MSN - SJO

$304 Find Cheap Flights from Madison to San José - Compare and Save

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1 adult, Economy, 0 bags

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Everything you should know

Cheapest round-trip
$439
Typical prices: $614-$885
American Airlines
Fri 11/16Sat 11/24
MSN - SJO • 2 stops
Cheapest one-way
$304
Typical prices: $262-$370
American Airlines
Sat 11/3
MSN - SJO • 2 stops
Nonstop flights
Not available
There are currently no direct flights between Madison and San José. You'll need to take a connecting flight to reach the destination.
Insights
Insights
When to travel
September
Cheapest • 24% price drop
February
Most popular
Good to know
+1
Good to know
+1
Top layover airports
Chicago O'Hare Intl (ORD)
Cheapest • Avg $674 (round-trip)
Charlotte Douglas (CLT)
Shortest trip • 7h 34m (one-way)
Insights
Insights
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We hope you love your trip to San José!
Flight Deals
Booking Insights
Flight Deals

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

 
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Madison to San José

Mon, Nov 16 - Tue, Nov 24
American Airlines Logo
8:42 pm - 1:05 pmMSN  Madison Truax Field-SJO San José Juan Santamaria Intl
16h 23m2 stops Chicago O'Hare Intl Charlotte Douglas
American Airlines Logo
3:54 pm - 8:24 amSJO  San José Juan Santamaria Intl-MSN Madison Truax Field
16h 30m2 stops Miami Chicago O'Hare Intl
$439American Airlines
Mon, Nov 16 - Mon, Nov 23
American Airlines Logo
8:42 pm - 1:05 pmMSN  Madison Truax Field-SJO San José Juan Santamaria Intl
16h 23m2 stops Chicago O'Hare Intl Charlotte Douglas
American Airlines Logo
12:30 am - 5:11 pmSJO  San José Juan Santamaria Intl-MSN Madison Truax Field
16h 41m1 stop Dallas/Fort Worth
$439American Airlines
Mon, Nov 16 - Mon, Nov 23
American Airlines Logo
12:23 pm - 1:05 pmMSN  Madison Truax Field-SJO San José Juan Santamaria Intl
24h 42m1 stop Charlotte Douglas
American Airlines Logo
12:30 am - 10:55 amSJO  San José Juan Santamaria Intl-MSN Madison Truax Field
10h 25m1 stop Dallas/Fort Worth
$443American Airlines
Sat, Jan 16 - Tue, Jan 26
American Airlines Logo
5:35 pm - 1:46 pmMSN  Madison Truax Field-SJO San José Juan Santamaria Intl
20h 11m1 stop Dallas/Fort Worth
American Airlines Logo
7:16 am - 9:46 pmSJO  San José Juan Santamaria Intl-MSN Madison Truax Field
14h 30m1 stop Dallas/Fort Worth
$494American Airlines
Thu, Dec 10 - Tue, Dec 15
Multiple Airlines Logo
10:40 am - 11:40 pmMSN  Madison Truax Field-SJO San José Juan Santamaria Intl
13h 00m2 stops Chicago O'Hare Intl San Salvador El Salvador Intl
Multiple Airlines Logo
5:00 am - 7:02 pmSJO  San José Juan Santamaria Intl-MSN Madison Truax Field
14h 02m2 stops San Salvador El Salvador Intl Chicago O'Hare Intl
$621Multiple Airlines
Mon, Oct 5 - Wed, Oct 14
Delta Logo
6:37 pm - 12:00 pmMSN  Madison Truax Field-SJO San José Juan Santamaria Intl
18h 23m2 stops Detroit Metropolitan Wayne County Atlanta Hartsfield-Jackson
Delta Logo
1:25 pm - 11:02 pmSJO  San José Juan Santamaria Intl-MSN Madison Truax Field
8h 37m1 stop Atlanta Hartsfield-Jackson
$623Delta
Mon, Oct 5 - Wed, Oct 14
United Airlines Logo
6:49 am - 7:37 pmMSN  Madison Truax Field-SJO San José Juan Santamaria Intl
13h 48m2 stops Chicago O'Hare Intl Houston George Bush Intcntl
United Airlines Logo
7:55 am - 10:35 pmSJO  San José Juan Santamaria Intl-MSN Madison Truax Field
13h 40m2 stops Houston George Bush Intcntl Chicago O'Hare Intl
$623United Airlines
Tue, Dec 8 - Sat, Dec 19
Delta Logo
11:32 am - 10:15 pmMSN  Madison Truax Field-SJO San José Juan Santamaria Intl
10h 43m1 stop Atlanta Hartsfield-Jackson
Delta Logo
7:00 am - 4:34 pmSJO  San José Juan Santamaria Intl-MSN Madison Truax Field
9h 34m1 stop Atlanta Hartsfield-Jackson
$630Delta
Thu, Oct 22 - Wed, Oct 28
Delta Logo
5:51 am - 12:00 pmMSN  Madison Truax Field-SJO San José Juan Santamaria Intl
7h 09m1 stop Atlanta Hartsfield-Jackson
Delta Logo
1:25 pm - 11:03 pmSJO  San José Juan Santamaria Intl-MSN Madison Truax Field
8h 38m1 stop Atlanta Hartsfield-Jackson
$633Delta
Thu, Jan 7 - Mon, Jan 11
United Airlines Logo
5:00 am - 12:15 pmMSN  Madison Truax Field-SJO San José Juan Santamaria Intl
7h 15m1 stop Chicago O'Hare Intl
United Airlines Logo
1:15 am - 3:00 pmSJO  San José Juan Santamaria Intl-MSN Madison Truax Field
13h 45m2 stops Houston George Bush Intcntl Chicago O'Hare Intl
$634United Airlines
Booking Insights

Price, demand and travel trends for Madison to San José flights

Use KAYAK data on prices, travel dates, airlines and seasonal trends to compare options and book flights from Madison to San José with more confidence.

