San José

$302+ Cheap flights from Madison (MSN) to San José (SJO)

MSN — SJO
Dec 9 — Dec 161
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1. Tell us where you want to go

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Cheap flight deals from Madison to San José

Cheapest flights from Madison to San José

Thu 12/314:33 pm -
2 stops18h 02m
Mon 3/12:49 pm -
2 stops17h 28m
Deal found 11/7$688
Wed 11/255:30 am -
1 stop7h 42m
Wed 12/27:00 am -
1 stop15h 52m
Deal found 11/4$719
Tue 12/85:00 am -
2 stops9h 52m
Sat 12/196:22 am -
2 stops13h 05m
Deal found 11/4$729
Wed 11/258:41 pm -
2 stops17h 05m
Wed 12/21:42 pm -
2 stops21h 03m
Deal found 11/4$734
Wed 12/305:40 am -
1 stop7h 19m
Tue 4/271:20 pm -
1 stop8h 14m
Deal found 11/6$739
Thu 12/36:00 am -
1 stop13h 53m
Thu 12/1011:28 pm -
2 stops12h 29m
Deal found 11/5$753
Thu 12/315:40 am -
1 stop16h 06m
Tue 4/271:20 pm -
1 stop8h 14m
Deal found 11/6$759
Tue 12/89:55 am -
2 stops12h 22m
Sat 12/197:00 am -
1 stop9h 26m
Deal found 11/5$763

Find flight deals from Madison to San José

Most accurate provider

Ovago
3 stars

Most trusted provider

Ovago
3 stars

Round-trip from

$439
(American Airlines)

One-way from

$302
(Avianca)

Popular in

December

Cheapest in

July

Average price

$742
Provider with most accurate pricing for Madison Truax Field-San José Juan Santamaria Intl flight deals.
Provider most trusted by Cheapflights users for Madison Truax Field-San José Juan Santamaria Intl flights.
From Madison Truax Field to San José Juan Santamaria Intl
One-way flight from Madison Truax Field to San José Juan Santamaria Intl
Highest demand for flights based on searches. 10% potential increase in price ($92 potential increase over avg. RT price).
Cheapest flight prices on average. 4% potential price decrease ($32 potential savings vs. average RT price).
Average for round-trip flights in November 2026

Cheapflights Fare Finder

 
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 Madison Truax Field - SJO San José Juan Santamaria Intl

