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Puerto Rico

$118+ Cheap flights from Madison (MSN) to Puerto Rico

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 2/9. Fares are subject to change and may not be available on all flights or dates of travel.
MSN — SJU
Jan 11 — Jan 181
Sun 1/11
Sun 1/18
1 adult, Economy
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Cheap flight deals from Madison to Puerto Rico

Cheapest flights from Madison to Puerto Rico
Explore the most affordable flight options available from Madison to Puerto Rico. Find the lowest fares from popular airlines and budget airlines, with prices last updated on December 12, 2025.

This American Airlines deal was found by Cheapflights users on 12/11. 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 12/308:10 pmMSN - SJU
1 stop6h 50mAmerican Airlines
Fri 1/92:31 pmSJU - MSN
2 stops10h 09mAmerican Airlines
Deal found 12/11$479
This American Airlines deal was found by Cheapflights users on 12/11. 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 12/1612:18 pmMSN - SJU
1 stop7h 51mAmerican Airlines
Sat 12/276:00 amSJU - MSN
1 stop15h 40mAmerican Airlines
Deal found 12/11$539
This American Airlines deal was found by Cheapflights users on 12/10. 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 12/187:00 amMSN - SJU
1 stop13h 05mAmerican Airlines
Thu 1/81:24 pmSJU - MSN
2 stops11h 16mAmerican Airlines
Deal found 12/10$602
This American Airlines deal was found by Cheapflights users on 12/11. 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 12/187:00 amMSN - SJU
1 stop13h 05mAmerican Airlines
Thu 12/256:00 amSJU - MSN
1 stop13h 42mAmerican Airlines
Deal found 12/11$632
This United Airlines deal was found by Cheapflights users on 12/9. 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.
Wed 12/106:30 amMSN - SJU
1 stop7h 10mUnited Airlines
Wed 12/105:50 pmSJU - MSN
2 stops22h 01mUnited Airlines
Deal found 12/9$634
This eDestinos deal was found by Cheapflights users on 12/10. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/222:56 pmMSN - SJU
3 stops32h 43mMultiple Airlines
Fri 1/92:29 amSJU - MSN
2 stops17h 07mMultiple Airlines
Deal found 12/10$646
This American Airlines deal was found by Cheapflights users on 12/10. 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.
Mon 12/229:51 amMSN - SJU
2 stops10h 14mAmerican Airlines
Fri 12/262:44 pmSJU - MSN
1 stop11h 15mAmerican Airlines
Deal found 12/10$662
This American Airlines deal was found by Cheapflights users on 12/10. 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.
Sun 12/288:10 pmMSN - SJU
1 stop6h 50mAmerican Airlines
Thu 1/16:18 amSJU - MSN
1 stop12h 02mAmerican Airlines
Deal found 12/10$693
This United Airlines deal was found by Cheapflights users on 12/11. 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.
Wed 12/2410:45 amMSN - BQN
2 stops11h 12mUnited Airlines
Sun 1/111:09 amBQN - MSN
2 stops12h 42mUnited Airlines
Deal found 12/11$955

Find flight deals from Madison to Puerto Rico

Keep the following information in mind while searching for Madison to Puerto Rico flight deals. Data was last updated December 12, 2025.

Round-trip from

$235
(United Airlines)

One-way from

$118
(American Airlines)

Popular in

March

Cheapest in

September

Average price

$617
From Madison Truax Field to Puerto Rico
Search Deals
One-way flight from Madison Truax Field to Puerto Rico
Search Deals
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 ($13 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
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Cheapflights Fare Finder

 
Customize your flight search to find flights from Madison to Puerto Rico 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 December 12, 2025.
Use the filters below to find and compare flights from Madison to Puerto Rico that are best for you.

