$203 Find Cheap Flights from Puerto Rico to Madison - Compare and Save

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 7/8. 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
Travelers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

Save 21% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Bundle and saveSave money when you bundle your flight + hotel.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Flight Deals
Booking Insights
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

Fri, Nov 6 - Tue, Nov 10
American Airlines Logo
3:53 pm - 11:33 pm
SJU
-
MSN
9h 40m
1 stop
American Airlines Logo
8:12 pm - 3:02 pm
MSN
-
SJU
16h 50m
1 stop
$372American Airlines
Tue, Sep 29 - Sat, Oct 3
United Airlines Logo
1:00 am - 1:37 pm
SJU
-
MSN
13h 37m
2 stops
United Airlines Logo
6:42 am - 8:38 pm
MSN
-
SJU
12h 56m
2 stops
$381United Airlines
Fri, Nov 6 - Tue, Nov 10
American Airlines Logo
3:53 pm - 11:33 pm
SJU
-
MSN
9h 40m
1 stop
American Airlines Logo
6:00 am - 5:52 pm
MSN
-
SJU
9h 52m
2 stops
$413American Airlines
Tue, Sep 29 - Sat, Oct 3
United Airlines Logo
1:00 am - 1:37 pm
SJU
-
MSN
13h 37m
2 stops
United Airlines Logo
6:42 am - 8:38 pm
MSN
-
SJU
12h 56m
2 stops
$430United Airlines
Wed, Jul 8 - Tue, Jul 14
American Airlines Logo
7:00 am - 9:41 pm
SJU
-
MSN
15h 41m
1 stop
American Airlines Logo
7:00 am - 10:59 pm
MSN
-
SJU
14h 59m
1 stop
$449American Airlines
Fri, Nov 6 - Tue, Nov 10
American Airlines Logo
2:05 pm - 10:50 pm
SJU
-
MSN
10h 45m
2 stops
American Airlines Logo
6:00 am - 5:52 pm
MSN
-
SJU
9h 52m
2 stops
$457American Airlines
Wed, Jul 8 - Thu, Jul 16
American Airlines Logo
7:00 am - 5:22 pm
SJU
-
MSN
11h 22m
1 stop
American Airlines Logo
6:00 am - 6:24 pm
MSN
-
SJU
11h 24m
2 stops
$486American Airlines
Wed, Jul 8 - Thu, Jul 16
American Airlines Logo
7:00 am - 9:41 pm
SJU
-
MSN
15h 41m
1 stop
American Airlines Logo
6:00 am - 6:24 pm
MSN
-
SJU
11h 24m
2 stops
$492American Airlines
Wed, Jul 8 - Thu, Jul 16
American Airlines Logo
7:25 am - 5:22 pm
SJU
-
MSN
10h 57m
2 stops
American Airlines Logo
6:00 am - 6:24 pm
MSN
-
SJU
11h 24m
2 stops
$529American Airlines
Tue, Jul 14 - Wed, Jul 29
American Airlines Logo
7:00 am - 9:41 pm
SJU
-
MSN
15h 41m
1 stop
American Airlines Logo
7:00 am - 10:59 pm
MSN
-
SJU
14h 59m
1 stop
$534American 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 are the most popular airlines flying to Madison?

The most popular airline among KAYAK users flying to Madison is American Airlines, followed by Delta and Southwest.

Good to know

Low seasonAugust
Cheapest flight$203
Best time to beat the crowds with an average 4% drop in price.
Most popular time to fly and prices are also 14% lower on average.
Flight from San Juan to Madison

FAQs - booking Madison flights

  • 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 956 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 11660 reviews
7.5Boarding
7.9Crew
7.2Comfort
6.4Food
6.8Entertainment
Airline reviews

Awfully rude American worker at door when we started boarding flight. Then, walk into a blazing hot airplane with no air conditioning until twenty minutes into the flight. Free entertainment was non existent! My husband, along with the fellow passenger in our row, and I could not get entertainment to work, no WIFI! Really?? Been flying American a long time. Was very disappointed.

2.0 MediocreKimberly, Jun 2026
RDU - DFW
Read more American Airlines reviews

Awfully rude American worker at door when we started boarding flight. Then, walk into a blazing hot airplane with no air conditioning until twenty minutes into the flight. Free entertainment was non existent! My husband, along with the fellow passenger in our row, and I could not get entertainment to work, no WIFI! Really?? Been flying American a long time. Was very disappointed.

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

Check in was easy. Flights were smooth. Flight attendants were courteous and friendly.

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

Crew was nice, aircraft dated, entertainment same. Internet is expensive and terribly slow. Food pretty bad

Horrible experience. Food was ridiculous, insufficient, and not appetizing at all. They served sugary granola bar for breakfast. Furthermore, my bags were delayed and delivered damaged and American made it impossible to file for damages. Furthermore, the flights were delayed causing unnecessary stress given the connecting flights. It was awful experience, would never want to fly American.

My flight times changed 4 times since I originally booked the flight. The last time being the day of flight - a 2 hour delay. This meant instead of getting into IAH at 9:30p, I got in at 2:30a. This was very disappointing!!!

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.

My table was broken so it made it difficult to eat the food during the service. I was also informed that my luggage did not make it with me to Phoenix. I live two hours away so this makes it even more stressful to try and arrange a time for pick up

Traveling to a place near Madison?

Book flights to Madison if you plan to visit one of these locations
Baraboo
Windsor
Evansville
Cambridge
Oxford

Everything you need to know for your flight to Madison

Information on the airport you'll fly into in Madison