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Madison

Cheap flights from San Juan to Madison (MSN) - Compare and Save

SJU — MSN
Oct 26 — Nov 21
Sun 10/26
Sun 11/2
1 adult, Economy
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Cheap flight deals from San Juan to Madison

Discover tips and strategies to find the most affordable flight options for your journey from San Juan (PR1) to Madison (MSN). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated September 26, 2025.

Round-trip from

$398
(American Airlines)

One-way from

$118
(United Airlines)

Popular in

November

Cheapest in

September

Average price

$285
From San Juan to Madison Truax Field
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One-way flight from San Juan to Madison Truax Field
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Highest demand for flights based on searches. 7% potential increase in price ($41 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($23 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Find flight deals from San Juan to Madison

Cheapest flights from San Juan to Madison
Explore the most affordable flight options available from San Juan to Madison. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 26, 2025.

This American Airlines deal was found by Cheapflights users on 9/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/295:30 amSJU - MSN
1 stop12h 09mAmerican Airlines
Tue 11/44:34 pmMSN - SJU
2 stops15h 43mAmerican Airlines
Deal found 9/26$235
This American Airlines deal was found by Cheapflights users on 9/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/295:30 amSJU - MSN
1 stop7h 45mAmerican Airlines
Tue 11/48:00 amMSN - SJU
1 stop10h 48mAmerican Airlines
Deal found 9/26$268
This United Airlines deal was found by Cheapflights users on 9/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/281:05 amSJU - MSN
2 stops11h 40mUnited Airlines
Tue 11/412:26 pmMSN - SJU
2 stops10h 10mUnited Airlines
Deal found 9/26$279
This United Airlines deal was found by Cheapflights users on 9/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/281:05 amSJU - MSN
2 stops13h 58mUnited Airlines
Tue 11/46:30 amMSN - SJU
1 stop7h 10mUnited Airlines
Deal found 9/26$330
This American Airlines deal was found by Cheapflights users on 9/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/48:20 amSJU - MSN
1 stop17h 10mAmerican Airlines
Wed 11/55:00 amMSN - SJU
2 stops13h 48mAmerican Airlines
Deal found 9/24$398
This American Airlines deal was found by Cheapflights users on 9/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/22:50 pmSJU - MSN
2 stops10h 40mAmerican Airlines
Wed 12/312:18 pmMSN - SJU
1 stop7h 51mAmerican Airlines
Deal found 9/25$465
This United Airlines deal was found by Cheapflights users on 9/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/32:05 amSJU - MSN
2 stops11h 40mUnited Airlines
Wed 11/56:30 amMSN - SJU
1 stop7h 10mUnited Airlines
Deal found 9/24$467
This United Airlines deal was found by Cheapflights users on 9/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/254:52 pmSJU - MSN
1 stop7h 38mUnited Airlines
Fri 1/28:15 amMSN - SJU
2 stops11h 11mUnited Airlines
Deal found 9/25$471
This American Airlines deal was found by Cheapflights users on 9/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/268:00 amSJU - MSN
1 stop17h 51mAmerican Airlines
Sun 11/309:15 pmMSN - SJU
2 stops11h 57mAmerican Airlines
Deal found 9/24$477
This American Airlines deal was found by Cheapflights users on 9/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/254:38 pmSJU - MSN
2 stops19h 30mAmerican Airlines
Fri 1/27:00 amMSN - SJU
1 stop13h 05mAmerican Airlines
Deal found 9/25$508
This American Airlines deal was found by Cheapflights users on 9/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/268:00 amSJU - MSN
2 stops10h 02mAmerican Airlines
Sun 11/309:15 pmMSN - SJU
2 stops11h 57mAmerican Airlines
Deal found 9/24$513
This United Airlines deal was found by Cheapflights users on 9/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/32:05 amSJU - MSN
2 stops11h 40mUnited Airlines
Wed 11/56:30 amMSN - SJU
2 stops12h 56mUnited Airlines
Deal found 9/24$526

Cheapflights Fare Finder

 
Customize your flight search to find flights from San Juan to Madison that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated September 26, 2025.
Use the filters below to find and compare flights from San Juan to Madison that are best for you.

