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Cheap flights from Madison to San José from $555

This is the cheapest round-trip flight price found by a momondo user in the last 72 hours by searching for a flight from Madison to San José departing on 12/8. 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
1 adult, Economy, 0 bags

Discover deals from 900+ travel sites with momondo.

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
7:05 pm - 2:02 pm
MSN
-
SJO
18h 57m
2 stops
American Airlines Logo
12:34 am - 10:37 am
SJO
-
MSN
10h 03m
1 stop
$555American Airlines
Tue, Dec 8 - Fri, Dec 18
American Airlines Logo
3:55 pm - 2:02 pm
MSN
-
SJO
22h 07m
1 stop
American Airlines Logo
12:34 am - 5:00 pm
SJO
-
MSN
16h 26m
1 stop
$560American Airlines
Tue, Dec 8 - Fri, Dec 18
American Airlines Logo
11:37 am - 1:57 pm
MSN
-
SJO
27h 20m
1 stop
American Airlines Logo
1:00 pm - 10:51 am
SJO
-
MSN
20h 51m
1 stop
$562American Airlines
Sat, Sep 26 - Sat, Oct 3
American Airlines Logo
8:05 pm - 1:57 pm
MSN
-
SJO
18h 52m
2 stops
American Airlines Logo
1:00 pm - 10:51 am
SJO
-
MSN
20h 51m
1 stop
$566American Airlines
Sat, Sep 26 - Sat, Oct 3
American Airlines Logo
6:52 pm - 12:26 pm
MSN
-
SJO
18h 34m
2 stops
American Airlines Logo
2:56 pm - 10:40 am
SJO
-
MSN
18h 44m
2 stops
$580American Airlines
Sun, Aug 16 - Thu, Aug 20
American Airlines Logo
7:17 am - 1:57 pm
MSN
-
SJO
7h 40m
1 stop
American Airlines Logo
1:00 pm - 10:36 pm
SJO
-
MSN
8h 36m
1 stop
$590American Airlines
Thu, Oct 1 - Tue, Oct 6
American Airlines Logo
3:55 pm - 12:21 pm
MSN
-
SJO
20h 26m
2 stops
American Airlines Logo
6:20 am - 10:46 pm
SJO
-
MSN
16h 26m
2 stops
$595American Airlines
Tue, Dec 8 - Sat, Dec 19
American Airlines Logo
11:19 am - 2:02 pm
MSN
-
SJO
26h 43m
1 stop
American Airlines Logo
12:34 am - 5:00 pm
SJO
-
MSN
16h 26m
1 stop
$600American Airlines
Tue, Dec 8 - Fri, Dec 18
American Airlines Logo
7:00 am - 9:00 pm
MSN
-
SJO
14h 00m
2 stops
American Airlines Logo
3:56 pm - 8:06 am
SJO
-
MSN
16h 10m
2 stops
$620American Airlines
Thu, Dec 31 - Mon, Mar 1
American Airlines Logo
6:52 pm - 1:52 pm
MSN
-
SJO
20h 00m
2 stops
American Airlines Logo
2:53 pm - 10:40 am
SJO
-
MSN
18h 47m
2 stops
$622American Airlines
Sat, Aug 15 - Sat, Aug 22

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American Airlines flights from Madison to San José

Our best American Airlines deals on Madison to San José flight tickets
American Airlines
Dec 8
MSN3:55 pmMadison Truax Field
20h 26m
2 stops
SJO12:21 pmSan José Juan Santamaria Intl
Dec 19
SJO6:20 amSan José Juan Santamaria Intl
16h 26m
2 stops
MSN10:46 pmMadison Truax Field
$555
American Airlines
Dec 8
MSN3:55 pmMadison Truax Field
22h 07m
1 stop
SJO2:02 pmSan José Juan Santamaria Intl
Dec 18
SJO12:34 amSan José Juan Santamaria Intl
16h 26m
1 stop
MSN5:00 pmMadison Truax Field
$560
American Airlines
Sep 26
MSN11:37 amMadison Truax Field
27h 20m
1 stop
SJO1:57 pmSan José Juan Santamaria Intl
Oct 3
SJO1:00 pmSan José Juan Santamaria Intl
20h 51m
1 stop
MSN10:51 amMadison Truax Field
$562

