$113 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 4/15. 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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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 14 - Mon, May 18
American Airlines Logo
6:00 am - 11:28 pm
SJU
-
MSN
18h 28m
1 stop
American Airlines Logo
6:20 am - 10:05 pm
MSN
-
SJU
14h 45m
1 stop
$306American Airlines
Thu, May 7 - Tue, May 12
American Airlines Logo
6:00 am - 11:28 pm
SJU
-
MSN
18h 28m
1 stop
American Airlines Logo
6:20 am - 10:05 pm
MSN
-
SJU
14h 45m
1 stop
$338American Airlines
Thu, May 7 - Tue, May 12
American Airlines Logo
6:00 am - 11:28 pm
SJU
-
MSN
18h 28m
1 stop
American Airlines Logo
11:33 am - 8:51 pm
MSN
-
SJU
8h 18m
1 stop
$356American Airlines
Thu, May 14 - Mon, May 18
American Airlines Logo
11:38 am - 10:11 pm
SJU
-
MSN
11h 33m
2 stops
American Airlines Logo
6:45 am - 8:51 pm
MSN
-
SJU
13h 06m
1 stop
$378American Airlines
Thu, May 7 - Tue, May 12
United Airlines Logo
3:56 pm - 10:54 pm
SJU
-
MSN
7h 58m
1 stop
United Airlines Logo
12:18 pm - 8:34 pm
MSN
-
SJU
7h 16m
1 stop
$389United 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
7:00 am - 10:45 pm
MSN
-
SJU
14h 45m
1 stop
$399American Airlines
Thu, May 7 - Tue, May 12
American Airlines Logo
1:31 pm - 11:54 pm
SJU
-
MSN
11h 23m
2 stops
American Airlines Logo
6:20 am - 10:05 pm
MSN
-
SJU
14h 45m
1 stop
$401American Airlines
Thu, May 7 - Tue, May 12
American Airlines Logo
6:00 am - 11:28 pm
SJU
-
MSN
18h 28m
1 stop
American Airlines Logo
6:45 am - 6:10 pm
MSN
-
SJU
10h 25m
2 stops
$406American Airlines
Thu, May 7 - Sun, May 10
American Airlines Logo
6:00 am - 11:28 pm
SJU
-
MSN
18h 28m
1 stop
American Airlines Logo
6:20 am - 10:05 pm
MSN
-
SJU
14h 45m
1 stop
$428American Airlines
Thu, May 7 - Tue, May 12
American Airlines Logo
4:30 pm - 11:54 pm
SJU
-
MSN
8h 24m
1 stop
American Airlines Logo
6:45 am - 8:51 pm
MSN
-
SJU
13h 06m
1 stop
$448American 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 $306 return. The most popular connection is from Denver to Madison and KAYAK users have found round-trip deals for as low as $213 in the last 3 days.

Good to know

Low seasonAugust
Cheapest flight$113
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 $306 return. The most popular connection is from Denver to Madison and KAYAK users have found round-trip deals for as low as $213 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 510 direct flights from within Puerto Rico to Madison. The most common day for departures is Sunday, with 16% 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 11507 reviews
7.5Boarding
6.4Food
7.2Comfort
7.9Crew
6.9Entertainment
Airline reviews

The flight changed gates multiple times and flight had to be delayed multiple times

4.0 OkayFaraz, Mar 2026
DFW - BWI
Read more American Airlines reviews

The flight changed gates multiple times and flight had to be delayed multiple times

We called Kayak for a change due to the TSA situation in Atlanta. What we got was a canceled return flight (in error) and we had to find the mistake. Not happy with Kayak who blamed it on AA.

I was in last row so that is never great bc the person in front of me leaned his seat all the way back into me.

Delayed for mechanical and no updates on what was happening and how long the delay might be.

My flight from LGA was cancelled and my rebooked flight from JFK was delayed numerous times. I will now be getting home after 2am.

Flight was delayed half hour before boarding, but when I checked flight aware the plane that would Pick us up had a delay of more than an hour. AA should let us know in advance to avoid waiting several hours in the airport

On the return flight, arriving in Denver we sat on the tarmac in Denver for over 20 minutes.

Typical AA - late by 90+ mn. Gate changed twice... Changed the departure time 6 times No explanation, no communication on reasons for delay I travel with AA twice a year... and it is consistently very poor.. I will continue to use AA only when i have to.

The flight attendant in business class was excellent! Professional, friendly and attentive.

Delays with no explanation. It could have been handled better.

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Everything you need to know for your flight to Madison

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