$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 7/30. 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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Flight Deals

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
American Airlines Logo
1:25 pm - 11:28 pm
SJU
-
MSN
11h 03m
1 stop
American Airlines Logo
6:45 am - 6:10 pm
MSN
-
SJU
10h 25m
2 stops
$326American Airlines
Fri, Jun 5 - Mon, Jun 8
American Airlines Logo
7:00 am - 11:59 pm
SJU
-
MSN
17h 59m
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
Delta Logo
6:15 am - 4:25 pm
SJU
-
MSN
11h 10m
1 stop
Delta Logo
5:43 am - 4:33 pm
MSN
-
SJU
9h 50m
1 stop
$408Delta
Fri, Jun 5 - Mon, Jun 8
American Airlines Logo
7:00 am - 11:59 pm
SJU
-
MSN
17h 59m
1 stop
American Airlines Logo
6:01 am - 6:25 pm
MSN
-
SJU
11h 24m
2 stops
$448American Airlines
Fri, Jul 3 - Mon, Jul 13
Multiple Airlines Logo
9:53 pm - 9:47 am
SJU
-
MSN
12h 54m
2 stops
Multiple Airlines Logo
6:50 pm - 4:34 pm
MSN
-
SJU
20h 44m
1 stop
$453Multiple Airlines
Tue, May 5 - Sat, May 9
Multiple Airlines Logo
2:56 pm - 9:14 am
SJU
-
MSN
19h 18m
1 stop
Multiple Airlines Logo
7:55 pm - 3:12 pm
MSN
-
SJU
18h 17m
2 stops
$465Multiple Airlines
Thu, May 21 - Mon, May 25
Multiple Airlines Logo
9:00 am - 8:25 am
SJU
-
MSN
24h 25m
1 stop
Multiple Airlines Logo
6:50 pm - 3:55 pm
MSN
-
SJU
20h 05m
2 stops
$478Multiple Airlines
Sat, May 16 - Sat, May 23
American Airlines Logo
6:00 am - 11:28 pm
SJU
-
MSN
18h 28m
1 stop
American Airlines Logo
7:00 am - 10:45 pm
MSN
-
SJU
14h 45m
1 stop
$488American Airlines
Thu, May 7 - Sun, May 10
American Airlines Logo
1:31 pm - 11:28 pm
SJU
-
MSN
10h 57m
2 stops
American Airlines Logo
8:24 pm - 2:18 pm
MSN
-
SJU
16h 54m
1 stop
$490American Airlines
Sat, May 16 - Sat, May 23
Multiple Airlines Logo
2:47 pm - 8:25 am
SJU
-
MSN
42h 38m
2 stops
Multiple Airlines Logo
7:55 pm - 8:04 am
MSN
-
SJU
11h 09m
1 stop
$496Multiple 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 $326 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.

Find deals

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 16% 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 $326 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 480 direct flights from within Puerto Rico to Madison. The most common day for departures is Monday, 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 11644 reviews
6.4Food
7.9Crew
6.9Entertainment
7.5Boarding
7.2Comfort
Airline reviews

The crew was very kind, but no in-flight entertainment monitors and a 2 hour and 30 minute delay was extremely frustrating.

6.0 GoodMichael, Apr 2026
DFW - SLC
Read more American Airlines reviews

The crew was very kind, but no in-flight entertainment monitors and a 2 hour and 30 minute delay was extremely frustrating.

Everything was delayed and the staff sent me to the wrong gate, causing me to miss one of my flights. I arrived at my destination 6 hours later than I was supposed to.

Got home at 3am after deboarding the plane. No compensation offered by American

Delayed flight. Missed connection, AA put us on a later connecting flight. The connection flight was delayed 4 times and we had to deplane. Didnt get home until 3am, when I was supposed to be home at 8:30p. Zero compensation offered from American. I would not fly them again.

The seats need better cushioning for a nearly 5-hour flight, it was a bit uncomfortable. I'm glad American has free wi-fi but there were was a bout 30 minutes in the middle of the flight when there was no connection which was frustrating.

My original flight got delayed day of so I had to rebook it from one layover to two layovers. The flight also left earlier which was a slight inconvenience but manageable. Then my first connection flight got delayed 3 separate times for a total of 2 hours delayed, causing me to miss my second connection flight back to Santa Barbara. Now, because of this missed flight, I am missing my college classes that I pay for.

Flight: Started on time. Comfortable flight. Arrived on time. Crew: Very cordial and helpful. Drinks and snack was served with a smile. Overall enjoyed the trip. Regards, Hari Doss Chanchala Doss

It was good, the staff was great, and the food, was as usual, tea and biscuit. Bathroom was clean, and the plane was clean as well.

Early departure meant on time arrival. Only real problem was free internet had issues, although chatting with the internet help desk (you can do this via aainflight.com) got the issue resolved.

It was really a terrific experience both going and returning on AA. Staff and crew were professional.

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Everything you need to know for your flight to Madison

Information on the airport you'll fly into in Madison

Madison (MSN)