$123 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 4/18. 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$364
Mayagüez
Mayagüez2 stops$1,406
Aguadilla
Aguadilla2 stops$364
Mayagüez
Mayagüez2 stops$1,406

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

Mon, Apr 27 - Mon, May 4
American Airlines Logo
11:50 am - 4:32 am
MSN
-
SJU
15h 42m
1 stop
American Airlines Logo
6:45 am - 10:32 pm
SJU
-
MSN
16h 47m
1 stop
$335American Airlines
Sat, Apr 11 - Wed, Apr 22
American Airlines Logo
5:00 am - 8:51 pm
MSN
-
SJU
14h 51m
2 stops
American Airlines Logo
11:59 pm - 11:05 am
SJU
-
MSN
12h 06m
1 stop
$338American Airlines
Wed, Apr 15 - Mon, Apr 27
United Airlines Logo
10:05 am - 8:34 pm
MSN
-
SJU
9h 29m
1 stop
United Airlines Logo
1:00 am - 10:11 am
SJU
-
MSN
10h 11m
2 stops
$345United Airlines
Sun, May 3 - Sat, May 9
Delta Logo
5:30 am - 4:23 pm
MSN
-
SJU
9h 53m
1 stop
Delta Logo
7:30 am - 5:34 pm
SJU
-
MSN
11h 04m
2 stops
$348Delta
Mon, Aug 10 - Fri, Aug 21
Multiple Airlines Logo
6:50 pm - 11:05 pm
MSN
-
SJU
27h 15m
1 stop
Multiple Airlines Logo
5:56 pm - 9:47 am
SJU
-
MSN
16h 51m
2 stops
$349Multiple Airlines
Sat, Apr 25 - Sun, May 10
American Airlines Logo
8:05 am - 8:51 pm
MSN
-
SJU
11h 46m
2 stops
American Airlines Logo
6:00 am - 11:28 pm
SJU
-
MSN
18h 28m
1 stop
$352American Airlines
Sat, May 16 - Fri, May 22
United Airlines Logo
6:30 am - 9:24 pm
MSN
-
SJU
13h 54m
2 stops
United Airlines Logo
1:00 am - 11:38 am
SJU
-
MSN
11h 38m
2 stops
$356United Airlines
Wed, Apr 22 - Wed, Apr 29
American Airlines Logo
11:50 am - 4:32 am
MSN
-
SJU
15h 42m
1 stop
American Airlines Logo
11:59 pm - 11:05 am
SJU
-
MSN
12h 06m
1 stop
$363American Airlines
Sat, Mar 21 - Fri, Mar 27
Multiple Airlines Logo
6:36 pm - 1:57 am
MSN
-
BQN
30h 21m
1 stop
Multiple Airlines Logo
2:42 am - 5:56 pm
BQN
-
MSN
16h 14m
1 stop
$927Multiple Airlines
Sat, Mar 21 - Fri, Mar 27
Frontier Logo
5:48 pm - 1:57 am
MSN
-
BQN
7h 09m
1 stop
Frontier Logo
2:42 am - 1:19 pm
BQN
-
MSN
11h 37m
1 stop
$1,040Frontier
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 April and March, when the average cost of round-trip tickets is $643 and $640 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 2 weeks before departure, which saves you about 10% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 5 weeks before departure.

Good to know

Low seasonOctober
Cheapest flight$123
Best time to beat the crowds with an average 20% drop in price.
Most popular time to fly with an average 26% 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.
7.9
DeltaOverall score based on 8242 reviews
7.2Food
7.9Comfort
7.8Entertainment
8.5Crew
8.1Boarding
Airline reviews

I was happy that I was able to get a last minute flight but unfortunately my seat was a middle seat. Even with Delta Comfort I wasn't comfortable

8.0 ExcellentSheila, Mar 2026
ATL - EWR
Read more Delta reviews

I was happy that I was able to get a last minute flight but unfortunately my seat was a middle seat. Even with Delta Comfort I wasn't comfortable

There’s not much to say about a one hour flight. This is a connection from LA to RNO that I missed the previous night due to a mechanical check delay on my originating flight from JFK to LAX. The short flight itself was fine. Instructions from the pilot and crew were per usual. The coffee was barely lukewarm, which possibly was purposeful so we would down it quickly. Bags were already on carousel upon reaching baggage claim, which was excellent.

Flight was warm for first few hours and quite rough

Seat was extremely hard which made even a short 1 hour 20 minute flight fairly uncomfortable.

Everything was good except wifi and a leaking drink chiller. The floor was all wet and my bag was soaked. Did not notice until debarking. Have not heard back from Delta. Even though this was leg one of an international flight in first class, they denied access to their Sky Club - very disappointing!

