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Puerto Rico

$148+ 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 11/11. Fares are subject to change and may not be available on all flights or dates of travel.
MSN — SJU
ago. 4 — ago. 111
lun. 8/4
lun. 8/11
1 adult, Economy
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Cheap 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 julio 30, 2025.

Round-trip from

$255
(American Airlines)

One-way from

$148
(American Airlines)

Popular in

December

Cheapest in

September

Average price

$555
From Madison Truax Field to Puerto Rico
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One-way flight from Madison Truax Field to Puerto Rico
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Highest demand for flights based on searches. 1% potential increase in price ($7 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($15 potential savings vs. average RT price).
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Average for round-trip flights in July 2025
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Find 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 julio 30, 2025.

This American Airlines deal was found by Cheapflights users on 7/30. 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. 9/296:20 amMSN - SJU
2 stops10h 55mAmerican Airlines
mar. 10/73:00 pmSJU - MSN
1 stop9h 36mAmerican Airlines
Deal found 7/30$255
This United Airlines deal was found by Cheapflights users on 7/29. 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.
lun. 9/296:30 amMSN - SJU
1 stop7h 14mUnited Airlines
mar. 10/71:30 pmSJU - MSN
1 stop10h 03mUnited Airlines
Deal found 7/29$385
This Delta deal was found by Cheapflights users on 7/28. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 9/201:20 pmMSN - SJU
1 stop7h 40mDelta
mié. 9/247:30 amSJU - MSN
1 stop9h 48mDelta
Deal found 7/28$397
This United Airlines deal was found by Cheapflights users on 7/30. 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. 8/148:20 amMSN - BQN
3 stops13h 49mUnited Airlines
dom. 8/1712:15 amBQN - MSN
2 stops12h 28mUnited Airlines
Deal found 7/30$1,043
This United Airlines deal was found by Cheapflights users on 7/30. 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. 8/145:20 pmMSN - CPX
2 stops46h 31mUnited Airlines
lun. 8/1810:13 amCPX - MSN
2 stops28h 36mUnited Airlines
Deal found 7/30$1,944

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 julio 30, 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

lun. 9/29

6:20 am-6:15 pm

2 stops10h 55m

San Juan Luis Munoz Marin Intl

mar. 10/7

3:00 pm-11:36 pm

1 stop9h 36m

$255

MadisonSan Juan

MSN - SJU

MSNSJU

Madison Truax Field

lun. 9/29

6:30 am-2:44 pm

1 stop7h 14m

San Juan Luis Munoz Marin Intl

mar. 10/7

1:30 pm-10:33 pm

1 stop10h 03m

$385

MadisonSan Juan

MSN - SJU

MSNSJU

Madison Truax Field

sáb. 9/20

1:20 pm-10:00 pm

1 stop7h 40m

San Juan Luis Munoz Marin Intl

mié. 9/24

7:00 am-4:09 pm

2 stops10h 09m

$397

MadisonAguadilla

MSN - BQN

MSNBQN

Madison Truax Field

jue. 8/14

8:20 am-11:09 pm

3 stops13h 49m

Aguadilla Borinquen

dom. 8/17

12:15 am-11:43 am

2 stops12h 28m

$1,043

MadisonCulebra

MSN - CPX

MSNCPX

Madison Truax Field

jue. 8/14

5:20 pm-4:51 pm

2 stops46h 31m

Culebra

lun. 8/18

10:13 am-1:49 pm

2 stops28h 36m

$1,944

MadisonSan Juan

MSN - SJU

MSNSJU

Madison Truax Field

mar. 11/11

5:00 am-5:05 pm

2 stops10h 05m

$148

MadisonAguadilla

MSN - BQN

MSNBQN

Madison Truax Field

mar. 11/11

12:26 pm-11:57 pm

2 stops9h 31m

$153

MadisonSan Juan

MSN - SJU

MSNSJU

Madison Truax Field

mar. 11/11

2:48 pm-6:25 pm

3 stops25h 37m

$330

MadisonSan Juan

MSN - SJU

MSNSJU

Madison Truax Field

dom. 11/30

6:30 am-2:40 pm

2 stops30h 10m

$512

MadisonSan Juan

MSN - SJU

MSNSJU

Madison Truax Field

dom. 12/21

6:24 pm-4:13 pm

2 stops43h 49m

$543

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/30

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, September is the cheapest month in which you can book a flight from Madison to Puerto Rico (average of $254). Flying from Madison to Puerto Rico in June is currently the most expensive (average of $339). 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 julio 30, 2025.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Madison to Puerto Rico as you normally would.

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 julio 30, 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
8.0
Very good
7,980 reviews

Boarding

8.2

Crew

8.5

Food

7.3

Overall

8.0

Comfort

7.9

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Delta
8.0
Very good
7,980 reviews
Delta
8.0
Very good
7,980 reviews

Boarding

8.2

Crew

8.5

Food

7.3

Overall

8.0

Comfort

7.9

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
United Airlines
7.4
Good
8,896 reviews
Delta
8.0
Very good
7,980 reviews

Boarding

8.2

Crew

8.5

Food

7.3

Overall

8.0

Comfort

7.9

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
American Airlines
7.2
Good
10,000 reviews
Delta
8.0
Very good
7,980 reviews

Boarding

8.2

Crew

8.5

Food

7.3

Overall

8.0

Comfort

7.9

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Sun Country Air
6.9
Okay
334 reviews
Delta
8.0
Very good
7,980 reviews

Boarding

8.2

Crew

8.5

Food

7.3

Overall

8.0

Comfort

7.9

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!

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.

  • What are the cheapest airlines to fly from Madison to Puerto Rico one-way?

    The cheapest airline one-way is American Airlines, with whom users have recently found tickets for as low as $148. However, be on the lookout for offers from United Airlines and Sun Country Air, as they are both options that can get you from Madison to Puerto Rico for a low price.

  • 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 - Culebra or Madison Truax Field - Mayagüez Eugenio M De Hostos 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, September is the cheapest month in which you can book a flight from Madison to Puerto Rico (average of $254). Flying from Madison to Puerto Rico in June is currently the most expensive (average of $339). 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 julio 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$264Average$469FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$269Average$542FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$331Average$496FlexibilityNo cancel feeOn-time69%

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