$118 Find Cheap Flights from Madison to Puerto Rico

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 2/9. 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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Flight Deals

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

ti., jan. 20 - on., jan. 28
Delta Logo
5:38 am - 5:17 pmMSN-SJU
9h 39m1 stop
Delta Logo
3:20 pm - 10:50 pmSJU-MSN
9h 30m2 stops
$235Delta
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ti., jan. 20 - ti., jan. 27
United Airlines Logo
6:30 am - 3:40 pmMSN-SJU
7h 10m1 stop
United Airlines Logo
2:05 am - 12:03 pmSJU-MSN
11h 58m2 stops
$257United Airlines
Find Deal
ti., jan. 20 - ti., jan. 27
United Airlines Logo
10:45 am - 12:36 amMSN-SJU
11h 51m2 stops
United Airlines Logo
2:05 am - 12:03 pmSJU-MSN
11h 58m2 stops
$267United Airlines
Find Deal
ti., jan. 20 - ti., jan. 27
American Airlines Logo
5:22 pm - 10:48 amMSN-SJU
15h 26m2 stops
American Airlines Logo
6:00 am - 3:27 pmSJU-MSN
11h 27m2 stops
$268American Airlines
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ti., feb. 24 - on., mar. 4
Delta Logo
11:20 am - 11:58 pmMSN-SJU
10h 38m1 stop
Delta Logo
6:15 am - 4:17 pmSJU-MSN
12h 02m1 stop
$278Delta
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ma., jan. 26 - on., jan. 28
American Airlines Logo
6:00 am - 3:18 pmMSN-SJU
7h 18m1 stop
American Airlines Logo
6:00 am - 12:46 pmSJU-MSN
8h 46m1 stop
$295American Airlines
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lø., jan. 31 - to., feb. 5
American Airlines Logo
11:23 am - 11:59 pmMSN-SJU
10h 36m2 stops
American Airlines Logo
6:00 am - 12:46 pmSJU-MSN
8h 46m1 stop
$298American Airlines
Find Deal
lø., jan. 31 - to., feb. 5
American Airlines Logo
11:23 am - 11:59 pmMSN-SJU
10h 36m2 stops
American Airlines Logo
6:00 am - 3:27 pmSJU-MSN
11h 27m2 stops
$301American Airlines
Find Deal
ti., mar. 31 - on., apr. 8
United Airlines Logo
6:30 am - 8:38 pmMSN-SJU
13h 08m2 stops
United Airlines Logo
3:56 pm - 10:40 pmSJU-MSN
7h 44m1 stop
$312United Airlines
Find Deal
to., apr. 9 - fr., apr. 17
Delta Logo
6:00 am - 2:20 pmMSN-SJU
7h 20m1 stop
Delta Logo
1:50 pm - 8:40 pmSJU-MSN
7h 50m1 stop
$315Delta
Find Deal
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 September, when tickets cost $310 (return) on average. On the other hand, the most expensive months are March and December, when the average cost of round-trip tickets is $662 and $638 respectively.

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

The average price of all round-trip flights from Madison to Puerto Rico clicked on KAYAK for each day over the last 12 months.

If you are looking for a flight deal from Madison to Puerto Rico, look for departures on Mondays and avoid leaving on a Thursday, as it's usually the priciest day. When flying back from Puerto Rico, Tuesday is the cheapest day to fly and Saturday is the most expensive.

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 1 week before departure. For the absolute cheapest price, our data suggests you should book 5 weeks before departure.

Good to know

Low seasonOctober
Cheapest flight$118
Best time to beat the crowds with an average 18% drop in price.
Most popular time to fly with an average 30% 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.

  • What is the cheapest time of day to fly to Puerto Rico?

    The cheapest time of day to fly to Puerto Rico is generally in the evening, when round-trip flights cost $370 on average. Morning departures are around 50% more expensive than evening flights, on average. The most expensive time of day to fly to Puerto Rico is generally in the afternoon, which is peak travel time and where the average cost of a ticket is $701.

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.
7.9
DeltaOverall score based on 8011 reviews
8.5Crew
7.9Entertainment
7.9Comfort
8.1Boarding
7.3Food
Airline reviews

Good seats in Main cabin, excellent service and excellent landing

10.0 ExcellentAnonymous, Dec 2025SEA - MSP
Read more Delta reviews

Good seats in Main cabin, excellent service and excellent landing

My flight was cancelled with no explanation after I had already cleared security. I was given 4 options to rebook, only one being non-stop like I had paid for. I grabbed it. It was 4 plus hours later and then took off even later. Biggest complaint is that I booked early and had an aisle seat. They gave me a "window" seat in front of the exit row, so the seat did not decline. I weigh all of 103 #s and it was tight for me! For what I paid, I feel I was kind of ripped off. I think they should have given me the empty comfort seat for the inconvenience. There was no apology nor any explanation as to why the flight was cancelled. My guess is it benefitted Delta in some way.

