
MSN
-
SJO
1 stop21h 06m
American Airlines
Sat 9/122:57 pm
SJO
-
MSN
2 stops20h 13m
American Airlines
Deal found 7/29$529
This American Airlines deal was found by Cheapflights users on 7/29. 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 9/1211:37 am
MSN
-
SJO
1 stop27h 20m
American Airlines
Sat 9/191:00 pm
SJO
-
MSN
1 stop20h 51m
American Airlines
Deal found 7/29$536
This American Airlines deal was found by Cheapflights users on 7/26. 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.
Tue 12/83:55 pm
MSN
-
SJO
2 stops21h 44m
American Airlines
Fri 12/1812:34 am
SJO
-
MSN
1 stop16h 26m
American Airlines
Deal found 7/26$565
This American Airlines deal was found by Cheapflights users on 7/28. 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.
Thu 11/512:24 pm
MSN
-
SJO
1 stop24h 43m
American Airlines
Thu 11/122:07 pm
SJO
-
MSN
1 stop9h 52m
American Airlines
Deal found 7/28$571
This American Airlines deal was found by Cheapflights users on 7/26. 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.
Thu 12/317:00 am
MSN
-
SJO
2 stops14h 00m
American Airlines
Mon 3/17:45 am
SJO
-
MSN
2 stops15h 06m
American Airlines
Deal found 7/26$615
This American Airlines deal was found by Cheapflights users on 7/29. 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 11/66:00 am
MSN
-
SJO
2 stops14h 50m
American Airlines
Sun 11/153:54 pm
SJO
-
MSN
2 stops16h 31m
American Airlines
Deal found 7/29$620

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 July 30, 2026.

Most accurate provider

Ovago
3 stars

Most trusted provider

Ovago
3 stars

Round-trip from

$521
(American Airlines)

Popular in

December

Cheapest in

September

Average price

$628
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.
Search Deals
From Madison Truax Field to San José Juan Santamaria Intl
Search Deals
Highest demand for flights based on searches. 3% potential increase in price ($24 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($33 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in July 2026
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 July 30, 2026.
Use the filters below to find and compare flights from Madison to San José that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

MadisonSan José

MSN - SJO

MSNSJO

Madison Truax Field

Sun 1/17

5:00 am-12:56 pm

1 stop7h 56m

San José Juan Santamaria Intl

Sat 1/23

1:15 am-1:50 pm

2 stops12h 35m

$565

MadisonSan José

MSN - SJO

MSNSJO

Madison Truax Field

Tue 12/8

3:55 pm-2:02 pm

1 stop22h 07m

San José Juan Santamaria Intl

Fri 12/18

12:34 am-5:00 pm

1 stop16h 26m

$570

MadisonSan José

MSN - SJO

MSNSJO

Madison Truax Field

Sat 1/16

11:23 am-11:43 pm

1 stop12h 20m

San José Juan Santamaria Intl

Tue 1/26

8:00 am-10:59 pm

2 stops14h 59m

$615
Quickest round-trip

MadisonSan José

MSN - SJO

MSNSJO

Madison Truax Field

Sat 1/16

3:09 pm-11:43 pm

1 stop8h 34m

San José Juan Santamaria Intl

Mon 1/25

6:38 am-5:11 pm

1 stop10h 33m

$660

MadisonSan José

MSN - SJO

MSNSJO

Madison Truax Field

Sat 10/31

9:00 am-9:00 pm

1 stop13h 00m

San José Juan Santamaria Intl

Wed 11/4

1:55 pm-11:37 pm

1 stop9h 42m

$680

MadisonSan José

MSN - SJO

MSNSJO

Madison Truax Field

Sat 1/16

2:50 pm-1:00 pm

2 stops22h 10m

San José Juan Santamaria Intl

Sat 1/23

1:15 am-1:50 pm

2 stops12h 35m

$735
Cheapest one-way
Quickest one-way

MadisonSan José

MSN - SJO

MSNSJO

Madison Truax Field

Mon 12/28

5:55 pm-12:29 pm

1 stop18h 34m

$551

MadisonSan José

MSN - SJO

MSNSJO

Madison Truax Field

Sat 12/26

3:44 pm-1:22 pm

2 stops21h 38m

$699

MadisonSan José

MSN - SJO

MSNSJO

Madison Truax Field

Sat 12/26

3:20 pm-2:29 pm

1 stop23h 09m

$806

MadisonSan José

MSN - SJO

MSNSJO

Madison Truax Field

Sat 12/26

5:50 pm-11:55 pm

3 stops30h 05m

$908

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/27

Sorted by cheapest first

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 July.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
OvagoPrice Accuracy3 starsTrust 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 Madison-San José flights, users find the pricing of Ovago to be most consistent on Cheapflights vs. Ovago Users can find the same prices on Madison-San José flight deals on Cheapflights vs. Ovago >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 Ovago the most. Ovago 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

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

Currently, September is the cheapest month in which you can book a flight from Madison to San José (average of $539). Flying from Madison to San José in December is currently the most expensive (average of $1,093). 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.

How much does it cost to fly round-trip from Madison to San José?

Airfare is below average for this route at the moment.

Madison to San José flights typically cost between $671 and $885 in September.
The cheapest round-trip price found within the last 5 days was $521 on American Airlines (Sep 10-Sep 17).

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 July 30, 2026.
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
7.8
Good
8,487 reviews

Food

7.2

Boarding

8.1

Overall

7.8

Comfort

7.8

Crew

8.5

Entertainment

7.8

Reviews

1 / 20
10.0
Excellent

Anonymous,May 2026

SEA - KOA

The snacks were not very good, not everyone was very friendly and professional
Delta
7.8
Good
8,487 reviews
Delta
7.8
Good
8,487 reviews

Food

7.2

Boarding

8.1

Overall

7.8

Comfort

7.8

Crew

8.5

Entertainment

7.8

Reviews

1 / 20
10.0
Excellent

Anonymous,May 2026

SEA - KOA

The snacks were not very good, not everyone was very friendly and professional
American Airlines
7.1
Good
11,841 reviews
Delta
7.8
Good
8,487 reviews

Food

7.2

Boarding

8.1

Overall

7.8

Comfort

7.8

Crew

8.5

Entertainment

7.8

Reviews

1 / 20
10.0
Excellent

Anonymous,May 2026

SEA - KOA

The snacks were not very good, not everyone was very friendly and professional

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 7h 56m. Fly via United Airlines or American 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 $448. Another airline that can offer you cheap pricing is American Airlines. Delta is currently priced 39% 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, September is the cheapest month in which you can book a flight from Madison to San José (average of $539). Flying from Madison to San José in December is currently the most expensive (average of $1,093). 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
Alajuela
Jacó
Heredia
Dominical
Manuel Antonio

Browse thousands of different options on Cheapflights for your next trip

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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 July 30, 2026.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$448Average$885FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$476Average$678FlexibilityNo cancel feeOn-time71%

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