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Cheap flights from Madison (MSN) to Caribbean from $212

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 9/3. 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.
MSN — SJU
May 21 — May 281
From?
To?
Tue 5/21
Tue 5/28
1 adult, Economy
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How far in advance should I book a flight from Madison to Caribbean?

To save up to 106% on this flight, we recommend booking at least 9 days prior to travel. The price may fluctuate and will likely increase closer to your departure date. Users on Cheapflights have found tickets from Madison to Caribbean from $312 1-2 weeks out and tickets from $643 for flights departing within the next 72 hours.

What is the cheapest month to fly from Madison to Caribbean?

September is one of the best times of the year to fly to Caribbean from Madison. Prices for September average $534 per person but you can even find prices for as low as $290. The most expensive prices can be found in the month of June. Opting for a September flight can save you 37% on your journey compared to booking in June

When is the cheapest time to fly from Madison to Caribbean (MSN - CB)?

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Madison to Caribbean as you normally would.

Cheap United Airlines flights from Madison to Caribbean

Explore cheap flight options specifically provided by United Airlines for the route between Madison and Caribbean. Find affordable fares and compare prices with other airlines to secure the best deal for your journey. Over the last 7 days, Cheapflights users made 2,637,452 searches. Data last updated May 16, 2024.
Sat 9/286:35 amMSN - SJU
1 stop7h 00mUnited Airlines
Mon 9/301:05 amSJU - MSN
2 stops10h 05mUnited Airlines
Deal found 5/14$424
Wed 6/58:35 amMSN - NAS
2 stops26h 03mUnited Airlines
Sun 6/94:05 pmNAS - MSN
1 stop6h 22mUnited Airlines
Deal found 5/15$528
Wed 7/36:32 amMSN - SJU
1 stop7h 10mUnited Airlines
Sun 7/73:50 pmSJU - MSN
1 stop7h 42mUnited Airlines
Deal found 5/15$614
Fri 5/244:02 pmMSN - NAS
2 stops22h 51mUnited Airlines
Tue 5/284:55 pmNAS - MSN
2 stops23h 10mUnited Airlines
Deal found 5/15$621
Thu 8/14:02 pmMSN - NAS
2 stops20h 48mUnited Airlines
Sun 8/41:15 pmNAS - MSN
2 stops34h 12mUnited Airlines
Deal found 5/14$652
Thu 6/138:35 amMSN - GCM
2 stops28h 00mUnited Airlines
Mon 6/171:40 pmGCM - MSN
2 stops20h 25mUnited Airlines
Deal found 5/15$665
Tue 6/116:20 amMSN - SJU
1 stop7h 22mUnited Airlines
Sat 6/151:05 amSJU - MSN
2 stops15h 10mUnited Airlines
Deal found 5/16$734
Sat 8/246:30 amMSN - SJU
2 stops16h 27mUnited Airlines
Fri 8/301:05 amSJU - MSN
2 stops11h 46mUnited Airlines
Deal found 5/15$800
Fri 6/286:32 amMSN - SJU
1 stop7h 10mUnited Airlines
Mon 7/11:05 amSJU - MSN
2 stops16h 39mUnited Airlines
Deal found 5/15$844