Fly from

San Juan

Fly to

Madison

Route

Depart

Return

Price

San JuanMadison

SJU - MSN

SJUMSN

San Juan Luis Munoz Marin Intl

Wed 10/29

7:45 am-6:59 pm

2 stops12h 14m

Madison Truax Field

Tue 11/4

4:34 pm-10:17 am

2 stops15h 43m

$235

San JuanMadison

SJU - MSN

SJUMSN

San Juan Luis Munoz Marin Intl

Wed 10/29

5:30 am-4:39 pm

1 stop12h 09m

Madison Truax Field

Tue 11/4

4:34 pm-10:17 am

2 stops15h 43m

$235

San JuanMadison

SJU - MSN

SJUMSN

San Juan Luis Munoz Marin Intl

Wed 10/29

5:30 am-12:15 pm

1 stop7h 45m

Madison Truax Field

Tue 11/4

8:00 am-8:48 pm

1 stop10h 48m

$268

San JuanMadison

SJU - MSN

SJUMSN

San Juan Luis Munoz Marin Intl

Tue 10/28

1:05 am-11:45 am

2 stops11h 40m

Madison Truax Field

Tue 11/4

12:26 pm-12:36 am

2 stops10h 10m

$279

San JuanMadison

SJU - MSN

SJUMSN

San Juan Luis Munoz Marin Intl

Tue 10/28

1:05 am-2:03 pm

2 stops13h 58m

Madison Truax Field

Tue 11/4

6:30 am-3:40 pm

1 stop7h 10m

$330

San JuanMadison

SJU - MSN

SJUMSN

San Juan Luis Munoz Marin Intl

Tue 11/4

11:13 am-10:05 pm

2 stops12h 52m

Madison Truax Field

Wed 11/5

5:00 am-5:52 pm

2 stops10h 52m

$398

San JuanMadison

SJU - MSN

SJUMSN

San Juan Luis Munoz Marin Intl

Tue 11/4

5:59 pm-11:30 pm

1 stop7h 31m

Madison Truax Field

Wed 11/5

12:20 pm-8:48 pm

1 stop6h 28m

$398

San JuanMadison

SJU - MSN

SJUMSN

San Juan Luis Munoz Marin Intl

Tue 11/4

8:20 am-11:30 pm

1 stop17h 10m

Madison Truax Field

Wed 11/5

5:00 am-8:48 pm

2 stops13h 48m

$398

San JuanMadison

SJU - MSN

SJUMSN

San Juan Luis Munoz Marin Intl

Tue 12/2

5:59 pm-11:30 pm

1 stop7h 31m

Madison Truax Field

Wed 12/3

12:18 pm-10:09 pm

1 stop7h 51m

$465

San JuanMadison

SJU - MSN

SJUMSN

San Juan Luis Munoz Marin Intl

Mon 11/3

2:05 am-11:45 am

2 stops11h 40m

Madison Truax Field

Wed 11/5

6:30 am-3:40 pm

1 stop7h 10m

$467

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/25

Showing 1-10 of 24 results
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Best time to book a flight from San Juan to Madison

Have a flexible travel schedule? Discover the best time to fly to Madison from San Juan with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from San Juan to Madison

What is the cheapest month to book a flight from San Juan to Madison?

Currently, January is the cheapest month in which you can book a flight from San Juan to Madison (average of $338). Flying from San Juan to Madison in March is currently the most expensive (average of $422). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from SJU to MSN?

Find hourly flight availability from San Juan to Madison. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated September 26, 2025.

It’s optimal to fly from San Juan to Madison in the morning. By choosing this option you can save up to 22% on the cost of your flight, compared to a flight in the afternoon.

How much does it cost to fly round-trip from San Juan to Madison?

Reviews of airlines servicing Madison

Get insights into the airlines that provide service to Madison. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Madison. Reviews last updated September 26, 2025.
See what other customers who have flown with American Airlines from San Juan to Madison have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
American Airlines
7.2
Good
10,000 reviews

Boarding

7.5

Overall

7.2

Comfort

7.2

Crew

8.0

Food

6.4

Entertainment

6.9

Reviews

1 / 20
2.0
Mediocre

Nordia,Sep 2025

KIN - MIA

We were to land in Miami sometime after 3pm but couldn’t due to bad weather, we flew around for 2 hrs until we had to land in Forth Myers to refuel, we had to sit another 2 hrs at Forth Myers until given the clearance to refuel, we were hungry, thirsty and frustrated at that point. All the had on the flight to offer was a small plastic glass of water and a pack of biscoff, I requested a cup of tea and was told none was there. We were basically at another airport and not one of the staff could consider that the passengers might be hungry or thirsty being on a plane for around 8 hrs, which you weren’t prepared for, at least find some hot water on board.
American Airlines
7.2
Good
10,000 reviews
American Airlines
7.2
Good
10,000 reviews

Boarding

7.5

Overall

7.2

Comfort

7.2

Crew

8.0

Food

6.4

Entertainment

6.9

Reviews

1 / 20
2.0
Mediocre

Nordia,Sep 2025

KIN - MIA

We were to land in Miami sometime after 3pm but couldn’t due to bad weather, we flew around for 2 hrs until we had to land in Forth Myers to refuel, we had to sit another 2 hrs at Forth Myers until given the clearance to refuel, we were hungry, thirsty and frustrated at that point. All the had on the flight to offer was a small plastic glass of water and a pack of biscoff, I requested a cup of tea and was told none was there. We were basically at another airport and not one of the staff could consider that the passengers might be hungry or thirsty being on a plane for around 8 hrs, which you weren’t prepared for, at least find some hot water on board.

Related info for your journey

Find useful and relevant information for your journey from San Juan to Madison. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly into for flights to Madison from San Juan?

    If you book a flight to Madison from San Juan, you will be flying to Truax Field, which is the city’s only airport. Madison Truax Field (MSN) is located 5.4 mi from the center of Madison. There are 0 flights from San Juan to Truax Field per day from 1 airline.

  • How long is the flight from San Juan to Madison?

    Airlines like American Airlines and United Airlines fly from San Juan to Madison in about 11h 40m. The time it takes to get you to your destination can typically vary by up to 34m. The distance from San Juan to Madison is about 2180 mi. This flight may include one or multiple stops.

  • What is the cheapest airline to fly from San Juan to Madison round-trip?

    According to our current data, American Airlines ($265), offers the cheapest pricing from San Juan to Madison. You may be able to fly from San Juan to Madison for 46% less than the average price by searching for this airline.

  • Can I find deals for flights from San Juan to Madison that include hotel bookings?

    Yes. In addition to deals on San Juan to Madison flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from San Juan to Madison?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from San Juan to Madison.

  • Can I find deals for business class flights from San Juan to Madison?

    Yes. Cheapflights offers flight deals from San Juan to Madison by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from San Juan to Madison?

    Currently, January is the cheapest month in which you can book a flight from San Juan to Madison (average of $338). Flying from San Juan to Madison in March is currently the most expensive (average of $422). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Traveling to a place near Madison?

Book flights to Madison if you plan to visit one of these locations
Portage
Middleton
Baraboo
Fitchburg

Browse thousands of different options on Cheapflights for your next trip

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Top airline flying from San Juan to Madison

Discover the top airline that operate flights from San Juan to Madison. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated September 26, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$265Average$450FlexibilityNo cancel feeOn-time71%

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