MSNSJO

Madison Truax Field

Wed 2/17

6:39 pm-12:15 pm

1 stop17h 36m

San José Juan Santamaria Intl

Wed 12/31

12:00 am-12:00 am

Nonstop0h 00m

$344

MadisonSan José

MSN Madison Truax Field - SJO San José Juan Santamaria Intl

MSNSJO

Madison Truax Field

Tue 3/23

7:00 am-9:24 pm

2 stops15h 24m

San José Juan Santamaria Intl

Wed 12/31

12:00 am-12:00 am

Nonstop0h 00m

$344
Quickest round-trip

MadisonSan José

MSN Madison Truax Field - SJO San José Juan Santamaria Intl

MSNSJO

Madison Truax Field

Thu 2/18

6:00 am-7:53 pm

1 stop13h 53m

San José Juan Santamaria Intl

Wed 12/31

12:00 am-12:00 am

Nonstop0h 00m

$344

MadisonSan José

MSN Madison Truax Field - SJO San José Juan Santamaria Intl

MSNSJO

Madison Truax Field

Sun 3/21

7:55 pm-9:24 pm

2 stops26h 29m

San José Juan Santamaria Intl

Wed 12/31

12:00 am-12:00 am

Nonstop0h 00m

$349

MadisonSan José

MSN Madison Truax Field - SJO San José Juan Santamaria Intl

MSNSJO

Madison Truax Field

Mon 3/22

11:00 am-11:55 am

2 stops25h 55m

San José Juan Santamaria Intl

Wed 12/31

12:00 am-12:00 am

Nonstop0h 00m

$386

MadisonSan José

MSN Madison Truax Field - SJO San José Juan Santamaria Intl

MSNSJO

Madison Truax Field

Mon 3/22

6:39 pm-11:15 am

1 stop17h 36m

San José Juan Santamaria Intl

Wed 12/31

12:00 am-12:00 am

Nonstop0h 00m

$409

MadisonSan José

MSN Madison Truax Field - SJO San José Juan Santamaria Intl

MSNSJO

Madison Truax Field

Fri 3/26

12:33 pm-12:22 pm

2 stops24h 49m

San José Juan Santamaria Intl

Wed 12/31

12:00 am-12:00 am

Nonstop0h 00m

$491

MadisonSan José

MSN Madison Truax Field - SJO San José Juan Santamaria Intl

MSNSJO

Madison Truax Field

Sat 3/20

6:30 am-11:15 am

1 stop29h 45m

San José Juan Santamaria Intl

Wed 12/31

12:00 am-12:00 am

Nonstop0h 00m

$561

MadisonSan José

MSN Madison Truax Field - SJO San José Juan Santamaria Intl

MSNSJO

Madison Truax Field

Wed 11/25

5:30 am-1:12 pm

1 stop7h 42m

San José Juan Santamaria Intl

Wed 12/2

7:00 am-10:52 pm

1 stop15h 52m

$719

MadisonSan José

MSN Madison Truax Field - SJO San José Juan Santamaria Intl

MSNSJO

Madison Truax Field

Tue 2/2

6:36 am-6:16 pm

2 stops11h 40m

San José Juan Santamaria Intl

Tue 2/9

9:05 am-9:38 pm

1 stop12h 33m

$719

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/4

Showing 1-10 of 19 resultsSorted by cheapest first
1
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Compare providers for flights from Madison to San José

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 November.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
OvagoPrice Accuracy3 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
eDreamsPrice Accuracy2 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

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, July is the cheapest month in which you can book a flight from Madison to San José (average of $628). Flying from Madison to San José in December is currently the most expensive (average of $1,118). 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 San José

Read through reviews of airlines operating flights from Madison to San José, such as Delta,United Airlines, andAmerican Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.

Boarding

8.1

Comfort

7.8

Entertainment

7.8

Overall

7.8

Food

7.2

Crew

8.5

Reviews

1 / 20
6.0
Good

Ellen,Oct 2026

GRR - ATL

The flight was delayed more then 30 minutes after I hurried and stressed to get to my connecting gate in Atlanta.

Boarding

8.1

Comfort

7.8

Entertainment

7.8

Overall

7.8

Food

7.2

Crew

8.5

Reviews

1 / 20
6.0
Good

Ellen,Oct 2026

GRR - ATL

The flight was delayed more then 30 minutes after I hurried and stressed to get to my connecting gate in Atlanta.

Boarding

8.1

Comfort

7.8

Entertainment

7.8

Overall

7.8

Food

7.2

Crew

8.5

Reviews

1 / 20
6.0
Good

Ellen,Oct 2026

GRR - ATL

The flight was delayed more then 30 minutes after I hurried and stressed to get to my connecting gate in Atlanta.

Boarding

8.1

Comfort

7.8

Entertainment

7.8

Overall

7.8

Food

7.2

Crew

8.5

Reviews

1 / 20
6.0
Good

Ellen,Oct 2026

GRR - ATL

The flight was delayed more then 30 minutes after I hurried and stressed to get to my connecting gate in Atlanta.

Related info for your journey

  • 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 42m. Fly via Delta, 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 $382. Other airlines that can offer you cheap pricing are American Airlines, from $476, and Delta, from $539. United Airlines is currently priced 50% 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, July is the cheapest month in which you can book a flight from Madison to San José (average of $628). Flying from Madison to San José in December is currently the most expensive (average of $1,118). 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
Heredia
Dominical
Manuel Antonio

Browse thousands of different options on Cheapflights for your next trip

Top 3 airlines flying from Madison to San José

AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$382Average$702FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$476Average$712FlexibilityNo cancel feeOn-time71%
DeltaCheapest$539Average$959FlexibilityNo cancel feeOn-timeN/A

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