$133 Find Cheap Flights from Madison to Puerto Rico - Compare and Save

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Madison to Puerto Rico departing on 9/8. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy, 0 bags

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Cheap Flights from Madison to Puerto Rico

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Aguadilla
Aguadilla2 stops$366
Culebra
Culebra2 stops$1,302
Mayagüez
Mayagüez2 stops$1,220
Aguadilla
Aguadilla2 stops$366
Culebra
Culebra2 stops$1,302
Mayagüez
Mayagüez2 stops$1,220

Book Cheap Madison to Puerto Rico Plane Tickets

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Madison to Puerto Rico that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Madison to Puerto Rico

Tue, Nov 3 - Tue, Nov 10
United Airlines Logo
10:40 am - 9:00 pm
MSN
-
SJU
8h 20m
1 stop
United Airlines Logo
8:25 am - 3:00 pm
SJU
-
MSN
8h 35m
1 stop
$266United Airlines
Tue, Sep 15 - Fri, Sep 18
United Airlines Logo
5:00 am - 2:44 pm
MSN
-
SJU
8h 44m
1 stop
United Airlines Logo
1:00 am - 1:42 pm
SJU
-
MSN
13h 42m
2 stops
$296United Airlines
Sun, Sep 6 - Wed, Sep 16
American Airlines Logo
9:48 am - 11:15 pm
MSN
-
SJU
12h 27m
1 stop
American Airlines Logo
6:00 am - 3:51 pm
SJU
-
MSN
10h 51m
2 stops
$326American Airlines
Wed, Sep 2 - Sat, Sep 5
Multiple Airlines Logo
10:27 am - 12:56 am
MSN
-
SJU
13h 29m
1 stop
Multiple Airlines Logo
12:11 pm - 7:15 pm
SJU
-
MSN
8h 04m
1 stop
$328Multiple Airlines
Wed, Sep 30 - Mon, Oct 5
American Airlines Logo
8:05 pm - 3:40 pm
MSN
-
SJU
18h 35m
2 stops
American Airlines Logo
2:27 pm - 9:21 pm
SJU
-
MSN
7h 54m
1 stop
$331American Airlines
Thu, Sep 17 - Tue, Sep 22
United Airlines Logo
6:30 am - 2:44 pm
MSN
-
SJU
7h 14m
1 stop
United Airlines Logo
1:25 pm - 8:13 pm
SJU
-
MSN
7h 48m
1 stop
$340United Airlines
Wed, Sep 2 - Sat, Sep 5
United Airlines Logo
8:10 am - 8:38 pm
MSN
-
SJU
11h 28m
2 stops
United Airlines Logo
7:00 am - 6:56 pm
SJU
-
MSN
12h 56m
2 stops
$346United Airlines
Sun, Sep 6 - Tue, Sep 15
United Airlines Logo
6:30 am - 2:44 pm
MSN
-
SJU
7h 14m
1 stop
United Airlines Logo
1:00 am - 10:14 am
SJU
-
MSN
10h 14m
1 stop
$356United Airlines
Mon, Aug 10 - Sat, Aug 15
American Airlines Logo
6:00 am - 10:24 pm
MSN
-
SJU
15h 24m
1 stop
American Airlines Logo
7:03 am - 11:29 pm
SJU
-
MSN
17h 26m
1 stop
$358American Airlines
Mon, Aug 10 - Fri, Aug 14
American Airlines Logo
7:47 am - 11:15 pm
MSN
-
SJU
14h 28m
1 stop
American Airlines Logo
12:55 am - 9:26 am
SJU
-
MSN
9h 31m
1 stop
$366American Airlines
Booking Insights

KAYAK's insights & trends for Madison to Puerto Rico flights

Get data-powered insights and trends into flights from Madison to Puerto Rico to help you find the cheapest flights, the best time to fly and much more.

What is the cheapest month to fly from Madison to Puerto Rico?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Madison to Puerto Rico, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Madison to Puerto Rico is March, when tickets cost $163 (return) on average. On the other hand, the most expensive months are July and June, when the average cost of round-trip tickets is $418 and $359 respectively.

How far in advance should I book a flight from Madison to Puerto Rico?

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Madison to Puerto Rico, removes the top 0.1% to account for outliers, and then takes the average of all the values for each week.

To get a below average price on the flight from Madison to Puerto Rico, you should book around 3 weeks before departure, which saves you about 20% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 17 weeks before departure.

