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Madison

$113+ Cheap flights from San Juan to Madison (MSN)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 4/24. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — MSN
Apr 29 — May 61
Wed 4/29
Wed 5/6
1 adult, Economy
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Cheap flight deals from San Juan to Madison

Cheapest flights from San Juan to Madison
Explore the most affordable flight options available from San Juan to Madison. Find the lowest fares from popular airlines and budget airlines, with prices last updated on March 30, 2026.

This American Airlines deal was found by Cheapflights users on 3/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/64:30 pm
SJU
-
MSN
1 stop8h 34m
American Airlines
Sat 5/1611:35 am
MSN
-
SJU
1 stop8h 20m
American Airlines
Deal found 3/30$334
This American Airlines deal was found by Cheapflights users on 3/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/76:00 am
SJU
-
MSN
1 stop18h 28m
American Airlines
Tue 5/1211:33 am
MSN
-
SJU
1 stop8h 18m
American Airlines
Deal found 3/26$356
This Delta deal was found by Cheapflights users on 3/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/12:45 pm
SJU
-
MSN
1 stop8h 42m
Delta
Wed 5/66:00 am
MSN
-
SJU
2 stops13h 26m
Delta
Deal found 3/30$358
This American Airlines deal was found by Cheapflights users on 3/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/56:20 am
SJU
-
MSN
1 stop16h 00m
American Airlines
Mon 6/86:01 am
MSN
-
SJU
1 stop16h 00m
American Airlines
Deal found 3/26$378
This United Airlines deal was found by Cheapflights users on 3/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/73:56 pm
SJU
-
MSN
1 stop7h 58m
United Airlines
Tue 5/128:10 am
MSN
-
SJU
2 stops12h 14m
United Airlines
Deal found 3/29$412
This American Airlines deal was found by Cheapflights users on 3/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/76:00 am
SJU
-
MSN
1 stop18h 28m
American Airlines
Sun 5/106:20 am
MSN
-
SJU
1 stop14h 45m
American Airlines
Deal found 3/25$428
This United Airlines deal was found by Cheapflights users on 3/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/301:00 am
SJU
-
MSN
2 stops11h 37m
United Airlines
Wed 5/66:30 am
MSN
-
SJU
2 stops13h 54m
United Airlines
Deal found 3/30$436
This United Airlines deal was found by Cheapflights users on 3/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/57:20 am
SJU
-
MSN
2 stops12h 47m
United Airlines
Sat 5/99:55 am
MSN
-
SJU
2 stops10h 29m
United Airlines
Deal found 3/29$439

Find flight deals from San Juan to Madison

Discover tips and strategies to find the most affordable flight options for your journey from San Juan (PR1) to Madison (MSN). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated March 30, 2026.

Round-trip from

$334
(American Airlines)

One-way from

$113
(United Airlines)

Popular in

March

Cheapest in

August

Average price

$588
From San Juan to Madison Truax Field
Search Deals
One-way flight from San Juan to Madison Truax Field
Search Deals
Highest demand for flights based on searches. 12% potential increase in price ($65 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($15 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in March 2026
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Cheapflights Fare Finder

 
Customize your flight search to find flights from San Juan to Madison that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated March 30, 2026.
Use the filters below to find and compare flights from San Juan to Madison that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

