$163 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 9/13. 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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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, Aug 18 - Tue, Aug 25
United Airlines Logo
7:00 am - 6:56 pm
SJU
-
MSN
12h 56m
2 stops
United Airlines Logo
5:00 am - 2:44 pm
MSN
-
SJU
8h 44m
1 stop
$280United Airlines
Tue, Aug 18 - Tue, Aug 25
American Airlines Logo
6:51 am - 5:17 pm
SJU
-
MSN
11h 26m
1 stop
American Airlines Logo
11:33 am - 11:59 pm
MSN
-
SJU
11h 26m
1 stop
$326American Airlines
Sat, Aug 1 - Sat, Aug 15
American Airlines Logo
7:25 am - 11:59 pm
SJU
-
MSN
17h 34m
1 stop
American Airlines Logo
6:00 am - 6:20 pm
MSN
-
SJU
11h 20m
2 stops
$409American Airlines
Tue, Jul 7 - Tue, Jul 14
American Airlines Logo
3:40 pm - 11:42 pm
SJU
-
MSN
9h 02m
1 stop
American Airlines Logo
6:00 am - 10:57 pm
MSN
-
SJU
15h 57m
1 stop
$449American Airlines
Sun, Jul 26 - Sun, Aug 2
JetBlue Logo
2:42 pm - 10:38 pm
SJU
-
MSN
8h 56m
1 stop
JetBlue Logo
5:48 am - 4:45 pm
MSN
-
SJU
9h 57m
1 stop
$461JetBlue
Fri, Jun 5 - Mon, Jun 8
American Airlines Logo
6:21 am - 9:20 pm
SJU
-
MSN
15h 59m
1 stop
American Airlines Logo
6:01 am - 11:00 pm
MSN
-
SJU
15h 59m
1 stop
$510American Airlines
Tue, Jul 14 - Wed, Jul 29
American Airlines Logo
5:45 am - 10:53 pm
SJU
-
MSN
18h 08m
1 stop
American Airlines Logo
6:00 am - 10:57 pm
MSN
-
SJU
15h 57m
1 stop
$537American Airlines
Fri, Jun 5 - Mon, Jun 8
American Airlines Logo
10:29 am - 9:20 pm
SJU
-
MSN
11h 51m
2 stops
American Airlines Logo
6:01 am - 6:25 pm
MSN
-
SJU
11h 24m
2 stops
$550American Airlines
Tue, Jul 14 - Wed, Jul 29
American Airlines Logo
5:45 am - 10:53 pm
SJU
-
MSN
18h 08m
1 stop
American Airlines Logo
9:18 am - 10:59 pm
MSN
-
SJU
12h 41m
2 stops
$577American Airlines
Tue, Jul 14 - Wed, Jul 29
Delta Logo
7:30 am - 3:51 pm
SJU
-
MSN
9h 21m
1 stop
Delta Logo
6:00 am - 4:45 pm
MSN
-
SJU
9h 45m
2 stops
$578Delta
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 3 days.

In the last 3 days, the cheapest flight deal to Madison was found on the route from San Juan, at $280 return. The most popular connection is from Denver to Madison and KAYAK users have found round-trip deals for as low as $260 in the last 3 days.

Good to know

Low seasonAugust
Cheapest flight$163
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 $280 return. The most popular connection is from Denver to Madison and KAYAK users have found round-trip deals for as low as $260 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 1,246 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 11644 reviews
6.9Entertainment
6.4Food
7.5Boarding
7.9Crew
7.2Comfort
Airline reviews

The homeless eat better than what was served on that plane. Pretzels and ice cream? My last trip to Europe. Everything is small, but the bill.

4.0 OkayAnonymous, May 2026
ATH - ORD
Read more American Airlines reviews

The homeless eat better than what was served on that plane. Pretzels and ice cream? My last trip to Europe. Everything is small, but the bill.

Cancelled flight. Still waiting to get home for grand daughter’s graduation .

So overall the flight was just average and nothing special. They overbooked some of the flights and they ended up running out of overhead storage space so we had to check our carry-ons which wasn't terrible but we were inconvenienced because of the second connecting flight with a long layover we couldn't get our bags until the final destination. Most of the flight attendants were pretty good and overall the meals were not that great because the chicken was dry and overcooked. They also didn't provide butter or any kind of spread with the bread which is cheap and concerning. The American airlines staff at the check-in counter was kind of unprofessional because this lady just started singing in the middle of checking us in and that's weird. The worst part of the flights was the terrible conditions of the bathrooms which were unclean and did not have toilet paper or toilet tissue available which is kind of insane for a 14-hour and 8 and 1/2 hour flight.

The seat when "flat" was not flat and pad was too thin to cover it.

Awful customer service, horrible experience. We travel a lot domestic & international- worst flights to/from ever. Brief bkgd as Inhate to relive this experience: booked and chose 2 seats 4 months prior in Premium Economy - last row end seats close to bathroom, no one behind us, plenty of legroom;, underwear storage — flown this was on other airlines, love it. We receive notice 4 days before scheduled overseas flight - plane has changed, new seats assigned. Seats are split into single seats, opposites of the plane, FRONT Row so no reachable storage. Called BOTH British Air & America. American “switched planes and the seats you want are taken;” British Air “Yes, we’ll be glad to accommodate you (type type type). Just ask at the Gate and someone will give you new boarding passes with seats together in middle, OK?” — OK. —At Gate the attendant looks us up saying “No, it is an overbooked flight and yours are the only seats available.” But but but wait, “We were TOLD our seats had been switched and seated together?” Gate attendant “Well they were wrong and don’t change your seats. Your original seats are where you’ll sit.”. Right. No help WHATSOEVER. We sit opposite on way there, wife VERY disgruntled, a Tol 5 worst ways to start a 3-week bus tour of UK. We promise to NEVER FLY AMERICAN OR BROTISH AIR EVER, and we have 3 more extensive trips planned..

Requested early boarding to disinfect seat, tray table, etc. before general boarding. Instructed to board after wheelchair passengers. Waited on jet bridge behind 12 wheelchair passengers. Stopped immediately after entering plane to wait for gate agent in rear of plane cleaning a seat that was wet, got to my row and found both seats adjacent to mine already occupied, with the lack of room making it impossible for me to clean my own space and defeating the purpose of my boarding early. Cleaned the armrests and tray table as best I could.

Seat bottom cushions are not good. I’m 165# & they hurt my butt. Plenty of legroom.

The wifi experience is awful. I had to try again and again, taking over 30 minutes, to connect to the wifi. I had to watch the same two ads over and over until I was finally successful. Once connected, it was anything but "high speed" and disconnected at least three times during the flight.

Fine. Nothing to write home about. The plane left on time, and arrived on time.

I was downgraded from first class to coach due to an airplane change. They pulled me out of line and I was the very last person to board the plane stuck in the middle seat with no overhead place to put my carry-.on. Very poor customer service.

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Everything you need to know for your flight to Madison

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