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Cheap flights from Madison to Puerto Rico from $118

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Madison to Puerto Rico departing on 11/18. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
0 bags

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Find the cheapest flights from Madison to Puerto Rico

Cheap round-trip flights

United Airlines Logo
2:56 pm - 6:11 amMSN-SJU
13h 15m2 stops
United Airlines Logo
8:35 am - 2:10 pmSJU-MSN
7h 35m1 stop
$235United Airlines
Find Deal
Sat, Jan 31 - Thu, Feb 5
United Airlines Logo
8:15 am - 10:22 pmMSN-SJU
12h 07m2 stops
United Airlines Logo
2:05 am - 11:44 amSJU-MSN
11h 39m2 stops
$267United Airlines
Find Deal
Tue, Dec 9 - Mon, Dec 15
American Airlines Logo
12:19 pm - 8:50 pmMSN-SJU
6h 31m1 stop
American Airlines Logo
4:40 pm - 11:42 pmSJU-MSN
9h 02m1 stop
$268American Airlines
Find Deal
Tue, Jan 20 - Wed, Jan 28
American Airlines Logo
4:17 pm - 11:45 amMSN-SJU
17h 28m1 stop
American Airlines Logo
4:40 pm - 10:27 amSJU-MSN
19h 47m2 stops
$295American Airlines
Find Deal
Sun, Jan 11 - Wed, Jan 21
American Airlines Logo
4:17 pm - 11:45 amMSN-SJU
17h 28m1 stop
American Airlines Logo
7:20 am - 6:42 pmSJU-MSN
13h 22m1 stop
$298American Airlines
Find Deal
Sat, Jan 31 - Thu, Feb 5
American Airlines Logo
11:22 am - 4:55 amMSN-SJU
15h 33m1 stop
American Airlines Logo
7:20 am - 5:30 pmSJU-MSN
12h 10m1 stop
$301American Airlines
Find Deal
Sat, Feb 21 - Wed, Feb 25
Delta Logo
5:40 am - 4:31 pmMSN-SJU
9h 51m1 stop
Delta Logo
7:00 am - 8:21 pmSJU-MSN
14h 21m2 stops
$317Delta
Find Deal
Mon, Sep 29 - Tue, Oct 7
Delta Logo
5:40 am - 4:31 pmMSN-SJU
9h 51m1 stop
Delta Logo
7:00 am - 8:21 pmSJU-MSN
14h 21m2 stops
$360Delta
Find Deal
Mon, Sep 29 - Tue, Oct 7
Multiple Airlines Logo
9:48 am - 1:05 pmMSN-SJU
25h 17m1 stop
Multiple Airlines Logo
10:59 am - 9:08 amSJU-MSN
24h 09m2 stops
$424Multiple Airlines
Find Deal
Sat, Jan 10 - Tue, Jan 20
Multiple Airlines Logo
6:16 pm - 9:54 amMSN-SJU
13h 38m1 stop
Multiple Airlines Logo
10:59 am - 9:08 amSJU-MSN
24h 09m2 stops
$458Multiple Airlines
Find Deal
Wed, Jan 14 - Tue, Jan 20

United Airlines flights from Madison to Puerto Rico

Our best United Airlines deals on Madison to Puerto Rico flight tickets
United Airlines
Jan 31
MSN2:56 pmMadison Truax Field
13h 15m
2 stops
SJU6:11 amSan Juan Luis Munoz Marin Intl
Feb 5
SJU8:35 amSan Juan Luis Munoz Marin Intl
7h 35m
1 stop
MSN2:10 pmMadison Truax Field
$235
Find similar
United Airlines
Dec 9
MSN8:15 amMadison Truax Field
12h 07m
2 stops
SJU10:22 pmSan Juan Luis Munoz Marin Intl
Dec 15
SJU2:05 amSan Juan Luis Munoz Marin Intl
11h 39m
2 stops
MSN11:44 amMadison Truax Field
$267
Find similar
United Airlines
Dec 9
MSN6:30 amMadison Truax Field
7h 10m
1 stop
SJU3:40 pmSan Juan Luis Munoz Marin Intl
Dec 15
SJU2:05 amSan Juan Luis Munoz Marin Intl
11h 39m
2 stops
MSN11:44 amMadison Truax Field
$311
Find similar

