$128 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 3/3. 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

Tue, Feb 24 - Tue, Mar 3
United Airlines Logo
6:30 am - 3:40 pm
MSN
-
SJU
7h 10m
1 stop
United Airlines Logo
2:05 am - 2:57 pm
SJU
-
MSN
14h 52m
2 stops
$256United Airlines
Sun, May 3 - Sat, May 9
Delta Logo
6:00 am - 8:06 pm
MSN
-
SJU
13h 06m
2 stops
Delta Logo
7:00 am - 8:40 pm
SJU
-
MSN
14h 40m
2 stops
$287Delta
Tue, Apr 14 - Tue, Apr 21
American Airlines Logo
6:10 am - 8:51 pm
MSN
-
SJU
13h 41m
2 stops
American Airlines Logo
4:25 pm - 11:01 pm
SJU
-
MSN
7h 36m
1 stop
$289American Airlines
Wed, Feb 18 - Wed, Mar 18
American Airlines Logo
8:24 pm - 5:24 am
MSN
-
SJU
7h 00m
1 stop
American Airlines Logo
3:40 pm - 9:11 am
SJU
-
MSN
18h 31m
2 stops
$316American Airlines
Tue, Mar 3 - Wed, Mar 11
American Airlines Logo
5:00 am - 4:52 pm
MSN
-
SJU
9h 52m
2 stops
American Airlines Logo
9:50 am - 8:49 pm
SJU
-
MSN
11h 59m
2 stops
$319American Airlines
Wed, Feb 4 - Wed, Feb 11
American Airlines Logo
7:25 am - 8:50 pm
MSN
-
SJU
11h 25m
2 stops
American Airlines Logo
6:00 am - 4:20 pm
SJU
-
MSN
12h 20m
2 stops
$322American Airlines
Thu, Feb 19 - Thu, Feb 26
American Airlines Logo
8:24 pm - 5:24 am
MSN
-
SJU
7h 00m
1 stop
American Airlines Logo
6:33 am - 2:32 pm
SJU
-
MSN
9h 59m
1 stop
$326American Airlines
Sun, Mar 1 - Thu, Mar 5
United Airlines Logo
3:53 pm - 6:11 am
MSN
-
SJU
12h 18m
2 stops
United Airlines Logo
8:30 am - 2:02 pm
SJU
-
MSN
7h 32m
1 stop
$331United Airlines
Sat, Jan 31 - Wed, Feb 4
Multiple Airlines Logo
6:16 pm - 9:47 am
MSN
-
SJU
13h 31m
1 stop
Multiple Airlines Logo
6:00 am - 5:56 pm
SJU
-
MSN
13h 56m
1 stop
$332Multiple Airlines
Sat, Jan 31 - Thu, Feb 5
American Airlines Logo
7:00 am - 10:26 pm
MSN
-
SJU
13h 26m
1 stop
American Airlines Logo
7:00 am - 4:20 pm
SJU
-
MSN
11h 20m
1 stop
$338American 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 March and December, when the average cost of round-trip tickets is $665 and $621 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 8% 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$128
Best time to beat the crowds with an average 19% drop in price.
Most popular time to fly and prices are also 13% lower on average.
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 8066 reviews
8.5Crew
7.8Entertainment
7.9Comfort
8.1Boarding
7.2Food
Airline reviews

No in flight service, no explanation - FC got service, C+ did not, unsure about Economy. No turbulence to speak of, so I guess another way to cut cost, or promote health and well being of Delta employees? Also, boarding in MEM combined zones, and with overhead space already full on both flights after Zone 2/ Diamond, presents a huge challenge to find a space for a bag. Delta, other than point A to B, is no longer reasonable to fly - very poor experiences, not even taking into account the chastising at the gate and rude crews, across the board.

4.0 OkayUros, Jan 2026
MEM - ATL
Read more Delta reviews

No in flight service, no explanation - FC got service, C+ did not, unsure about Economy. No turbulence to speak of, so I guess another way to cut cost, or promote health and well being of Delta employees? Also, boarding in MEM combined zones, and with overhead space already full on both flights after Zone 2/ Diamond, presents a huge challenge to find a space for a bag. Delta, other than point A to B, is no longer reasonable to fly - very poor experiences, not even taking into account the chastising at the gate and rude crews, across the board.

