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

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 11/20. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — MSN
Nov 6 — Nov 131
Thu 11/6
Thu 11/13
1 adult, Economy
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Find flight deals from Puerto Rico to Madison

Cheapest flights from Puerto Rico to Madison
Explore the most affordable flight options available from Puerto Rico to Madison. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 7, 2025.

This United Airlines deal was found by Cheapflights users on 10/5. 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.
Tue 11/118:10 amSJU - MSN
1 stop7h 53mUnited Airlines
Sat 11/158:25 amMSN - SJU
2 stops11h 57mUnited Airlines
Deal found 10/5$275
This American Airlines deal was found by Cheapflights users on 10/5. 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 11/115:59 pmSJU - MSN
1 stop7h 31mAmerican Airlines
Sat 11/1510:58 amMSN - SJU
1 stop8h 26mAmerican Airlines
Deal found 10/5$298
This United Airlines deal was found by Cheapflights users on 10/5. 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.
Sun 11/28:10 amSJU - MSN
1 stop8h 44mUnited Airlines
Sun 11/96:30 amMSN - SJU
1 stop7h 10mUnited Airlines
Deal found 10/5$342
This American Airlines deal was found by Cheapflights users on 10/5. 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.
Wed 10/83:00 pmSJU - MSN
1 stop9h 36mAmerican Airlines
Thu 10/96:29 amMSN - SJU
1 stop16h 30mAmerican Airlines
Deal found 10/5$399
This United Airlines deal was found by Cheapflights users on 10/6. 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.
Mon 10/201:05 amSJU - MSN
2 stops9h 50mUnited Airlines
Sat 10/256:30 amMSN - SJU
1 stop7h 14mUnited Airlines
Deal found 10/6$416
This American Airlines deal was found by Cheapflights users on 10/7. 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 11/258:00 amSJU - MSN
1 stop17h 51mAmerican Airlines
Tue 12/26:00 amMSN - SJU
2 stops12h 48mAmerican Airlines
Deal found 10/7$431
This American Airlines deal was found by Cheapflights users on 10/5. 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 11/23:43 pmSJU - MSN
1 stop10h 15mAmerican Airlines
Sun 11/96:50 amMSN - SJU
1 stop12h 08mAmerican Airlines
Deal found 10/5$461

Cheap flight deals from Puerto Rico to Madison

Keep the following information in mind while searching for Puerto Rico to Madison flight deals. Data was last updated October 7, 2025.

Round-trip from

$275
(United Airlines)

One-way from

$118
(American Airlines)

Popular in

June

Cheapest in

September

Average price

$296
From Puerto Rico to Madison Truax Field
Search Deals
One-way flight from Puerto Rico to Madison Truax Field
Search Deals
Highest demand for flights based on searches. 19% potential increase in price ($109 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($12 potential savings vs. average RT price).
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Average for round-trip flights in October 2025
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Cheapflights Fare Finder

 
Customize your flight search to find flights from Puerto Rico to Madison 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 October 7, 2025.
Use the filters below to find and compare flights from Puerto Rico to Madison that are best for you.

