MSN - SJO

$555 Find Cheap Flights from Madison to San José - Compare and Save

This is the cheapest round-trip flight price found by a KAYAK user in the last 72 hours by searching for a flight from Madison to San José departing on 12/8. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy, 0 bags

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Everything you should know

Cheapest round-trip
$555
Typical prices: $586-$1,583
American Airlines
Tue 12/8Fri 12/18
MSN - SJO • 2 stops
Top airlines
Cheapest • from $555 (round-trip)
Best reviews • 7.8 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Nonstop flights
Not available
There are currently no direct flights between Madison and San José. You'll need at least 1 connection.
Insights
Insights
Insights
Insights
Top layover airports
Cheapest • Avg $718 (round-trip)
Shortest trip • 7h 04m (one-way)
Insights
Insights
Insights
Insights
When to travel
Cheapest • 27% price drop
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
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KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to San José!
Flight Deals
Booking Insights
Flight Deals

Cheap Flights from Madison to San José (MSN-SJO)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Madison to San José that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Madison to San José

Tue, Dec 8 - Fri, Dec 18
American Airlines Logo
7:05 pm - 2:02 pm
MSN
-
SJO
18h 57m
2 stops
American Airlines Logo
12:34 am - 2:55 pm
SJO
-
MSN
14h 21m
2 stops
$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
Sat, Sep 26 - Sat, Oct 3
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
Sun, Aug 16 - Thu, Aug 20
American Airlines Logo
6:00 am - 12:26 pm
MSN
-
SJO
7h 26m
1 stop
American Airlines Logo
2:56 pm - 10:40 am
SJO
-
MSN
18h 44m
2 stops
$580American Airlines
Sat, Aug 15 - Sat, Aug 22
American Airlines Logo
11:53 am - 12:26 pm
MSN
-
SJO
25h 33m
1 stop
American Airlines Logo
2:53 pm - 10:40 am
SJO
-
MSN
18h 47m
2 stops
$589American Airlines
Sun, Sep 6 - Sat, Sep 12
American Airlines Logo
7:00 am - 1:52 pm
MSN
-
SJO
7h 52m
1 stop
American Airlines Logo
2:57 pm - 12:26 pm
SJO
-
MSN
20h 29m
2 stops
$595American Airlines
Sat, Aug 15 - Sat, Aug 22
American Airlines Logo
6:52 pm - 12:03 pm
MSN
-
SJO
18h 11m
2 stops
American Airlines Logo
2:53 pm - 9:22 am
SJO
-
MSN
17h 29m
2 stops
$622American Airlines
Mon, Jul 27 - Mon, Aug 10
American Airlines Logo
4:11 pm - 1:00 pm
MSN
-
SJO
21h 49m
1 stop
American Airlines Logo
2:56 pm - 10:23 am
SJO
-
MSN
18h 27m
2 stops
$630American Airlines
Sat, Aug 15 - Sat, Aug 22
American Airlines Logo
5:46 pm - 1:52 pm
MSN
-
SJO
21h 06m
1 stop
American Airlines Logo
2:53 pm - 9:22 am
SJO
-
MSN
17h 29m
2 stops
$631American Airlines
Booking Insights

KAYAK's insights & trends for Madison to San José flights

Get data-powered insights and trends into flights from Madison to San José to help you find the cheapest flights, the best time to fly and much more.

What is the cheapest month to fly from Madison to San José?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Madison to San José, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Madison to San José is September, where tickets cost $539 (return) on average. On the other hand, the most expensive months are December and May, where the average cost of round-trip tickets is $1,118 and $861 respectively.

Good to know

Low seasonJuly
Cheapest flight$555
Best time to beat the crowds with an average 15% drop in price.
Most popular time to fly and prices are also 6% lower on average.
Flight from Madison to San José

When to book flights from Madison to San José

Are your dates flexible? Find out the best times to travel from Madison to San José based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking flights from Madison to San José

  • What is the cheapest flight from Madison to San José?

    In the last 5 days, the lowest price for a flight from Madison to San José was $555 for a round-trip ticket.

  • Do I need a passport to fly between Madison and San José?

    A passport is required to fly from Madison to San José.

  • Which airports will I be using when flying from Madison to San José?

    When flying out of Madison you will be using Madison Truax Field. You will be landing at San José, also known as San José Juan Santamaria Intl.

  • Which aircraft models fly most regularly from Madison to San José?

    We unfortunately don’t have that data for this specific route.