It would have been better if the flight wasn't delayed by 2.5 hours

Delta’s staff is unmatched. From the gate agents, to the pilots, to the flight attendants… all top of the industry.

Delta flight Delay for ,more that two hours i.e original flight was 6.30 PM and it starts at 8.45 PM, When we connect Delta team for meal vouchers as it is late arrival in designation,But we did not get it as per delta policy , which is not good for mid night arrival,

Inexperienced boarding crew allowed too many bags on to a full flight and delayed takeoff causing a missed connection and unplanned overnight stay. There was a hotel at the airport but Delta would not pay for it offering only to shuttle me to an area hotel. Never even offerred so much as an apology by anyone working for Delta.

Staff was great! Kind and cordial! Middle seat row 28 seat B has a hump in it. Trays were getting stuck when putting down and up. Good flight

Departure was delayed resulting in me missing my connection. Delta did not autimatically find me another flight.

The seats weren’t reclining even though it wasn’t as exit seat

It was good because we traveled without luggage, carry on only.

I usually get upgraded so my experience is usually amazing. I did not get upgraded this time - which was fine - but the wifi had issues, the monitors were going in & out, & (though not Delta's fault) one of the gentlemen next to me desperately needed a shower.

Food should be changed in menu Many muslims travels in this airlime they need to add one Halal meal

Delayed, toilets did not flush, pilot parked to far away from Gate

Was happy we finally got upgraded in 1st class. The seat getting old. The cushiness need some improvement.

Yet another flight in which beverage and snack service was skipped. Other that that, firmly mediocre. Landed early, to gate late due to congestion at the gates. Airline's fault or airports fault: unknown.

Ineffective communication with United resulted in lost baggage. Their Baggage Tracing counter at MUC was shut down from 11:00-14:15 on my arrival. Undertrained, underinformed staff had me Running all over MUC to find someone to help me to no avail. Staff was rude, unhelpful, and unable to effectively use the systems they did have operational. They refused to contact United in any way or provide any accommodation or other resources while I waited for my luggage. This has destroyed my downstream itinerary. If they had even the slightest visibility I may have been able to reschedule/plan, but again, their staff provided nothing, and did nothing more than their website, which doesn’t even work on a standard phone browser. Miserable failure at all levels that weren’t associated with the operation of the aircraft.

Miserable. They moved my seat, but canceled the next leg of my flight. I resolved the issue at my transfer, but that resulted in lost luggage that has taken days off my schedule with no resolution. Worse, they fail to interface effectively with Lufthansa, forcing me to bounce between two equally useless help desks. The apps are unable to handle the situation, the bag dropped off the tracker, and while the call centers are polite, they do not provide written information to assist with cross-airline communication.

left on time, reasonable boarding process arrived early luggage came out quickly

I like flying first class, and United has a nice one

Teeny tiny bathrooms, crew was not realistic about when we'd arrive.

Check-in, boarding and the flight from Phoenix to Houston was quick and easy. The flight from Houston to Shreveport was delayed 5 hours. It was frustrating but I think United handled it the best they could.

The seat cushions were very worn so they were extremely uncomfortable.

Delayed, no updates, had a rewards number but was not working

The seats from lax to DFW was so tight that I could not move my legs . No WiFi and had to pay . Not a good selection of entertainment

AA should improve their in air internet & entertainment options. Seems unreasonable to charge $20/hr and should have some form of free connections. The entertainment options are also pretty limited, movies are outdated and the series only show 3-5 episodes.

The professionals have excellent customer service, the seats don´t have enough space.

We were upgraded to First Class and it was a great flight

Amazing I love American. I’ll never fly anyone else if I can help it.

I love American. I’ll never fly anyone else if I can help it.

Flight delay and multiple gate changes including a change near boarding time to another terminal, which in DFW is a pain. Pre-boarding delay and also a further delay on the ground after boarding. About an hour and a half total delay.

On the plus side, crew was attentive, drinks were cold, and in-flight entertainment selection was better than some other airlines. On the negative aide, Plane was delayed almost an hour, either no announcements from the gate crew. Biscoff cookies are gross, appreciate airlines that give a choice. Also, crew had no personality or enthusiasm at all.

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

Information on your arrival and departure airports