MSN - SJO

$255 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 3/6. 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
$389
Overall average: $625
American Airlines
Thu 4/16Tue 4/21
MSN - SJO • 2 stops
Cheapest one-way
$255
Multiple Airlines
Fri 3/6
MSN - SJO • 2 stops
Top airlines
American Airlines
Cheapest • from $389 (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 $742 (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

Thu, Apr 16 - Tue, Apr 21
American Airlines Logo
8:05 am - 7:07 pm
MSN
-
SJO
12h 02m
2 stops
American Airlines Logo
2:22 pm - 10:55 am
SJO
-
MSN
19h 33m
2 stops
$389American Airlines
Thu, Apr 16 - Tue, Apr 21
American Airlines Logo
8:05 am - 7:07 pm
MSN
-
SJO
12h 02m
2 stops
American Airlines Logo
2:22 pm - 10:55 am
SJO
-
MSN
19h 33m
2 stops
$409American Airlines
Wed, Mar 4 - Tue, Mar 10
United Airlines Logo
6:30 am - 8:39 pm
MSN
-
SJO
14h 09m
2 stops
United Airlines Logo
1:05 pm - 10:32 pm
SJO
-
MSN
8h 27m
1 stop
$435United Airlines
Mon, Mar 2 - Tue, Mar 10
Delta Logo
6:15 pm - 1:00 pm
MSN
-
SJO
18h 45m
2 stops
Delta Logo
7:00 am - 12:41 pm
SJO
-
MSN
28h 41m
2 stops
$440Delta
Thu, Mar 5 - Tue, Mar 10
Delta Logo
5:38 am - 1:00 pm
MSN
-
SJO
7h 22m
1 stop
Delta Logo
7:00 am - 10:34 pm
SJO
-
MSN
14h 34m
1 stop
$453Delta
Wed, Mar 4 - Tue, Mar 10
American Airlines Logo
6:14 am - 10:43 pm
MSN
-
SJO
16h 29m
1 stop
American Airlines Logo
11:35 pm - 10:39 am
SJO
-
MSN
10h 04m
1 stop
$455American Airlines
Thu, Mar 5 - Wed, Mar 11
Delta Logo
7:00 am - 10:02 pm
MSN
-
SJO
15h 02m
2 stops
Delta Logo
7:00 am - 9:06 pm
SJO
-
MSN
13h 06m
2 stops
$458Delta
Wed, Mar 4 - Tue, Mar 10
Delta Logo
5:38 am - 10:02 pm
MSN
-
SJO
16h 24m
1 stop
Delta Logo
7:00 am - 12:41 pm
SJO
-
MSN
28h 41m
2 stops
$460Delta
Thu, Mar 5 - Tue, Mar 10
Delta Logo
5:38 am - 1:00 pm
MSN
-
SJO
7h 22m
1 stop
Delta Logo
7:00 am - 10:34 pm
SJO
-
MSN
14h 34m
1 stop
$473Delta
Thu, Mar 5 - Tue, Mar 10
Delta Logo
7:00 am - 10:02 pm
MSN
-
SJO
15h 02m
2 stops
Delta Logo
7:00 am - 10:34 pm
SJO
-
MSN
14h 34m
1 stop
$478Delta
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$255
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 $255 for a one-way ticket and $389 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 $887 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 $638 and an overall rating of 7.2.

  • 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 8212 reviews
8.1Boarding
7.9Comfort
8.5Crew
7.8Entertainment
7.2Food
Airline reviews

Boarding and crew were fantastic, but I paid for a window seat with no window. Seat 11D on a CRJ-900 apparently does not have a window. Lesson learned.

6.0 GoodAnthony, Feb 2026
LGA - CMH
Read more Delta reviews

Boarding and crew were fantastic, but I paid for a window seat with no window. Seat 11D on a CRJ-900 apparently does not have a window. Lesson learned.

Terrible. Four hour delay because Delta could not find crew to man the aircraft. Terrible communication. Terrible insight into the delays. One of the worst flight experiences I’ve had.

It was good. The leg room was not great in Row 1.

The landing was the worst I’ve experienced with a flight.

The crew, and fellow passengers, were super gracious and kind. There seemed to be plenty of bin space even though the plane was full. It’s nice to get a glass of wine with dinner in Premiere seating, and there was a lot of food.

First flight out and was 85 minutes delayed. Notification came out way too late

Delta flights recently are always delayed AND at jfk tney get the gates further away (need To walk 20’ to get to them/all the way at the end of the terminal). Not sure whats happening but price doesnt match experience!

Everything I mentioned earlier - the airbus was more comfortable indeed and the experience was further enhanced.

Delta continues to set the benchmark for traveler-friendly service with minimal disruption and clear communication within the mainland US (coast to coast). I am consistently pleased to be a Delta customer, and this experience once again met my expectations. There was a brief delay departing from MIA due to a technical issue that required the aircraft to return to the gate. However, the situation was handled professionally and transparently. Fortunately, my planned layover allowed ample buffer time, so the adjustment caused no stress. Overall, another smooth and reassuring experience.

Good experience and the flight landed early. There was no food I had or entertainment.

Flight was on time and there was an empty seat next to me. That makes for a good flight!

Maintenance took a very long time and then we were in a holding pattern. While a one-off maintenance issue is standard, there were delays on both of my flights for this trip based on maintenance issues with the planes, which delayed both flights over 45 minutes. Thankfully, I didn't have any connections but it wasn't an experience that would make me pick AA if I have other options.

I like that the flight attendant was very attentive and helpful. The meal menu could have more of an variety of food choices.

Everything was good. Flight was very full so crew was busy. After we boarded and plane pulled away from the gate, we were delayed about 40 minutes- sitting on the runway - due to weather en route or at the destination. While weather is not the fault of the airline- it’s terrible to sit on a plane and not moving.

We missed our flight and got stranded in Miami where we had to rent a hotel we could not afford. they would not work with us because they said it was weather related even though the gate attendant said it was not. I could go on but trying to get satisfaction has wore me down, which I believe is the intent. My only solution is to never fly AA again.

No Snacks or Entertainment. The flight was short, snacks should still be given.

We lost a day of our vacation because AA did not get the plane to the gate on time. Even though the gate attendant was very clear that it was not weather related, AA would do nothing because there was some snow that day. They basically said the gate attendant was wrong even though she was on the front line of the situation and they were not.

See prior comment about how Kayak mishandled my reservation and delayed my arrival by 6 hours.

American Airlines was great and worked very hard to change my ticket so I could get an earlier, direct flight back to Dallas. However, I was informed that Kayak made mistakes with my itinerary and classified my ticket as desiring to be on the earlier flight instead of taking the necessary step of calling AA to get me on the standby list. This ended up keeping me from being added to the standby list and delayed me getting home by 6 hours. I am happy to discuss this further with Kayak so they can correct their procedures so this won't happen again.

The flight was fine. It's the satellite terminal that supports American eagle flights is what sucks. There is only one food option and everything there is way overpriced. I mean I know it's airport pricing, but it's even crazier than that. I bought a sandwich in a plastic container for $18.

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

Information on your arrival and departure airports