Cheap Delta flights from Madison to Caribbean

Explore cheap flight options specifically provided by Delta for the route between Madison and Caribbean. Find affordable fares and compare prices with other airlines to secure the best deal for your journey. Over the last 7 days, Cheapflights users made 2,637,452 searches. Data last updated May 16, 2024.
Sat 9/2810:55 amMSN - SJU
2 stops11h 04mDelta
Tue 10/12:25 pmSJU - MSN
1 stop9h 08mDelta
Deal found 5/15$429
Mon 8/265:55 amMSN - NAS
1 stop5h 12mDelta
Wed 8/282:27 pmNAS - MSN
1 stop9h 15mDelta
Deal found 5/15$443
Mon 8/266:38 pmMSN - NAS
2 stops16h 29mDelta
Wed 8/282:27 pmNAS - MSN
2 stops19h 16mDelta
Deal found 5/15$448
Mon 5/277:20 amMSN - NAS
1 stop6h 43mDelta
Thu 5/302:38 pmNAS - MSN
1 stop9h 25mDelta
Deal found 5/14$483
Mon 5/277:20 amMSN - NAS
1 stop6h 43mDelta
Thu 5/305:49 pmNAS - MSN
2 stops15h 55mDelta
Deal found 5/14$488
Sat 9/75:55 amMSN - STT
1 stop7h 40mDelta
Wed 9/112:24 pmSTT - MSN
1 stop9h 09mDelta
Deal found 5/15$493
Sat 9/75:55 amMSN - STT
1 stop7h 40mDelta
Wed 9/112:24 pmSTT - MSN
1 stop9h 09mDelta
Deal found 5/14$508
Thu 10/175:55 amMSN - NAS
1 stop5h 12mDelta
Tue 10/222:27 pmNAS - MSN
1 stop9h 06mDelta
Deal found 5/16$512
Wed 9/45:25 pmMSN - AUA
2 stops18h 35mDelta
Wed 9/113:35 pmAUA - MSN
1 stop7h 58mDelta
Deal found 5/16$541

Cheap Madison to Caribbean flights in May & June 2024

Find cheap flight options from Madison to Caribbean specifically for the months of May and June 2024. Explore affordable fares based on user searches. Over the last 7 days, Cheapflights users made 2,637,452 searches. Prices were last updated on May 16, 2024.
Mon 5/277:20 amMSN - NAS
1 stop6h 43mDelta
Thu 5/302:38 pmNAS - MSN
1 stop9h 25mDelta
Deal found 5/14$483
Mon 5/277:20 amMSN - NAS
1 stop6h 43mDelta
Thu 5/305:49 pmNAS - MSN
2 stops15h 55mDelta
Deal found 5/14$488
Wed 6/58:35 amMSN - NAS
2 stops26h 03mUnited Airlines
Sun 6/94:05 pmNAS - MSN
1 stop6h 22mUnited Airlines
Deal found 5/15$528
Wed 6/55:35 amMSN - NAS
1 stop6h 55mAmerican Airlines
Sun 6/910:33 amNAS - MSN
1 stop12h 57mAmerican Airlines
Deal found 5/15$535
Mon 5/277:00 amMSN - NAS
2 stops10h 59mAmerican Airlines
Thu 5/3010:51 amNAS - MSN
2 stops12h 32mAmerican Airlines
Deal found 5/14$571
Wed 6/56:00 amMSN - NAS
2 stops13h 54mAmerican Airlines
Sun 6/97:50 amNAS - MSN
2 stops27h 09mAmerican Airlines
Deal found 5/15$575
Fri 6/76:45 amMSN - SJU
1 stop16h 30mAmerican Airlines
Tue 6/113:49 pmSJU - MSN
1 stop7h 41mAmerican Airlines
Deal found 5/15$580
Tue 6/186:45 amMSN - SJU
1 stop16h 30mAmerican Airlines
Sun 6/236:00 amSJU - MSN
1 stop15h 06mAmerican Airlines
Deal found 5/15$584
Fri 5/246:11 pmMSN - NAS
1 stop18h 14mAmerican Airlines
Tue 5/282:25 pmNAS - MSN
1 stop8h 58mAmerican Airlines
Deal found 5/15$592

