$203 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 7/28. 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$256
Mayagüez
Mayagüez2 stops$2,207
Aguadilla
Aguadilla2 stops$256
Mayagüez
Mayagüez2 stops$2,207

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

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 - 1:42 pm
SJU
-
MSN
13h 42m
2 stops
$256United Airlines
Tue, Nov 10 - Tue, Nov 17
United Airlines Logo
9:44 am - 11:57 pm
MSN
-
BQN
12h 13m
2 stops
United Airlines Logo
1:09 am - 9:53 am
BQN
-
MSN
10h 44m
2 stops
$256United Airlines
Wed, Oct 7 - Sat, Oct 10
United Airlines Logo
6:49 am - 2:44 pm
MSN
-
SJU
6h 55m
1 stop
United Airlines Logo
3:56 pm - 10:35 pm
SJU
-
MSN
7h 39m
1 stop
$311United Airlines
Sun, Sep 6 - Tue, Sep 15
United Airlines Logo
6:30 am - 8:38 pm
MSN
-
SJU
13h 08m
2 stops
United Airlines Logo
1:00 am - 11:58 am
SJU
-
MSN
11h 58m
2 stops
$313United Airlines
Sat, Aug 22 - Tue, Aug 25
American Airlines Logo
6:01 am - 10:24 pm
MSN
-
SJU
15h 23m
1 stop
American Airlines Logo
7:30 am - 11:09 pm
SJU
-
MSN
16h 39m
1 stop
$326American Airlines
Tue, Nov 10 - Wed, Nov 18
United Airlines Logo
6:45 am - 10:22 pm
MSN
-
SJU
13h 37m
2 stops
United Airlines Logo
4:52 pm - 10:50 pm
SJU
-
MSN
7h 58m
1 stop
$330United Airlines
Wed, Aug 19 - Wed, Aug 26
American Airlines Logo
9:48 am - 11:15 pm
MSN
-
SJU
12h 27m
1 stop
American Airlines Logo
3:47 pm - 11:59 pm
SJU
-
MSN
9h 12m
2 stops
$331American Airlines
Tue, Aug 25 - Mon, Aug 31
Delta Logo
5:43 am - 4:38 pm
MSN
-
SJU
9h 55m
1 stop
Delta Logo
12:56 pm - 10:38 pm
SJU
-
MSN
10h 42m
1 stop
$340Delta
Tue, Aug 25 - Fri, Aug 28
Delta Logo
9:32 am - 10:29 pm
MSN
-
SJU
11h 57m
2 stops
Delta Logo
12:56 pm - 10:38 pm
SJU
-
MSN
10h 42m
1 stop
$357Delta
Sat, Aug 22 - Tue, Aug 25
American Airlines Logo
6:30 am - 9:55 pm
MSN
-
SJU
14h 25m
2 stops
American Airlines Logo
6:00 am - 5:06 pm
SJU
-
MSN
12h 06m
2 stops
$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 August, when the average cost of round-trip tickets is $418 and $380 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 30% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 17 weeks before departure.

Good to know

Low seasonAugust
Cheapest flight$203
Best time to beat the crowds but there is an average 15% 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.
7.9
DeltaOverall score based on 8396 reviews
8.1Boarding
7.8Comfort
8.5Crew
7.8Entertainment
7.2Food
Airline reviews

Flight delayed four separate times. I’m now one hour hours late to landing.

2.0 MediocreTravis, Jun 2026
SFO - LAX
Read more Delta reviews

Flight delayed four separate times. I’m now one hour hours late to landing.

worst flight ever from Delta, it got delayed and kept on delaying..

Should never have had to go to Detroit from Orlando back to Tennessee!

Got rerouted from a straight flight from Orlando to Atlanta to Knoxville to a flight from Orlando to Detroit to Knoxville! Seriously!! Flight delay out of Detroit! Long day for what should have been a pretty easy travel day!

Two delays on two separate planes with parts they could not easily find and replace.

Checkin was good, fllight ws good. Onlly complaint is lack of foot on 6 hour flight from Seattle to Boston. Snacks were flimsy - chips and cookies. could have offered something more substantial for such a long flight. I know you can buy food in airport but for the price you pay for a ticket, they should step up for the passengers.

Only beverages were offered to first class and I thought the flight attendant could have also served the Delta Comfort as well instead of sitting down and staring at her phone and walking past all of us to the back of the plane to charge her phone more. There was a complete lack of turbulence and was safe enough for flights attendant to walk around in the front of the plane, collect trash and serve a few people water and turn off the seat belt light. Also didn’t enforce people putting their seats into the upright position and allowed two passengers to remain reclined during landing. They seemed out to lunch completely. Usually my experience on Delta is much better.

Long story short, it was one of the better flight experiences I've had in some time when compared with other airlines.

Flight was great! This flight from Atlanta was even better than when I paid for Comfort from SNA to Atlanta.

Connection flights should be spaced out farther because too close I missed my connection.

This planes staff was top tier. Everything went great and had a great flight home.