  • Which airline alliances offer flights from Madison to San José?

    SkyTeam, and oneworld are the airline alliances operating flights between Madison and San José, with SkyTeam being the most commonly used for this route.

  • Which is the best airline for flights from Madison to San José, Delta or American Airlines?

    The two airlines most popular with KAYAK users for flights from Madison to San José are Delta and American Airlines. With an average price for the route of $854 and an overall rating of 7.8, Delta is the most popular choice. American Airlines is also a great choice for the route, with an average price of $649 and an overall rating of 7.1.

  • How does KAYAK find such low prices on flights from Madison to San José?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Madison to San José.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Madison to San José?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to San José from Madison is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Madison to San José?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to San José with an airline and back to Madison with another airline. Booking your flights between Madison and SJO can sometimes prove cheaper using this method.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Madison to San José?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to San José from Madison up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Reviews of the top airlines flying from Madison to San José

 
See real verified KAYAK customer reviews for airlines flying from Madison to San José. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Madison to San José? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
7.8
DeltaOverall score based on 8453 reviews
7.8Entertainment
8.1Boarding
8.5Crew
7.8Comfort
7.2Food
Airline reviews

Probably not the fault of Delta but there was delay after delay after delay and I ended up getting home 4 hours later then I should have at 1:30 in the morning

4.0 Okaybyron, Jan 2026
CWA - MSP
Read more Delta reviews

Probably not the fault of Delta but there was delay after delay after delay and I ended up getting home 4 hours later then I should have at 1:30 in the morning

Easiest airport experience ever in my life at MSP with Delta check-in and flight attendant gave us a bottle of champagne in celebration of our 10-year wedding anniversary, so overall amazing!

Staff was exceptional! Everyone was kind, professional and friendly making the trip very pleasant. Thank you!

Great. Seamless. Check in agent at kiosk international was amazing and extremely helpful.

Very late arrival at PWM. Late jet getting to ATL. Equipment problem with aircraft - could not get enough water onto plane., Another delay getting FAA approval for flight with bottled H2O. Not the crew’s problem.

A little bumpy ride . No food was being provided due the the turbulence. That was ok it was a short flight to my standards.

Pretty standard flight. Delta has a good selection of movies.

The flight was so late that I had to change connecting flights, turning a five-hour trip into a fourteen-hour nightmare.

Delta planes have the WORST seat comfort of any plane in history. It's the opposite of ergonomic, in every sense. They also recline minimally, are covered in a vinyl and have no feet rests. Then the disembarking process is chaotic and time consuming (because of the way they load the plane and deal with luggage). Overall, somewhat frustrating but we arrived safely :)

Despite being delayed, we would still give a high score for this flight experience. For the first time in quite some time we had excellent customer service throughout our entire round trip. The flight attendants were the most polite we have experienced in our last ten flights at least (non of which were Delta and include business class). The food offered was a better selection than most—we just didn’t have any of it. Overall, almost as good as flying used to be. Thank you to Delta.

I found the seats ergonomically uncomfortable forcing the body to seat slightly hunched. For a short flight I worked on adjustments but for a longer flight, it would be difficult.

Crew was helpful and cheerful especially when they had no refreshments to work with. The plane was never serviced and had nothing but limited water and coffee onboard. For the price point, a concern of services.

I bought wifi and most of the flight could not even use it my apps would just spin. I couldn't even listen to music. super frustrating.

Seating was horrible. Small seats. Access to flight information and extras very iser unfriendly. Kept losing internet after paying for it. Staff in madison was as unprofessional and unhelpful.

There were several different delays but we ended up being delayed a total of 40 mins or so. It was annoying we had a gate change which made it take longer to leave DFW, and we had to check our carry on. Ugh

The counter/baggage counter was busy and so many people missed flights. We got stuck sitting on the plane over 2 hours at the gate while they were doing an inspection is wrong. Many of us missed our connecting flights because of it.

A much better flight than our previous. The flight attendant took care of us and regularly checked in to see if we needed anything. Brought us drinks prior to the departure and then a couple more times. Totally makes the difference in how you travel when the crew is checking on their passengers. Great job on this leg of our trip.

Our flight was changed from Madison to DC to Madison to Charlotte.

We were told we had no flights before our flight was continually delayed then cancelled.

Boarding was relatively fast and easy and the crew was attentive throughout.

Everything you need to know for your flight from Madison to San José

Information on your arrival and departure airports