Madison to Caribbean 2024 flight deals

Discover exclusive flight deals for travel between Madison and Caribbean in 2024. Find excellent offers based on user searches. Over the last 7 days, Cheapflights users made 2,637,452 searches. Data last updated May 16, 2024.
Tue 9/36:50 amMSN - PUJ
1 stop7h 59mAmerican Airlines
Fri 9/65:27 pmPUJ - MSN
1 stop17h 56mAmerican Airlines
Deal found 5/15$392
Tue 9/34:24 pmMSN - PUJ
2 stops19h 18mAmerican Airlines
Fri 9/64:51 pmPUJ - MSN
2 stops18h 32mAmerican Airlines
Deal found 5/15$397
Sat 8/246:34 amMSN - SJU
2 stops13h 46mAmerican Airlines
Sat 8/311:19 pmSJU - MSN
1 stop8h 07mAmerican Airlines
Deal found 5/15$399
Sat 9/286:35 amMSN - SJU
1 stop7h 00mUnited Airlines
Mon 9/301:05 amSJU - MSN
2 stops10h 05mUnited Airlines
Deal found 5/14$424
Sat 9/2810:55 amMSN - SJU
2 stops11h 04mDelta
Tue 10/12:25 pmSJU - MSN
1 stop9h 08mDelta
Deal found 5/15$429
Sat 8/246:50 amMSN - SJU
1 stop7h 10mAmerican Airlines
Sat 8/311:19 pmSJU - MSN
1 stop8h 07mAmerican Airlines
Deal found 5/15$443
Mon 8/265:55 amMSN - NAS
1 stop5h 12mDelta
Wed 8/282:27 pmNAS - MSN
1 stop9h 15mDelta
Deal found 5/15$443
Sat 9/287:17 amMSN - SJU
2 stops15h 33mAmerican Airlines
Tue 10/16:33 amSJU - MSN
2 stops10h 01mAmerican Airlines
Deal found 5/14$447
Mon 8/265:55 amMSN - NAS
1 stop6h 23mDelta
Wed 8/282:27 pmNAS - MSN
2 stops19h 16mDelta
Deal found 5/15$448

Madison to Caribbean flights leaving soon

Find last-minute flight options from Madison to Caribbean for spontaneous travel. Discover available flights and compare prices based on user searches. Secure great deals and offers for spontaneous trips with quick booking options. Over the last 7 days, Cheapflights users made 2,637,452 searches. Data last updated May 16, 2024.
Fri 5/246:11 pmMSN - NAS
1 stop18h 14mAmerican Airlines
Tue 5/282:25 pmNAS - MSN
1 stop8h 58mAmerican Airlines
Deal found 5/15$592
Wed 5/225:45 amMSN - PUJ
1 stop9h 00mAmerican Airlines
Thu 5/234:20 pmPUJ - MSN
1 stop7h 03mAmerican Airlines
Deal found 5/15$603
Thu 5/237:00 amMSN - SJU
1 stop10h 32mAmerican Airlines
Sun 5/265:55 pmSJU - MSN
1 stop17h 18mAmerican Airlines
Deal found 5/16$604
Thu 5/236:30 amMSN - SJU
2 stops11h 02mAmerican Airlines
Sun 5/265:55 pmSJU - MSN
1 stop17h 18mAmerican Airlines
Deal found 5/16$605
Thu 5/236:30 amMSN - SJU
2 stops11h 02mAmerican Airlines
Sun 5/266:30 amSJU - MSN
2 stops11h 18mAmerican Airlines
Deal found 5/16$607
Fri 5/244:02 pmMSN - NAS
2 stops22h 51mUnited Airlines
Tue 5/284:55 pmNAS - MSN
2 stops23h 10mUnited Airlines
Deal found 5/15$621
Fri 5/246:11 pmMSN - NAS
1 stop18h 14mAmerican Airlines
Tue 5/288:00 amNAS - MSN
2 stops10h 52mAmerican Airlines
Deal found 5/15$626
Wed 5/225:45 amMSN - PUJ
1 stop9h 00mAmerican Airlines
Thu 5/234:20 pmPUJ - MSN
2 stops19h 57mAmerican Airlines
Deal found 5/15$674
Wed 5/226:10 amMSN - PUJ
2 stops10h 05mAmerican Airlines
Thu 5/236:15 pmPUJ - MSN
2 stops18h 02mAmerican Airlines
Deal found 5/15$787