Good to know

Low seasonJune
Cheapest flight$133
Best time to beat the crowds but there is an average 22% increase in price.
Most popular time to fly with an average 31% increase in price.
Flight from Madison to San Juan

FAQs - booking Puerto Rico flights

  • How does KAYAK find such low prices on flights from Madison to Puerto Rico?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Madison to Puerto Rico.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Madison to Puerto Rico?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Madison to Puerto Rico is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Madison to Puerto Rico?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly from Madison to Puerto Rico with an airline and back with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Madison to Puerto Rico?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying from Madison to Puerto Rico up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Reviews of the top 3 airlines serving from Madison to Puerto Rico

 
Need help choosing which airline to fly with from Madison to Puerto Rico? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
7.8
DeltaOverall score based on 8462 reviews
8.1Boarding
7.8Entertainment
8.5Crew
7.8Comfort
7.2Food
Airline reviews

It was good. The leg room was not great in Row 1.

8.0 ExcellentDaniel, Feb 2026
JFK - SJU
Read more Delta reviews

It was good. The leg room was not great in Row 1.

Probably not the fault of Delta but there was delay after delay after delay and I ended up getting home 4 hours later then I should have at 1:30 in the morning

Staff was exceptional! Everyone was kind, professional and friendly making the trip very pleasant. Thank you!

Very late arrival at PWM. Late jet getting to ATL. Equipment problem with aircraft - could not get enough water onto plane., Another delay getting FAA approval for flight with bottled H2O. Not the crew’s problem.

A little bumpy ride . No food was being provided due the the turbulence. That was ok it was a short flight to my standards.

Pretty standard flight. Delta has a good selection of movies.

The flight was so late that I had to change connecting flights, turning a five-hour trip into a fourteen-hour nightmare.

When we checked in my friend and I were sitting seperate. By the time we got to boarding, they automatically switched our seats. I really liked that.

Despite being delayed, we would still give a high score for this flight experience. For the first time in quite some time we had excellent customer service throughout our entire round trip. The flight attendants were the most polite we have experienced in our last ten flights at least (non of which were Delta and include business class). The food offered was a better selection than most—we just didn’t have any of it. Overall, almost as good as flying used to be. Thank you to Delta.

I trust Delta. I travel comfortable. The snacks could improve or could go to something as a little sandwich.

Have not had a flight out or returning to Norfolk that has not required maintenance, and a gate delay. Properly staff the crew so maintenance can be performed without last minute emergencies on each flight and there is enough staff to have gates prepared for inbound flights. Staff to ensure the safety and on time service vs. profit.

Always pretty good as far as I see it. Staff was friendly and process was quick to get on and off.

The flight was delayed by two de-icings. The seatbelt did not work correctly. It did not stay tight.

My flight was completely full. Making me very stressful with people walking around all the time. I believe airlines can do better for entertain people during the flight.

The seats on the aircraft are like sitting in a rock. During the boarding process they recognize Active Duty Military, why don’t they recognize Retired Military. I’ve always preferred Delta, this flight confirmed why I still prefer Delta.

It was literally one of the worst travel experiences ever. My flight got delayed by over an hour and there was no communication of this from the gate staff. I realized it by checking the screen periodically. Once on board the flight attendants continued to serve alcohol to a man who was clearly already drunk and that was making a bunch of commotion. Never again will I fly United!

At least the delays were short. Business class, even in the new planes is very crowded now with crappy tray tables

All good except paid for wifi that did not work

Flight cancelled due to fog. No other flights available for 36 hours. Directed by United to book passage on another carrier, and submit receipts for reimbursement. Did that. United now states they will not reimburse. Currently out 2 grand.

The United website was easy to use and had all the information I needed. I needed to change my flight and it was accomplished easily on line. I was also easily able to upgrade and for a reasonable price. Boarding went smoothly and the flight was in time. The service was good in board but the crew did not seem happy at all. Limited availability of meals - not much choice for purchase and in business class they ran out of one of the meal choices by row 4. .

Delayed delayed. Poor professionalism. Our seats changed and we pay for them

Crew was helpful and cheerful especially when they had no refreshments to work with. The plane was never serviced and had nothing but limited water and coffee onboard. For the price point, a concern of services.

I bought wifi and most of the flight could not even use it my apps would just spin. I couldn't even listen to music. super frustrating.

The plane was broken so we had to change planes.

Seating was horrible. Small seats. Access to flight information and extras very iser unfriendly. Kept losing internet after paying for it. Staff in madison was as unprofessional and unhelpful.

There were several different delays but we ended up being delayed a total of 40 mins or so. It was annoying we had a gate change which made it take longer to leave DFW, and we had to check our carry on. Ugh

The counter/baggage counter was busy and so many people missed flights. We got stuck sitting on the plane over 2 hours at the gate while they were doing an inspection is wrong. Many of us missed our connecting flights because of it.

Our flight was changed from Madison to DC to Madison to Charlotte.

We were told we had no flights before our flight was continually delayed then cancelled.

Boarding was relatively fast and easy and the crew was attentive throughout.

Everything you need to know for your flight from Madison to Puerto Rico

Information on your arrival and departure airports