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San Juan

$118+ Cheap flights from Madison (MSN) to San Juan

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 4/10. Fares are subject to change and may not be available on all flights or dates of travel.
MSN — SJU
nov. 28 — dic. 51
vie. 11/28
vie. 12/5
1 adult, Economy
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Cheapflights Tip: The best prices from Madison Truax Field to San Juan are usually found in September or January, booked 21 days in advance, depart on a Monday or Wednesday and return on a Tuesday

Find flight deals from Madison to San Juan

Cheapest flights from Madison to San Juan
Explore the most affordable flight options available from Madison to San Juan. Find the lowest fares from popular airlines and budget airlines, with prices last updated on octubre 29, 2025.

This United Airlines deal was found by Cheapflights users on 10/28. 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.
mar. 12/96:30 amMSN - SJU
2 stops12h 56mUnited Airlines
mar. 12/168:10 amSJU - MSN
1 stop7h 51mUnited Airlines
Deal found 10/28$257
This American Airlines deal was found by Cheapflights users on 10/28. 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.
mar. 12/912:18 pmMSN - SJU
1 stop7h 51mAmerican Airlines
mar. 12/165:56 pmSJU - MSN
1 stop7h 44mAmerican Airlines
Deal found 10/28$268
This American Airlines deal was found by Cheapflights users on 10/27. 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.
sáb. 12/611:00 amMSN - SJU
2 stops21h 09mAmerican Airlines
mar. 12/98:20 amSJU - MSN
1 stop17h 20mAmerican Airlines
Deal found 10/27$295
This American Airlines deal was found by Cheapflights users on 10/27. 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.
mar. 12/95:00 amMSN - SJU
2 stops15h 09mAmerican Airlines
lun. 12/155:56 pmSJU - MSN
1 stop7h 44mAmerican Airlines
Deal found 10/27$301
This United Airlines deal was found by Cheapflights users on 10/28. 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.
jue. 12/183:46 pmMSN - SJU
2 stops12h 25mUnited Airlines
jue. 12/258:10 amSJU - MSN
1 stop7h 44mUnited Airlines
Deal found 10/28$325
This American Airlines deal was found by Cheapflights users on 10/28. 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.
mié. 12/1010:20 amMSN - SJU
1 stop11h 32mAmerican Airlines
lun. 12/152:36 pmSJU - MSN
2 stops11h 04mAmerican Airlines
Deal found 10/28$331
This American Airlines deal was found by Cheapflights users on 10/27. 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.
lun. 12/88:05 amMSN - SJU
1 stop12h 04mAmerican Airlines
mar. 12/165:56 pmSJU - MSN
1 stop7h 44mAmerican Airlines
Deal found 10/27$340
This Frontier deal was found by Cheapflights users on 10/26. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 11/78:00 pmMSN - SJU
2 stops17h 19mFrontier
jue. 11/137:30 amSJU - MSN
2 stops13h 45mFrontier
Deal found 10/26$366
This American Airlines deal was found by Cheapflights users on 10/27. 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.
vie. 12/512:18 pmMSN - SJU
1 stop7h 51mAmerican Airlines
mié. 12/108:20 amSJU - MSN
1 stop17h 20mAmerican Airlines
Deal found 10/27$382

Cheap flight deals from Madison to San Juan

Discover tips and strategies to find the most affordable flight options for your journey from Madison (MSN) to San Juan (PR1). 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 octubre 29, 2025.

Round-trip from

$235
(Delta)

One-way from

$118
(Delta)

Popular in

March

Cheapest in

September

Average price

$420
From Madison Truax Field to San Juan
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One-way flight from Madison Truax Field to San Juan
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Highest demand for flights based on searches. 3% potential increase in price ($16 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($15 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in October 2025
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Cheapflights Fare Finder

 
Customize your flight search to find flights from Madison to San Juan 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 octubre 29, 2025.
Use the filters below to find and compare flights from Madison to San Juan that are best for you.