One-way flights to Caribbean from Madison

Search for one-way flight options from Madison to Caribbean. Find affordable one-way fares based on user searches. Compare prices and availability to plan your one-way journey according to your preferred dates and budget. Over the last 7 days, Cheapflights users made 2,637,452 searches. Data last updated May 16, 2024.
Tue 9/34:24 pmMSN - MBJ
2 stops18h 43mAmerican Airlines
Deal found 5/15$212
Mon 9/26:38 pmMSN - MBJ
2 stops16h 58mDelta
Deal found 5/14$219
Thu 10/317:22 amMSN - SJU
2 stops30h 17mAmerican Airlines
Deal found 5/15$229
Thu 10/314:30 pmMSN - SJU
1 stop17h 13mAmerican Airlines
Deal found 5/15$268
Fri 6/219:05 pmMSN - SJU
2 stops17h 16mFrontier
Deal found 5/15$399
Thu 10/311:00 pmMSN - SJU
3 stops23h 40mUnited Airlines
Deal found 5/15$479
Thu 10/315:20 pmMSN - SJU
3 stops19h 20mUnited Airlines
Deal found 5/15$482

Find flights from Madison to Caribbean within your budget

Customize your flight search to find flights from Madison to Caribbean 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 2,637,452 searches. Data last updated May 16, 2024.

Fly from

Any airport

Fly to

Any airport

Budget

$392 - $494

Route

Depart

Return

Price

Madison Truax FieldPunta Cana

MSN - PUJ

MSNPUJ

Madison Truax Field

Tue 9/3

1 stop7h 59m

Punta Cana

Fri 9/6

1 stop17h 56m

$392

Madison Truax FieldPunta Cana

MSN - PUJ

MSNPUJ

Madison Truax Field

Tue 9/3

2 stops19h 18m

Punta Cana

Fri 9/6

2 stops18h 32m

$397

Madison Truax FieldSan Juan Luis Munoz Marin Intl

MSN - SJU

MSNSJU

Madison Truax Field

Sat 8/24

2 stops13h 46m

San Juan Luis Munoz Marin Intl

Sat 8/31

1 stop8h 07m

$399

Madison Truax FieldSan Juan Luis Munoz Marin Intl

MSN - SJU

MSNSJU

Madison Truax Field

Sat 9/28

1 stop7h 00m

San Juan Luis Munoz Marin Intl

Mon 9/30

2 stops10h 05m

$424

Madison Truax FieldSan Juan Luis Munoz Marin Intl

MSN - SJU

MSNSJU

Madison Truax Field

Sat 9/28

2 stops11h 04m

San Juan Luis Munoz Marin Intl

Tue 10/1

1 stop9h 08m

$429

Madison Truax FieldNassau Intl

MSN - NAS

MSNNAS

Madison Truax Field

Mon 8/26

1 stop5h 12m

Nassau Intl

Wed 8/28

1 stop9h 15m

$443

Madison Truax FieldNassau Intl

MSN - NAS

MSNNAS

Madison Truax Field

Mon 8/26

2 stops16h 29m

Nassau Intl

Wed 8/28

2 stops19h 16m

$448

Madison Truax FieldSan Juan Luis Munoz Marin Intl

MSN - SJU

MSNSJU

Madison Truax Field

Wed 7/3

2 stops21h 45m

San Juan Luis Munoz Marin Intl

Sun 7/7

2 stops17h 17m

$454

Madison Truax FieldSan Juan Luis Munoz Marin Intl

MSN - SJU

MSNSJU

Madison Truax Field

Wed 7/3

2 stops21h 45m

San Juan Luis Munoz Marin Intl

Sun 7/7

2 stops17h 17m

$494

Flights are sorted by cheapest first

Deals found on 5/15

No data available for this route at this time. Please check back soon.