Food was great. Staff was phenomenal. Seats were a bit hard and could use a lot more entertainment options as far as movies to choose from. WiFi was good. Overall great trip.

This was an overnight flight, and in the morning they did know coffee service. How you can throw passengers in a San Francisco airport at 5:40 a.m. in the morning and not giving them Coffee is a crime.

I was promised by United Airline (operated by ANA) that I will be seated together with my kids as I am the only adult flying with two minors. We did not get seats together in our 11 hours flight from LA to Tokyo. When asked at the gate, ANA representative said United Airline should have informed them that there is a parent flying with two minors. He said they can’t do anything in the system as the flight is full. He ask me to ask passengers next to me and the kids if they are willing to change seats. This is ridiculous! However, I went in the flight and asked other passages but no one willing to change seats. 11 hours and we were seating separately. I was very disappointed with this. It made things super inconvenient for me.

Our flight was delayed several Times due to mechanical issues. Although I understand this may happen at times, it was very inconvenient and we had to book a hotel for an overnight stay. We were traveling with my 3-yo grandson and waiting at the airport from noon until 6:30pm with no reassurance that our next rescheduled flight would depart, we had to decide what’s best for him. A day later, I found out that I may be able to demand compensation if my flight is delayed more than 4 hours. I will hav to read the fine print next time.

Flight cancelled instead of leaving Friday am now, maybe, leaving Sunday

The pilot had to extend the flight time from san antonio to Houston to burn off fuel. This caused a lot of unnecessary stress since we had a tight connection to Aruba. And with no other flights going to Aruba we were worried about spending a night in Houston. We had to to run to our connection because of the flight crews mistake. Not happy.

Service was professional and quick. Premium economy seat was comfortable given the class

one of the flight attendants on the Dallas to frankfurt leg was somewhat rude..

I'm a United 1K member and have ben for 10 years. The gate agent had no control over the boarding process and had us passengers queued for hours as delays were announced. On the plane, the overhead air nozzle was broken so col over was powering through on me and the passenger next to me. Not a great experience for a million miler on United. Feel free to contact me. Josh Smigel - DM426089

Flight was delayed by 6 hours... the level of incompetence was truly astounding. I won't be flying American Airlines again. I don't care if AA is direct and there is a layover with another airline, I'll take the layover.

Leave on time. We waited on the plane for hour hours and it was hot and smelly

Two hours delay, probably one hour because they didn’t bring catering and they had to bring water in board. There a change of aircraft. But delays galore at CLT so it must be a CLT and/or AA operation issue. The 1 hr additional delays because nobody could bring 2 packs of water sooner is probably the best example of this airline operates

Flight was delayed 5 hours. Initial reason for delay was 'maintenance' - which makes sense. Then, the additional 2 hours continued to say it was maintenance - when I know EWR had a 2 hour delay. AA did not say that. Additionally, when boarding, there was only one agent at the counter for a long time - until another came to help. After boarding, we had to wait another 45 minutes due to 'no catering'. So while we waited for catering, AA continued to board additional passengers - which seemed odd - and raised questions about what really was going on. I sat in First Class. During the flight, the flight crew allowed a significant number of non-First Class passengers to use the front bathroom - which created a very crowded environment in First Class which was uncomfortable. This also delayed First Class passengers from using the bathroom. Overall, horrible experience.

The Charleston, WV airport was cute. Very good staff and small enough to feel comfortable. The plane had more leg room than bigger planes. Much more comfortable.

Another uncoordinated American experience. Always surprises me at DFW for them of all places. Have to take this flight as there are no other good time options. We knew from the start that something was wrong, but the pilot wouldn't tell us. I just watched my Kayak app grow the delay by 10 minutes as it went to 3.5 hours. They were uncoordinated with maintenance (as maintenance, when finally arriving, knew within 15 minutes the plane wasn't going. No 'sorry' or 'this is what is going on' comment. The pilot seemed unfazed / didn't care about the process we were going through.

The seats. The seat in front of me was awful and when the guy sat down, it flew back and hit my head when I was putting my backpack under the seat, It didn't make for a pleasant experience,

Luggage did not make it onto my plane. Business seats were economy with empty row seat. Just horrible experience. Why would the company allow for transfers that don’t give employees enough time to transfer luggages??

I’ve got 31F seat and window seat . My 2 co passengers was AA crew members and they were very rude attitude and when I was going to use bathroom their gestures was very different and awkward and the guy beside me completely occupied the hand rest and I was really uncomfortable

The gate experience at LAX was abysmal (same for the arrival experience two days prior). Despite the LAX -> SAT schedule of two flights daily, our departure gate was at a smaller hub that we had to be bussed to from Terminal 4. Fortunately, I arrived at LAX extra early and had time to spare, but if I had not known, I might have missed my flight. I looked at the LAX airport map in the AA app and there was no indication of the additional boarding process. Lastly the gate area we were bussed to was crowded with limited food and beverage options. On flight, the fight attendant was hospitable and attentive, the flight was smooth, and AA's free (and working) wifi for AA members were all on the positive side.

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

Information on your arrival and departure airports