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Cheap flights from Madison to San José from $208

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Madison to San José departing on 3/7. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
0 bags

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Find the cheapest flights from Madison to San José

Cheap round-trip flights

Enter your travel dates to find the best prices.
American Airlines Logo
5:17 pm - 10:24 am
MSN
-
SJO
17h 07m
2 stops
American Airlines Logo
12:35 am - 10:36 am
SJO
-
MSN
10h 01m
1 stop
$328American Airlines
Sat, Feb 28 - Wed, Mar 4
American Airlines Logo
7:15 am - 8:12 pm
MSN
-
SJO
12h 57m
2 stops
American Airlines Logo
2:20 pm - 10:39 am
SJO
-
MSN
19h 19m
1 stop
$335American Airlines
Tue, Mar 3 - Tue, Mar 10
American Airlines Logo
8:24 pm - 8:12 pm
MSN
-
SJO
23h 48m
1 stop
American Airlines Logo
2:20 pm - 10:39 am
SJO
-
MSN
19h 19m
1 stop
$336American Airlines
Tue, Mar 3 - Tue, Mar 10
American Airlines Logo
8:09 am - 8:33 pm
MSN
-
SJO
12h 24m
2 stops
American Airlines Logo
2:59 pm - 9:08 am
SJO
-
MSN
17h 09m
2 stops
$382American Airlines
Tue, Mar 3 - Tue, Mar 10
American Airlines Logo
7:00 am - 7:33 pm
MSN
-
SJO
13h 33m
2 stops
American Airlines Logo
6:00 am - 11:22 pm
SJO
-
MSN
16h 22m
1 stop
$407American Airlines
Mon, Mar 9 - Tue, Mar 17
United Airlines Logo
7:25 pm - 11:56 am
MSN
-
SJO
17h 31m
1 stop
United Airlines Logo
1:05 pm - 10:32 pm
SJO
-
MSN
8h 27m
1 stop
$422United Airlines
Mon, Mar 9 - Tue, Mar 17
American Airlines Logo
9:41 am - 8:12 pm
MSN
-
SJO
10h 31m
1 stop
American Airlines Logo
12:35 am - 10:36 am
SJO
-
MSN
10h 01m
1 stop
$430American Airlines
Tue, Feb 24 - Wed, Mar 4
American Airlines Logo
7:15 am - 8:33 pm
MSN
-
SJO
13h 18m
2 stops
American Airlines Logo
12:35 am - 10:36 am
SJO
-
MSN
10h 01m
1 stop
$435American Airlines
Tue, Feb 24 - Wed, Mar 4
United Airlines Logo
6:30 am - 6:53 pm
MSN
-
SJO
13h 23m
2 stops
United Airlines Logo
1:05 pm - 10:32 pm
SJO
-
MSN
8h 27m
1 stop
$441United Airlines
Tue, Mar 10 - Tue, Mar 17
American Airlines Logo
8:00 am - 7:33 pm
MSN
-
SJO
12h 33m
2 stops
American Airlines Logo
7:00 am - 9:39 pm
SJO
-
MSN
13h 39m
2 stops
$446American Airlines
Mon, Mar 9 - Tue, Mar 17

United Airlines flights from Madison to San José

Our best United Airlines deals on Madison to San José flight tickets
United Airlines
Mar 10
MSN6:30 amMadison Truax Field
13h 23m
2 stops
SJO6:53 pmSan José Juan Santamaria Intl
Mar 17
SJO1:05 pmSan José Juan Santamaria Intl
8h 27m
1 stop
MSN10:32 pmMadison Truax Field
$441
United Airlines
Apr 6
MSN8:35 pmMadison Truax Field
16h 46m
2 stops
SJO12:21 pmSan José Juan Santamaria Intl
Apr 13
SJO1:25 pmSan José Juan Santamaria Intl
17h 36m
2 stops
MSN8:01 amMadison Truax Field
$517
United Airlines
Feb 25
MSN2:48 pmMadison Truax Field
22h 27m
2 stops
SJO1:15 pmSan José Juan Santamaria Intl
Mar 5
SJO2:20 pmSan José Juan Santamaria Intl
32h 12m
2 stops
MSN10:32 pmMadison Truax Field
$574

LATAM Airlines flights from Madison to San José

Our best LATAM Airlines deals on Madison to San José flight tickets
LATAM Airlines
Mar 10
MSN5:30 amMadison Truax Field
16h 45m
1 stop
SJO9:15 pmSan José Juan Santamaria Intl
Mar 17
SJO7:00 amSan José Juan Santamaria Intl
14h 34m
1 stop
MSN10:34 pmMadison Truax Field
$471
LATAM Airlines
Mar 6
MSN5:38 amMadison Truax Field
16h 24m
1 stop
SJO10:02 pmSan José Juan Santamaria Intl
Mar 9
SJO7:00 amSan José Juan Santamaria Intl
14h 34m
1 stop
MSN10:34 pmMadison Truax Field
$557

momondo 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, momondo users made 832,500 searches. Data last updated February 8, 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

