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Puerto Rico

$128+ 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 5/5. Fares are subject to change and may not be available on all flights or dates of travel.
MSN — SJU
fev 27 — mar 61
sex 2/27
sex 3/6
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 janeiro 28, 2026.

This United Airlines deal was found by Cheapflights users on 1/26. 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.
ter 2/246:30 am
MSN
-
SJU
2 stops12h 56m
United Airlines
qua 3/48:30 am
SJU
-
MSN
1 stop7h 37m
United Airlines
Deal found 1/26$256
This Delta deal was found by Cheapflights users on 1/26. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
qua 4/86:00 am
MSN
-
SJU
1 stop7h 15m
Delta
qua 4/156:15 am
SJU
-
MSN
1 stop11h 02m
Delta
Deal found 1/26$304
This American Airlines deal was found by Cheapflights users on 1/27. 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.
ter 4/146:10 am
MSN
-
SJU
2 stops13h 41m
American Airlines
ter 4/217:25 am
SJU
-
MSN
1 stop16h 36m
American Airlines
Deal found 1/27$319
This American Airlines deal was found by Cheapflights users on 1/27. 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.
seg 4/208:25 pm
MSN
-
SJU
1 stop16h 43m
American Airlines
qua 4/294:30 pm
SJU
-
MSN
1 stop8h 25m
American Airlines
Deal found 1/27$324
This United Airlines deal was found by Cheapflights users on 1/26. 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.
sáb 2/285:44 pm
MSN
-
SJU
2 stops10h 27m
United Airlines
ter 3/32:05 am
SJU
-
MSN
2 stops11h 48m
United Airlines
Deal found 1/26$325
This Delta deal was found by Cheapflights users on 1/27. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
qua 4/86:00 am
MSN
-
SJU
1 stop7h 15m
Delta
sáb 5/27:15 am
SJU
-
MSN
2 stops15h 00m
Delta
Deal found 1/27$338
This United Airlines deal was found by Cheapflights users on 1/27. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
ter 4/216:30 am
MSN
-
SJU
2 stops13h 54m
United Airlines
ter 4/281:00 am
SJU
-
MSN
2 stops11h 38m
United Airlines
Deal found 1/27$346
This United Airlines deal was found by Cheapflights users on 1/26. 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.
dom 3/13:53 pm
MSN
-
SJU
2 stops12h 18m
United Airlines
qui 3/58:30 am
SJU
-
MSN
1 stop7h 32m
United Airlines
Deal found 1/26$350
This Delta deal was found by Cheapflights users on 1/27. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
ter 3/246:00 am
MSN
-
SJU
1 stop7h 15m
Delta
sex 4/177:30 am
SJU
-
MSN
2 stops11h 19m
Delta
Deal found 1/27$352
This Faresmojo deal was found by Cheapflights users on 1/26. 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 Faresmojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
qui 2/195:38 am
MSN
-
SJU
1 stop6h 54m
JetBlue
qui 2/267:30 am
SJU
-
MSN
1 stop10h 47m
JetBlue
Deal found 1/26$356
This American Airlines deal was found by Cheapflights users on 1/27. 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.
ter 3/38:09 am
MSN
-
SJU
2 stops11h 25m
American Airlines
qua 3/111:23 pm
SJU
-
MSN
2 stops11h 12m
American Airlines
Deal found 1/27$359
This Kiwi.com deal was found by Cheapflights users on 1/27. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
qua 4/226:36 pm
MSN
-
SJU
1 stop13h 11m
Multiple Airlines
qua 4/296:30 am
SJU
-
MSN
1 stop12h 26m
Multiple Airlines
Deal found 1/27$361

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 janeiro 28, 2026.

