$123 Find Cheap Flights from Puerto Rico to Madison

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight to Madison departing on 5/15. 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

KAYAK searches hundreds of travel sites at once for deals on flights to Madison

 
These are the airlines KAYAK users have selected most often from within our search results for flights to Madison, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results for flights to Madison, as well as popular online travel agencies
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Cheap Flights from Puerto Rico to Madison

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Puerto Rico to Madison 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 Puerto Rico to Madison

Thu, May 7 - Tue, May 12
United Airlines Logo
3:56 pm - 10:54 pm
SJU
-
MSN
7h 58m
1 stop
United Airlines Logo
9:55 am - 8:34 pm
MSN
-
SJU
9h 39m
1 stop
$308United Airlines
Thu, May 7 - Sun, May 10
JetBlue Logo
2:48 pm - 10:44 pm
SJU
-
MSN
8h 56m
1 stop
JetBlue Logo
5:43 am - 4:33 pm
MSN
-
SJU
9h 50m
1 stop
$316JetBlue
Thu, May 7 - Tue, May 12
American Airlines Logo
11:59 pm - 11:05 am
SJU
-
MSN
12h 06m
1 stop
American Airlines Logo
6:45 am - 6:10 pm
MSN
-
SJU
10h 25m
2 stops
$326American Airlines
Wed, Apr 22 - Wed, Apr 29
United Airlines Logo
7:40 am - 1:51 pm
SJU
-
MSN
7h 11m
1 stop
United Airlines Logo
8:30 am - 9:24 pm
MSN
-
SJU
11h 54m
2 stops
$328United Airlines
Fri, Jun 5 - Mon, Jun 8
American Airlines Logo
6:20 am - 9:20 pm
SJU
-
MSN
16h 00m
1 stop
American Airlines Logo
6:01 am - 11:01 pm
MSN
-
SJU
16h 00m
1 stop
$366American Airlines
Thu, May 7 - Tue, May 12
American Airlines Logo
6:45 am - 10:32 pm
SJU
-
MSN
16h 47m
1 stop
American Airlines Logo
6:10 am - 10:05 pm
MSN
-
SJU
14h 55m
1 stop
$379American Airlines
Fri, May 1 - Wed, May 6
United Airlines Logo
3:56 pm - 10:54 pm
SJU
-
MSN
7h 58m
1 stop
United Airlines Logo
6:30 am - 9:24 pm
MSN
-
SJU
13h 54m
2 stops
$386United Airlines
Thu, Apr 23 - Sat, Apr 25
United Airlines Logo
3:56 pm - 11:49 pm
SJU
-
MSN
8h 53m
1 stop
United Airlines Logo
5:00 am - 8:38 pm
MSN
-
SJU
14h 38m
2 stops
$391United Airlines
Thu, Apr 23 - Sat, Apr 25
United Airlines Logo
3:56 pm - 11:49 pm
SJU
-
MSN
8h 53m
1 stop
United Airlines Logo
10:05 am - 8:34 pm
MSN
-
SJU
9h 29m
1 stop
$396United Airlines
Thu, Aug 20 - Mon, Aug 31
Multiple Airlines Logo
5:15 pm - 8:25 am
SJU
-
MSN
16h 10m
2 stops
Multiple Airlines Logo
6:50 pm - 4:34 pm
MSN
-
SJU
20h 44m
1 stop
$399Multiple Airlines
Booking Insights

KAYAK's insights & trends for flights to Madison

Get data-powered insights and trends for flights to Madison to help you find the cheapest flights, the best time to fly and much more.

What is the cheapest flight to Madison?

These are the best round-trip prices found by users searching on KAYAK in the last 72 hours.

In the last 3 days, the cheapest flight deal to Madison was found on the route from San Juan, at $308 return. The most popular connection is from Denver to Madison and KAYAK users have found round-trip deals for as low as $208 in the last 3 days.

Good to know

Low seasonAugust
Cheapest flight$123
Best time to beat the crowds with an average 4% drop in price.
Most popular time to fly with an average 13% increase in price.
Flight from San Juan to Madison

FAQs - booking Madison flights

  • What is the cheapest flight to Madison?

    In the last 3 days, the cheapest flight deal to Madison was found on the route from San Juan, at $308 return. The most popular connection is from Denver to Madison and KAYAK users have found round-trip deals for as low as $208 in the last 3 days.

  • How far is Madison Truax Field Airport from central Madison?