Price

MadisonSan José

MSN - SJO

MSNSJO

Madison Truax Field

Sat 2/28

5:17 pm-10:24 am

2 stops17h 07m

San José Juan Santamaria Intl

Wed 3/4

12:35 am-10:36 am

1 stop10h 01m

$328

MadisonSan José

MSN - SJO

MSNSJO

Madison Truax Field

Tue 3/3

7:15 am-8:12 pm

2 stops12h 57m

San José Juan Santamaria Intl

Tue 3/10

2:20 pm-10:39 am

1 stop19h 19m

$335

MadisonSan José

MSN - SJO

MSNSJO

Madison Truax Field

Tue 3/3

8:24 pm-8:12 pm

1 stop23h 48m

San José Juan Santamaria Intl

Tue 3/10

2:20 pm-10:39 am

1 stop19h 19m

$336

MadisonSan José

MSN - SJO

MSNSJO

Madison Truax Field

Tue 3/3

8:09 am-8:33 pm

2 stops12h 24m

San José Juan Santamaria Intl

Tue 3/10

2:59 pm-9:08 am

2 stops17h 09m

$382

MadisonSan José

MSN - SJO

MSNSJO

Madison Truax Field

Mon 3/9

7:00 am-7:33 pm

2 stops13h 33m

San José Juan Santamaria Intl

Tue 3/17

6:00 am-11:22 pm

1 stop16h 22m

$407

MadisonSan José

MSN - SJO

MSNSJO

Madison Truax Field

Mon 3/9

7:25 pm-11:56 am

1 stop17h 31m

San José Juan Santamaria Intl

Tue 3/17

1:05 pm-10:32 pm

1 stop8h 27m

$422

MadisonSan José

MSN - SJO

MSNSJO

Madison Truax Field

Tue 2/24

9:41 am-8:12 pm

1 stop10h 31m

San José Juan Santamaria Intl

Wed 3/4

12:35 am-10:36 am

1 stop10h 01m

$430

MadisonSan José

MSN - SJO

MSNSJO

Madison Truax Field

Tue 2/24

7:15 am-8:33 pm

2 stops13h 18m

San José Juan Santamaria Intl

Wed 3/4

12:35 am-10:36 am

1 stop10h 01m

$435

MadisonSan José

MSN - SJO

MSNSJO

Madison Truax Field

Tue 3/10

6:30 am-6:53 pm

2 stops13h 23m

San José Juan Santamaria Intl

Tue 3/17

1:05 pm-10:32 pm

1 stop8h 27m

$441

MadisonSan José

MSN - SJO

MSNSJO

Madison Truax Field

Mon 3/9

8:00 am-7:33 pm

2 stops12h 33m

San José Juan Santamaria Intl

Tue 3/17

7:00 am-9:39 pm

2 stops13h 39m

$446

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to San José from

How to get the cheapest flight ticket from Madison to San José

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest month to fly to San José?

In general, September is the cheapest month to fly from Madison to San José. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around $505. If you don’t want to visit San José in September, then you should wait until October to fly from Madison, when ticket prices are also cheap, with an average price of $590.

Can stopping save me money on Madison to San José flights?

You could potentially save up to 63% on your flight if you consider stops on a Madison to San José flight.

When to book flights from Madison to San José

Are you open to changing your travel dates? Check out the ideal times to fly from Madison to San José according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Madison to San José (MSN to SJO) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Madison to San José

Fastest flight time

10h 49m

Direct flights

None
The fastest flight from Madison to San José takes 10h 49m
There are no direct flights from Madison to San José. There are no popular flight routes from Madison to San José.
Search flight deals

  • How far is Madison Truax Field to San José Juan Santamaria Intl by plane?

    Madison Truax Field and San José Juan Santamaria Intl are 2310.4 mi apart from one another. Flights usually cover this in 10h 49m, depending on flying conditions and air traffic around both airports.

  • When did momondo last update prices for flights from Madison Truax Field Airport to San José Juan Santamaria Intl Airport?

    Prices for flights from Madison Truax Field Airport to San José Juan Santamaria Intl Airport were last updated today.

  • How many operators does momondo search for flights from Madison Truax Field Airport to San José Juan Santamaria Intl Airport?

  • How old do you have to be to fly from Madison Truax Field Airport to San José Juan Santamaria Intl Airport?

    The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Madison Truax Field Airport to San José Juan Santamaria Intl Airport.

  • What documentation or ID do you need to fly to San José Juan Santamaria Intl Airport?

    The travel and health documents required for your trip to San José Juan Santamaria Intl Airport can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at San José Juan Santamaria Intl Airport. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

  • What is the most popular airline from Madison to San José?

Best airlines flying from Madison to San José

Compare and see reviews for airlines that fly from Madison to San José with momondo
Airline
Rating
Free Cancellation
Price
American AirlinesPriceFrom $475Free CancellationRating
7.2
11,258 reviews
Search American Airlines flights
DeltaPriceFrom $495Free CancellationRating
7.9
8,174 reviews
Search Delta flights

Traveling to a place near San José?

Book flights to San José if you plan to visit one of these locations
Manuel Antonio
Jacó
Monteverde
Alajuela
Heredia
Dominical
San Gerardo de Dota
Santa Elena
Esterillos Este

Why use momondo?

Why should I use momondo to find a flight deal from Madison to San José?

To find the flight that best suits your needs, momondo gathers a range of flights from a large pool of different airlines and agents; you can then use our insights and filters to find and book the right flight to San José from Madison.

Can I find flights from Madison to San José with flexible booking policies on momondo?

Yes. momondo enables you to select and highlight flights to San José from Madison with this policy.

How can momondo help me find flights from Madison to San José?

momondo provides multiple filters to help you find the best flight to San José from Madison. Filter by price, airline, airports, cabin, aircraft, payment method, number of stops and more.

I’m not ready to book a flight from Madison to San José right now. Can momondo alert me if prices change?

If you are not ready to book a flight from Madison to San José now, use our insights above to find helpful tips or alternatively set up a price alert, where momondo will track prices on flights to San José and let you know when they change.

An easier way to manage your San José trip

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