Delta flights from Madison to Puerto Rico

Our best Delta deals on Madison to Puerto Rico flight tickets
Delta
Sep 29
MSN5:40 amMadison Truax Field
9h 51m
1 stop
SJU4:31 pmSan Juan Luis Munoz Marin Intl
Oct 7
SJU7:00 amSan Juan Luis Munoz Marin Intl
14h 21m
2 stops
MSN8:21 pmMadison Truax Field
$317
Find similar
Delta
Sep 29
MSN5:40 amMadison Truax Field
9h 51m
1 stop
SJU4:31 pmSan Juan Luis Munoz Marin Intl
Oct 7
SJU7:00 amSan Juan Luis Munoz Marin Intl
14h 21m
2 stops
MSN8:21 pmMadison Truax Field
$360
Find similar
Delta
Sep 27
MSN5:40 amMadison Truax Field
9h 51m
1 stop
SJU4:31 pmSan Juan Luis Munoz Marin Intl
Oct 1
SJU7:20 amSan Juan Luis Munoz Marin Intl
9h 49m
2 stops
MSN4:09 pmMadison Truax Field
$399
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Madison to Puerto Rico 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, momondo users made 832,500 searches. Data last updated September 17, 2025.
Use the filters below to find and compare flights from Madison to Puerto Rico that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

MadisonSan Juan

MSN - SJU

MSNSJU

Madison Truax Field

Sat 1/31

2:56 pm-6:11 am

2 stops13h 15m

San Juan Luis Munoz Marin Intl

Thu 2/5

8:35 am-2:10 pm

1 stop7h 35m

$235

MadisonSan Juan

MSN - SJU

MSNSJU

Madison Truax Field

Tue 12/9

8:15 am-10:22 pm

2 stops12h 07m

San Juan Luis Munoz Marin Intl

Mon 12/15

2:05 am-11:44 am

2 stops11h 39m

$267

MadisonSan Juan

MSN - SJU

MSNSJU

Madison Truax Field

Tue 1/20

12:19 pm-8:50 pm

1 stop6h 31m

San Juan Luis Munoz Marin Intl

Wed 1/28

4:40 pm-11:42 pm

1 stop9h 02m

$268

MadisonSan Juan

MSN - SJU

MSNSJU

Madison Truax Field

Sun 1/11

4:17 pm-11:45 am

1 stop17h 28m

San Juan Luis Munoz Marin Intl

Wed 1/21

4:40 pm-10:27 am

2 stops19h 47m

$295

MadisonSan Juan

MSN - SJU

MSNSJU

Madison Truax Field

Sat 1/31

4:17 pm-11:45 am

1 stop17h 28m

San Juan Luis Munoz Marin Intl

Thu 2/5

7:20 am-6:42 pm

1 stop13h 22m

$298

MadisonSan Juan

MSN - SJU

MSNSJU

Madison Truax Field

Sat 2/21

11:22 am-4:55 am

1 stop15h 33m

San Juan Luis Munoz Marin Intl

Wed 2/25

7:20 am-5:30 pm

1 stop12h 10m

$301

MadisonSan Juan

MSN - SJU

MSNSJU

Madison Truax Field

Mon 9/29

5:40 am-4:31 pm

1 stop9h 51m

San Juan Luis Munoz Marin Intl

Tue 10/7

7:00 am-8:21 pm

2 stops14h 21m

$317

MadisonSan Juan

MSN - SJU

MSNSJU

Madison Truax Field

Mon 9/29

5:40 am-4:31 pm

1 stop9h 51m

San Juan Luis Munoz Marin Intl

Tue 10/7

7:00 am-8:21 pm

2 stops14h 21m

$360

MadisonSan Juan

MSN - SJU

MSNSJU

Madison Truax Field

Sat 1/10

9:48 am-1:05 pm

1 stop25h 17m

San Juan Luis Munoz Marin Intl

Tue 1/20

10:59 am-9:08 am

2 stops24h 09m

$424

MadisonSan Juan

MSN - SJU

MSNSJU

Madison Truax Field

Wed 1/14

6:16 pm-9:54 am

1 stop13h 38m

San Juan Luis Munoz Marin Intl

Tue 1/20

10:59 am-9:08 am

2 stops24h 09m

$458

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to Puerto Rico from

How to get the cheapest flight ticket from Madison to Puerto Rico

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest month to fly to Puerto Rico?

