$159 Find Cheap Flights from Puerto Rico to Madison - Compare and Save

1 adult
1 adult, Economy, 0 bags

Save 21% or more on flights. Compare deals from all over the web.

Never overpay with our price tracking tools.

Filter searches by price, airline and more to find your best flights.

Flight Deals
Booking Insights
Flight Deals

Cheap Flights from Puerto Rico to Madison

 
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Puerto Rico to Madison

Tue, Jan 12 - Tue, Jan 19
United Airlines Logo
1:09 am - 10:10 amBQN  Aguadilla Borinquen-MSN Madison Truax Field
11h 01m2 stops Newark Chicago O'Hare Intl
United Airlines Logo
8:15 am - 11:57 pmMSN  Madison Truax Field-BQN Aguadilla Borinquen
13h 42m2 stops Chicago O'Hare Intl Newark
$356United Airlines
Wed, Dec 2 - Wed, Dec 9
United Airlines Logo
1:09 am - 10:01 amBQN  Aguadilla Borinquen-MSN Madison Truax Field
10h 52m2 stops Newark Chicago O'Hare Intl
United Airlines Logo
8:15 am - 11:57 pmMSN  Madison Truax Field-BQN Aguadilla Borinquen
13h 42m2 stops Chicago O'Hare Intl Newark
$356United Airlines
Mon, Nov 2 - Tue, Nov 10
United Airlines Logo
1:09 am - 11:49 amBQN  Aguadilla Borinquen-MSN Madison Truax Field
12h 40m2 stops Newark Chicago O'Hare Intl
United Airlines Logo
8:15 am - 11:57 pmMSN  Madison Truax Field-BQN Aguadilla Borinquen
13h 42m2 stops Chicago O'Hare Intl Newark
$356United Airlines
Fri, Dec 11 - Sat, Jan 9
American Airlines Logo
2:28 pm - 11:19 pmSJU  San Juan Luis Munoz Marin Intl-MSN Madison Truax Field
10h 51m2 stops Charlotte Douglas Chicago O'Hare Intl
American Airlines Logo
6:00 am - 9:11 pmMSN  Madison Truax Field-SJU San Juan Luis Munoz Marin Intl
13h 11m2 stops Washington, D.C. Reagan-National Charlotte Douglas
$386American Airlines
Sat, Oct 31 - Sat, Nov 7
American Airlines Logo
2:54 pm - 11:12 pmSJU  San Juan Luis Munoz Marin Intl-MSN Madison Truax Field
9h 18m1 stop Chicago O'Hare Intl
American Airlines Logo
8:10 am - 9:13 pmMSN  Madison Truax Field-SJU San Juan Luis Munoz Marin Intl
11h 03m1 stop Charlotte Douglas
$386American Airlines
Sat, Oct 31 - Sat, Nov 7
American Airlines Logo
6:30 am - 5:13 pmSJU  San Juan Luis Munoz Marin Intl-MSN Madison Truax Field
11h 43m2 stops Miami Dallas/Fort Worth
American Airlines Logo
9:15 am - 9:13 pmMSN  Madison Truax Field-SJU San Juan Luis Munoz Marin Intl
9h 58m2 stops Chicago O'Hare Intl Charlotte Douglas
$386American Airlines
Sat, Oct 31 - Sat, Nov 7
United Airlines Logo
3:55 pm - 11:07 pmSJU  San Juan Luis Munoz Marin Intl-MSN Madison Truax Field
8h 12m1 stop Chicago O'Hare Intl
United Airlines Logo
8:15 am - 10:22 pmMSN  Madison Truax Field-SJU San Juan Luis Munoz Marin Intl
12h 07m2 stops Chicago O'Hare Intl Washington, D.C. Dulles Intl
$386United Airlines
Thu, Dec 24 - Thu, Jan 7
Delta Logo
3:00 pm - 8:45 pmSJU  San Juan Luis Munoz Marin Intl-MSN Madison Truax Field
7h 45m1 stop Detroit Metropolitan Wayne County
Delta Logo
6:15 am - 4:10 pmMSN  Madison Truax Field-SJU San Juan Luis Munoz Marin Intl
7h 55m1 stop Minneapolis St Paul
$431Delta
Tue, Oct 20 - Sat, Oct 24
Multiple Airlines Logo
6:21 pm - 9:58 amSJU  San Juan Luis Munoz Marin Intl-MSN Madison Truax Field
16h 37m1 stop Tampa
Multiple Airlines Logo
10:38 am - 1:31 pmMSN  Madison Truax Field-SJU San Juan Luis Munoz Marin Intl
25h 53m2 stops Tampa Fort Lauderdale
$432Multiple Airlines
Mon, Nov 30 - Tue, Dec 8
Multiple Airlines Logo
3:47 am - 9:50 amBQN  Aguadilla Borinquen-MSN Madison Truax Field
8h 03m1 stop Orlando
Multiple Airlines Logo
10:30 am - 2:52 amMSN  Madison Truax Field-BQN Aguadilla Borinquen
14h 22m1 stop Orlando
$439Multiple 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 Southwest and United Airlines.

