$219 Cheap flight deals from San José (SJO) to Madison (MSN)

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Airfares from $219 One Way, $390 Round Trip from San José to Madison

Prices starting at $390 for return flights and $219 for one-way flights to Madison were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Fri, Aug 29 - Sun, Sep 7
SJO
San José
MSN
Madison
$390 Roundtrip, found 8 hours ago
$390
Roundtrip
found 8 hours ago
Select American Airlines flight, departing Fri, Aug 29 from San José to Madison, returning Sun, Sep 7, priced at $390 found 8 hours ago
Fri, Oct 31 - Mon, Nov 3
SJO
San José
MSN
Madison
$396 Roundtrip, found 5 days ago
$396
Roundtrip
found 5 days ago
Select American Airlines flight, departing Fri, Oct 31 from San José to Madison, returning Mon, Nov 3, priced at $396 found 5 days ago
Fri, Aug 29 - Sun, Sep 7
SJO
San José
MSN
Madison
$398 Roundtrip, found 8 hours ago
$398
Roundtrip
found 8 hours ago
Select American Airlines flight, departing Fri, Aug 29 from San José to Madison, returning Sun, Sep 7, priced at $398 found 8 hours ago
Fri, Aug 29 - Sun, Sep 7
SJO
San José
MSN
Madison
$426 Roundtrip, found 8 hours ago
$426
Roundtrip
found 8 hours ago
Select American Airlines flight, departing Fri, Aug 29 from San José to Madison, returning Sun, Sep 7, priced at $426 found 8 hours ago
Fri, Sep 5 - Sat, Sep 13
SJO
San José
MSN
Madison
$431 Roundtrip, found 17 hours ago
$431
Roundtrip
found 17 hours ago
Select United flight, departing Fri, Sep 5 from San José to Madison, returning Sat, Sep 13, priced at $431 found 17 hours ago

Madison first class flight packages

Price found within the past 48 hours. Click for updated prices.
Hilton Garden Inn Madison West/Middleton
3.0-star property

Hilton Garden Inn Madison West/Middleton

9/10 Wonderful! (933 reviews)

Jul 28 - Aug 5

8 night stay

San José (SJO) to Madison (MSN)

United • Non-stop • FirstClass

Madison (MSN) to San José (SJO)

American Airlines • Non-stop • FirstClass
per person
found 3 hours ago
Great location & a nice, little bar.

Reviewed on Mar 2, 2025

Graduate by Hilton Madison
4.0-star property

Graduate by Hilton Madison

9/10 Wonderful! (1,002 reviews)

Jul 28 - Aug 5

8 night stay

San José (SJO) to Madison (MSN)

United • Non-stop • FirstClass

Madison (MSN) to San José (SJO)

American Airlines • Non-stop • FirstClass
per person
found 3 hours ago
The staff is extremely friendly and helpful. The bed in our first room was not comfortable and the hotel was accommodating and moved us to a new room. The bed in the new room was more comfortable. Easy walking distance to The terrace, restaurants, campus and the capital.

Reviewed on Aug 11, 2024

The Madison Concourse Hotel and Governor's Club
3.5-star property

The Madison Concourse Hotel and Governor's Club

9.4/10 Exceptional! (2,680 reviews)

Jul 28 - Aug 5

8 night stay

San José (SJO) to Madison (MSN)

United • Non-stop • FirstClass

Madison (MSN) to San José (SJO)

American Airlines • Non-stop • FirstClass
per person
found 3 hours ago
Very comfortable hotel in perfect location for enjoying downtown Madison.

Reviewed on Jun 1, 2025

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More About Flying To Madison from San José

Route Information for Flights from San José to Madison

Origin Airport IATA Code
SJO
Destination Airport IATA Code
MSN
Distance
Direct Flight Airlines
Earliest Flight Arrival
Latest Flight Arrival

San José to Madison

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Guaranteed low prices for San José to Madison flights makes Orbitz the perfect online budget travel source.

Frequently asked questions

What is the shortest flight from San Jose to Madison?
Flying from Juan Santamaria Intl. Airport to Truax Field will take you at least 5 hours and 56 minutes. Indulge in a tipple and watch a show or two --- here's your chance to sit back and chill out.
What is the cheapest day of the week to fly?
Consider flying out early in the week to save on your airfare. Orbitz data from 2021 shows that Monday is the cheapest day to depart, followed by Tuesday. Saturday showed the highest average ticket prices likely because many travelers prefer to start their vacation on a weekend.
What is the cheapest month to fly?
We won't keep you guessing, according to Orbitz data from 2021, the cheapest month to fly is February. Perfect for those who need a weekend getaway, or just a break from it all in the shortest month of the year. Be aware that the most expensive time to fly is during the height of summer in July, and in the holiday month of December.*According to flight demand on Orbitz.com from January to December 2021. Savings are subject to change based on departure location, date and destination.

Fare, taxes & fees: Fares include all taxes and fees, except baggage fees. Rates shown reflect fares found by other Orbitz users over the past 7 days. Due to rapidly changing airline prices & seat availability, these fares may no longer be available.

Refunds/changes/cancellations: Itinerary changes, if permitted for the fare, will have a $30 service fee charged by Orbitz. Additional airline charges may apply.

Other conditions: Schedules, fares and rules are subject to change without notice. Seats are limited and may not be available on all flights/dates or in all markets. Lower fares may be available. Fares will not be honored retroactively or in exchange for any wholly/partially unused ticket. Tickets are non-transferable and non-refundable. Fare rules are provided for the selected itinerary before booking.