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$229+ Cheap flights from Madison (MSN) to Costa Rica

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 1/25. Fares are subject to change and may not be available on all flights or dates of travel.
MSN — SJO
Jan 31 — Feb 71
Sat 1/31
Sat 2/7
1 adult, Economy
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Cheap flight deals from Madison to Costa Rica

Cheapest flights from Madison to Costa Rica
Explore the most affordable flight options available from Madison to Costa Rica. Find the lowest fares from popular airlines and budget airlines, with prices last updated on January 1, 2026.

This American Airlines deal was found by Cheapflights users on 12/29. 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.
Tue 12/305:55 pmMSN - SJO
2 stops16h 37mAmerican Airlines
Tue 1/67:30 amSJO - MSN
2 stops15h 10mAmerican Airlines
Deal found 12/29$716
This American Airlines deal was found by Cheapflights users on 12/30. 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 12/316:00 amMSN - SJO
1 stop14h 14mAmerican Airlines
Mon 1/57:00 amSJO - MSN
1 stop16h 28mAmerican Airlines
Deal found 12/30$724
This United Airlines deal was found by Cheapflights users on 12/30. 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.
Wed 12/312:29 pmMSN - SJO
2 stops22h 46mUnited Airlines
Mon 1/58:45 amSJO - MSN
2 stops29h 25mUnited Airlines
Deal found 12/30$836
This Delta deal was found by Cheapflights users on 12/30. 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 12/305:03 pmMSN - LIR
2 stops19h 47mDelta
Thu 1/13:05 pmLIR - MSN
2 stops25h 18mDelta
Deal found 12/30$897
This American Airlines deal was found by Cheapflights users on 12/30. 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 12/305:55 pmMSN - LIR
1 stop18h 29mAmerican Airlines
Thu 1/12:37 pmLIR - MSN
1 stop8h 51mAmerican Airlines
Deal found 12/30$993

Find flight deals from Madison to Costa Rica

Keep the following information in mind while searching for Madison to Costa Rica flight deals. Data was last updated January 1, 2026.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$482
(American Airlines)

One-way from

$229
(American Airlines)

Popular in

December

Cheapest in

September

Average price

$640
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 Costa Rica
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One-way flight from Madison Truax Field to Costa Rica
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Highest demand for flights based on searches. 11% potential increase in price ($93 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 5% potential price decrease ($35 potential savings vs. average RT price).
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Average for round-trip flights in January 2026
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Cheapflights Fare Finder

 
Customize your flight search to find flights from Madison to Costa Rica 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 January 1, 2026.
Use the filters below to find and compare flights from Madison to Costa Rica that are best for you.