Reviews of airlines servicing Caribbean

Get insights into the airlines that provide service to Caribbean. 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 Caribbean. Reviews last updated May 16, 2024.
Delta
8.0
Very good
10,673 reviews
Check prices

Crew

8.6

Overall

8.0

Comfort

7.9

Food

7.4

Entertainment

8.0

Boarding

8.2

Reviews

1 / 10

Bad experience with the staff boarding the gate. I couldn’t board with my carry on, personal item and a funny bag. I had to put my passport inside my pockets and put the funny bag inside the personal item. Then after passing the staff pull out everything again.

Delta
8.0
Very good
10,673 reviews
Delta
8.0
Very good
10,673 reviews
Check prices

Crew

8.6

Overall

8.0

Comfort

7.9

Food

7.4

Entertainment

8.0

Boarding

8.2

Reviews

1 / 10

Bad experience with the staff boarding the gate. I couldn’t board with my carry on, personal item and a funny bag. I had to put my passport inside my pockets and put the funny bag inside the personal item. Then after passing the staff pull out everything again.

United Airlines
7.4
Good
10,924 reviews
Delta
8.0
Very good
10,673 reviews
Check prices

Crew

8.6

Overall

8.0

Comfort

7.9

Food

7.4

Entertainment

8.0

Boarding

8.2

Reviews

1 / 10

Bad experience with the staff boarding the gate. I couldn’t board with my carry on, personal item and a funny bag. I had to put my passport inside my pockets and put the funny bag inside the personal item. Then after passing the staff pull out everything again.

American Airlines
7.3
Good
14,514 reviews
Delta
8.0
Very good
10,673 reviews
Check prices

Crew

8.6

Overall

8.0

Comfort

7.9

Food

7.4

Entertainment

8.0

Boarding

8.2

Reviews

1 / 10

Bad experience with the staff boarding the gate. I couldn’t board with my carry on, personal item and a funny bag. I had to put my passport inside my pockets and put the funny bag inside the personal item. Then after passing the staff pull out everything again.

Frontier
6.3
Okay
4,060 reviews
Delta
8.0
Very good
10,673 reviews
Check prices

Crew

8.6

Overall

8.0

Comfort

7.9

Food

7.4

Entertainment

8.0

Boarding

8.2

Reviews

1 / 10

Bad experience with the staff boarding the gate. I couldn’t board with my carry on, personal item and a funny bag. I had to put my passport inside my pockets and put the funny bag inside the personal item. Then after passing the staff pull out everything again.

Related info for your journey

Find useful and relevant information for your journey from Madison to Caribbean. 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 from for flights from Madison to Caribbean?

    Most people fly from Madison Truax Field (MSN) if they book a flight from Madison to Caribbean. Madison Truax Field is conveniently located just 5.4 mi from Madison’s city center.

  • Can I find flights from Madison to Caribbean for under $400 on Cheapflights?

    Yes, there are multiple flights from Madison to Caribbean for under $400. The cheapest flight booked recently is on American Airlines for just $392, but on average you can expect to pay $454.

  • Are there last-minute flights available from Madison to Caribbean for under $600?

    There are currently 15+ open flights from Madison to Caribbean within the next 7 days for less than $600.

  • What are the cheapest airlines to fly from Madison to Caribbean one-way?

    For one-way options, check prices for American Airlines. According to our data, you can fly for as low as $212. Users have also found prices from $219 and $399 on Delta and Frontier, respectively.

  • What are the most popular routes from Madison to Caribbean?

    The most popular flight routes from Madison to Caribbean are Madison Truax Field - San Juan Luis Munoz Marin Intl, Madison Truax Field - Simpson Bay Princess Juliana and Madison Truax Field - Saint Thomas Island Cyril E King.

  • What are the most popular airlines that fly from Madison to Caribbean?