If you don’t want to visit Puerto Rico in September, then you should wait until January to fly from Madison, when ticket prices are also cheap, with an average price of $433.

What is the cheapest day to depart on your flight to Puerto Rico?

On average, the least expensive day to fly to Puerto Rico from Madison is on a Monday. momondo users have found tickets for Monday departures for as low as $494. However, this price may fluctuate depending on the airline, the season, and holidays. The most expensive day to fly to Puerto Rico is Thursday, with ticket prices averaging around $609.

What is the cheapest time of day to depart on your flight to Puerto Rico?

Our most recent data shows that the best time of day to fly to Puerto Rico is in the afternoon. Flights from Madison to Puerto Rico during this time can be as low as $370. In contrast, the most expensive time of day to depart to Puerto Rico is at noon when prices are around $701.

How far in advance should I book a flight to Puerto Rico?

You are more likely to see cheaper flights to Puerto Rico from Madison when booking weeks ahead of your departure date. In general, you can expect to find flights to Puerto Rico for around $503 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Puerto Rico from Madison for as low as $365 on momondo.

Cheap Madison to Puerto Rico flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Madison to Puerto Rico

Direct flights

None
There are no direct flights from Madison to Puerto Rico. There are no popular flight routes from Madison to Puerto Rico.
Search flight deals

  • When did momondo last update prices for flights from Madison Truax Field Airport to Puerto Rico?

    Prices for flights from Madison Truax Field Airport to Puerto Rico refresh daily.

  • How many operators does momondo search for flights from Madison Truax Field Airport to Puerto Rico?

  • How old do you have to be to fly from Madison Truax Field Airport to Puerto Rico?

    The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Madison Truax Field Airport to Puerto Rico.

  • What documentation or ID do you need to fly to Puerto Rico?

    The required travel and health documents for your Puerto Rico trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Puerto Rico. We recommend that you seek guidance from your airline or a reliable third party such as IATA.

Best airlines flying from Madison to Puerto Rico

Compare and see reviews for airlines that fly from Madison to Puerto Rico with momondo
Airline
Rating
Free Cancellation
Price
DeltaPriceFrom $254Free CancellationRating
7.9
7,961 reviews
Search Delta flights
American AirlinesPriceFrom $279Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
United AirlinesPriceFrom $293Free CancellationRating
7.4
8,926 reviews
Search United Airlines flights

Why use momondo?

Why should I use momondo to find a flight deal from Madison to Puerto Rico?

Finding the right flight to Puerto Rico from Madison is quick and easy when you have a range of options in front of you, from reputable agents and recognisable airlines. Options that can then be filtered down to find the best fit. That is what momondo does. We make finding flights to Puerto Rico quick and easy, saving you time and money.

Can I find flights from Madison to Puerto Rico with flexible booking policies on momondo?

momondo does allow users to show only those flights to Puerto Rico from Madison which offer a flexible booking policy as well as other useful filters and features.

How can momondo help me find flights from Madison to Puerto Rico?

momondo provides multiple filters to help you find the best flight to Puerto Rico from Madison. Filter by price, airline, airports, cabin, aircraft, payment method, number of stops and more.

I’m not ready to book a flight from Madison to Puerto Rico right now. Can momondo alert me if prices change?

Yes. momondo can track prices for Madison to Puerto Rico flights and alert you when they change. Perform a search to set up the price alert. All that is required is a valid email address.

An easier way to manage your Puerto Rico trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.
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Find better results for your trip to Puerto Rico

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