MSN - SJO

$339 Find Cheap Flights from Madison to San José

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Madison to San José departing on 3/7. 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

KAYAK searches hundreds of travel sites at once for deals on flights to San José

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Madison to San José, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Madison to San José, as well as popular online travel agencies
Travelers love KAYAK
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Everything you should know

Cheapest round-trip
$339
Overall average: $625
American Airlines
Tue 4/14Tue 4/21
MSN - SJO • 2 stops
Cheapest one-way
$286
Typical prices: $341-$424
Delta
Sat 3/7
MSN - SJO • 2 stops
Top airlines
American Airlines
Cheapest • from $339 (round-trip)
Delta
Best reviews • 7.9 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
Dallas (DFW)
Cheapest • Avg $714 (round-trip)
Charlotte (CLT)
Shortest trip • 7h 04m (one-way)
Insights
Insights
Insights
Insights
When to travel
September
Cheapest • 28% price drop
March
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
Start a new search
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, Apr 14 - Tue, Apr 21
American Airlines Logo
4:51 pm - 11:07 am
MSN
-
SJO
19h 16m
2 stops
American Airlines Logo
2:22 pm - 10:55 am
SJO
-
MSN
19h 33m
2 stops
$339American Airlines
Mon, Apr 20 - Fri, Apr 24
GOL Logo
8:24 pm - 1:08 pm
MSN
-
SJO
17h 44m
2 stops
GOL Logo
2:22 pm - 11:05 am
SJO
-
MSN
19h 43m
2 stops
$404GOL
Mon, Apr 20 - Fri, Apr 24
GOL Logo
5:08 pm - 11:35 am
MSN
-
SJO
19h 27m
1 stop
GOL Logo
11:35 pm - 11:05 am
SJO
-
MSN
10h 30m
1 stop
$408GOL
Mon, Apr 20 - Fri, Apr 24
GOL Logo
5:08 pm - 11:35 am
MSN
-
SJO
19h 27m
1 stop
GOL Logo
2:22 pm - 10:55 am
SJO
-
MSN
19h 33m
2 stops
$412GOL
Tue, Apr 14 - Tue, Apr 21
American Airlines Logo
4:51 pm - 11:07 am
MSN
-
SJO
19h 16m
2 stops
American Airlines Logo
12:35 pm - 11:01 pm
SJO
-
MSN
9h 26m
1 stop
$491American Airlines
Mon, Apr 20 - Fri, Apr 24
American Airlines Logo
5:08 pm - 11:35 am
MSN
-
SJO
19h 27m
1 stop
American Airlines Logo
11:35 pm - 5:22 pm
SJO
-
MSN
16h 47m
1 stop
$494American Airlines
Wed, Apr 8 - Mon, Apr 27
American Airlines Logo
8:24 pm - 11:25 am
MSN
-
SJO
16h 01m
2 stops
American Airlines Logo
2:08 pm - 8:45 am
SJO
-
MSN
17h 37m
2 stops
$526American Airlines
Wed, Apr 8 - Mon, Apr 27
American Airlines Logo
3:29 pm - 1:22 pm
MSN
-
SJO
22h 53m
1 stop
American Airlines Logo
2:22 pm - 9:48 am
SJO
-
MSN
18h 26m
2 stops
$534American Airlines
Wed, Apr 8 - Mon, Apr 27
American Airlines Logo
6:45 am - 7:07 pm
MSN
-
SJO
13h 22m
2 stops
American Airlines Logo
2:08 pm - 8:45 am
SJO
-
MSN
17h 37m
2 stops
$565American Airlines
Tue, Apr 14 - Tue, Apr 21
United Airlines Logo
2:44 pm - 12:21 pm
MSN
-
SJO
22h 37m
2 stops
United Airlines Logo
1:25 pm - 10:11 am
SJO
-
MSN
19h 46m
2 stops
$571United 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 $505 (return) on average. On the other hand, the most expensive months are December and June, where the average cost of round-trip tickets is $1,059 and $786 respectively.

Good to know

Low seasonJuly
Cheapest flight$286
Best time to beat the crowds with an average 1% drop in price.
Most popular time to fly with an average 8% increase in price.
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 3 days, the lowest price for a flight from Madison to San José was $286 for a one-way ticket and $339 for a round-trip.

