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Cheap flights from Madison to San José from $314

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 6/23. 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.
Delta Logo
5:45 am - 11:56 am
MSN
-
SJO
7h 11m
1 stop
Delta Logo
1:25 pm - 8:50 am
SJO
-
MSN
18h 25m
2 stops
$565Delta
Sun, Sep 6 - Mon, Oct 5
Delta Logo
5:45 am - 11:56 am
MSN
-
SJO
7h 11m
1 stop
Delta Logo
1:25 pm - 10:35 pm
SJO
-
MSN
8h 10m
1 stop
$574Delta
Sun, Sep 6 - Mon, Oct 5
American Airlines Logo
5:47 pm - 12:03 pm
MSN
-
SJO
19h 16m
2 stops
American Airlines Logo
2:53 pm - 10:40 am
SJO
-
MSN
18h 47m
2 stops
$579American Airlines
Sat, Aug 15 - Sat, Aug 22
American Airlines Logo
11:29 am - 1:52 pm
MSN
-
SJO
27h 23m
1 stop
American Airlines Logo
2:53 pm - 10:40 am
SJO
-
MSN
18h 47m
2 stops
$588American Airlines
Sat, Aug 15 - Sat, Aug 22
American Airlines Logo
5:47 pm - 11:34 am
MSN
-
SJO
18h 47m
2 stops
American Airlines Logo
2:52 pm - 10:40 am
SJO
-
MSN
18h 48m
2 stops
$589American Airlines
Sat, Aug 15 - Sat, Aug 22
Multiple Airlines Logo
7:55 pm - 8:20 am
MSN
-
SJO
13h 25m
1 stop
Multiple Airlines Logo
7:07 am - 5:25 pm
SJO
-
MSN
9h 18m
1 stop
$597Multiple Airlines
Sat, Aug 1 - Wed, Aug 5
American Airlines Logo
11:29 am - 1:52 pm
MSN
-
SJO
27h 23m
1 stop
American Airlines Logo
2:52 pm - 10:40 am
SJO
-
MSN
18h 48m
2 stops
$599American Airlines
Sat, Aug 15 - Sat, Aug 22
Delta Logo
5:43 am - 11:49 am
MSN
-
SJO
7h 06m
1 stop
Delta Logo
1:14 pm - 11:26 am
SJO
-
MSN
21h 12m
2 stops
$603Delta
Mon, Aug 3 - Fri, Aug 7
American Airlines Logo
5:46 pm - 11:34 am
MSN
-
SJO
18h 48m
2 stops
American Airlines Logo
2:52 pm - 10:40 am
SJO
-
MSN
18h 48m
2 stops
$604American Airlines
Sat, Aug 15 - Sat, Aug 22
Delta Logo
5:45 am - 11:56 am
MSN
-
SJO
7h 11m
1 stop
Delta Logo
1:25 pm - 8:50 am
SJO
-
MSN
18h 25m
2 stops
$609Delta
Sat, Sep 5 - Mon, Oct 5

American Airlines flights from Madison to San José

Our best American Airlines deals on Madison to San José flight tickets
American Airlines
Aug 15
MSN5:47 pmMadison Truax Field
19h 16m
2 stops
SJO12:03 pmSan José Juan Santamaria Intl
Aug 22
SJO2:53 pmSan José Juan Santamaria Intl
18h 47m
2 stops
MSN10:40 amMadison Truax Field
$579
American Airlines
Aug 15
MSN11:29 amMadison Truax Field
27h 23m
1 stop
SJO1:52 pmSan José Juan Santamaria Intl
Aug 22
SJO2:53 pmSan José Juan Santamaria Intl
18h 47m
2 stops
MSN10:40 amMadison Truax Field
$588
American Airlines
Aug 15
MSN5:47 pmMadison Truax Field
18h 47m
2 stops
SJO11:34 amSan José Juan Santamaria Intl
Aug 22
SJO2:52 pmSan José Juan Santamaria Intl
18h 48m
2 stops
MSN10:40 amMadison Truax Field
$589

