HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
San José

$183+ 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 8/18. Fares are subject to change and may not be available on all flights or dates of travel.
MSN — SJO
Jun 17 — Jun 241
Tue 6/17
Tue 6/24
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Madison to San José with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

Cheapflights Tip: The best prices from Madison Truax Field to San José Juan Santamaria Intl are usually found in August or July, booked 27 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 June 12, 2025.

Round-trip from

$392
(American Airlines)

One-way from

$183
(American Airlines)

Popular in

December

Cheapest in

August

Average price

$777
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. 8% potential increase in price ($64 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($26 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in June 2025
Search Deals

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 June 12, 2025.

This American Airlines deal was found by Cheapflights users on 6/11. 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 11/411:30 amMSN - SJO
1 stop8h 32mAmerican Airlines
Tue 11/117:00 amSJO - MSN
1 stop14h 23mAmerican Airlines
Deal found 6/11$392
This Kiwi.com deal was found by Cheapflights users on 6/10. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/2710:19 amMSN - SJO
1 stop27h 21mMultiple Airlines
Fri 9/51:41 pmSJO - MSN
1 stop26h 47mMultiple Airlines
Deal found 6/10$397
This United Airlines deal was found by Cheapflights users on 6/11. 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.
Sun 11/93:58 pmMSN - SJO
2 stops19h 27mUnited Airlines
Thu 11/132:20 pmSJO - MSN
2 stops30h 15mUnited Airlines
Deal found 6/11$530
This Delta deal was found by Cheapflights users on 6/10. 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 9/255:45 amMSN - SJO
1 stop7h 08mDelta
Tue 9/301:18 pmSJO - MSN
1 stop8h 16mDelta
Deal found 6/10$564
This Avianca deal was found by Cheapflights users on 6/11. 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 Avianca is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/110:35 amMSN - SJO
2 stops14h 40mAvianca
Fri 12/52:15 amSJO - MSN
2 stops14h 36mAvianca
Deal found 6/11$1,764
This Air Canada deal was found by Cheapflights users on 6/10. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/297:00 amMSN - SJO
2 stops15h 25mAir Canada
Fri 1/28:55 amSJO - MSN
2 stops31h 56mAir Canada
Deal found 6/10$2,285

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 June 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

Tue 11/4

11:30 am-8:02 pm

1 stop8h 32m

San José Juan Santamaria Intl

Tue 11/11

7:00 am-9:23 pm

1 stop14h 23m

$392

MadisonSan José

MSN - SJO

MSNSJO

Madison Truax Field

Wed 8/27

10:19 am-12:40 pm

1 stop27h 21m

San José Juan Santamaria Intl

Fri 9/5

1:41 pm-5:28 pm

1 stop26h 47m

$397

MadisonSan José

MSN - SJO

MSNSJO

Madison Truax Field

Sun 11/9

3:58 pm-11:25 am

2 stops19h 27m

San José Juan Santamaria Intl

Fri 11/14

11:28 pm-11:44 am

2 stops12h 16m

$530

MadisonSan José

MSN - SJO

MSNSJO

Madison Truax Field

Thu 9/25

5:45 am-11:53 am

1 stop7h 08m

San José Juan Santamaria Intl

Tue 9/30

1:18 pm-10:34 pm

1 stop8h 16m

$564

MadisonSan José

MSN - SJO

MSNSJO

Madison Truax Field

Sat 11/1

10:35 am-12:15 am

2 stops14h 40m

San José Juan Santamaria Intl

Fri 12/5

2:15 am-4:51 pm

2 stops14h 36m

$1,764

MadisonSan José

MSN - SJO

MSNSJO

Madison Truax Field

Mon 8/18

6:46 am-6:15 pm

1 stop12h 29m

$183

MadisonSan José

MSN - SJO

MSNSJO

Madison Truax Field

Tue 8/26

5:40 am-12:10 pm

1 stop7h 30m

$227

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/9

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 June 9, 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 26 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 June 12, 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.

Rainfall in San José by month

Plan your trip to San José by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in San José, San José Province ranges from 0.0 - 11.8 inches per month. September is typically the wettest month, when rainfall can reach 11.8 in. February is typically the driest time to visit San José, San José Province when rainfall is around 0.0 in.

Temperature in San José by month

Plan your trip to San José by taking into account the average temperature totals by month.

If weather is an important factor for your trip to San José, San José Province, use this chart to help with planning. For those seeking warmer temperatures, April is the ideal time of year to visit, when temperatures reach an average of 69.8 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 64.4 F).

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 June 12, 2025.
Delta
8.0
Very good
7,950 reviews

Overall

8.0

Entertainment

7.9

Food

7.3

Boarding

8.2

Comfort

7.9

Crew

8.5

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
7,950 reviews
Delta
8.0
Very good
7,950 reviews

Overall

8.0

Entertainment

7.9

Food

7.3

Boarding

8.2

Comfort

7.9

Crew

8.5

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
8,790 reviews
Delta
8.0
Very good
7,950 reviews

Overall

8.0

Entertainment

7.9

Food

7.3

Boarding

8.2

Comfort

7.9

Crew

8.5

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
7,950 reviews

Overall

8.0

Entertainment

7.9

Food

7.3

Boarding

8.2

Comfort

7.9

Crew

8.5

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!
Avianca
6.7
Okay
2,345 reviews
Delta
8.0
Very good
7,950 reviews

Overall

8.0

Entertainment

7.9

Food

7.3

Boarding

8.2

Comfort

7.9

Crew

8.5

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.

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

    Flying on American Airlines is currently your cheapest option to San José, San José Province, with prices starting at $392. Additional round-trip tickets that might be worth considering are offered by United Airlines and Delta, with the lowest prices starting at $530 and $564, respectively. American Airlines is priced at 42% 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 Madison?

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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

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 June 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$495Average$710FlexibilityNo cancel feeOn-time71%
DeltaCheapest$505Average$887FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$557Average$852FlexibilityNo cancel feeOn-time69%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.