The staff was fine. The plane was extremely tight, and I paid for the wifi and it did not work at all. I was actually going to ask for a refund.

two hour delay and the Delta representative on the PA system was unable to understand

An awesome flight crew. FC seat cushion just doesn’t cut it for a 3+ hour flight.

2+hrs delay without any reason provided and a cramped flight

We waited an hour on the runway to get a gate in Orlando

Good flight. Efficient boarding and competent flight crew. No problems until we arrived at our destination gate. We were early so there was an aircraft at the gate that had to move before we could pull in. Then, due to the type of aircraft we flew, the cabin door could not be opened until some luggage from the cargo bay was offloaded to preserve center of gravity characteristics. So, that further delayed deplaning. Despite being 20 minutes early on landing, we ended up being 5 to 10 minutes late after all the delays.

Everything went well except the turbulence what no one have a control of but pilot and crew handled very good!

There was no WiFi available, there were mechanical problems with the plane and we landed at C 124, then the gate was switched to A 26, then all the way back to C126! For a 75 yo woman traveling alone, this was a difficult journey, indeed!

This trip did not start off well. The inbound flight was delayed about 20 minutes. Then, after initial onboarding, the passengers had to deplane due to a mechanical problem. That took about 30 minutes to fix and be cleared. Then, reboarding was chaotic. It took a long time to sort passengers and two passengers on standby were ticketed but there was no seat. So, they had to deplane. One of the flight crew was trying to help passengers figure out a place to put their carry-on bags and that took more time. In the end, our scheduled 10:30 am departure did not actually take off until about 12:05 pm CST. The flight itself was long but we got to Houston. Some passengers missed their connecting flights and had to rebook. Not the best of flights I've had.

Staff were good. My seat was in need of repair, but for a short flight was not problematic. Usual basic snack and drink setup that you'll find on any US carrier. Over, a decent, basic flight.

Complimentary light meal would be appreciated. But great flight crew service on all legs

Terrible because it was cancelled due to volcanic ash clouds in Guatemala while all other airlines kept flying. Had to pay for a hotel to stay overnight in Houston and try to fly next day.

Flight delayed for more than 16 hrs and no effort was spent to provide an alternate

We got delayed three hours and nobody thought to have the bathroom fixed while we were sitting waiting to board? took a full hour to have maintenance come and check it off. Had to shut the bathroom down twice so that the pilots could go to the bathroom. Everyone missed their connections.

Flight left on time and we arrived 25 minutes early! There was a gate available when we arrived so early on a busy Sunday afternoon! Flight attendants came around twice with the drinks cart.

My seat was assigned last row behind restrooms No legroom’s I’m very Pettit Still was not comfortable Food choice was excellent

Delayed initially because they couldn’t print the flight details. Poor instruction on delay. When I got on the plane the flight attendant argued with me about whether my carry on would fit (it did, although she didn’t acknowledge that). No greeting (other than arguing with me) getting on or off the plane.

Overall good. The pilots and flight attendants are excellent! The equipment was the issue on my First flight as they had to wait for a part to be installed. So the take off was at least 30 minutes later.

The worst Airline ever. They centered my second flight and leave me in NY. They don’t have any representatives at the airport and they don’t respond to calls. Basically I got stuck. I will never purchase through there again.

It was an older plane. First Class was not especially roomy or comfortable. It was a short flight so there were no meal but they did offer mixed nuts which used to be normal but now is rare. Crew member was very polite and professional.

The chicken wrap was tiny ($13 for what looked like a 1/3 of a normal wrap?) and disgusting.

It was a train wreck but on an airplane. First off, flight was delayed then we board only to hear two announcements, First weather delays in Orlando and second backup battery warning on emergency lights. After sitting on the plane for almost 2 hours they have us deplane due to the maintenance issue. We were told they were getting another plane. In the mean time, I notice another American- Orlando flight and ask the gate agent if I can switch. He says he cant help me and I'd have to walk to A13 from A37. Really!? I get down there and get a seat only to get an announcement my original flight was RE-boarding. The Then inflight there's no communication and I notice on flightaware were circling over the Gulf of America. I call the flight attendant and of course she has no clue and apparently 5m later the pilot finally tells us about another delay. Why does American always have these service and delay issues? They are my LAST choice in flights now!

Mediocre would be best description. Food bland. Seat biz class uncomfortable to sleep. Crew never dimmed lights completely in an overnight flight to Europe. Would avoid AA if possible.

For my arriving destination, we were delayed multiple times to the point that we arrived 6 hours after we were originally scheduled. On my flight home, they overbooked and involuntarily removed passengers (including me) from the plane. It was not a good experience.

It was good experience this time. The flight was on time.

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

Information on your arrival and departure airports