MSN - SJO

$161 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 5/26. 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
41.299.237 searches in the past 7 days on KAYAK

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Everything you should know

Cheapest round-trip
$392
Overall average: $717
American Airlines
Sat 5/2Sat 5/9
MSN - SJO • 1 stop
Cheapest one-way
$161
American Airlines
Tue 5/26
MSN - SJO • 2 stops
Top airlines
Cheapest • from $392 (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

Sat, May 2 - Sat, May 9
American Airlines Logo
3:29 pm - 1:22 pm
MSN
-
SJO
22h 53m
1 stop
American Airlines Logo
12:31 pm - 11:55 pm
SJO
-
MSN
10h 24m
1 stop
$392American Airlines
Sat, May 2 - Sat, May 9
American Airlines Logo
5:08 pm - 11:25 am
MSN
-
SJO
19h 17m
1 stop
American Airlines Logo
6:30 am - 11:55 pm
SJO
-
MSN
16h 25m
2 stops
$396American Airlines
Sat, May 2 - Sat, May 9
American Airlines Logo
5:00 am - 7:07 pm
MSN
-
SJO
15h 07m
2 stops
American Airlines Logo
6:30 am - 11:55 pm
SJO
-
MSN
16h 25m
2 stops
$419American Airlines
Wed, Aug 12 - Wed, Aug 19
American Airlines Logo
6:00 am - 8:14 pm
MSN
-
SJO
15h 14m
2 stops
American Airlines Logo
12:57 pm - 9:22 am
SJO
-
MSN
19h 25m
2 stops
$471American Airlines
Wed, Aug 12 - Wed, Aug 19
American Airlines Logo
6:00 am - 8:14 pm
MSN
-
SJO
15h 14m
2 stops
American Airlines Logo
12:57 pm - 9:22 am
SJO
-
MSN
19h 25m
2 stops
$477American Airlines
Sat, May 2 - Sat, May 9
American Airlines Logo
5:08 pm - 11:25 am
MSN
-
SJO
19h 17m
1 stop
American Airlines Logo
12:31 pm - 11:55 pm
SJO
-
MSN
10h 24m
1 stop
$509American Airlines
Thu, Sep 3 - Wed, Sep 16
American Airlines Logo
7:05 am - 1:58 pm
MSN
-
SJO
7h 53m
1 stop
American Airlines Logo
7:00 am - 10:19 pm
SJO
-
MSN
14h 19m
2 stops
$526American Airlines
Wed, Apr 8 - Mon, Apr 27
United Airlines Logo
8:30 am - 10:11 am
MSN
-
SJO
26h 41m
2 stops
United Airlines Logo
7:55 am - 10:11 am
SJO
-
MSN
25h 16m
2 stops
$529United Airlines
Thu, Sep 3 - Wed, Sep 16
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
$542Delta
Mon, May 4 - Thu, May 7
United Airlines Logo
8:55 pm - 12:21 pm
MSN
-
SJO
16h 26m
2 stops
United Airlines Logo
1:25 pm - 10:54 pm
SJO
-
MSN
32h 29m
2 stops
$545United 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 $765 respectively.

Good to know

Low seasonJuly
Cheapest flight$161
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 $161 for a one-way ticket and $392 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 8319 reviews
7.8Entertainment
8.5Crew
8.1Boarding
7.2Food
7.9Comfort
Airline reviews

Kayak botched up the booking, i had to call delta and fix. In the process Delta failed to honor my comfort plus seat assignment that i had previously.

2.0 MediocreSreekumar, Mar 2026
FLL - DTW
Read more Delta reviews

Kayak botched up the booking, i had to call delta and fix. In the process Delta failed to honor my comfort plus seat assignment that i had previously.

Entertainment is ok! Boarding and seat with zone is terrible. I paid for the seats but you didn’t give me what I paid for which is exit isles.

the crew cancel the morning service due to the weather. Then the flight got deverted to Nashville . we were on the ground for over two hours the only gave us water once... no food or any snacks.... the crew should have handled better and offered something to passengers.

My recent experience was excellent on Delta! I flew with Delta Comfort and I was really comfortable in my seat. I enjoyed the in-flight service. The flight attendants were so friendly and hospitable. I love the snack on the flight as well. This was my first time flying on Delta and I will definitely consider flying with them again.

My flight was cencaled due with the bad weather on Sunday the crew was poorly mistaken my luggage supposed depart with my flight instead I didn’t have my luggage for almost 3 days the website is poorly respond to my complain until I have someone to do it my connection smooth their not even respon or email me even the have my luggage

Delta needs to step its game up get a more reliable internet service. Internet service was non-existent for this flight.

Mechanical Delay of over an hour with multiple gate changes. Entertainment system down for rejuvenation.

This was a Latam operated flight. Seats seemed a bit narrow in business class. Older aircraft.

I had a flight cancel and had it rerouted. When the rerouted they put me at a window seat instead of an isle. It was hard sitting by the window because the couple with masks on were making out. I get motion sickness which is why I need to have the isle seat.

NEVER MADE THE FLIGHT BECAUSE DELTA SAID THEY CAN NOT

The experience at checkin for my American Airlines flight from Sacramento to LAX was very good including the assistance I received in getting my bags checked in and boarding passes printed. Was pleasantly surprised the my bags were checked through all the way to my destination at Clark International Airport in Angeles, Philippines.

Absolutely terrible. Would never fly American again. 2 deplaned incidents and delayed by close to 24 hours. $12 meal voucher for first class passengers was an insult to the injury. Pathetic.

Terrible planning. And even worse gate agents. Absolutely rude behavior.

Half of the TSA checkpoints at PHL are closed. Also, there is no standby for first class passengers. You can only standby for coach. Very dated policy and inconsistent with peers.

Flight was scheduled at 11:26am but they keep Delaying until midnight. They waited at airport restless.

Rough flight No beverage service due to turbulence Bottom Seat cushion was non existent

Great experience. Good dinner and service. FA's were very nice and attentive.

It was great. Smooth flight, comfortable, left on time and landed on time.

Perhaps this is an airport issue, but being in a takeoff queue for over an hour in the taxiing lane is unacceptable. We will definitely be seeking alternative avenues for air travel in the future.

We hoarded. Then we deplaned. Then we waited for 10 hours in the MSP airport due to a wheel misfunction. We understand safety but communication between crew and airport staff was horrible. When we did finally board, we were rushed on and because we were waiting for a “fresh” pilot and crew, we sat in a roasting plane with no A/C for an hour. My question is why was this flight not cancelled right away when they knew this would be a huge issue OR, why did AA not get a substitute plane, considering this was already a full flight? To me, this appears to be a complete breakdown in leadership and utter systems failure. The compensation for completely disrupting travel plans for hundreds, which we paid dearly for, was measly. While we appreciated the lodging for the night, $12 in meal vouchers isn’t going to sustain anyone for over 12 hours. “We apologize; our hands are tied” is no longer an acceptable explanation. We are so completely turned off by this experience and will definitely seek alternative avenues when we need to fly.

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

Information on your arrival and departure airports