$418+ 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 11/10. Fares are subject to change and may not be available on all flights or dates of travel.
MSN — SJO
Jul 15 — Jul 221
Round-trip
1 adult, Economy
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Find cheap flights from Madison to San José with Cheapflights
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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 San José
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Best
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Cheapest flights from Madison to San JoséExplore 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 15, 2026.
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 15, 2026.
This American Airlines 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/106:00 am
MSN
- SJO
1 stop8h 10m
American Airlines
Wed 11/256:22 am
SJO
- MSN
1 stop10h 37m
American Airlines
Deal found 6/10![American Airlines logo]()
$418
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 11/106:00 am
MSN
- SJO
1 stop16h 59m
American Airlines
Thu 11/197:00 am
SJO
- MSN
2 stops15h 50m
American Airlines
Deal found 6/11![American Airlines logo]()
$423
This American Airlines 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/56:00 am
MSN
- SJO
1 stop8h 10m
American Airlines
Fri 11/201:23 pm
SJO
- MSN
1 stop10h 28m
American Airlines
Deal found 6/10![American Airlines logo]()
$499
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.
Wed 10/216:49 am
MSN
- SJO
2 stops13h 48m
United Airlines
Sun 10/2511:35 am
SJO
- MSN
2 stops11h 37m
United Airlines
Deal found 6/11![United Airlines logo]()
$504
This American Airlines deal was found by Cheapflights users on 6/13. 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 10/274:16 pm
MSN
- SJO
2 stops19h 49m
American Airlines
Tue 11/36:22 am
SJO
- MSN
2 stops13h 20m
American Airlines
Deal found 6/13![American Airlines logo]()
$515
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/105:30 pm
MSN
- SJO
2 stops17h 55m
United Airlines
Wed 11/258:45 am
SJO
- MSN
2 stops25h 08m
United Airlines
Deal found 6/10![United Airlines logo]()
$543
This Delta deal was found by Cheapflights users on 6/13. 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 10/2411:00 am
MSN
- SJO
2 stops25h 58m
Delta
Tue 11/32:23 pm
SJO
- MSN
1 stop8h 11m
Delta
Deal found 6/13![Delta logo]()
$550
This Delta deal was found by Cheapflights users on 6/13. 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 10/2411:00 am
MSN
- SJO
2 stops25h 58m
Delta
Wed 11/42:23 pm
SJO
- MSN
2 stops18h 27m
Delta
Deal found 6/13![Delta logo]()
$579
This Delta deal was found by Cheapflights users on 6/13. 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 10/283:30 pm
MSN
- SJO
2 stops21h 28m
Delta
Tue 11/32:23 pm
SJO
- MSN
2 stops22h 33m
Delta
Deal found 6/13![Delta logo]()
$580
Best flights from Madison to San JoséDiscover carefully curated flight deals from Madison to San José that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated June 15, 2026.
Discover carefully curated flight deals from Madison to San José that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated June 15, 2026.
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 11/103:10 pm
MSN
- SJO
1 stop7h 49m
American Airlines
Thu 11/196:22 am
SJO
- MSN
1 stop15h 32m
American Airlines
Deal found 6/11![American Airlines logo]()
$418
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.
Wed 10/216:49 am
MSN
- SJO
2 stops13h 48m
United Airlines
Sun 10/2511:35 am
SJO
- MSN
2 stops11h 37m
United Airlines
Deal found 6/11![United Airlines logo]()
$504
This Delta deal was found by Cheapflights users on 6/13. 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 10/255:45 am
MSN
- SJO
1 stop7h 13m
Delta
Tue 11/32:23 pm
SJO
- MSN
1 stop8h 11m
Delta
Deal found 6/13![Delta logo]()
$734
This American Airlines 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/106:00 am
MSN
- SJO
1 stop8h 10m
American Airlines
Wed 11/256:22 am
SJO
- MSN
1 stop10h 37m
American Airlines
Deal found 6/10![American Airlines logo]()
$418
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/108:25 pm
MSN
- SJO
2 stops16h 50m
United Airlines
Wed 11/258:45 am
SJO
- MSN
2 stops25h 08m
United Airlines
Deal found 6/10![United Airlines logo]()
$543
This American Airlines 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/13:10 pm
MSN
- SJO
1 stop7h 49m
American Airlines
Mon 11/161:23 pm
SJO
- MSN
1 stop10h 28m
American Airlines
Deal found 6/10![American Airlines logo]()
$610
This United Airlines deal was found by Cheapflights users on 6/14. 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 9/286:06 am
MSN
- SJO
1 stop30h 32m
United Airlines
Thu 10/11:25 pm
SJO
- MSN
2 stops24h 39m
United Airlines
Deal found 6/14![United Airlines logo]()
$645
This United Airlines deal was found by Cheapflights users on 6/13. 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 11/26:45 am
MSN
- SJO
2 stops28h 40m
United Airlines
Thu 11/52:20 pm
SJO
- MSN
2 stops19h 33m
United Airlines
Deal found 6/13![United Airlines logo]()
$682
This American Airlines deal was found by Cheapflights users on 6/14. 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.