United Airlines flights from Madison to San José

Our best United Airlines deals on Madison to San José flight tickets
United Airlines
Jun 22
MSN6:30 amMadison Truax Field
17h 09m
2 stops
SJO10:39 pmSan José Juan Santamaria Intl
Jun 28
SJO7:55 amSan José Juan Santamaria Intl
25h 04m
2 stops
MSN9:59 amMadison Truax Field
$685
United Airlines
Oct 24
MSN4:31 pmMadison Truax Field
20h 44m
2 stops
SJO12:15 pmSan José Juan Santamaria Intl
Oct 28
SJO1:20 pmSan José Juan Santamaria Intl
18h 33m
2 stops
MSN8:53 amMadison Truax Field
$699
United Airlines
Oct 24
MSN6:30 pmMadison Truax Field
18h 45m
2 stops
SJO12:15 pmSan José Juan Santamaria Intl
Oct 28
SJO11:35 amSan José Juan Santamaria Intl
20h 18m
2 stops
MSN8:53 amMadison Truax Field
$709

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 May 24, 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

Cheapest round-trip

MadisonSan José

MSN - SJO

MSNSJO

Madison Truax Field

Sun 9/6

5:45 am-11:56 am

1 stop7h 11m

San José Juan Santamaria Intl

Mon 10/5

1:25 pm-8:50 am

2 stops18h 25m

$565
Quickest round-trip

MadisonSan José

MSN - SJO

MSNSJO

Madison Truax Field

Sun 9/6

5:45 am-11:56 am

1 stop7h 11m

San José Juan Santamaria Intl

Mon 10/5

1:25 pm-10:35 pm

1 stop8h 10m

$574

MadisonSan José

MSN - SJO

MSNSJO

Madison Truax Field

Sat 8/15

5:47 pm-12:03 pm

2 stops19h 16m

San José Juan Santamaria Intl

Sat 8/22

2:53 pm-10:40 am

2 stops18h 47m

$579

MadisonSan José

MSN - SJO

MSNSJO

Madison Truax Field

Sat 8/15

11:29 am-1:52 pm

1 stop27h 23m

San José Juan Santamaria Intl

Sat 8/22

2:53 pm-10:40 am

2 stops18h 47m

$588

MadisonSan José

MSN - SJO

MSNSJO

Madison Truax Field

Sat 8/15

5:47 pm-11:34 am

2 stops18h 47m

San José Juan Santamaria Intl

Sat 8/22

2:52 pm-10:40 am

2 stops18h 48m

$589

MadisonSan José

MSN - SJO

MSNSJO

Madison Truax Field

Sat 8/1

7:55 pm-8:20 am

1 stop13h 25m

San José Juan Santamaria Intl

Wed 8/5

7:07 am-5:25 pm

1 stop9h 18m

$597

MadisonSan José

MSN - SJO

MSNSJO

Madison Truax Field

Sat 8/15

11:29 am-1:52 pm

1 stop27h 23m

San José Juan Santamaria Intl

Sat 8/22

2:52 pm-10:40 am

2 stops18h 48m

$599

MadisonSan José

MSN - SJO

MSNSJO

Madison Truax Field

Mon 8/3

5:43 am-11:49 am

1 stop7h 06m

San José Juan Santamaria Intl

Fri 8/7

1:14 pm-11:26 am

2 stops21h 12m

$603

MadisonSan José

MSN - SJO

MSNSJO

Madison Truax Field

Sat 8/15

5:46 pm-11:34 am

2 stops18h 48m

San José Juan Santamaria Intl

Sat 8/22

2:52 pm-10:40 am

2 stops18h 48m

$604

MadisonSan José

MSN - SJO

MSNSJO

Madison Truax Field

Sat 9/5

5:45 am-11:56 am

1 stop7h 11m

San José Juan Santamaria Intl

Mon 10/5

1:25 pm-8:50 am

2 stops18h 25m

$609

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 typical price of a round-trip flight between Madison and San José?

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 November to fly from Madison, when ticket prices are also cheap, with an average price of $544.

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

You could potentially save up to 56% on your flight if you consider stops on a Madison to San José flight.

How have Madison to San José flight prices changed over time?

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

7h 06m

Direct flights

None
The fastest flight from Madison to San José takes 7h 06m
There are no direct flights from Madison to San José. There are no popular flight routes from Madison to San José.
Search flight deals

Frequently asked questions about flying from Madison to San José

  • 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 7h 06m, 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 $397Free CancellationRating
7.1
11,631 reviews
Search American Airlines flights
DeltaPriceFrom $495Free CancellationRating
7.9
8,436 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
Santa Elena
Dominical
San Gerardo de Dota
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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