San JuanMadison

SJU - MSN

SJUMSN

San Juan Luis Munoz Marin Intl

Thu 5/7

6:00 am-11:28 pm

1 stop18h 28m

Madison Truax Field

Tue 5/12

11:33 am-8:51 pm

1 stop8h 18m

$356

San JuanMadison

SJU - MSN

SJUMSN

San Juan Luis Munoz Marin Intl

Fri 6/5

6:20 am-9:20 pm

1 stop16h 00m

Madison Truax Field

Mon 6/8

7:00 am-10:45 pm

1 stop14h 45m

$399

San JuanMadison

SJU - MSN

SJUMSN

San Juan Luis Munoz Marin Intl

Thu 5/7

3:56 pm-10:54 pm

1 stop7h 58m

Madison Truax Field

Tue 5/12

8:10 am-9:24 pm

2 stops12h 14m

$412
Quickest round-trip

San JuanMadison

SJU - MSN

SJUMSN

San Juan Luis Munoz Marin Intl

Tue 5/5

7:40 am-3:00 pm

1 stop8h 20m

Madison Truax Field

Sat 5/9

9:55 am-9:24 pm

2 stops10h 29m

$439

San JuanMadison

SJU - MSN

SJUMSN

San Juan Luis Munoz Marin Intl

Thu 4/30

1:00 am-11:37 am

2 stops11h 37m

Madison Truax Field

Wed 5/6

6:30 am-2:44 pm

1 stop7h 14m

$451
Cheapest one-way

San JuanMadison

SJU - MSN

SJUMSN

San Juan Luis Munoz Marin Intl

Wed 4/15

6:15 am-4:17 pm

1 stop11h 02m

$153

San JuanMadison

SJU - MSN

SJUMSN

San Juan Luis Munoz Marin Intl

Tue 4/21

12:53 pm-11:01 pm

1 stop11h 08m

$163

San JuanMadison

SJU - MSN

SJUMSN

San Juan Luis Munoz Marin Intl

Wed 6/24

6:00 am-11:19 pm

2 stops18h 19m

$216

San JuanMadison

SJU - MSN

SJUMSN

San Juan Luis Munoz Marin Intl

Tue 4/14

7:25 am-11:01 pm

1 stop16h 36m

$245

San JuanMadison

SJU - MSN

SJUMSN

San Juan Luis Munoz Marin Intl

Wed 4/15

11:43 am-9:14 pm

2 stops10h 31m

$251

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/29

Showing 1-10 of 13 resultsSorted by cheapest first
1
2

Best time to book a flight from San Juan to Madison

Have a flexible travel schedule? Discover the best time to fly to Madison from San Juan with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

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

What is the cheapest month to book a flight from San Juan to Madison?

Currently, September is the cheapest month in which you can book a flight from San Juan to Madison (average of $113). Flying from San Juan to Madison in June is currently the most expensive (average of $337). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

How much does it cost to fly round-trip from San Juan to Madison?

Reviews of airlines servicing Madison

Get insights into the airlines that provide service to Madison. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Madison. Reviews last updated March 30, 2026.
See what other customers who have flown with American Airlines from San Juan to Madison have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
American Airlines
7.1
Good
11,531 reviews

Boarding

7.5

Crew

7.9

Entertainment

6.9

Overall

7.1

Food

6.4

Comfort

7.2

Reviews

1 / 20
4.0
Okay

Elizabeth,Mar 2026

ORD - MIA

Staff was rude and flight attendants 2 out of 3 looked like they had just been thru a hurricane.
American Airlines
7.1
Good
11,531 reviews
American Airlines
7.1
Good
11,531 reviews

Boarding

7.5

Crew

7.9

Entertainment

6.9

Overall

7.1

Food

6.4

Comfort

7.2

Reviews

1 / 20
4.0
Okay

Elizabeth,Mar 2026

ORD - MIA

Staff was rude and flight attendants 2 out of 3 looked like they had just been thru a hurricane.

Related info for your journey

Find useful and relevant information for your journey from San Juan to Madison. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly into for flights to Madison from San Juan?

    If you book a flight to Madison from San Juan, you will be flying to Truax Field, which is the city’s only airport. Madison Truax Field (MSN) is located 5.4 mi from the center of Madison. There are 0 flights from San Juan to Truax Field per day from 1 airline.

  • How long is the flight from San Juan to Madison?

    Airlines like American Airlines fly from San Juan to Madison in about 18h 28m. The time it takes to get you to your destination can typically vary by up to . The distance from San Juan to Madison is about 2180 mi.

  • What is the cheapest airline to fly from San Juan to Madison round-trip?

    According to our current data, American Airlines ($265), offers the cheapest pricing from San Juan to Madison. You may be able to fly from San Juan to Madison for 41% less than the average price by searching for this airline.

  • Can I find deals for flights from San Juan to Madison that include hotel bookings?

    Yes. In addition to deals on San Juan to Madison flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from San Juan to Madison?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from San Juan to Madison.

  • Can I find deals for business class flights from San Juan to Madison?

    Yes. Cheapflights offers flight deals from San Juan to Madison by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from San Juan to Madison?

    Currently, September is the cheapest month in which you can book a flight from San Juan to Madison (average of $113). Flying from San Juan to Madison in June is currently the most expensive (average of $337). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Traveling to a place near Madison?

Book flights to Madison if you plan to visit one of these locations
Portage
Middleton
Baraboo
Fitchburg

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Alternative routes for San Juan to Madison

See prices for flight routes from nearby airports that may be better suited for you.
Luis Munoz Marin Intl to O'Hare Intl flights
Luis Munoz Marin Intl to Milwaukee flights
Aguadilla to O'Hare Intl flights

Top airline flying from San Juan to Madison

Discover the top airline that operate flights from San Juan to Madison. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated March 30, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$265Average$550FlexibilityNo cancel feeOn-time71%

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