Very smooth, on-time, and pleasantly uneventful flight. The team at the gate and on board were professional and genuinely courteous. The pilot kept us well updated throughout, and both takeoff and landing were steady and enjoyable without any drama. Just a good, solid flight. Thank you! 💗

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

No lunch on a x-country flight scheduled for 10:50 am departure, arrived 5+ hrs later. That requires a black box label before you pay for the tickets. Worst, when I checked in online, it's specifically said that lunch was served on his flight for economy Plus passengers.

We had a lot of really rough weather but that was not Delta's fault. Pilot was amazing.

First, Delta needs more flights to/from Miami. Second, a 1000pm leaving at 1230pm is unacceptable from their biggest airport world hub. Another aircraft could have been used such as the aircraft scheduled to be used in the morning for that exact same route. Yes, I did get me there but the lack of sleep the next day didn't help me enjoy my entire trip since I was busy with activities during the weekend. This can be and is expected from Spirit (going bankrupt) and Frontier (despite they're nickel and dimers). But from Delta's World Hub? That's totally unacceptable!

This flight was straightforward and without difficulty. Service was OK, but I continue to be underwhelmed by level of attention given to Sky Priority passengers.

It would’ve been nice for all that money to have a more substantial snack for free. I remember once upon a time getting a very nice turkey sandwich with Swiss cheese on whole wheat bread for no charge along with a drink. I guess those days are gone. it’s a little insulting being given a cookie or a bag of baked chips Going forward I’ll just bring my own.

Great. Seamless. Check in agent at kiosk international was amazing and extremely helpful.

Flight was delayed 8 times. We were sitting at the airport for 14 hours. We got 2 hours of sleep (if that) on what was not meant to be a red-eye.

The movies offered were great. Staff were very pleasant and very efficient.

After a delay at the gate, C3, at Ohare on Sunday, I left my Blk ski coat on the bench at the gate, lost! Please review my lob claim, thx.

Very bad! They kept delaying my flight and wouldn’t do anything about it

They brought an empty plane to the gate. Then a flight delay was announced for maintenance and waiting on a part. I was then put on a flight to San Francisco instead with a connecting flight to my final destination. Arrived at my final destination 2 hours late.

The only downside was my cell phone charger wouldn’t work in the charging port but everyone else’s would work in them all. My cell phone cable works fine in my hotel room in Frankfurt.

Flight and crew were great. United didn't inform crew of immigration process which was disappointing!

Flight team stood out for perzonal attention, kindness at bright cheery attitudes at 8am. Very helpful.

Seats had less pitch than a regional jet. Food was OK. Have to buy alcohol on US based carriers flying international. Boarding was a mess. Did not have bags but overhead space was gone quick. Would like to see the airlines enforce the one bag over and one bag under policy

Ot was overall fine. Left on time and had basic snacks. Weather was finicky but that’s not the airlines fault.

AA delayed the flight for 3 hours and 50 minutes, but delayed the last 2 hours, 30 minutes at a time, so if we knew before, could have stayed at home and worked instead of being at the airport wasting time... The plane's crew was excellent, not their fault.

After arriving in Dallas, the aircraft taxied for an unusually long time and was unable to park at the gate, which caused a significant delay and made me miss my connecting flight. I then had to wait in a very long line to be rebooked, and I was told that no hotel or meal accommodations would be provided. What is even more unacceptable is that my luggage was mishandled and has still not been located. My suitcase contains important medications that I urgently need, and I have been unable to access them due to the airline’s mishandling. This situation has caused me considerable stress and inconvenience, and I need this issue to be resolved immediately.

RIC Staff was not enough. Elderly passengers had to wait 30 minutes to deplane, so we could board and still had to walk as no chairs were provided. And, passenger in front of my seat assignment rammed seat against my legs entire flight time. Was mildly bruised and left thigh still sore.

Liked that it was on time. Staff professional and friendly.

Things were delayed a little. But that didn’t affect my plans. It was fine. I was surprised it was so full thanksgiving day. The crew were friendly and professional.

I appreciated that it was on time, safe and professional. I didn’t like that I wasn’t in a place where I had a window at my window seat. It would have been nice to know that in advance. If it was mentioned in the ticketing, I didn’t notice it.

My flight was delayed about three hours. I got home at 3:30 in the morning very bad experience.

I like that the crew kept us informed but we moved back and forth from gate to gate before the aircraft arrived.

The flight was delayed multiple times, again no fault of American but again the extra cost, for everything makes it feel like a cheap airline! Especially when flights are outrageously expensive already

Horrible. Both legs of my flight were delayed more than 6 hours. No compensation, no screens on the plane, and the plane was not clean.

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

Information on your arrival and departure airports