$173 Find Cheap Flights from Madison to Puerto Rico - Compare and Save

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Price, demand and travel trends for Madison to Puerto Rico flights

Use KAYAK data on prices, travel dates, airlines and seasonal trends to compare options and book flights with more confidence.

Are flights from Madison to Puerto Rico cheaper or more expensive than last year?

Fares from Madison to Puerto Rico are running about the same as they were around this time last year, averaging $516 round-trip.

What are the cheapest fares from Madison to Puerto Rico right now?

The cheapest fares from Madison to Puerto Rico on KAYAK in the last week were to San Juan Luis Munoz Marin Intl (SJU) from $356 round-trip, and to Aguadilla Borinquen (BQN) from $471 round-trip.

What’s the cheapest month to fly from Madison to Puerto Rico?

August is the cheapest time of year to fly, with average fares of $341. Prices are highest in March, when average flight costs increase to around $793.

When is the best time to book flights from Madison to Puerto Rico?

Book your flights 15 weeks before your trip. KAYAK data collected over the past 12 months shows that booking in this window can save you around 30% compared to booking last-minute (within 2 weeks of departure).

Which airport in Puerto Rico is the cheapest to fly to from Madison?

Based on KAYAK data from the past 12 months, the cheapest airports to fly into Puerto Rico are:

• San Juan Luis Munoz Marin Intl (SJU) from $557
• Aguadilla Borinquen (BQN) from $967

What’s the cheapest day to fly from Madison to Puerto Rico?

Tuesday tends to be the cheapest day to fly from Madison to Puerto Rico, while Monday is the most expensive. Fares run about 45% higher that day, based on the past 12 months of KAYAK data.

What's the cheapest time of day to fly from Madison to Puerto Rico?

Data from the past 12 months shows it's cheapest to fly to Puerto Rico during the afternoon with average prices of $415. The evening is the most expensive time to fly, with average prices of $585.

Key details for Madison to Puerto Rico flights

Low season

October

Cheapest flight

$173
Beat the crowds with an average 56% drop in travelers.
The most popular month to fly with an average 12% increase in travelers.
One-way flight from Madison to Aguadilla

Your Madison to Puerto Rico flight questions, answered

Find helpful answers about this route, including flight times, airports, airlines and booking tips.

  • Is now a good time to book a flight from Madison to Puerto Rico?

    Yes. Fares from Madison to Puerto Rico are low right now. As a rule of thumb, a round-trip under $404 (cheaper than most fares this year) is a good deal, so if you spot one at or below that, it's a good time to book.

  • How much should I budget for a flight from Madison to Puerto Rico?

    Over the past 12 months, round-trip fares from Madison to Puerto Rico have ranged from $404 to $710.

  • What are the main airports serving Puerto Rico?

    Flights to Puerto Rico use two main airports, San Juan Luis Munoz Marin Intl (SJU) and Aguadilla Borinquen (BQN).

  • What airlines fly nonstop from Madison to Puerto Rico?

    Based on the flight schedule for the next 3 months, no airline regularly operates nonstop flights from Madison to Puerto Rico. One-stop options include:

    • Delta
    • United Airlines
    • American Airlines

  • Which cabin classes are available on flights from Madison to Puerto Rico?

    On flights from Madison to Puerto Rico you can book Economy Class or First Class.

  • What are some popular landmarks in Puerto Rico?

    KAYAK travelers' favorite landmarks in Puerto Rico include:

    • Viejo San Juan
    • Condado Beach
    • Puerto Rico Convention Center
    • Ocean Park

Your guide to booking Madison to Puerto Rico flights

Get tips on when to book, when to fly and what to know before your trip.
  • If you can plan ahead, the sweet spot for booking your flight is 15 weeks before your trip. KAYAK data shows fares in this window are around 30% lower than last-minute bookings (made within 2 weeks of departure). Not ready to commit? Set a Price Alert and we'll let you know when prices change.
  • If your travel dates are flexible, book your trip for August when flights are typically cheapest and avoid March when prices are at their highest.
  • Flying on Tuesday is usually the cheapest. Flights on Monday cost about 45% more on average, so being flexible with your travel dates could help you save.
  • If you're looking to save, San Juan Luis Munoz Marin Intl (SJU) is the cheapest airport to fly into from Madison. If you have onward travel, don't forget to factor in the cost of your journey by train, bus or domestic flight.
  • Start your trip in San Juan, which is the most popular destination in Puerto Rico. From there, it's easy to continue on to other popular destinations such as Carolina, Fajardo and Rio Grande.

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 8633 reviews
8.5Crew
8.1Boarding
7.8Comfort
7.8Entertainment
7.2Food
Airline reviews

The wait in the tunnel to enter the plane was too long. The counter personnel, specially ''Israel'' was really not welcoming considering Delta Standards. Other than this everything was good overall.

8.0 ExcellentKevin, Sep 2026
Read more Delta reviews

The wait in the tunnel to enter the plane was too long. The counter personnel, specially ''Israel'' was really not welcoming considering Delta Standards. Other than this everything was good overall.

The flights were on time; all went as expected which is a big positive! No delays! There was no food or drink service in any legs, which I understand due to the short flight time.

The Delta assistsed services were awesome for my aunt. So very helpful.

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.

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.

Entertainment was great. Seats were good. They did not have my pre-ordered hot food product available but did comp me something cold in place of the item.

Good, our flight was delayed but that was totally out of their control due to weather and a presidential visit.

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. .

My luggage was lost at some point during my layover between Chicago and LHR. I landed Tuesday morning, and did not get it until Thursday night. Ironically, the people at the ticket desk had added a “priority” sticker to my tracking tag.

The flight was delayed multiple times. Breakfast was not served and only an apology given and statement that we could find better pastries in Paris. Seats were extremely narrow and uncomfortable.

The flight could have actually taken place. Canceled flight and no option to rebook that day.

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.

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.

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

More options for your flight from Madison to Puerto Rico

Complete your trip to Puerto Rico with a hotel stay or car rental