United Airlines flights from Madison to San José

Our best United Airlines deals on Madison to San José flight tickets
United Airlines
Oct 24
MSN6:42 amMadison Truax Field
13h 55m
2 stops
SJO7:37 pmSan José Juan Santamaria Intl
Oct 28
SJO10:28 pmSan José Juan Santamaria Intl
15h 32m
2 stops
MSN3:00 pmMadison Truax Field
$675
United Airlines
Oct 28
MSN6:09 amMadison Truax Field
13h 44m
1 stop
SJO6:53 pmSan José Juan Santamaria Intl
Nov 9
SJO1:55 pmSan José Juan Santamaria Intl
9h 42m
1 stop
MSN11:37 pmMadison Truax Field
$710
United Airlines
Oct 24
MSN6:42 amMadison Truax Field
13h 55m
2 stops
SJO7:37 pmSan José Juan Santamaria Intl
Oct 28
SJO10:28 pmSan José Juan Santamaria Intl
15h 32m
2 stops
MSN3:00 pmMadison Truax Field
$715

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 July 6, 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

Tue 12/8

7:05 pm-2:02 pm

2 stops18h 57m

San José Juan Santamaria Intl

Fri 12/18

12:34 am-10:37 am

1 stop10h 03m

$555

MadisonSan José

MSN - SJO

MSNSJO

Madison Truax Field

Tue 12/8

3:55 pm-2:02 pm

1 stop22h 07m

San José Juan Santamaria Intl

Fri 12/18

12:34 am-5:00 pm

1 stop16h 26m

$560

MadisonSan José

MSN - SJO

MSNSJO

Madison Truax Field

Sat 9/26

11:37 am-1:57 pm

1 stop27h 20m

San José Juan Santamaria Intl

Sat 10/3

1:00 pm-10:51 am

1 stop20h 51m

$562

MadisonSan José

MSN - SJO

MSNSJO

Madison Truax Field

Sat 9/26

8:05 pm-1:57 pm

2 stops18h 52m

San José Juan Santamaria Intl

Sat 10/3

1:00 pm-10:51 am

1 stop20h 51m

$566

MadisonSan José

MSN - SJO

MSNSJO

Madison Truax Field

Sun 8/16

6:52 pm-12:26 pm

2 stops18h 34m

San José Juan Santamaria Intl

Thu 8/20

2:56 pm-10:40 am

2 stops18h 44m

$580
Quickest round-trip

MadisonSan José

MSN - SJO

MSNSJO

Madison Truax Field

Thu 10/1

7:17 am-1:57 pm

1 stop7h 40m

San José Juan Santamaria Intl

Tue 10/6

1:00 pm-10:36 pm

1 stop8h 36m

$590

MadisonSan José

MSN - SJO

MSNSJO

Madison Truax Field

Tue 12/8

3:55 pm-12:21 pm

2 stops20h 26m

San José Juan Santamaria Intl

Sat 12/19

6:20 am-10:46 pm

2 stops16h 26m

$595

MadisonSan José

MSN - SJO

MSNSJO

Madison Truax Field

Tue 12/8

11:19 am-2:02 pm

1 stop26h 43m

San José Juan Santamaria Intl

Fri 12/18

12:34 am-5:00 pm

1 stop16h 26m

$600

MadisonSan José

MSN - SJO

MSNSJO

Madison Truax Field

Thu 12/31

7:00 am-9:00 pm

2 stops14h 00m

San José Juan Santamaria Intl

Mon 3/1

3:56 pm-8:06 am

2 stops16h 10m

$620

MadisonSan José

MSN - SJO

MSNSJO

Madison Truax Field

Sat 8/15

6:52 pm-1:52 pm

2 stops20h 00m

San José Juan Santamaria Intl

Sat 8/22

2:53 pm-10:40 am

2 stops18h 47m

$622

Flights are sorted by cheapest round-trip flights first.

Sorted by cheapest first

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 $539. 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 $551.

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

You could potentially save up to 37% 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 35m

Direct flights

None
The fastest flight from Madison to San José takes 7h 35m
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 35m, 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 $420Free CancellationRating
7.1
11,784 reviews
Search American Airlines flights
DeltaPriceFrom $448Free CancellationRating
7.8
8,452 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.

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