Fly from

Puerto Rico

Fly to

Madison

Route

Depart

Return

Price

San JuanMadison

SJU - MSN

SJUMSN

San Juan Luis Munoz Marin Intl

Tue 11/11

8:10 am-2:03 pm

1 stop7h 53m

Madison Truax Field

Sat 11/15

8:25 am-10:22 pm

2 stops11h 57m

$275

San JuanMadison

SJU - MSN

SJUMSN

San Juan Luis Munoz Marin Intl

Sun 11/2

8:10 am-2:54 pm

1 stop8h 44m

Madison Truax Field

Sun 11/9

6:30 am-3:40 pm

1 stop7h 10m

$342

San JuanMadison

SJU - MSN

SJUMSN

San Juan Luis Munoz Marin Intl

Tue 10/21

3:34 pm-11:29 pm

1 stop8h 55m

Madison Truax Field

Sat 10/25

7:20 am-11:54 pm

1 stop15h 34m

$399

San JuanMadison

SJU - MSN

SJUMSN

San Juan Luis Munoz Marin Intl

Tue 10/21

1:30 pm-10:28 pm

2 stops9h 58m

Madison Truax Field

Sat 10/25

6:30 am-2:44 pm

1 stop7h 14m

$416

San JuanMadison

SJU - MSN

SJUMSN

San Juan Luis Munoz Marin Intl

Tue 11/25

7:15 am-9:54 pm

1 stop16h 39m

Madison Truax Field

Tue 12/2

8:00 am-5:05 pm

1 stop7h 05m

$431

San JuanMadison

SJU - MSN

SJUMSN

San Juan Luis Munoz Marin Intl

Sun 11/2

3:43 pm-11:58 pm

1 stop10h 15m

Madison Truax Field

Sun 11/9

6:50 am-8:58 pm

1 stop12h 08m

$461

San JuanMadison

SJU - MSN

SJUMSN

San Juan Luis Munoz Marin Intl

Thu 11/20

5:09 pm-9:50 am

1 stop18h 41m

$118

San JuanMadison

SJU - MSN

SJUMSN

San Juan Luis Munoz Marin Intl

Wed 11/19

2:05 am-2:54 pm

2 stops14h 49m

$195

San JuanMadison

SJU - MSN

SJUMSN

San Juan Luis Munoz Marin Intl

Fri 10/10

5:30 am-4:39 pm

1 stop12h 09m

$200

San JuanMadison

SJU - MSN

SJUMSN

San Juan Luis Munoz Marin Intl

Thu 11/20

9:30 pm-9:08 am

3 stops37h 38m

$255

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/6

Showing 1-10 of 17 results
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Best time to book a flight from Puerto Rico to Madison

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

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

Currently, September is the cheapest month in which you can book a flight from Puerto Rico to Madison (average of $113). Flying from Puerto Rico to Madison in July is currently the most expensive (average of $290). 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 PR to MSN?

Find hourly flight availability from Puerto Rico to Madison. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated October 7, 2025.

A simple way to save on the total cost of your ticket is to fly from Puerto Rico to Madison in the morning. If you’re flexible enough to do this you can expect to save up to 34% on your trip compared to booking a flight in the evening.

Reviews of airlines servicing Madison

Get insights into the airlines that provide service to Madison. 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 Madison. Reviews last updated October 7, 2025.
See what other customers who have flown with American Airlines from Puerto Rico to Madison have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
American Airlines
7.2
Good
11,041 reviews

Food

6.4

Boarding

7.5

Crew

8.0

Entertainment

6.9

Comfort

7.2

Overall

7.2

Reviews

1 / 20
2.0
Mediocre

Nordia,Sep 2025

KIN - MIA

We were to land in Miami sometime after 3pm but couldn’t due to bad weather, we flew around for 2 hrs until we had to land in Forth Myers to refuel, we had to sit another 2 hrs at Forth Myers until given the clearance to refuel, we were hungry, thirsty and frustrated at that point. All the had on the flight to offer was a small plastic glass of water and a pack of biscoff, I requested a cup of tea and was told none was there. We were basically at another airport and not one of the staff could consider that the passengers might be hungry or thirsty being on a plane for around 8 hrs, which you weren’t prepared for, at least find some hot water on board.
American Airlines
7.2
Good
11,041 reviews
American Airlines
7.2
Good
11,041 reviews

Food

6.4

Boarding

7.5

Crew

8.0

Entertainment

6.9

Comfort

7.2

Overall

7.2

Reviews

1 / 20
2.0
Mediocre

Nordia,Sep 2025

KIN - MIA

We were to land in Miami sometime after 3pm but couldn’t due to bad weather, we flew around for 2 hrs until we had to land in Forth Myers to refuel, we had to sit another 2 hrs at Forth Myers until given the clearance to refuel, we were hungry, thirsty and frustrated at that point. All the had on the flight to offer was a small plastic glass of water and a pack of biscoff, I requested a cup of tea and was told none was there. We were basically at another airport and not one of the staff could consider that the passengers might be hungry or thirsty being on a plane for around 8 hrs, which you weren’t prepared for, at least find some hot water on board.

Related info for your journey

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

    Madison Truax Field (MSN) is the airport you will fly into if you book a flight from Puerto Rico to Madison. It is only a 5.4 mi journey from Truax Field (MSN) to Madison’s city center.

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

    Departing from Puerto Rico to Madison will take you 7h 53m. Airlines will cover a distance of 2180 mi. This flight may include one or multiple stops.

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

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

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

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

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

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

    Currently, September is the cheapest month in which you can book a flight from Puerto Rico to Madison (average of $113). Flying from Puerto Rico to Madison in July is currently the most expensive (average of $290). 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

Traveling to a place near Madison?

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Portage
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Baraboo
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Alternative routes for Puerto Rico to Madison

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

Discover the top airline that operate flights from Puerto Rico to Madison. 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 October 7, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$265Average$450FlexibilityNo cancel feeOn-time71%

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