  • 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 $823 and an overall rating of 7.9, Delta is the most popular choice. American Airlines is also a great choice for the route, with an average price of $634 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.
7.9
DeltaOverall score based on 8237 reviews
7.9Comfort
7.8Entertainment
8.5Crew
7.2Food
8.1Boarding
Airline reviews

There’s not much to say about a one hour flight. This is a connection from LA to RNO that I missed the previous night due to a mechanical check delay on my originating flight from JFK to LAX. The short flight itself was fine. Instructions from the pilot and crew were per usual. The coffee was barely lukewarm, which possibly was purposeful so we would down it quickly. Bags were already on carousel upon reaching baggage claim, which was excellent.

10.0 ExcellentGrace, Feb 2026
JFK - LAX
Read more Delta reviews

There’s not much to say about a one hour flight. This is a connection from LA to RNO that I missed the previous night due to a mechanical check delay on my originating flight from JFK to LAX. The short flight itself was fine. Instructions from the pilot and crew were per usual. The coffee was barely lukewarm, which possibly was purposeful so we would down it quickly. Bags were already on carousel upon reaching baggage claim, which was excellent.

Flight was warm for first few hours and quite rough

Seat was extremely hard which made even a short 1 hour 20 minute flight fairly uncomfortable.

Everything was good except wifi and a leaking drink chiller. The floor was all wet and my bag was soaked. Did not notice until debarking. Have not heard back from Delta. Even though this was leg one of an international flight in first class, they denied access to their Sky Club - very disappointing!

The staff was fine. The plane was extremely tight, and I paid for the wifi and it did not work at all. I was actually going to ask for a refund.

two hour delay and the Delta representative on the PA system was unable to understand

An awesome flight crew. FC seat cushion just doesn’t cut it for a 3+ hour flight.

2+hrs delay without any reason provided and a cramped flight

We waited an hour on the runway to get a gate in Orlando

Flight was delayed by 3-hours and their fix was… complimentary pretzels.

It was an older plane. First Class was not especially roomy or comfortable. It was a short flight so there were no meal but they did offer mixed nuts which used to be normal but now is rare. Crew member was very polite and professional.

The chicken wrap was tiny ($13 for what looked like a 1/3 of a normal wrap?) and disgusting.

It was a train wreck but on an airplane. First off, flight was delayed then we board only to hear two announcements, First weather delays in Orlando and second backup battery warning on emergency lights. After sitting on the plane for almost 2 hours they have us deplane due to the maintenance issue. We were told they were getting another plane. In the mean time, I notice another American- Orlando flight and ask the gate agent if I can switch. He says he cant help me and I'd have to walk to A13 from A37. Really!? I get down there and get a seat only to get an announcement my original flight was RE-boarding. The Then inflight there's no communication and I notice on flightaware were circling over the Gulf of America. I call the flight attendant and of course she has no clue and apparently 5m later the pilot finally tells us about another delay. Why does American always have these service and delay issues? They are my LAST choice in flights now!

Mediocre would be best description. Food bland. Seat biz class uncomfortable to sleep. Crew never dimmed lights completely in an overnight flight to Europe. Would avoid AA if possible.

For my arriving destination, we were delayed multiple times to the point that we arrived 6 hours after we were originally scheduled. On my flight home, they overbooked and involuntarily removed passengers (including me) from the plane. It was not a good experience.

It was good experience this time. The flight was on time.

I very rarely fly American and my experience today reenforces that is the correct decision. While the staff were all very courteous, our flight was first thing in the morning so there was no reason to be delayed, yet appropriate maintenance checks weren’t completed prior to our flight so we were delayed multiple times. Not a great showing, American Airlines.

It's very confusing because Kayak has it as American Airlines, but it was Hawaiian Airlines, but operated by Alaska Airlines. I had to go to the airport for my boarding pass because American said I didn't have any trips.

Smooth flight. From the early boarding and all were on board before departure time and arrived early in ONT. Great crew. Thank you!!!!

Small plane, poor meal choices for first class, bad terminal and boarding experience at LAX

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

Information on your arrival and departure airports