$115 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 5/4. 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$424
Mayagüez
Mayagüez2 stops$1,708
Aguadilla
Aguadilla2 stops$424
Mayagüez
Mayagüez2 stops$1,708

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

Wed, Apr 22 - Wed, Apr 29
American Airlines Logo
11:35 am - 8:51 pm
MSN
-
SJU
8h 16m
1 stop
American Airlines Logo
1:31 pm - 11:28 pm
SJU
-
MSN
10h 57m
2 stops
$329American Airlines
Tue, Apr 14 - Tue, Apr 21
American Airlines Logo
11:33 am - 8:51 pm
MSN
-
SJU
8h 18m
1 stop
American Airlines Logo
6:45 am - 10:32 pm
SJU
-
MSN
16h 47m
1 stop
$340American Airlines
Wed, Apr 22 - Wed, Apr 29
American Airlines Logo
6:00 am - 6:10 pm
MSN
-
SJU
11h 10m
2 stops
American Airlines Logo
1:31 pm - 11:28 pm
SJU
-
MSN
10h 57m
2 stops
$344American Airlines
Mon, Apr 13 - Wed, Apr 15
American Airlines Logo
8:05 am - 8:51 pm
MSN
-
SJU
11h 46m
2 stops
American Airlines Logo
1:31 pm - 11:28 pm
SJU
-
MSN
10h 57m
2 stops
$352American Airlines
Sat, Apr 18 - Mon, Apr 27
United Airlines Logo
10:05 am - 9:24 pm
MSN
-
SJU
10h 19m
2 stops
United Airlines Logo
1:00 am - 10:11 am
SJU
-
MSN
10h 11m
2 stops
$354United Airlines
Tue, Apr 14 - Tue, Apr 21
American Airlines Logo
6:20 am - 10:05 pm
MSN
-
SJU
14h 45m
1 stop
American Airlines Logo
6:45 am - 5:22 pm
SJU
-
MSN
11h 37m
1 stop
$355American Airlines
Mon, Mar 23 - Fri, Mar 27
Frontier Logo
12:29 pm - 1:58 am
MSN
-
SJU
12h 29m
1 stop
Frontier Logo
3:08 am - 1:19 pm
SJU
-
MSN
11h 11m
1 stop
$361Frontier
Tue, Apr 21 - Tue, Apr 28
United Airlines Logo
10:05 am - 11:09 pm
MSN
-
BQN
12h 04m
2 stops
United Airlines Logo
12:15 am - 10:11 am
BQN
-
MSN
10h 56m
2 stops
$424United Airlines
Sat, Apr 18 - Fri, Apr 24
Multiple Airlines Logo
6:36 pm - 1:43 am
MSN
-
BQN
30h 07m
1 stop
Multiple Airlines Logo
2:38 am - 5:56 pm
BQN
-
MSN
16h 18m
1 stop
$522Multiple Airlines
Sat, Apr 18 - Fri, Apr 24
Multiple Airlines Logo
6:36 pm - 1:43 am
MSN
-
BQN
30h 07m
1 stop
Multiple Airlines Logo
2:38 am - 5:56 pm
BQN
-
MSN
16h 18m
1 stop
$553Multiple 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 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 $661 and $658 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 14% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 17 weeks before departure.

Good to know

Low seasonOctober
Cheapest flight$115
Best time to beat the crowds with an average 19% drop 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.
7.9
DeltaOverall score based on 8269 reviews
7.2Food
7.8Entertainment
8.5Crew
8.1Boarding
7.9Comfort
Airline reviews

Could not get my connecting flight boarding pass until four hrs before departure! Ver annoying especially since the staff could not explain why!

8.0 ExcellentAnonymous, Mar 2026
SEA - RDU
Read more Delta reviews

Could not get my connecting flight boarding pass until four hrs before departure! Ver annoying especially since the staff could not explain why!

The flight was flying with 30% capacity. The flight my seat from preferred seating to back of the seat. Even though i can understand that this was to balance the flight weight. The flight attendance decided to do the serving near my seat and in the middle , their noices woke me up from sleep , when i realized that the service has ended and when they were going back asked for a coffee, for which they answered they have completed teh service in my location. That really upset me as they woke me up and also rejected the coffee i asked. I ended up landing with a headache, thanks to the crew that screwed up my travel

Delayed. Hot. Passenger next to me was so large I couldn’t move.

Same experience as the flight from Norfolk to Atlanta where people are boarded in zones that don't make sense. People behind you on the plane will get on before you and they take the luggage space on your row.

The boarding process doesn't make sense since some people that will sit behind your rows are boarded before you and then they take up the luggage space above your head. I then have to wait for people to get off the plane before I can go back to get my luggage.

Good flight. Connector flight was delayed so made a short turnaround in Atlanta which was stressful. Otherwise, great crew, Staff in ATL was very informative about the delay and ensured people their connections were fine. Notified the ones that were not. Great communication.

The flight went very well, but the flight attendants didn't serve and food or drinks other than 1st class due to rough air but to be honest it wasn't that bumpy and I felt that they could've at least offered water and coffee perhaps. Also serving 1st class only is a bad look. I've been in 1st class many times and I would've felt that if the turbulence was too rough for the main cabin, it would be too rough for 1st class too.

There was an unruly family behind us that made the short flight miserable!!! The cabin crew did nothing to contain it.

My seatback screen didn’t work so that sucked because that’s what I was going to do on the plane.

Left a few minutes early. Got in 15 minutes early. Very attentive service on board. Very organized boarding.

The travel company that you have on your site did me so wrong. I don’t know how it happened, but they put my son‘s name on my plane ticket flying to Vietnam. Along with his birthday. They would not have let me fly from Fort Myers to Ho Chi Minh City. I don’t think that I can ever use your service again. I typed my information into the browser along with my passport number and four days before I’m leaving I have to quickly search another ticket to fly out here.

Seats are uncomfortable. This has been a trend in the industry for decades. Trying to fit more seats on each plane to increase profits at the expense of the passenger.

The flight was delayed so we were dead tired, and after that the turbulence was horrible. I was very scared.

It’s always a great time flying with united airlines.

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

Like all of the flights I took to get down to Dallas. They were delayed

Other than nearly three hour delay for maintenance issues, everything went smooth

Plane from partner PSA was filthy. Plastic needs to be thoroughly cleaned. Really disgusting to look at and wonder about cleanliness of parts less visible.

The baggage claim experience was poor. The plane crew and the AA app said that checked baggage in CLT would be at carousel 7 but the sign at Baggage Claim said carousel 1. The carousel 1 sign had the correct flight # listed above the belt. But the luggage never came. I went to an AA baggage claim office after about 1 hour and the clerk directed me to another AA room that was poorly marked, with a closed door and no obvious way to know what to do. Finally someone opened the door and my bag was inside. The clerk was totally unable to explain why.

They are rarely on time! Very hard to plan your travels when flights or connections keep getting delayed.

Flight delay for mechanical. Inbound arrived on time. No one said why mechanical delay.

Forced to check bags. Crew uninterested in collecting trash. Unclean seats.

why would I bother with this airline and pick seats when I am asked to move for a weight imbalance

Flight pulled out on time but sat on runway for 30 mins. It was extremely cold in the aircraft despite wearing a winter coat. Surprisingly they had a vegetarian meal but could have some better snack choices for a 8 hour flight.

We had a male flight attendant who was super attentive and wonderful! Very professional. I have both gluten and dairy intolerance, and was only able to get a gluten free part, and not the dairy free part of the meal. Easy to order ahead of time and I appreciate being able to do that.

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

Information on your arrival and departure airports