Fly from

Madison

Fly to

Puerto Rico

Route

Depart

Return

Price

MadisonSan Juan

MSN - SJU

MSNSJU

Madison Truax Field

Tue 2/10

8:15 am-9:26 pm

2 stops11h 11m

San Juan Luis Munoz Marin Intl

Tue 2/17

2:05 am-11:58 am

2 stops11h 53m

$235

MadisonSan Juan

MSN - SJU

MSNSJU

Madison Truax Field

Thu 1/29

7:25 am-8:50 pm

2 stops11h 25m

San Juan Luis Munoz Marin Intl

Tue 2/3

7:00 am-4:20 pm

1 stop11h 20m

$235

MadisonSan Juan

MSN - SJU

MSNSJU

Madison Truax Field

Tue 1/27

6:30 am-3:40 pm

1 stop7h 10m

San Juan Luis Munoz Marin Intl

Fri 1/30

2:05 am-11:51 am

2 stops11h 46m

$235

MadisonSan Juan

MSN - SJU

MSNSJU

Madison Truax Field

Mon 1/26

6:30 am-3:40 pm

1 stop7h 10m

San Juan Luis Munoz Marin Intl

Thu 1/29

2:05 am-11:51 am

2 stops11h 46m

$235

MadisonSan Juan

MSN - SJU

MSNSJU

Madison Truax Field

Sun 1/25

2:56 pm-6:11 am

2 stops13h 15m

San Juan Luis Munoz Marin Intl

Fri 1/30

8:35 am-2:52 pm

1 stop8h 17m

$235

MadisonSan Juan

MSN - SJU

MSNSJU

Madison Truax Field

Thu 1/29

7:00 am-10:26 pm

1 stop13h 26m

San Juan Luis Munoz Marin Intl

Thu 2/5

6:00 am-12:46 pm

1 stop8h 46m

$268

MadisonSan Juan

MSN - SJU

MSNSJU

Madison Truax Field

Sun 1/11

3:48 pm-6:11 am

2 stops12h 23m

San Juan Luis Munoz Marin Intl

Wed 1/21

8:10 am-5:47 pm

2 stops11h 37m

$312

MadisonAguadilla

MSN - BQN

MSNBQN

Madison Truax Field

Mon 1/26

8:15 am-11:57 pm

2 stops13h 42m

Aguadilla Borinquen

Thu 1/29

1:09 am-11:51 am

2 stops12h 42m

$318

MadisonSan Juan

MSN - SJU

MSNSJU

Madison Truax Field

Wed 1/21

6:30 am-9:26 pm

2 stops12h 56m

San Juan Luis Munoz Marin Intl

Wed 1/28

8:35 am-2:52 pm

1 stop8h 17m

$325

MadisonSan Juan

MSN - SJU

MSNSJU

Madison Truax Field

Tue 1/20

6:30 am-9:26 pm

2 stops12h 56m

San Juan Luis Munoz Marin Intl

Sat 1/24

7:45 am-9:05 pm

2 stops15h 20m

$325

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/11

Showing 1-10 of 35 results
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Best time to book a flight from Madison to Puerto Rico

Have a flexible travel schedule? Discover the best time to fly to Puerto Rico 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 Puerto Rico

What is the cheapest month to book a flight from Madison to Puerto Rico?

Currently, March is the cheapest month in which you can book a flight from Madison to Puerto Rico (average of $87). Flying from Madison to Puerto Rico 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 PR?

Find hourly flight availability from Madison to Puerto Rico. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated December 12, 2025.

It’s typically best to fly out from Madison to Puerto Rico in the afternoon. Doing so could potentially save you 71% on the flight price compared to flying in the morning, which is usually more expensive.

Reviews of airlines servicing Puerto Rico

Get insights into the airlines that provide service to Puerto Rico. 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 Puerto Rico. Reviews last updated December 12, 2025.
Peruse reviews from past customers who have flown with Delta, United Airlines, and American Airlines from Madison to Puerto Rico to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
7.9
Good
8,008 reviews

Comfort

7.9

Boarding

8.1

Food

7.3

Crew

8.5

Entertainment

7.9

Overall

7.9

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
Delta
7.9
Good
8,008 reviews
Delta
7.9
Good
8,008 reviews

Comfort

7.9

Boarding

8.1

Food

7.3

Crew

8.5

Entertainment

7.9

Overall

7.9

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
United Airlines
7.4
Good
9,095 reviews
Delta
7.9
Good
8,008 reviews

Comfort

7.9

Boarding

8.1

Food

7.3

Crew

8.5

Entertainment

7.9

Overall

7.9

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
American Airlines
7.2
Good
11,050 reviews
Delta
7.9
Good
8,008 reviews

Comfort

7.9

Boarding

8.1

Food

7.3

Crew

8.5

Entertainment

7.9

Overall

7.9

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.

Related info for your journey

Find useful and relevant information for your journey from Madison to Puerto Rico. 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 Puerto Rico?

    For a flight from Madison to Puerto Rico, you will be flying from Truax Field. Madison Truax Field (MSN) is just 5.4 mi from the center of the city.

  • How long is the flight from Madison to Puerto Rico?

    Airlines like United Airlines and American Airlines fly from Madison to Puerto Rico in about 11h 11m. The time it takes to get you to your destination can typically vary by up to 14m. There are 2180 mi between Madison and Puerto Rico. Both multi-stop and nonstop flights can be found to your destination and back.

  • What are the most popular routes from Madison to Puerto Rico?

    Most travelers choose Madison Truax Field - San Juan Luis Munoz Marin Intl, Madison Truax Field - Aguadilla Borinquen or Madison Truax Field - Culebra when deciding on the best route from Madison to Puerto Rico.

  • Can I find deals for flights from Madison to Puerto Rico that include hotel bookings?

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

  • How can I find direct flights from Madison to Puerto Rico?

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

  • Can I find deals for business class flights from Madison to Puerto Rico?

    Yes. Cheapflights offers flight deals from Madison to Puerto Rico 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 Puerto Rico?

    Currently, March is the cheapest month in which you can book a flight from Madison to Puerto Rico (average of $87). Flying from Madison to Puerto Rico 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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Alternative routes for Madison to Puerto Rico

See prices for flight routes from nearby airports that may be better suited for you.
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Top 3 airlines flying from Madison to Puerto Rico

Discover the top 3 airlines that operate flights from Madison to Puerto Rico. 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 December 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$225Average$458FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$257Average$473FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$269Average$517FlexibilityNo cancel feeOn-time71%

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