$311+ Cheap flights from Madison (MSN) to Costa Rica
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 1/6. Fares are subject to change and may not be available on all flights or dates of travel.
MSN — SJO
Oct 31 — Nov 71
Round-trip
1 adult, Economy
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Find cheap flights from Madison to Costa Rica 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
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Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from Madison to Costa Rica
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Last-minute
One-way
Cheapest flights from Madison to Costa RicaExplore 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 October 1, 2026.
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 October 1, 2026.
This American Airlines deal was found by Cheapflights users on 9/30. 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.
Sat 11/288:31 pm -
2 stops16h 36m
Sat 12/52:00 pm -
1 stop8h 36m
Deal found 9/30![American Airlines logo]()
$546
This American Airlines deal was found by Cheapflights users on 9/30. 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.
Thu 11/128:41 pm -
2 stops15h 52m
Thu 11/191:31 pm -
2 stops10h 28m
Deal found 9/30![American Airlines logo]()
$572
This Delta deal was found by Cheapflights users on 9/30. 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 12/811:45 am -
1 stop10h 32m
Sat 12/197:00 am -
1 stop9h 26m
Deal found 9/30![Delta logo]()
$650
This Delta deal was found by Cheapflights users on 9/30. 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.
Thu 11/261:42 pm -
1 stop8h 33m
Wed 12/27:00 am -
1 stop9h 30m
Deal found 9/30![Delta logo]()
$664
This Delta deal was found by Cheapflights users on 9/30. 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.
Thu 11/261:42 pm -
1 stop8h 33m
Sun 12/67:00 am -
1 stop15h 52m
Deal found 9/30![Delta logo]()
$670
This Delta deal was found by Cheapflights users on 9/30. 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.
Thu 11/266:30 am -
2 stops15h 45m
Mon 12/77:00 am -
1 stop9h 30m
Deal found 9/30![Delta logo]()
$675
This American Airlines deal was found by Cheapflights users on 9/30. 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.
Thu 12/317:00 am -
1 stop16h 01m
Mon 3/12:46 pm -
1 stop20h 10m
Deal found 9/30![American Airlines logo]()
$682
This American Airlines deal was found by Cheapflights users on 9/30. 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.
Thu 12/36:35 pm -
2 stops18h 00m
Mon 12/73:35 pm -
2 stops19h 20m
Deal found 9/30![American Airlines logo]()
$703
This United Airlines deal was found by Cheapflights users on 9/30. 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 11/115:43 pm -
2 stops19h 27m
Tue 11/175:20 pm -
2 stops23h 42m
Deal found 9/30![United Airlines logo]()
$801
This United Airlines deal was found by Cheapflights users on 9/29. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/28:15 am -
2 stops28h 55m
Thu 11/52:20 pm -
2 stops21h 35m
Deal found 9/29![United Airlines logo]()
$816
Best flights from Madison to Costa RicaDiscover carefully curated flight deals from Madison to Costa Rica that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated October 1, 2026.
Discover carefully curated flight deals from Madison to Costa Rica that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated October 1, 2026.
This United Airlines deal was found by Cheapflights users on 9/26. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/245:00 am -
1 stop7h 15m
Wed 3/101:25 pm -
1 stop9h 38m
Deal found 9/26![United Airlines logo]()
$630
This Delta deal was found by Cheapflights users on 9/26. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/87:00 am -
2 stops15h 17m
Sat 12/197:00 am -
1 stop9h 26m
Deal found 9/26![Delta logo]()
$655
This American Airlines deal was found by Cheapflights users on 9/28. 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.
Mon 2/812:59 pm -
1 stop23h 31m
Mon 3/17:45 am -
2 stops15h 06m
Deal found 9/28![American Airlines logo]()
$665
This United Airlines deal was found by Cheapflights users on 9/26. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 1/67:19 pm -
2 stops17h 51m
Wed 1/132:06 pm -
1 stop9h 04m
Deal found 9/26![United Airlines logo]()
$639
This United Airlines deal was found by Cheapflights users on 9/30. 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.
Sat 10/315:00 am -
1 stop7h 48m
Sat 11/77:30 am -
1 stop13h 13m
Deal found 9/30![United Airlines logo]()
$670
This Delta deal was found by Cheapflights users on 9/30. 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.
Sat 1/162:00 pm -
1 stop8h 05m
Tue 1/267:05 am -
1 stop9h 29m
Deal found 9/30![Delta logo]()
$746
This United Airlines deal was found by Cheapflights users on 9/30. 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.
Fri 10/308:15 am -
2 stops13h 45m
Sat 11/71:55 pm -
1 stop9h 12m
Deal found 9/30![United Airlines logo]()
$670
This Delta deal was found by Cheapflights users on 9/28. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 1/162:00 pm -
1 stop8h 05m
Mon 1/257:05 am -
1 stop9h 29m
Deal found 9/28![Delta logo]()
$746
This United Airlines deal was found by Cheapflights users on 9/30. 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.