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

Round-trip flights from Madison to San José start at $439. Prices are below average for this route right now, with typical round-trip fares ranging from $614 to $885. The lowest price found in the past 5 days was $439 on American Airlines.

What's the cheapest day of the week to fly from Madison to San José?

Friday is the cheapest day of the week to fly from Madison to San José, it is 14% cheaper than the average day. Saturday is the most expensive day with flight prices 52% higher than average. Based on deals found by KAYAK users in the last 12 months.

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

  • September is the cheapest month to fly from Madison to San José at $539 round-trip.
  • December ($1,118) and June ($894) are the most expensive months.
  • The price difference between flying in the cheapest and most expensive months is 107% on average.
This is based on KAYAK aggregated and averaged internal data over the past 12 months.

Find deals

Key details for Madison to San José flights

Low season

June

Cheapest flight

$304
Best time to beat the crowds but there is an average 26% increase in price.
Most popular time to fly with an average 7% 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

Your Madison to San José flight questions, answered

Find helpful route details based on KAYAK data, including flight times, airports, airlines and booking questions.

  • Which airports can I use when flying from Madison to San José?

    Flights from Madison to San José usually depart from Madison Truax Field (MSN) and arrive at San José Juan Santamaria Intl (SJO).

  • What cabin classes can I book on flights from Madison to San José?

    Only Economy Class is available on flights from Madison to San José.

  • Which airports do connecting flights from Madison to San José pass through?

    One-stop flights from Madison to San José most commonly connect through:

    • Dallas/Fort Worth (DFW) - 52% of one-stop connections
    • Atlanta Hartsfield-Jackson (ATL) - 31% of one-stop connections
    • Chicago O'Hare Intl (ORD) - 9% of one-stop connections
    • Charlotte Douglas (CLT) - 4% of one-stop connections

    Dallas/Fort Worth (DFW) handles the largest share of one-stop connections on this route.

  • Can I save money by using flexible dates for flights from Madison to San José?

    Yes. Being flexible with your travel dates can save you up to 44% on the Madison to San José route. Friday is the cheapest departure day at $614 round-trip on average, while Saturday is the most expensive at $1,085, a difference of $471. KAYAK's flexible dates feature shows options up to 3 days before and after your selected dates, making it easier to compare nearby fares.

  • What popular places can I visit in San José?

    Some of the most popular sights in San José are Parque Metropolitano La Sabana, Barrio Amón and Estadio Nacional de Costa Rica. These are among the most viewed places in San José on KAYAK.

  • How long is a flight from Madison to San José?

    A nonstop flight from Madison to San José takes 0h 00m, covering 2,309 miles.

  • What are the earliest and latest flights from Madison to San José?

    These are the earliest and latest flight times available from Madison to San José:

    • Earliest: departs at 12:00 am and lands at 12:00 am
    • Latest: departs at 12:00 am and lands at 12:00 am.

    The flight takes about 0h 00m.

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

    Yes, a valid passport is required for this international route. Many destinations require at least six months of validity beyond your travel dates. Check your passport expiry well before booking.

  • Have flight prices from Madison to San José changed much recently?

    Yes. Based on fares seen in the past 5 days, round-trip prices on this route showed a wide range, from about $439 to $3,209. That means the highest observed fare was about 7x higher than the lowest one.

  • How are flight prices from Madison to San José looking right now?

    One-way fares from Madison to San José are currently higher than usual. Average one-way flight prices are about $372, which is 23% above the typical average for this route.

  • How much time can I save by choosing a different layover airport from Madison to San José?

    Flying via Charlotte Douglas (CLT) gives the shortest average 1-stop total travel time at 7h 34m, compared with 7h 54m via Atlanta Hartsfield-Jackson (ATL) and 8h 48m via Miami (MIA).

  • What is the time difference between Madison and San José?

    San José is 1 hour behind Madison (Central Time vs Central Time). Plan for the time shift when scheduling connections or first-day activities.

  • What car rental options are available at San José Juan Santamaria Intl Airport (SJO)?

    San José Juan Santamaria Intl Airport (SJO) hosts 5 major car rental companies, with daily rates starting from around $1 for economy cars. Top options include:
    · Budget
    · Avis
    · Priceless
    · Routes Car & Truck Rentals
    · Payless

  • How much should I expect to pay for a Madison to San José flight?

    Round-trip flights from Madison to San José range from $614 to $885, with an average of $711 over the past 12 months. Anything below $614 counts as a good deal.

Your guide to booking Madison to San José flights

Get tips on when to book, when to fly and what to know before your trip.
  • If your dates can be flexible, aim for a Friday departure instead of Saturday. On this route, Friday flights average $614 - about $471 less than Saturday (43% savings) based on the last 12 months.
  • If you can choose when to travel, plan your Madison to San José trip for September. Fares historically average $539 round-trip in that month - typically $579 less than the most expensive month, which is December (based on the last 12 months).

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

Information on your arrival and departure airports

Madison (MSN)
San José (SJO)