Sun 9/67:00 am
MSN
- SJO
1 stop7h 52m
American Airlines
Sat 9/121:00 pm
SJO
- MSN
1 stop20h 51m
American Airlines
Deal found 6/14![American Airlines logo]()
$743
Last-minute flights from Madison to San JoséDiscover last-minute flight deals from Madison to San José. Data last updated June 15, 2026 and is based on user searches.
Discover last-minute flight deals from Madison to San José. Data last updated June 15, 2026 and is based on user searches.
This United Airlines deal was found by Cheapflights users on 6/13. 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.
Thu 7/25:00 am
MSN
- SJO
2 stops18h 39m
United Airlines
Sat 7/116:40 am
SJO
- MSN
1 stop13h 36m
United Airlines
Deal found 6/13![United Airlines logo]()
$777
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.
Wed 7/83:46 pm
MSN
- SJO
2 stops19h 25m
United Airlines
Thu 7/1611:13 am
SJO
- MSN
2 stops21h 34m
United Airlines
Deal found 6/11![United Airlines logo]()
$849
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.
Thu 7/910:48 am
MSN
- SJO
2 stops12h 51m
United Airlines
Wed 7/157:15 am
SJO
- MSN
1 stop12h 24m
United Airlines
Deal found 6/11![United Airlines logo]()
$826
This Kiwi.com deal was found by Cheapflights users on 6/14. 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 7/187:55 pm
MSN
- SJO
1 stop13h 25m
Multiple Airlines
Sat 8/159:45 am
SJO
- MSN
1 stop8h 30m
Multiple Airlines
Deal found 6/14![Multiple Airlines logo]()
$700
This Kiwi.com deal was found by Cheapflights users on 6/14. 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 7/187:55 pm
MSN
- SJO
1 stop13h 25m
Multiple Airlines
Thu 8/137:07 am
SJO
- MSN
2 stops24h 18m
Multiple Airlines
Deal found 6/14![Multiple Airlines logo]()
$776
This United Airlines deal was found by Cheapflights users on 6/14. 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 7/275:00 am
MSN
- SJO
2 stops30h 11m
United Airlines
Mon 8/1012:30 am
SJO
- MSN
2 stops15h 43m
United Airlines
Deal found 6/14![United Airlines logo]()
$856
This KAYAK deal was found by Cheapflights users on 6/12. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/284:11 pm
MSN
- SJO
2 stops20h 39m
GOL
Sat 8/13:37 pm
SJO
- MSN
2 stops20h 10m
GOL
Deal found 6/12![GOL logo]()
$775
This American Airlines deal was found by Cheapflights users on 6/14. 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 7/296:50 am
MSN
- SJO
1 stop16h 48m
American Airlines
Tue 8/112:56 pm
SJO
- MSN
2 stops18h 27m
American Airlines
Deal found 6/14![American Airlines logo]()
$823
This United Airlines deal was found by Cheapflights users on 6/14. 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 7/295:00 am
MSN
- SJO
2 stops18h 39m
United Airlines
Mon 8/1012:30 am
SJO
- MSN
2 stops15h 43m
United Airlines
Deal found 6/14![United Airlines logo]()
$837
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 June 15, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $418 (American Airlines) |
Popular in | December |
Cheapest in | October |
Average price | $874 |
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 15, 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
Cheapest round-trip
MadisonSan José
MSN - SJO
MSNSJO
Madison Truax Field
Tue 11/10
3:10 pm-10:59 pm
1 stop7h 49m
San José Juan Santamaria Intl
Thu 11/19
6:22 am-9:54 pm
1 stop15h 32m
$418
MadisonSan José
MSN - SJO
MSNSJO
Madison Truax Field
Tue 11/10
6:00 am-2:10 pm
1 stop8h 10m
San José Juan Santamaria Intl