Fly from

Madison

Fly to

San Juan

Route

Depart

Return

Price

MadisonSan Juan

MSN - SJU

MSNSJU

Madison Truax Field

mar. 1/20

7:00 am-11:44 pm

2 stops14h 44m

San Juan Luis Munoz Marin Intl

mié. 1/28

4:30 pm-10:40 pm

1 stop8h 10m

$235

MadisonSan Juan

MSN - SJU

MSNSJU

Madison Truax Field

mar. 1/20

5:22 pm-10:48 am

2 stops15h 26m

San Juan Luis Munoz Marin Intl

mié. 1/28

6:00 am-3:27 pm

2 stops11h 27m

$235

MadisonSan Juan

MSN - SJU

MSNSJU

Madison Truax Field

mar. 12/9

8:15 am-10:22 pm

2 stops12h 07m

San Juan Luis Munoz Marin Intl

lun. 12/15

2:05 am-11:44 am

2 stops11h 39m

$257

MadisonSan Juan

MSN - SJU

MSNSJU

Madison Truax Field

mar. 12/9

6:13 am-10:09 pm

2 stops13h 56m

San Juan Luis Munoz Marin Intl

mar. 12/16

8:20 am-11:40 pm

1 stop17h 20m

$268

MadisonSan Juan

MSN - SJU

MSNSJU

Madison Truax Field

mar. 3/10

6:30 am-2:40 pm

1 stop7h 10m

San Juan Luis Munoz Marin Intl

mar. 3/10

1:05 am-1:52 pm

2 stops13h 47m

$320

MadisonSan Juan

MSN - SJU

MSNSJU

Madison Truax Field

mar. 1/20

6:30 am-9:26 pm

2 stops12h 56m

San Juan Luis Munoz Marin Intl

mar. 1/27

2:05 am-2:52 pm

2 stops14h 47m

$325

MadisonSan Juan

MSN - SJU

MSNSJU

Madison Truax Field

jue. 12/18

3:46 pm-6:11 am

2 stops12h 25m

San Juan Luis Munoz Marin Intl

jue. 12/25

8:10 am-1:54 pm

1 stop7h 44m

$325

MadisonSan Juan

MSN - SJU

MSNSJU

Madison Truax Field

vie. 4/10

6:15 am-2:20 pm

1 stop7h 05m

$118

MadisonSan Juan

MSN - SJU

MSNSJU

Madison Truax Field

jue. 4/9

6:15 am-2:20 pm

1 stop7h 05m

$118

MadisonSan Juan

MSN - SJU

MSNSJU

Madison Truax Field

dom. 1/4

9:30 pm-11:39 am

2 stops12h 09m

$151

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/26

Showing 1-10 of 18 results
1
2

Best time to book a flight from Madison to San Juan

Have a flexible travel schedule? Discover the best time to fly to San Juan from Madison 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 Madison to San Juan

How far ahead should I book a flight from Madison to San Juan?

Use this chart to determine the optimal time to book a round-trip flight from Madison to San Juan. Price data was last updated on October 24, 2025.

The best time to book flights from Madison to San Juan is 21 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.

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

Currently, October is the cheapest month in which you can book a flight from Madison to San Juan (average of $143). Flying from Madison to San Juan in June is currently the most expensive (average of $379). 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 MSN to SJU?

Find hourly flight availability from Madison to San Juan. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated octubre 29, 2025.

It’s typically best to fly out from Madison to San Juan in the afternoon. Doing so could potentially save you 74% on the flight price compared to flying in the morning, which is usually more expensive.

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

Reviews of airlines servicing San Juan

Get insights into the airlines that provide service to San Juan. 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 San Juan. Reviews last updated octubre 29, 2025.
Read through reviews of airlines operating flights from Madison to San Juan, such as Delta, United Airlines, and American Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Delta
7.9
Good
7,992 reviews

Crew

8.5

Food

7.3

Boarding

8.2

Entertainment

7.9

Overall

7.9

Comfort

7.9

Reviews

1 / 20
8.0
Excellent

Matthew,Oct 2025

GSP - ATL

This is always a full flight since it is the connecting route to primary destinations through Atlanta. That said, the crew handles the full load well. Not much more to say, it is a short flight with no in-flight services due to the length.
Delta
7.9
Good
7,992 reviews
Delta
7.9
Good
7,992 reviews

Crew

8.5

Food

7.3

Boarding

8.2

Entertainment

7.9

Overall

7.9

Comfort

7.9

Reviews

1 / 20
8.0
Excellent

Matthew,Oct 2025

GSP - ATL

This is always a full flight since it is the connecting route to primary destinations through Atlanta. That said, the crew handles the full load well. Not much more to say, it is a short flight with no in-flight services due to the length.
United Airlines
7.4
Good
8,999 reviews
Delta
7.9
Good
7,992 reviews

Crew

8.5

Food

7.3

Boarding

8.2

Entertainment

7.9

Overall

7.9

Comfort

7.9

Reviews

1 / 20
8.0
Excellent

Matthew,Oct 2025

GSP - ATL

This is always a full flight since it is the connecting route to primary destinations through Atlanta. That said, the crew handles the full load well. Not much more to say, it is a short flight with no in-flight services due to the length.
American Airlines
7.2
Good
11,032 reviews
Delta
7.9
Good
7,992 reviews

Crew

8.5

Food

7.3

Boarding

8.2

Entertainment

7.9

Overall

7.9

Comfort

7.9

Reviews

1 / 20
8.0
Excellent

Matthew,Oct 2025

GSP - ATL

This is always a full flight since it is the connecting route to primary destinations through Atlanta. That said, the crew handles the full load well. Not much more to say, it is a short flight with no in-flight services due to the length.

Related info for your journey

Find useful and relevant information for your journey from Madison to San Juan. 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 from for flights from Madison to San Juan?

    Madison Truax Field (MSN), located 5.4 mi from the city center, is the airport you fly out of when you book flights from Madison to San Juan. 3 airlines have flights from Truax Field to San Juan on a regular basis. Booking flights from Madison Truax Field to San Juan should not be difficult; the airport handles an average of 0 outbound flights to San Juan per day.

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

    For as low as $257, Delta can have you in San Juan from Madison in 12h 07m. There are 2180 mi between Madison and San Juan. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • What are the cheapest airlines flying from Madison to San Juan round-trip?

    Delta, at $225, was found to be the cheapest airline from Madison to San Juan.Alternate airlines to your destination round-trip include United Airlines and American Airlines. Users have found that Delta is 55% cheaper than the other options available to this destination.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Madison to San Juan 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 Madison to San Juan?

    Currently, October is the cheapest month in which you can book a flight from Madison to San Juan (average of $143). Flying from Madison to San Juan in June is currently the most expensive (average of $379). 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

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Top 3 airlines flying from Madison to San Juan

Discover the top 3 airlines that operate flights from Madison to San Juan. 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 octubre 29, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$225Average$438FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$260Average$577FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$269Average$516FlexibilityNo cancel feeOn-time71%

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