Sun 2/285:00 am -
2 stops11h 10m
Fri 3/58:35 am -
2 stops14h 28m
Deal found 9/30![United Airlines logo]()
$749
This United Airlines deal was found by Cheapflights users on 9/29. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/175:45 am -
1 stop7h 11m
Sun 2/282:06 pm -
1 stop8h 57m
Deal found 9/29![United Airlines logo]()
$797
This United Airlines deal was found by Cheapflights users on 10/1. 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 11/113:00 pm -
2 stops22h 10m
Tue 11/175:20 pm -
2 stops23h 42m
Deal found 10/1![United Airlines logo]()
$801
Last-minute flights from Madison to Costa RicaDiscover last-minute flight deals from Madison to Costa Rica. Data last updated October 1, 2026 and is based on user searches.
Discover last-minute flight deals from Madison to Costa Rica. Data last updated October 1, 2026 and is based on user searches.
This American Airlines deal was found by Cheapflights users on 9/28. 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.
Mon 10/125:53 pm -
2 stops19h 07m
Thu 10/153:01 pm -
2 stops20h 43m
Deal found 9/28![American Airlines logo]()
$749
This Delta deal was found by Cheapflights users on 9/30. 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.
Sun 10/185:51 am -
1 stop7h 09m
Thu 10/291:25 pm -
1 stop8h 38m
Deal found 9/30![Delta logo]()
$698
This Delta deal was found by Cheapflights users on 9/30. 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.
Sun 10/185:51 am -
1 stop7h 09m
Fri 10/231:25 pm -
2 stops28h 41m
Deal found 9/30![Delta logo]()
$712
This Delta deal was found by Cheapflights users on 9/30. 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.
Sun 10/185:51 am -
1 stop7h 09m
Mon 10/261:25 pm -
1 stop8h 38m
Deal found 9/30![Delta logo]()
$734
This Delta deal was found by Cheapflights users on 9/30. 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.
Sun 10/185:51 am -
1 stop7h 09m
Tue 10/271:25 pm -
2 stops18h 22m
Deal found 9/30![Delta logo]()
$739
This Delta deal was found by Cheapflights users on 9/30. 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 10/205:51 am -
1 stop7h 09m
Wed 10/281:25 pm -
1 stop8h 38m
Deal found 9/30![Delta logo]()
$718
This Delta deal was found by Cheapflights users on 9/30. 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 10/205:51 am -
1 stop7h 09m
Tue 10/271:25 pm -
1 stop8h 38m
Deal found 9/30![Delta logo]()
$745
This United Airlines deal was found by Cheapflights users on 9/30. 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.
Fri 10/308:15 am -
2 stops13h 45m
Sat 11/71:55 pm -
1 stop9h 12m
Deal found 9/30![United Airlines logo]()
$670
This American Airlines deal was found by Cheapflights users on 9/30. 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.
Fri 10/306:00 am -
2 stops15h 21m
Sat 11/76:20 am -
2 stops16h 40m
Deal found 9/30![American Airlines logo]()
$675
This American Airlines deal was found by Cheapflights users on 9/30. 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.
Sat 10/317:05 pm -
2 stops19h 41m
Sat 11/73:54 pm -
2 stops16h 16m
Deal found 9/30![American Airlines logo]()
$669
This United Airlines deal was found by Cheapflights users on 9/30. 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 11/115:43 pm -
2 stops19h 27m
Tue 11/175:20 pm -
2 stops23h 42m
Deal found 9/30![United Airlines logo]()
$801
This American Airlines deal was found by Cheapflights users on 9/30. 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.
Thu 11/128:41 pm -
2 stops15h 52m
Thu 11/191:31 pm -
2 stops10h 28m
Deal found 9/30![American Airlines logo]()
$572
One-way flights from Madison to Costa RicaSearch for one-way flight options from Madison to Costa Rica. Find affordable one-way fares based on user searches. Data last updated October 1, 2026.
Search for one-way flight options from Madison to Costa Rica. Find affordable one-way fares based on user searches. Data last updated October 1, 2026.
This United Airlines deal was found by Cheapflights users on 9/26. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 1/65:00 am -
1 stop7h 56m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/26![United Airlines logo]()
$311
This Delta deal was found by Cheapflights users on 9/26. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 1/209:26 am -
2 stops12h 39m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/26![Delta logo]()
$314
This American Airlines deal was found by Cheapflights users on 9/26. 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.
Wed 1/65:00 am -
2 stops9h 42m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/26![American Airlines logo]()
$316
This Delta deal was found by Cheapflights users on 9/26. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 1/227:55 pm -
2 stops26h 10m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/26![Delta logo]()
$319
This American Airlines deal was found by Cheapflights users on 9/27. 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 2/66:00 am -
2 stops13h 54m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/27![American Airlines logo]()
$326
This United Airlines deal was found by Cheapflights users on 9/30. 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.
Fri 2/195:45 am -
2 stops12h 52m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/30![United Airlines logo]()
$338
This Delta deal was found by Cheapflights users on 9/26. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 1/251:45 pm -
2 stops23h 00m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/26![Delta logo]()
$341
This United Airlines deal was found by Cheapflights users on 9/26. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 1/255:00 am -
1 stop7h 15m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/26![United Airlines logo]()
$379
This Kiwi.com deal was found by Cheapflights users on 9/27. 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.