Wed 11/25
6:22 am-4:59 pm
1 stop10h 37m
$418
MadisonSan José
MSN - SJO
MSNSJO
Madison Truax Field
Wed 10/21
6:49 am-7:37 pm
2 stops13h 48m
San José Juan Santamaria Intl
Sun 10/25
11:35 am-12:12 am
2 stops11h 37m
$504
MadisonSan José
MSN - SJO
MSNSJO
Madison Truax Field
Tue 11/10
8:25 pm-1:15 pm
2 stops16h 50m
San José Juan Santamaria Intl
Wed 11/25
8:45 am-9:53 am
2 stops25h 08m
$543
MadisonSan José
MSN - SJO
MSNSJO
Madison Truax Field
Sun 11/1
3:10 pm-10:59 pm
1 stop7h 49m
San José Juan Santamaria Intl
Mon 11/16
1:23 pm-11:51 pm
1 stop10h 28m
$610
MadisonSan José
MSN - SJO
MSNSJO
Madison Truax Field
Mon 9/28
6:06 am-11:38 am
1 stop30h 32m
San José Juan Santamaria Intl
Thu 10/1
1:25 pm-3:04 pm
2 stops24h 39m
$645
MadisonSan José
MSN - SJO
MSNSJO
Madison Truax Field
Mon 11/2
6:45 am-11:25 am
2 stops28h 40m
San José Juan Santamaria Intl
Thu 11/5
2:20 pm-9:53 am
2 stops19h 33m
$682
Quickest round-trip
MadisonSan José
MSN - SJO
MSNSJO
Madison Truax Field
Sun 10/25
5:45 am-11:58 am
1 stop7h 13m
San José Juan Santamaria Intl
Tue 11/3
2:23 pm-10:34 pm
1 stop8h 11m
$734
MadisonSan José
MSN - SJO
MSNSJO
Madison Truax Field
Sun 9/6
7:00 am-1:52 pm
1 stop7h 52m
San José Juan Santamaria Intl
Sat 9/12
1:00 pm-10:51 am
1 stop20h 51m
$743
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 June.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars |
- Most accurate provider: When it comes to deals on Madison-San José flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Madison-San José flight deals on Cheapflights vs. FlightHub >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 FlightHub the most. FlightHub 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.
MSN-SJO
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, October is the cheapest month in which you can book a flight from Madison to San José (average of $448). 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?
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 15, 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.
Food
7.2
Comfort
7.8
Overall
7.9
Entertainment
7.8
Boarding
8.1
Crew
8.5
Reviews
1 / 20
10.0
ExcellentAnonymous,May 2026
SEA - KOA
Food
7.2
Comfort
7.8
Overall
7.9
Entertainment
7.8
Boarding
8.1
Crew
8.5
Reviews
1 / 20
10.0
ExcellentAnonymous,May 2026
SEA - KOA
Food
7.2
Comfort
7.8
Overall
7.9
Entertainment
7.8
Boarding
8.1
Crew
8.5
Reviews
1 / 20
10.0
ExcellentAnonymous,May 2026
SEA - KOA
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.
Traveling to a place near San José?
Book flights to San José if you plan to visit one of these locationsAlajuela
Jacó
Heredia
Dominical
Manuel Antonio
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Madison and San José flights
Browse other Madison and San José flight options. Last updated on June 15, 2026.
Other flights from Madison
Browse through other flights departing from Madison. Flights are based on user searches made on Cheapflights and were last updated on June 15, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Other flights to San José
Explore flights to San José departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on June 15, 2026.
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 June 15, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$397 | Average$638 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$495 | Average$906 | FlexibilityNo cancel fee | On-timeN/A |