Fly from

Madison

Fly to

Costa Rica

Route

Depart

Return

Price

MadisonSan José

MSN - SJO

MSNSJO

Madison Truax Field

Tue 1/27

11:29 am-10:30 pm

1 stop11h 01m

San José Juan Santamaria Intl

Tue 2/3

7:09 am-10:05 pm

1 stop14h 56m

$482

MadisonSan José

MSN - SJO

MSNSJO

Madison Truax Field

Tue 1/13

7:20 am-10:30 pm

1 stop15h 10m

San José Juan Santamaria Intl

Thu 1/22

7:09 am-4:52 pm

1 stop9h 43m

$499

MadisonSan José

MSN - SJO

MSNSJO

Madison Truax Field

Sat 1/31

11:29 am-10:30 pm

1 stop11h 01m

San José Juan Santamaria Intl

Tue 2/10

7:09 am-10:05 pm

1 stop14h 56m

$502

MadisonSan José

MSN - SJO

MSNSJO

Madison Truax Field

Tue 1/13

7:00 am-10:15 pm

2 stops15h 15m

San José Juan Santamaria Intl

Thu 1/22

7:00 am-4:17 pm

1 stop9h 17m

$504

MadisonSan José

MSN - SJO

MSNSJO

Madison Truax Field

Mon 1/12

6:00 am-9:02 pm

2 stops15h 02m

San José Juan Santamaria Intl

Thu 1/29

8:00 am-11:41 pm

2 stops15h 41m

$504

MadisonSan José

MSN - SJO

MSNSJO

Madison Truax Field

Tue 2/10

7:20 am-10:30 pm

1 stop15h 10m

San José Juan Santamaria Intl

Sat 2/14

12:35 am-5:04 pm

1 stop16h 29m

$507

MadisonSan José

MSN - SJO

MSNSJO

Madison Truax Field

Sat 1/24

4:30 pm-12:38 pm

1 stop20h 08m

San José Juan Santamaria Intl

Sat 1/31

7:09 am-6:55 pm

1 stop11h 46m

$511

MadisonLiberia

MSN - LIR

MSNLIR

Madison Truax Field

Mon 3/23

8:24 pm-1:25 pm

2 stops18h 01m

Liberia

Mon 3/30

12:30 pm-10:03 am

2 stops20h 33m

$549

MadisonLiberia

MSN - LIR

MSNLIR

Madison Truax Field

Wed 2/18

6:00 am-1:32 pm

1 stop7h 32m

Liberia

Wed 2/25

2:32 pm-11:26 pm

1 stop8h 54m

$557

MadisonLiberia

MSN - LIR

MSNLIR

Madison Truax Field

Mon 1/19

4:30 pm-2:13 pm

2 stops21h 43m

Liberia

Sun 1/25

3:23 pm-10:55 am

2 stops19h 32m

$586

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/31

Showing 1-10 of 15 results
1
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Best time to book a flight from Madison to Costa Rica

Have a flexible travel schedule? Discover the best time to fly to Costa Rica 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 Costa Rica

What is the cheapest month to book a flight from Madison to Costa Rica?

Currently, August is the cheapest month in which you can book a flight from Madison to Costa Rica (average of $184). Flying from Madison to Costa Rica in July is currently the most expensive (average of $485). 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 Costa Rica

Get insights into the airlines that provide service to Costa Rica. 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 Costa Rica. Reviews last updated January 1, 2026.
See what other customers who have flown with Delta and American Airlines from Madison to Costa Rica have to say. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
7.9
Good
8,013 reviews

Boarding

8.1

Comfort

7.9

Crew

8.5

Entertainment

7.8

Food

7.2

Overall

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
8,013 reviews
Delta
7.9
Good
8,013 reviews

Boarding

8.1

Comfort

7.9

Crew

8.5

Entertainment

7.8

Food

7.2

Overall

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
11,069 reviews
Delta
7.9
Good
8,013 reviews

Boarding

8.1

Comfort

7.9

Crew

8.5

Entertainment

7.8

Food

7.2

Overall

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 Costa Rica. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly from for flights from Madison to Costa Rica?

    Located just 5.4 mi from the city center, Madison Truax Field (MSN) is the airport most travelers will use when flying to Costa Rica from Madison.

  • How long is the flight from Madison to Costa Rica?

    Airlines like American Airlines fly from Madison to Costa Rica in about 11h 01m. The time it takes to get you to your destination can typically vary by up to . The distance from Madison to Costa Rica is about 2309 mi.

  • Can I find deals for flights from Madison to Costa Rica that include hotel bookings?

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

  • How can I find direct flights from Madison to Costa Rica?

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

  • Can I find deals for business class flights from Madison to Costa Rica?

    Yes. Cheapflights offers flight deals from Madison to Costa Rica 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 Costa Rica?

    Currently, August is the cheapest month in which you can book a flight from Madison to Costa Rica (average of $184). Flying from Madison to Costa Rica in July is currently the most expensive (average of $485). 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

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Alternative routes for Madison to Costa Rica

See prices for flight routes from nearby airports that may be better suited for you.
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Top 2 airlines flying from Madison to Costa Rica

Discover the top 2 airlines that operate flights from Madison to Costa Rica. 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 January 1, 2026.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$378Average$885FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$418Average$677FlexibilityNo cancel feeOn-time71%

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