$108 Cheap flight deals from Madison (MSN) to San Juan (SJU)

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This Weekend's Flight Deals from Madison to San Juan

This weekend's flight prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Sun, Apr 27 - Fri, May 2
MSN
Dane County Regional
SJU
Luis Munoz Marin Intl.
$369 Roundtrip, found 12 hours ago
$369
Roundtrip
found 12 hours ago
Select American Airlines flight, departing Sun, Apr 27 from Dane County Regional to Luis Munoz Marin Intl., returning Fri, May 2, priced at $369 found 12 hours ago

Airfares from $108 One Way, $292 Round Trip from Madison to San Juan

Prices starting at $292 for return flights and $108 for one-way flights to San Juan were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Wed, May 7 - Wed, May 14
MSN
Madison
SJU
San Juan
$292 Roundtrip, found 5 hours ago
$292
Roundtrip
found 5 hours ago
Select American Airlines flight, departing Wed, May 7 from Madison to San Juan, returning Wed, May 14, priced at $292 found 5 hours ago
Sat, May 24 - Wed, May 28
MSN
Madison
SJU
San Juan
$329 Roundtrip, found 1 day ago
$329
Roundtrip
found 1 day ago
Select Delta flight, departing Sat, May 24 from Madison to San Juan, returning Wed, May 28, priced at $329 found 1 day ago
Wed, May 7 - Wed, May 14
MSN
Madison
SJU
San Juan
$349 Roundtrip, found 5 hours ago
$349
Roundtrip
found 5 hours ago
Select American Airlines flight, departing Wed, May 7 from Madison to San Juan, returning Wed, May 14, priced at $349 found 5 hours ago
Tue, May 20 - Thu, May 29
MSN
Madison
SJU
San Juan
$368 Roundtrip, found 1 day ago
$368
Roundtrip
found 1 day ago
Select American Airlines flight, departing Tue, May 20 from Madison to San Juan, returning Thu, May 29, priced at $368 found 1 day ago
Sun, Apr 27 - Fri, May 2
MSN
Madison
SJU
San Juan
$369 Roundtrip, found 12 hours ago
$369
Roundtrip
found 12 hours ago
Select American Airlines flight, departing Sun, Apr 27 from Madison to San Juan, returning Fri, May 2, priced at $369 found 12 hours ago

San Juan economy flight packages

Price found within the past 48 hours. Click for updated prices.
Urbana Hotel
2.0-star property

Urbana Hotel

8.4/10 Very Good! (198 reviews)

Jun 10 - Jun 16

6 night stay

Madison (MSN) to San Juan (SJU)

United • Non-stop roundtrip • Coach
Save 100% on your flight
per person
just found
The Urbana is carved out of newly renovated historic buildings, making for a unique and centrally-located stay. The staff is friendly an helpful, and a bar across the street offers drinks and music. While I stayed there, a couple big music/dance events happened at an events venue also on the block, so the whole street felt alive and energetic. It is about a mile walk to the center of Old San Juan, and you pass lots of plazas and sites of interest on the way. A bakery is just down the block offering breakfast and lunch options, and a co-working space next door is available for guests who need to be on the clock while in town. The rooms are small, but with the beach only 10-15 minutes away on foot, and with San Juan all around you, who needs to be in the room? Even so, the hotel was meticulously clean and comfortable. Depending on the time of day, the water might be more warm than hot, but the in-room AC makes climate control easy. I will definitely seek to stay here again!

Reviewed on Mar 13, 2023

Hyatt Regency Grand Reserve Puerto Rico
4.0-star property

Hyatt Regency Grand Reserve Puerto Rico

8.8/10 Excellent! (2,095 reviews)

Jun 10 - Jun 16

6 night stay

Madison (MSN) to San Juan (SJU)

United • Non-stop roundtrip • Coach
per person
just found
I have nothing to complain about, one of the best stays I’ve had in a long time. All the staff were very attentive and willing to help.

Reviewed on Apr 5, 2025

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More About Flying To San Juan from Madison

Route Information for Flights from Madison to San Juan

Origin Airport IATA Code
MSN
Destination Airport IATA Code
SJU
Distance
Direct Flight Airlines
Earliest Flight Arrival
Latest Flight Arrival

Madison to San Juan

Getting a spectacularly low fare on Madison to San Juan flights is always possible when you use Orbitz as your personal travel planner. Orbitz is your essential travel resource for low cost flights from Madison to San Juan, discount hotel accommodations, cheap car rentals, and more.

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Stay in Your Budget and Still Get Great Accommodations

Orbitz shoppers can access affordable vacation packages and have the option of booking their departure and arrival flights through different airlines, making travel less costly and more convenient. The best prices on flights from Madison to San Juanare always found on Orbitz.

Frequently asked questions

Am I able to catch a flight from Madison to San Juan now?
If you’re agonizing over quarantine and travel restrictions when flying from Madison to San Juan, go right to the Covid-19 Travel Advisor.
What is the shortest flight from Madison to San Juan?
The shortest flight from MSN to Isla Verde Intl. Airport is 5 hours and 31 minutes. Order a refreshment from the drink trolley, work on your travel itinerary or read a few magazines — you’ll have the time on this medium-haul journey.
If I am not able to travel due to COVID-19, can I cancel my flight to San Juan?
We get that traveling right now has its challenges, so it’s good to know that many reservations booked through us are able to be cancelled or changed. If your travel plans to San Juan have been affected by COVID-19, a lot of airlines are making things easier by offering credits to use at a later date. Just sign in to your account and you’ll quickly see what options are available. Our Customer Service Portal is the place to go for more information.
Are there flights to San Juan with flexible change policies?
In most cases you’ll have the option to reschedule your flight to San Juan without a change fee. All you have to do then is pay the difference between the old flight and the new one. Look for the “no change fees” filter and book with confidence.
What is the cheapest day of the week to fly?
Consider flying out early in the week to save on your airfare. Orbitz data from 2020 shows that Monday is the cheapest day to depart, followed by Tuesday. Saturday showed the highest average ticket prices likely because many travelers prefer to start their vacation on a weekend.
What is the cheapest month to fly?
We won’t keep you guessing, according to Orbitz data the cheapest month to fly is August. Perfect for those who need a weekend getaway, or just a break from it all before the weather changes. Be aware that the most expensive time to fly is the height of summer, with ticket prices peaking in the month of June.
How can I save money on flights?
To really save big on your next vacation, think outside the box. Select two different airlines or fare types for your return trip and you’ll generally get a much better deal. Those who tried this on Orbitz in 2020 saved up to 45% on their airfares. Get mixing and matching today!

Fare, taxes & fees: Fares include all taxes and fees, except baggage fees. Rates shown reflect fares found by other Orbitz users over the past 7 days. Due to rapidly changing airline prices & seat availability, these fares may no longer be available.

Refunds/changes/cancellations: Itinerary changes, if permitted for the fare, will have a $30 service fee charged by Orbitz. Additional airline charges may apply.

Other conditions: Schedules, fares and rules are subject to change without notice. Seats are limited and may not be available on all flights/dates or in all markets. Lower fares may be available. Fares will not be honored retroactively or in exchange for any wholly/partially unused ticket. Tickets are non-transferable and non-refundable. Fare rules are provided for the selected itinerary before booking.