SJU - MSN

$133 Find Cheap Flights from San Juan 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 from San Juan to Madison departing on 4/22. 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 in flight searches from San Juan to Madison, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from San Juan to Madison, as well as popular online travel agencies
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41,299,237 searches in the past 7 days on KAYAK

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Everything you should know

Cheapest round-trip
$520
United Airlines
Tue 2/24Sat 2/28
SJU - MSN • 2 stops
Cheapest one-way
$133
Typical prices: $196-$351
American Airlines
Wed 4/22
SJU - MSN • 1 stop
Top airlines
American Airlines
Cheapest • from $510 (round-trip)
American Airlines
Best reviews • 7.2 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Nonstop flights
Not available
There are currently no direct flights between San Juan and Madison. You'll need at least 1 connection.
Insights
Insights
Insights
Insights
Top layover airports
Chicago (ORD)
Cheapest • Avg $471 (round-trip)
Philadelphia (PHL)
Shortest trip • 7h 53m (one-way)
Insights
Insights
Insights
Insights
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KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Madison!
Flight Deals
Booking Insights
Flight Deals

Cheap Flights from San Juan to Madison (SJU-MSN)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from San Juan 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 San Juan to Madison

Tue, Feb 24 - Sat, Feb 28
United Airlines Logo
2:05 am - 11:53 am
SJU
-
MSN
11h 48m
2 stops
United Airlines Logo
3:53 pm - 6:11 am
MSN
-
SJU
12h 18m
2 stops
$520United Airlines
Tue, Feb 24 - Sat, Feb 28
United Airlines Logo
2:05 am - 11:53 am
SJU
-
MSN
11h 48m
2 stops
United Airlines Logo
2:48 pm - 6:11 am
MSN
-
SJU
13h 23m
2 stops
$540United Airlines
Wed, Feb 25 - Sat, Feb 28
United Airlines Logo
2:10 pm - 8:15 pm
SJU
-
MSN
8h 05m
1 stop
United Airlines Logo
5:44 pm - 3:40 pm
MSN
-
SJU
19h 56m
1 stop
$670United Airlines
Wed, Feb 25 - Sat, Feb 28
United Airlines Logo
8:30 am - 2:57 pm
SJU
-
MSN
8h 27m
1 stop
United Airlines Logo
2:48 pm - 3:40 pm
MSN
-
SJU
22h 52m
1 stop
$690United Airlines
Wed, Feb 25 - Sat, Feb 28
United Airlines Logo
3:46 pm - 10:14 am
SJU
-
MSN
20h 28m
2 stops
United Airlines Logo
3:53 pm - 6:11 am
MSN
-
SJU
12h 18m
2 stops
$740United Airlines
Wed, Feb 25 - Sat, Feb 28
United Airlines Logo
4:52 pm - 2:57 pm
SJU
-
MSN
24h 05m
1 stop
United Airlines Logo
2:48 pm - 9:00 pm
MSN
-
SJU
28h 12m
1 stop
$820United Airlines
Booking Insights

KAYAK's insights & trends for San Juan to Madison flights

Get data-powered insights and trends into flights from San Juan to Madison to help you find the cheapest flights, the best time to fly and much more.

Which airlines provide the cheapest flights from San Juan to Madison?

The cheapest round-trip price for the route for each airline clicked by KAYAK users in the last 72 hours.

In the past 3 days, the cheapest round-trip tickets from San Juan to Madison were found on American Airlines ($510) and United Airlines ($781).

Good to know

Low seasonAugust
Cheapest flight$133
Best time to beat the crowds with an average 40% drop in price.
Most popular time to fly with an average 19% increase in price.
Flight from San Juan to Madison

When to book flights from San Juan to Madison

Are your dates flexible? Find out the best times to travel from San Juan to Madison based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking San Juan to Madison flights

  • What is the cheapest flight from San Juan Luis Munoz Marin Intl Airport to Madison?

    In the last 3 days, the lowest price for a flight from San Juan Luis Munoz Marin Intl Airport to Madison was $133 for a one-way ticket and $510 for a round-trip.

  • Do I need a passport to fly between San Juan and Madison?

    A passport is required to fly from San Juan to Madison.

  • Which airports will I be using when flying from San Juan to Madison?

    San Juan airport is called San Juan Luis Munoz Marin Intl and the only airport in Madison is Madison Truax Field.

  • Which aircraft models fly most regularly from San Juan to Madison?

    We unfortunately don’t have that data for this specific route.

  • Which airline alliances offer flights from San Juan to Madison?

    oneworld is the only airline alliance operating flights between San Juan and Madison.

  • How does KAYAK find such low prices on flights from San Juan 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 from San Juan to Madison.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from San Juan to Madison?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Madison from San Juan is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from San Juan 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 to San Juan with another airline. Booking your flights between San Juan and MSN can sometimes prove cheaper using this method.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from San Juan 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 from San Juan up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Reviews of the top airline flying from San Juan to Madison

 
See real verified KAYAK customer reviews for airlines flying from San Juan to Madison. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from San Juan 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.
7.2
American AirlinesOverall score based on 11339 reviews
8.0Crew
6.4Food
7.5Boarding
6.9Entertainment
7.2Comfort
Airline reviews

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

6.0 GoodGovinda, Feb 2026
DFW - MSN
Read more American Airlines reviews

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

Arriving plane went to wrong gate. Flight Attendant was late. Was in no Hurry when he arrived. Flight was fine. Plane had to wait 20 minutes to get assigned a gate due to designated gate tied up. barely connected.. Boarded extremely late on final leg of trip.

We arrived 25 minutes early only to be told our gate was occupied and so we sat for close to 30 minutes to pull into a gate. That’s not an early arrival!

Experience was great. The best part is the free Wi-Fi connection which helps me to work on the flight

The gate agent had a really bad attitude and refused to help me get on the standby list. She just handed me a card and said I needed to call a number. I asked her to help with the AA app on my phone and she just shrugged and said she didnt know. After a few phone calls, I eventually just went to a different gate agent on the other side of the terminal and got the help I needed.

The TSA check in took 1.5 hours to get through in Austin and I missed my flights back to DC

As previously stated the delay I experienced flying from Wichita to Chicago caused a host of issues. When I finally was able to be booked on the last remaining American flight from Chicago to Cincinnati, the gate changed four times with the last change occurring very near the scheduled boarding time. While I didn't have a problem moving from gate to gate, I did notice and make note of others that had mobility issues and had to move each time for the gate change.

Overall, my last three trips on American Airlines have all been either delayed or "rescheduled" due to mechanical issues. At least on delay caused me to miss two possible connecting flights each later than the first. My last option for my last connection required the assistance of the onsite service desk (O'Hare Airport). The wait time for the service desk was such that it jeopardized getting booked on the last connecting flight available for the night. Suffice it to say, my latest experiences with American Airlines have caused me extensive loss of productive business and personal time and can therefore be classified as significantly less than satisfactory.

There was free WiFi (definitely a plus), but the flight was delayed 45 minutes waiting on a catering truck that never arrived. The pilot said there would be food vouchers given out at the end of the gangway to make up for the inconvenience, but there was no one offering those. Delay made me late for work!

Waiting for gate in RDU for more than 20mins is crazy.

Everything you need to know for your flight from San Juan to Madison

Information on your arrival and departure airports