$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 4/24. 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 23% 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

Tue, Sep 29 - Tue, Oct 6
United Airlines Logo
3:56 pm - 12:12 am
SJU
-
MSN
9h 16m
1 stop
United Airlines Logo
6:45 am - 8:38 pm
MSN
-
SJU
12h 53m
2 stops
$266United Airlines
Thu, May 7 - Sun, May 10
JetBlue Logo
7:30 am - 4:25 pm
SJU
-
MSN
9h 55m
1 stop
JetBlue Logo
5:43 am - 1:38 pm
MSN
-
SJU
6h 55m
1 stop
$286JetBlue
Thu, May 7 - Sun, May 10
JetBlue Logo
7:30 am - 4:25 pm
SJU
-
MSN
9h 55m
1 stop
JetBlue Logo
11:04 am - 10:17 pm
MSN
-
SJU
10h 13m
1 stop
$316JetBlue
Mon, Jun 1 - Tue, Jun 16
JetBlue Logo
2:48 pm - 10:44 pm
SJU
-
MSN
8h 56m
1 stop
JetBlue Logo
5:48 am - 1:31 pm
MSN
-
SJU
6h 43m
1 stop
$321JetBlue
Thu, May 7 - Tue, May 12
American Airlines Logo
2:42 pm - 11:28 pm
SJU
-
MSN
9h 46m
1 stop
American Airlines Logo
7:50 am - 8:51 pm
MSN
-
SJU
12h 01m
2 stops
$326American Airlines
Wed, May 6 - Sat, May 16
American Airlines Logo
4:30 pm - 12:04 am
SJU
-
MSN
8h 34m
1 stop
American Airlines Logo
11:35 am - 8:55 pm
MSN
-
SJU
8h 20m
1 stop
$334American 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
8:10 am - 9:24 pm
MSN
-
SJU
12h 14m
2 stops
$349United Airlines
Mon, Jun 1 - Thu, Jun 11
JetBlue Logo
7:30 am - 4:25 pm
SJU
-
MSN
9h 55m
1 stop
JetBlue Logo
5:48 am - 1:31 pm
MSN
-
SJU
6h 43m
1 stop
$356JetBlue
Fri, May 1 - Wed, May 6
Delta Logo
2:45 pm - 10:27 pm
SJU
-
MSN
8h 42m
1 stop
Delta Logo
6:00 am - 8:26 pm
MSN
-
SJU
13h 26m
2 stops
$358Delta
Wed, May 6 - Sat, May 16
American Airlines Logo
1:31 pm - 12:04 am
SJU
-
MSN
11h 33m
2 stops
American Airlines Logo
9:18 am - 8:55 pm
MSN
-
SJU
10h 37m
2 stops
$375American 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 $266 return. The most popular connection is from Denver to Madison and KAYAK users have found round-trip deals for as low as $206 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 $266 return. The most popular connection is from Denver to Madison and KAYAK users have found round-trip deals for as low as $206 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 469 direct flights from within Puerto Rico to Madison. The most common day for departures is Friday, 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 11550 reviews
7.5Boarding
6.9Entertainment
7.2Comfort
6.4Food
8.0Crew
Airline reviews

Early morning flight and no food in First Class except a "salmon" box. No thank you. Was informed before take off by Captain that the plane was not serviced before we boarded in Phoenix. How does that happen? Need more frequent additions/turn over on the Entertainment. Thanks

2.0 MediocreKathryn, Apr 2026
PHX - OMA
Read more American Airlines reviews

Early morning flight and no food in First Class except a "salmon" box. No thank you. Was informed before take off by Captain that the plane was not serviced before we boarded in Phoenix. How does that happen? Need more frequent additions/turn over on the Entertainment. Thanks

Moved to earlier flight which unexpectedly had maintenance issues initially indicated as quick fix to ultimately plane changes. Moved back to original flight, also delayed. In all cases customer updates and communication very unclear, no updates on drivers for delays.

Flight was delayed. No urgency by American Airlines team to assist those with connecting flights. It was basically you are on your own to run through the terminals to try and make your connection. Thanks, Mary

I have never been assaulted they way I was today in Charlotte - shame on American

One of our group members was struggling to walk. In Charlotte we asked for a wheelchair and she was accompanied by Desmond. I was impressed by his patience and attention. In Boston she received the same service. I didn’t get the name of the helper but she went above and beyond in assisting us. A great AA service

Delayed 24 hours. Should have called it much earlier They provided quality accommodations, food vouchers etc. FINALLY The issues started at 8 AM and they cancelled the flight at 11:30 PM, with no plans for a new flight.

Better snacks but flight and crew were amazing on this flight

Found that the plane used for this short flight is smaller and therefore the seats are really squeezed tight.

It was the most un-special flight experience in my life.

Plane was super cold. No entertainment unless you were with mileage program Getting off the plane was super slow

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