MSN - SJO

$244 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 5/1. 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
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Everything you should know

Cheapest round-trip
$347
Typical prices: $740-$590
American Airlines
Mon 5/4Fri 5/8
MSN - SJO • 2 stops
Cheapest one-way
$244
GOL
Fri 5/1
MSN - SJO • 2 stops
Top airlines
Cheapest • from $372 (round-trip)
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
Cheapest • Avg $721 (round-trip)
Shortest trip • 7h 04m (one-way)
Insights
Insights
Insights
Insights
When to travel
Cheapest • 25% price drop
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

Mon, May 4 - Fri, May 8
American Airlines Logo
5:37 pm - 11:07 am
MSN
-
SJO
18h 30m
2 stops
American Airlines Logo
11:35 pm - 5:22 pm
SJO
-
MSN
16h 47m
1 stop
$347American Airlines
Mon, May 4 - Fri, May 8
American Airlines Logo
5:08 pm - 11:35 am
MSN
-
SJO
19h 27m
1 stop
American Airlines Logo
12:35 pm - 11:54 pm
SJO
-
MSN
10h 19m
1 stop
$350American Airlines
Sat, May 2 - Tue, May 12
American Airlines Logo
11:50 am - 9:36 pm
MSN
-
SJO
10h 46m
1 stop
American Airlines Logo
12:35 pm - 10:56 pm
SJO
-
MSN
9h 21m
1 stop
$360American Airlines
Sat, May 2 - Tue, May 12
American Airlines Logo
11:50 am - 9:36 pm
MSN
-
SJO
10h 46m
1 stop
American Airlines Logo
6:30 am - 9:14 pm
SJO
-
MSN
13h 44m
2 stops
$365American Airlines
Sat, May 2 - Sat, May 9
American Airlines Logo
3:29 pm - 1:22 pm
MSN
-
SJO
22h 53m
1 stop
American Airlines Logo
6:30 am - 11:55 pm
SJO
-
MSN
16h 25m
2 stops
$372American Airlines
Sat, May 2 - Sat, May 9
American Airlines Logo
11:50 am - 9:36 pm
MSN
-
SJO
10h 46m
1 stop
American Airlines Logo
6:30 am - 11:55 pm
SJO
-
MSN
16h 25m
2 stops
$383American Airlines
Thu, Apr 16 - Wed, Apr 22
GOL Logo
5:37 pm - 11:25 am
MSN
-
SJO
18h 48m
2 stops
GOL Logo
2:22 pm - 10:55 am
SJO
-
MSN
19h 33m
2 stops
$443GOL
Thu, May 28 - Sun, May 31
American Airlines Logo
11:23 am - 10:42 pm
MSN
-
SJO
12h 19m
1 stop
American Airlines Logo
11:59 pm - 10:38 am
SJO
-
MSN
9h 39m
1 stop
$465American Airlines
Tue, May 26 - Tue, Jun 2
Delta Logo
6:15 pm - 11:52 am
MSN
-
SJO
18h 37m
2 stops
Delta Logo
1:20 pm - 8:49 am
SJO
-
MSN
18h 29m
2 stops
$475Delta
Thu, May 28 - Fri, May 29
United Airlines Logo
6:30 am - 10:39 pm
MSN
-
SJO
17h 09m
2 stops
United Airlines Logo
12:30 am - 10:27 pm
SJO
-
MSN
20h 57m
2 stops
$493United 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.

How much is a round-trip flight from Madison to San José?

This analysis is based on the cheapest round-trip price found on KAYAK in the last 12 months by searching for a flight from Madison to San José departing in May.

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 $765 respectively.

Good to know

Low seasonJuly
Cheapest flight$244
Best time to beat the crowds with an average 18% drop in price.
Most popular time to fly with an average 57% 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 $341 for a one-way ticket and $372 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 8356 reviews
8.5Crew
7.8Entertainment
7.2Food
7.9Comfort
8.1Boarding
Airline reviews

Delta is always a wonderful experience. A clean plane and the crew is really friendly.

10.0 ExcellentCharlean, Mar 2026
LAS - ATL
Read more Delta reviews

Delta is always a wonderful experience. A clean plane and the crew is really friendly.

Too many people are taking up space in the overhead bins with their extra piece of luggage. Since they cannot fit their backpacks or extra luggage piece under the seat in front of them, they store it in the overheads and thus taking up room for other passengers. It wasn’t only one or two persons; more like 12 or 13 passengers.

Excellent service, I love the soft blush pink mood lighting on the 767-400ER during meal service. The overhead gasper vents on the 767-400ER were also very strong with a lot of airflow to keep me comfortable on my flight.

This was the worse experience. They delayed our flight twice and we still had to find another flight to get home sooner which was alos delayed. Also, the flight attendant named Ginny on DL9890 leaving at 4:13pm on 3/23/26 was extremely rude.

I love Delta the flight attendants were personable and the flight arrived 1/2 earlier thanks expected. All a plus. The gate agent was a bit flustered but even with that I still had a good experience. Her supervisor assisted me.

Got to fly my favorite plane, the Boeing 767-400ER, to Milan. The soft blush pink mood lighting during meal service was very beautiful and gorgeous. The service was top-notch, and our flights were on time. I highly recommend Delta.

I am still at the Airport! Delayed Delayed and Delyaed

I took seat 15A in anticipation of window seat, there is no window.

The first class flight attendant was awful to everyone. Very rude; no customer service. She should not be working in first class.

Snacks and included beverages were appreciated. Boarding went smoothly. Plenty of overhead bin space. Seats get very uncomfortable after a couple of hours. After waiting 10 painful minutes for my walker, a very nice Delta guest agent pushed me in a wheelchair to the gate. It was finally delivered to me after another 15 minutes . Our checked bag was on the carousel long b4 I was able to retrieve it. Fortunately it was still there but somewhere along the way the straps we used to secure it were removed and and were not reattached. Wish I had made note of the agents name.

The flight changed gates multiple times and flight had to be delayed multiple times

We called Kayak for a change due to the TSA situation in Atlanta. What we got was a canceled return flight (in error) and we had to find the mistake. Not happy with Kayak who blamed it on AA.

Tv screens and movie selection v good. Friendly staff. They were really worried about max capacity and room for carryons. That is never fun but i had no problem finding space when I boarded.

I was in last row so that is never great bc the person in front of me leaned his seat all the way back into me.

Delayed for mechanical and no updates on what was happening and how long the delay might be.

My flight from LGA was cancelled and my rebooked flight from JFK was delayed numerous times. I will now be getting home after 2am.

Flight was delayed half hour before boarding, but when I checked flight aware the plane that would Pick us up had a delay of more than an hour. AA should let us know in advance to avoid waiting several hours in the airport

On the return flight, arriving in Denver we sat on the tarmac in Denver for over 20 minutes.

Typical AA - late by 90+ mn. Gate changed twice... Changed the departure time 6 times No explanation, no communication on reasons for delay I travel with AA twice a year... and it is consistently very poor.. I will continue to use AA only when i have to.

The flight attendant in business class was excellent! Professional, friendly and attentive.

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

Information on your arrival and departure airports