Good to know

Low season

December

Cheapest flight

$159
Best time to beat the crowds with an average 18% drop in price.
Most popular time to fly and prices are also 16% 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 972 direct flights from within Puerto Rico to Madison. The most common day for departures is Sunday, with 17% 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 airlines flying from Puerto Rico to Madison

 
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.
7.4
United AirlinesOverall score based on 10283 reviews
6.7Food
7.3Comfort
7.1Entertainment
7.7Boarding
8.1Crew
Airline reviews

There were no vegan options for first class. Even though we were promised the satellite internet for free, we received NO wifi at all. Even though we were promised a 20-min early arrival, we ended up over 30 mins late.

4.0 OkayMila, Oct 2026
Read more United Airlines reviews

There were no vegan options for first class. Even though we were promised the satellite internet for free, we received NO wifi at all. Even though we were promised a 20-min early arrival, we ended up over 30 mins late.

No water or beverage was provided. I had to ask for water. The sole flight attendant had more interest in selling the credit card. In addition when we got to Dulles the plane and gate were misaligned and it took at least 15 minutes to get off the plane.

Really delayed, no effort to support customers other than “sometimes we run late.”

Awful. There was a minor problem with a fridge and they had us 2 hours in the runway before take off. The paper work alone took them half hour. There was no attemp to make up time up while in teansit and when we arrived, they had us another half hour in the plane because of traffic. I, and a bunch of people, lost their onnection flights for 5 to 10 minutes. Not even the attemp to wait given thar all delays, but the taxing, were United's fault. Then another 45 mins to get an agent and no flight alternatives for 2 days. Im am very disapointed with this "premium carrier".

Deplaning was delayed because of Jetbridge equipment issues in MKE, causing an issue on an otherwise great flight.

Delays took 2hours and thirty minutes making me miss my connecting flight and make me sit in the Chicago airport for 9 hours

IT WAS A LONG TIME SINCE THE LAST TIME I TRAVELED. I THOUGHT I WAS TO BE LOST BUT EVERYONE WAS PRETTY NICE WITH ME AND MADE MY EXPERIENCE NICE. THANKS

No real agent onsite helping you for missing luggage there. Not like the other airline next to UA desk, they have staff attending in their desk assisting answer/helping luggage issue, even after midnight.

There was a delay that was unexpected. The seats were uncomfortable for the length of the flight.

The wi-fi was awful. I paid $8 each way and got little , except frustration. .

Our gate was changed several times, and the gate agents were just as in the dark as all of us in knowing when our plane would arrive at PHL.

The flight from Milwaukee to Dallas was great the staff absolutely amazing. After that EVERYTHING WENT DOWN HILL!!! ABSOLUTELY HORRIBLE!!! WILL NOT FLY THIS AIRLINE AGAIN

not sure why you ask about food, I n3ver get food on flights except maybe cookies or pretzels. wifi was slow and in and out most of the flight not good.

there are no options s for snack besides cookies would ve nice to have a salty option n

Never ontime and always delays. Long waits for customer service and often app doesn’t work

We were upgraded to First Class and it was a great flight

it was fine, decent flight... dont get food besides cookies or pretzels so not sure why you ask about food. same for entertainment..

this plane was really old, had exit row seats and tray was in arm of seat so super uncomfortable to use. another seat they could t even use the tray it was broke. seat i. front of me had duct tape on it cause seat was ripped open... this plane should either be updated or retired.

American airlines suck they delay the flights all the time made me sleep in an airport because my flight was delayed and I miss my connecting flight

American cancelled our flight home. Zero option for hotel, alternative transportation and took 3 hours to find our bags so we could take a 3 hour UBER ride home on our dime. Never flying AA again.

Traveling to a place near Madison?

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

More options for your flight to Madison