Sat 2/610:38 am -
3 stops37h 21m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/27![Multiple Airlines logo]()
$442
This Kiwi.com deal was found by Cheapflights users on 9/26. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 1/2611:05 am -
3 stops23h 33m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/26![Multiple Airlines logo]()
$472
This Kiwi.com deal was found by Cheapflights users on 9/26. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 1/2310:38 am -
3 stops34h 27m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/26![Multiple Airlines logo]()
$478
This Kiwi.com deal was found by Cheapflights users on 9/26. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 1/246:00 pm -
3 stops30h 30m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/26![Multiple Airlines logo]()
$489
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 October 1, 2026.
Most accurate provider | Ovago 3 stars |
|---|---|
Most trusted provider | Ovago 3 stars |
Round-trip from | $434 (American Airlines) |
One-way from | $311 (United Airlines) |
Popular in | December |
Cheapest in | July |
Average price | $691 |
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 7,457,451 searches. Data last updated October 1, 2026.
Use the filters below to find and compare flights from Madison to Costa Rica that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
MadisonLiberia
MSN Madison Truax Field - LIR Liberia
MSNLIR
Madison Truax Field
Wed 1/6
5:00 am-12:56 pm
1 stop7h 56m
Liberia
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$311
MadisonSan José
MSN Madison Truax Field - SJO San José Juan Santamaria Intl
MSNSJO
Madison Truax Field
Thu 1/21
11:11 am-10:05 pm
1 stop10h 54m
San José Juan Santamaria Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$314
MadisonSan José
MSN Madison Truax Field - SJO San José Juan Santamaria Intl
MSNSJO
Madison Truax Field
Sun 1/24
9:26 am-10:05 pm
2 stops12h 39m
San José Juan Santamaria Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$314
MadisonSan José
MSN Madison Truax Field - SJO San José Juan Santamaria Intl
MSNSJO
Madison Truax Field
Tue 1/26
7:55 pm-10:05 pm
2 stops26h 10m
San José Juan Santamaria Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$319
MadisonSan José
MSN Madison Truax Field - SJO San José Juan Santamaria Intl
MSNSJO
Madison Truax Field
Fri 1/22
7:55 pm-10:05 pm
2 stops26h 10m
San José Juan Santamaria Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$319
MadisonSan José
MSN Madison Truax Field - SJO San José Juan Santamaria Intl
MSNSJO
Madison Truax Field
Sat 2/6
6:00 am-7:54 pm
2 stops13h 54m
San José Juan Santamaria Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$326
MadisonLiberia
MSN Madison Truax Field - LIR Liberia
MSNLIR
Madison Truax Field
Fri 2/19
5:00 am-12:56 pm
1 stop7h 56m
Liberia
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$338
Quickest round-trip
MadisonSan José
MSN Madison Truax Field - SJO San José Juan Santamaria Intl
MSNSJO
Madison Truax Field
Mon 1/25
5:00 am-12:15 pm
1 stop7h 15m
San José Juan Santamaria Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$379
MadisonSan José
MSN Madison Truax Field - SJO San José Juan Santamaria Intl
MSNSJO
Madison Truax Field
Sat 2/6
10:38 am-11:59 pm
3 stops37h 21m
San José Juan Santamaria Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$442
MadisonSan José
MSN Madison Truax Field - SJO San José Juan Santamaria Intl
MSNSJO
Madison Truax Field
Wed 2/24
5:00 am-12:15 pm
1 stop7h 15m
San José Juan Santamaria Intl
Wed 3/10
1:25 pm-11:03 pm
1 stop9h 38m
$630
Showing 1-10 of 21 resultsSorted by cheapest first
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.
MSN-SJO
MSN-LIR
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
MSN-CR0
MSN-SJO
MSN-LIR
What is the cheapest month to book a flight from Madison to Costa Rica?
Currently, September is the cheapest month in which you can book a flight from Madison to Costa Rica (average of $688). Flying from Madison to Costa Rica in December is currently the most expensive (average of $1,216). 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 October 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.
Comfort
7.8
Overall
7.8
Crew
8.5
Boarding
8.1
Entertainment
7.8
Food
7.2
Reviews
1 / 20
4.0
OkayJennifer,Sep 2026
ORD - LGA
Comfort
7.8
Overall
7.8
Crew
8.5
Boarding
8.1
Entertainment
7.8
Food
7.2
Reviews
1 / 20
4.0
OkayJennifer,Sep 2026
ORD - LGA
Comfort
7.8
Overall
7.8
Crew
8.5
Boarding
8.1
Entertainment
7.8
Food
7.2
Reviews
1 / 20
4.0
OkayJennifer,Sep 2026
ORD - LGA
Related info for your journey
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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 7,457,451 searches. Data last updated October 1, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$448 | Average$869 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$476 | Average$762 | FlexibilityNo cancel fee | On-time71% |