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$123+ 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 8/6. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — MSN
Jun 15 — Jun 221
Mon 6/15
Mon 6/22
1 adult, Economy
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Cheap 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 May 16, 2026.

This American Airlines deal was found by Cheapflights users on 5/13. 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.
Fri 6/57:00 am
SJU
-
MSN
1 stop17h 59m
American Airlines
Mon 6/86:01 am
MSN
-
SJU
1 stop15h 59m
American Airlines
Deal found 5/13$416
This American Airlines deal was found by Cheapflights users on 5/13. 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 7/297:00 am
SJU
-
MSN
1 stop11h 22m
American Airlines
Tue 8/46:00 am
MSN
-
SJU
1 stop15h 57m
American Airlines
Deal found 5/13$419
This American Airlines deal was found by Cheapflights users on 5/15. 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 7/612:59 am
SJU
-
MSN
1 stop12h 31m
American Airlines
Tue 7/146:00 am
MSN
-
SJU
1 stop15h 57m
American Airlines
Deal found 5/15$459
This American Airlines deal was found by Cheapflights users on 5/14. 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 7/147:25 am
SJU
-
MSN
1 stop17h 17m
American Airlines
Wed 7/292:55 pm
MSN
-
SJU
1 stop8h 03m
American Airlines
Deal found 5/14$464
This American Airlines deal was found by Cheapflights users on 5/12. 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 5/276:20 am
SJU
-
MSN
1 stop12h 02m
American Airlines
Sun 5/316:02 am
MSN
-
SJU
1 stop15h 59m
American Airlines
Deal found 5/12$510

Find 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 May 16, 2026.

Round-trip from

$416
(American Airlines)

One-way from

$123
(Delta)

Popular in

March

Cheapest in

August

Average price

$562
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. 13% potential increase in price ($68 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($16 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in May 2026
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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 May 16, 2026.
Use the filters below to find and compare flights from Puerto Rico to Madison that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

San JuanMadison

SJU - MSN

SJUMSN

San Juan Luis Munoz Marin Intl

Fri 6/5

7:00 am-11:59 pm

1 stop17h 59m

Madison Truax Field

Mon 6/8

6:01 am-11:00 pm

1 stop15h 59m

$416

San JuanMadison

SJU - MSN

SJUMSN

San Juan Luis Munoz Marin Intl

Tue 7/14

7:25 am-11:42 pm

1 stop17h 17m

Madison Truax Field

Wed 7/29

1:00 pm-11:58 pm

1 stop9h 58m

$464

San JuanMadison

SJU - MSN

SJUMSN

San Juan Luis Munoz Marin Intl

Mon 7/6

12:59 am-7:51 am

1 stop7h 52m

Madison Truax Field

Tue 7/14

6:00 am-10:57 pm

1 stop15h 57m

$484

San JuanMadison

SJU - MSN

SJUMSN

San Juan Luis Munoz Marin Intl

Tue 7/7

3:02 pm-11:42 pm

2 stops9h 40m

Madison Truax Field

Fri 7/17

7:00 am-10:59 pm

1 stop14h 59m

$538
Quickest round-trip

San JuanMadison

SJU - MSN

SJUMSN

San Juan Luis Munoz Marin Intl

Tue 8/25

1:00 am-1:42 pm

2 stops13h 42m

Madison Truax Field

Sun 8/30

6:30 am-2:44 pm

1 stop7h 14m

$586

San JuanMadison

SJU - MSN

SJUMSN

San Juan Luis Munoz Marin Intl

Wed 5/27

6:00 am-4:31 pm

2 stops11h 31m

Madison Truax Field

Sun 5/31

6:02 am-11:01 pm

1 stop15h 59m

$613
Cheapest one-way
Quickest one-way

San JuanMadison

SJU - MSN

SJUMSN

San Juan Luis Munoz Marin Intl

Thu 8/6

12:56 pm-10:32 pm

1 stop10h 36m

$123

San JuanMadison

SJU - MSN

SJUMSN

San Juan Luis Munoz Marin Intl

Thu 8/6

6:51 am-11:30 pm

1 stop17h 39m

$168

San JuanMadison

SJU - MSN

SJUMSN

San Juan Luis Munoz Marin Intl

Fri 8/14

3:47 pm-8:22 am

1 stop17h 35m

$208

San JuanMadison

SJU - MSN

SJUMSN

San Juan Luis Munoz Marin Intl

Tue 6/9

7:00 am-12:09 am

1 stop18h 09m

$246

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/13

Showing 1-10 of 13 resultsSorted by cheapest first
1
2

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
No data available for this route at this time. Please check back soon.

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 May 16, 2026.
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
7.1
Good
11,662 reviews

Boarding

7.5

Entertainment

6.9

Food

6.4

Comfort

7.2

Crew

7.9

Overall

7.1

Reviews

1 / 20
10.0
Excellent

Beatriz,May 2026

HEL - DFW

Very modern and confortable plane. Dinner was delicious. Whole crew were polite and perfect.
American Airlines
7.1
Good
11,662 reviews
American Airlines
7.1
Good
11,662 reviews

Boarding

7.5

Entertainment

6.9

Food

6.4

Comfort

7.2

Crew

7.9

Overall

7.1

Reviews

1 / 20
10.0
Excellent

Beatriz,May 2026

HEL - DFW

Very modern and confortable plane. Dinner was delicious. Whole crew were polite and perfect.

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 17h 59m. Airlines will cover a distance of 2180 mi.

  • 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.

See more FAQs

Traveling to a place near Madison?

Book flights to Madison if you plan to visit one of these locations
Portage
Sun Prairie
Middleton
Baraboo
Fitchburg

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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 May 16, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$265Average$539FlexibilityNo cancel feeOn-time71%

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