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Puerto Rico

$190+ 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 5/14. Fares are subject to change and may not be available on all flights or dates of travel.
MSN — SJU
May 6 — May 131
Tue 5/6
Tue 5/13
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 May 1, 2025.

Round-trip from

$225
(American Airlines)

One-way from

$190
(American Airlines)

Popular in

December

Cheapest in

August

Average price

$596
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 ($6 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 May 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 May 1, 2025.

This American Airlines deal was found by Cheapflights users on 4/29. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/138:27 pmMSN - SJU
2 stops18h 53mAmerican Airlines
Sat 9/203:55 pmSJU - MSN
1 stop6h 33mAmerican Airlines
Deal found 4/29$225
This United Airlines deal was found by Cheapflights users on 4/30. 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.
Wed 7/162:35 pmMSN - SJU
1 stop8h 19mUnited Airlines
Tue 7/293:56 pmSJU - MSN
1 stop7h 37mUnited Airlines
Deal found 4/30$389
This Delta deal was found by Cheapflights users on 4/30. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/26:45 amMSN - SJU
1 stop7h 27mDelta
Sat 8/94:25 pmSJU - MSN
1 stop8h 02mDelta
Deal found 4/30$405
This United deal was found by Cheapflights users on 4/29. 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/226:40 amMSN - MAZ
2 stops11h 02mMultiple Airlines
Mon 7/285:00 pmMAZ - MSN
2 stops30h 33mMultiple Airlines
Deal found 4/29$665

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 May 1, 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

Sat 9/13

8:27 pm-4:20 pm

2 stops18h 53m

San Juan Luis Munoz Marin Intl

Sat 9/20

3:55 pm-9:28 pm

1 stop6h 33m

$225

MadisonSan Juan

MSN - SJU

MSNSJU

Madison Truax Field

Wed 7/16

2:35 pm-11:54 pm

1 stop8h 19m

San Juan Luis Munoz Marin Intl

Tue 7/29

3:56 pm-10:33 pm

1 stop7h 37m

$389

MadisonSan Juan

MSN - SJU

MSNSJU

Madison Truax Field

Sat 8/2

6:45 am-3:12 pm

1 stop7h 27m

San Juan Luis Munoz Marin Intl

Sat 8/9

4:25 pm-11:27 pm

1 stop8h 02m

$405

MadisonMayagüez

MSN - MAZ

MSNMAZ

Madison Truax Field

Tue 7/22

6:40 am-6:42 pm

2 stops11h 02m

Mayagüez Eugenio M De Hostos

Mon 7/28

5:00 pm-10:33 pm

2 stops30h 33m

$665

MadisonSan Juan

MSN - SJU

MSNSJU

Madison Truax Field

Wed 5/14

6:13 am-8:33 pm

1 stop13h 20m

$190

MadisonSan Juan

MSN - SJU

MSNSJU

Madison Truax Field

Mon 5/26

2:35 pm-11:54 pm

1 stop8h 19m

$235

MadisonSan Juan

MSN - SJU

MSNSJU

Madison Truax Field

Wed 5/14

10:45 am-10:53 pm

3 stops35h 08m

$312

MadisonAguadilla

MSN - BQN

MSNBQN

Madison Truax Field

Fri 5/30

8:20 am-11:09 pm

2 stops13h 49m

$318

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/30

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 December is currently the most expensive (average of $336). 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 May 1, 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.

Rainfall in Puerto Rico by month

Plan your trip to Puerto Rico by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Puerto Rico ranges from 2.2 - 6.1 inches per month. November is typically the wettest month, when rainfall can reach 6.1 in. February is typically the driest time to visit Puerto Rico when rainfall is around 2.2 in.

Temperature in Puerto Rico by month

Plan your trip to Puerto Rico by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Puerto Rico, use this chart to help with planning. For those seeking warmer temperatures, June is the ideal time of year to visit, when temperatures reach an average of 82.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 77.0 F).

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 May 1, 2025.
See what other customers who have flown with Delta, United Airlines and American Airlines from Madison to Puerto Rico have to say. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
7,934 reviews

Entertainment

7.9

Crew

8.5

Boarding

8.2

Overall

8.0

Comfort

7.9

Food

7.3

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.
Delta
8.0
Very good
7,934 reviews
Delta
8.0
Very good
7,934 reviews

Entertainment

7.9

Crew

8.5

Boarding

8.2

Overall

8.0

Comfort

7.9

Food

7.3

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.
United Airlines
7.4
Good
8,696 reviews
Delta
8.0
Very good
7,934 reviews

Entertainment

7.9

Crew

8.5

Boarding

8.2

Overall

8.0

Comfort

7.9

Food

7.3

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.
American Airlines
7.2
Good
10,000 reviews
Delta
8.0
Very good
7,934 reviews

Entertainment

7.9

Crew

8.5

Boarding

8.2

Overall

8.0

Comfort

7.9

Food

7.3

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.

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 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, 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 December is currently the most expensive (average of $336). 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 May 1, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$264Average$457FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$330Average$575FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$331Average$534FlexibilityNo cancel feeOn-time69%

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