Round-trip from

$256
(United Airlines)

One-way from

$128
(American Airlines)

Popular in

March

Cheapest in

September

Average price

$409
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. 7% potential increase in price ($42 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($14 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
Search Deals

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 janeiro 28, 2026.
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

sáb 4/11

6:00 am-2:15 pm

1 stop7h 15m

San Juan Luis Munoz Marin Intl

ter 5/5

2:34 pm-10:27 pm

1 stop8h 53m

$256

MadisonSan Juan

MSN - SJU

MSNSJU

Madison Truax Field

qua 4/8

6:00 am-2:15 pm

1 stop7h 15m

San Juan Luis Munoz Marin Intl

qua 4/15

6:15 am-4:17 pm

1 stop11h 02m

$304

MadisonSan Juan

MSN - SJU

MSNSJU

Madison Truax Field

ter 3/3

5:38 am-2:32 pm

1 stop6h 54m

San Juan Luis Munoz Marin Intl

qua 3/11

7:00 am-9:06 pm

2 stops15h 06m

$304

MadisonSan Juan

MSN - SJU

MSNSJU

Madison Truax Field

seg 3/16

7:00 am-10:58 pm

2 stops14h 58m

San Juan Luis Munoz Marin Intl

qui 4/9

11:59 pm-11:04 am

1 stop12h 05m

$324

MadisonSan Juan

MSN - SJU

MSNSJU

Madison Truax Field

ter 3/24

6:00 am-2:15 pm

1 stop7h 15m

San Juan Luis Munoz Marin Intl

sex 4/17

6:15 am-5:49 pm

2 stops12h 34m

$352

MadisonAguadilla

MSN - BQN

MSNBQN

Madison Truax Field

dom 3/8

6:29 pm-1:57 am

1 stop6h 28m

Aguadilla Borinquen

sáb 3/14

2:42 am-11:29 am

1 stop9h 47m

$363

MadisonSan Juan

MSN - SJU

MSNSJU

Madison Truax Field

dom 4/5

6:00 am-2:15 pm

1 stop7h 15m

San Juan Luis Munoz Marin Intl

qua 4/29

2:34 pm-10:27 pm

1 stop8h 53m

$371

MadisonSan Juan

MSN - SJU

MSNSJU

Madison Truax Field

seg 4/13

7:00 am-8:24 pm

2 stops12h 24m

San Juan Luis Munoz Marin Intl

sex 4/17

6:15 am-5:49 pm

2 stops12h 34m

$386

MadisonSan Juan

MSN - SJU

MSNSJU

Madison Truax Field

ter 4/7

6:30 am-9:24 pm

2 stops13h 54m

San Juan Luis Munoz Marin Intl

sex 5/1

7:40 am-3:00 pm

1 stop8h 20m

$389

MadisonSan Juan

MSN - SJU

MSNSJU

Madison Truax Field

ter 4/14

11:33 am-8:51 pm

1 stop8h 18m

San Juan Luis Munoz Marin Intl

sex 5/8

11:59 pm-11:04 am

1 stop12h 05m

$408

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/27

Showing 1-10 of 28 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 $92). Flying from Madison to Puerto Rico in June is currently the most expensive (average of $378). 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.

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 janeiro 28, 2026.
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
8,124 reviews

Food

7.2

Boarding

8.1

Crew

8.5

Entertainment

7.8

Comfort

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
8,124 reviews
Delta
7.9
Good
8,124 reviews

Food

7.2

Boarding

8.1

Crew

8.5

Entertainment

7.8

Comfort

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
9,212 reviews
Delta
7.9
Good
8,124 reviews

Food

7.2

Boarding

8.1

Crew

8.5

Entertainment

7.8

Comfort

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
11,201 reviews
Delta
7.9
Good
8,124 reviews

Food

7.2

Boarding

8.1

Crew

8.5

Entertainment

7.8

Comfort

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 Delta, American Airlines, and Frontier fly from Madison to Puerto Rico in about 6h 28m. The time it takes to get you to your destination can typically vary by up to 8h 30m. There are 2137 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 $92). Flying from Madison to Puerto Rico in June is currently the most expensive (average of $378). 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

Browse thousands of different options on Cheapflights for your next trip

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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 janeiro 28, 2026.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$214Average$457FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$257Average$446FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$268Average$513FlexibilityNo cancel feeOn-time71%

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