    Madison Truax Field Airport is 5 miles from the center of Madison.

  • What is the name of Madison’s airport?

    Madison is served by Madison Truax Field Airport, also commonly referred to as Truax Field. The airport code is MSN.

  • How does KAYAK find such low prices on flights to Madison?

    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 to Madison.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket to Madison?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Madison is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights to Madison?

    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 to Madison 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 to Madison?

    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 to Madison up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

  • How many direct flights to Madison are there each week?

    Each week there are around 504 direct flights from within Puerto Rico to Madison. The most common day for departures is Friday, with 15% of flights taking off on this day.

Top tips for finding cheap flights to Madison

  • Enter your preferred departure airport and travel dates into the search form above to unlock the latest Madison flight deals.

Reviews of the top airline flying from Puerto Rico to Madison

 
See real verified KAYAK customer reviews for airlines flying to Madison. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline from Puerto Rico to Madison. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with to Madison? 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.
7.1
American AirlinesOverall score based on 11549 reviews
7.9Crew
7.2Comfort
7.5Boarding
6.4Food
6.9Entertainment
Airline reviews

I'm not sure American is capable of on-time arrivals and departures. When you land at ORD, you almost always get held on the tarmac because your gate is still occupied. I may have missed my connection, but that ended up up being significantly delayed as well. Once again, I finally got home well after midnight.

2.0 MediocreMark, Apr 2026
PHX - ORD
Read more American Airlines reviews

I'm not sure American is capable of on-time arrivals and departures. When you land at ORD, you almost always get held on the tarmac because your gate is still occupied. I may have missed my connection, but that ended up up being significantly delayed as well. Once again, I finally got home well after midnight.

Same plane as RDU to LGA — internet not working. Pilot issue of some sort at end of prior flight - I was on same plane for my connection. Late/delayed —

Good flight, seated and had a water within 5 minutes. Crew was hospitable.

Didn't make it back on American Airlines due to a maintenance issue. The communication and updates were terrible. I ended up returning on Aero Mexico which had a much nicer aircraft with a large entertainment screen with movies and shows AND they had a nice inflight meal. That was a treat after being delayed 26 hours! I think some additional flight miles, or something should be offered for that long of a delay ---it was not pleasant at all---very physical and emotional experience.

Message about flight cancelation was received late due to being in the air. No explanation, just canceled and booked on morning flight. We had to stay in the airport overnight because there was no transportation offered to get to the hotel that AA had available. Actual inflight was fine.

Buying ticket from kayak instant booking was a huge mistake, never to be repeated again! The Kayak didn’t book the tickets directly, it handed it off to a third party Underpricer, that booked a code shared American Airlines flight operated by Cathay Pacific!! When managing the booking American Airlines would recognize the itinerary but wouldn’t let me do anything stating, the flight is operated by Cathay Pacific so go to their website. Cathay Pacific would recognize the itinerary, neither by reservation ID or ticket number…asking to reach out to the third party Underpricer….calling Underpricer resulted in no help like seat requests, mileage number or upgrade request, 15hr layover accommodation voucher guidance…so net in net avoid booking through three layers of intermediaries

I didn't go from Reno to Phoenix I ended up going from Reno to Dallas to Tucson because my flight rebooked because my Amtrak was late I tried notifying you guys I also don't know what you ask me about my flight because you guys didn't book my flight

A chaotic and uncomfortable experience from start to finish. The boarding process was a disaster; despite group numbers, it was a free-for-all that the staff failed to manage (especially after group 5). Once on board, the "entertainment" was non-existent. There are no seatback screens, and the mobile app selection is incredibly thin. The hardware is severely dated. My seat had zero cushioning left—it felt like sitting on a hard board for the entire flight—and the legroom was cramped. To make matters worse, the bathroom was repulsive, with toilet paper, soiled paper towels and liquid/pee all over the floor. When I did interact with the crew, they provided the absolute bare minimum and made me feel like an inconvenience for asking for anything. Avoid this flight if you can.

Delays experienced in boarding/take off due to incoming plane delayed. However, the boarding time/depart time in the app was significantly delayed in providing these updates. Usually not updated until an hour after we should have already boarded. Poorly managed.

Bag drop was very disorganized in Miami. All main cabin passengers were shunted to just a few lanes and they had an equal number of lanes for first class passengers but there was nobody on those lines. They did nothing to bring the main cab and passengers over to the open lines and they just had employees standing there and doing nothing

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Everything you need to know for your flight to Madison

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