    Consider American Airlines, Delta or Frontier when booking your flight. These represent the most popular airlines when flying from Madison to Caribbean.

  • What does MSN to SJU mean?

    Great question - MSN to SJU just means Madison Truax Field Airport to San Juan Luis Munoz Marin Intl Airport. Now you’ll know what these unique codes when you look for flights! Punta Cana Airport (PUJ), Santo Domingo Las Americas Airport (SDQ), Montego Bay Sangster Intl Airport (MBJ), Oranjestad Reina Beatrix Airport (AUA), Santiago de los Caballeros Airport (STI) are some additional IATA codes for airports related to your trip.

  • Can I find deals for flights from Madison to Caribbean that include extra baggage allowance?

    The amount of baggage you can bring on your Madison to Caribbean flight depends on the airline and the type of fare you've chosen. After entering your flight details, you'll be able to view the specific baggage policies for each deal in the search results. Keep in mind that certain deals may offer additional baggage allowance.

  • Can I find deals on flights from Madison to Caribbean with specific airlines?

    Yes, Cheapflights allows you to browse and filter Madison to Caribbean flight deals by airline. After entering your origin and destination, use the available filters to view flights offered by airlines.

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

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

  • How can I find direct flights from Madison to Caribbean?

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

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

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

  • Can I find deals for flights from Madison to Caribbean that allow pets onboard?

    Many airlines flying from Madison to Caribbean offer the option to travel with pets. After selecting a flight deal, you can find more information about the airline's pet policy on their official website or by contacting the airline directly. Please note that additional fees and restrictions may apply.

  • Can I find deals on last-minute flights from Madison to Caribbean?

    Yes, you can often find last-minute deals on Madison to Caribbean flights on Cheapflights. However, these deals can vary and may not always be available. We recommend checking back frequently or signing up for price alerts for the most up-to-date deals.

  • How recently were the Madison to Caribbean flight deals updated?

    The Madison to Caribbean flight deals you see on this page were last updated on 5/15.

See more FAQs

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Top 4 airlines flying from Madison to Caribbean

Discover the top 4 airlines that operate flights from Madison to Caribbean. 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 2,637,452 searches. Data last updated May 16, 2024.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$234Average$275FlexibilityNo cancel feeOn-time62%
Search Frontier flights
American AirlinesCheapest$310Average$690FlexibilityNo cancel feeOn-time71%
Search American Airlines flights
DeltaCheapest$330Average$636FlexibilityNo cancel feeOn-timeN/A
Search Delta flights
United AirlinesCheapest$384Average$651FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
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Search flights from Madison to Caribbean by cabin class

Find flights from Madison to Caribbean, based on your preferred cabin class, be it economy, premium economy, business, or first class.
First Class
Business Class
Prem Econ Class
Economy Class

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Fly with Cheapflights

Find the best flight deals on Cheapflights, where travelers can enjoy low prices and a wide availability of flights to their desired destinations.

How does Cheapflights help users find flights from Madison to Caribbean?

Cheapflights makes it easy to find Madison to Caribbean flights by helping our users search from 900+ travel sites for deals. We also provide you with filters for cabin, price, airline, airports, number of stops, and many more to narrow down that perfect flight.

Why should you use Cheapflights to find cheap flight tickets from Madison to Caribbean?

It’s simple! Cheapflights, which is free to use for everyone, saves millions of users time and money every year by helping them find the cheapest and most suitable flights from Madison to Caribbean.

Can Cheapflights find flights from Madison to Caribbean with no change fees?

Certainly. Search results for flights to Caribbean from Madison shown to you on Cheapflights can be narrowed down with different useful search filters, which includes flexible booking options.

Can Cheapflights notify me if prices for flights from Madison to Caribbean become cheaper?

Of course! You can now track prices for flights from Madison to Caribbean and get an alert from Cheapflights when they change. Have a valid email address ready and click the bell icon next to the flight deals above to set up your price alerts.

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