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Jamaica

$539+ Cheap flights from Madison (MSN) to Jamaica

This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 11/18. Fares are subject to change and may not be available on all flights or dates of travel.
MSN — MBJ
Nov 7 — Nov 141
Fri 11/7
Fri 11/14
1 adult, Economy
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Cheap flight deals from Madison to Jamaica

Keep the following information in mind while searching for Madison to Jamaica flight deals. Data was last updated October 8, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$539
(Delta)

Popular in

July

Cheapest in

October

Average price

$470
Provider with most accurate pricing for Madison Truax Field-Montego Bay Sangster Intl flight deals.
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Provider most trusted by Cheapflights users for Madison Truax Field-Montego Bay Sangster Intl flights.
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From Madison Truax Field to Jamaica
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Highest demand for flights based on searches. 9% potential increase in price ($63 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($11 potential savings vs. average RT price).
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Average for round-trip flights in October 2025
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Find flight deals from Madison to Jamaica

Cheapest flights from Madison to Jamaica
Explore the most affordable flight options available from Madison to Jamaica. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 8, 2025.

This American Airlines deal was found by Cheapflights users on 10/6. 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.
Tue 11/186:00 amMSN - MBJ
1 stop8h 00mAmerican Airlines
Tue 11/251:55 pmMBJ - MSN
1 stop10h 56mAmerican Airlines
Deal found 10/6$539
This American Airlines deal was found by Cheapflights users on 10/8. 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.
Tue 12/27:00 amMSN - MBJ
1 stop7h 28mAmerican Airlines
Mon 12/83:12 pmMBJ - MSN
1 stop9h 09mAmerican Airlines
Deal found 10/8$564
This American Airlines deal was found by Cheapflights users on 10/7. 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 11/145:00 amMSN - MBJ
1 stop9h 28mAmerican Airlines
Mon 11/173:13 pmMBJ - MSN
1 stop9h 45mAmerican Airlines
Deal found 10/7$589
This American Airlines deal was found by Cheapflights users on 10/8. 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.
Sat 10/254:15 pmMSN - MBJ
1 stop16h 58mAmerican Airlines
Thu 10/3011:50 amMBJ - MSN
1 stop9h 53mAmerican Airlines
Deal found 10/8$629
This United Airlines deal was found by Cheapflights users on 10/6. 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.
Mon 12/86:15 amMSN - MBJ
1 stop7h 14mUnited Airlines
Thu 12/182:48 pmMBJ - MSN
1 stop7h 15mUnited Airlines
Deal found 10/6$649

Cheapflights Fare Finder

 
Customize your flight search to find flights from Madison to Jamaica 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 October 8, 2025.
Use the filters below to find and compare flights from Madison to Jamaica that are best for you.

Fly from

Madison

Fly to

Jamaica

Route

Depart

Return

Price

MadisonMontego Bay

MSN - MBJ

MSNMBJ

Madison Truax Field

Mon 4/6

6:15 am-1:40 pm

1 stop7h 25m

Montego Bay Sangster Intl

Wed 4/8

1:10 pm-8:48 pm

1 stop7h 38m

$539

MadisonMontego Bay

MSN - MBJ

MSNMBJ

Madison Truax Field

Sun 2/15

4:19 pm-10:05 am

1 stop16h 46m

Montego Bay Sangster Intl

Thu 2/19

11:45 am-9:26 pm

1 stop10h 41m

$539

MadisonMontego Bay

MSN - MBJ

MSNMBJ

Madison Truax Field

Tue 1/6

6:30 am-1:46 pm

1 stop6h 16m

Montego Bay Sangster Intl

Tue 1/13

3:55 pm-10:10 am

2 stops19h 15m

$544

MadisonMontego Bay

MSN - MBJ

MSNMBJ

Madison Truax Field

Tue 1/6

5:23 pm-1:44 pm

2 stops19h 21m

Montego Bay Sangster Intl

Wed 1/14

11:32 am-10:05 pm

2 stops11h 33m

$544

MadisonMontego Bay

MSN - MBJ

MSNMBJ

Madison Truax Field

Tue 11/18

4:34 pm-1:01 pm

2 stops19h 27m

Montego Bay Sangster Intl

Tue 11/25

3:13 pm-10:23 pm

1 stop8h 10m

$544

MadisonMontego Bay

MSN - MBJ

MSNMBJ

Madison Truax Field

Thu 3/5

6:15 am-2:40 pm

1 stop7h 25m

Montego Bay Sangster Intl

Tue 3/10

11:35 am-10:38 pm

1 stop11h 03m

$564

MadisonMontego Bay

MSN - MBJ

MSNMBJ

Madison Truax Field

Thu 12/4

8:08 pm-1:20 pm

1 stop16h 12m

Montego Bay Sangster Intl

Wed 12/10

3:48 pm-11:40 pm

1 stop8h 52m

$564

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/5

Best time to book a flight from Madison to Jamaica

Have a flexible travel schedule? Discover the best time to fly to Jamaica from Madison 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 Madison to Jamaica

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

Currently, October is the cheapest month in which you can book a flight from Madison to Jamaica (average of $312). Flying from Madison to Jamaica in July is currently the most expensive (average of $595). 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.

What is the cheapest time of day to fly from MSN to JM?

Find hourly flight availability from Madison to Jamaica. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated October 8, 2025.

When flying from Madison to Jamaica, the time of day you fly usually plays a role in the price. Save by searching for a flight at noon, which can drop the price by up to 65% versus a flight in the evening.

Reviews of airlines servicing Jamaica

Get insights into the airlines that provide service to Jamaica. 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 Jamaica. Reviews last updated October 8, 2025.
Get a feel of what it's like to fly with Delta, United Airlines, and American Airlines from Madison to Jamaica by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
7,969 reviews

Entertainment

7.9

Overall

8.0

Crew

8.5

Boarding

8.2

Comfort

7.9

Food

7.3

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Delta
8.0
Very good
7,969 reviews
Delta
8.0
Very good
7,969 reviews

Entertainment

7.9

Overall

8.0

Crew

8.5

Boarding

8.2

Comfort

7.9

Food

7.3

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
United Airlines
7.4
Good
8,964 reviews
Delta
8.0
Very good
7,969 reviews

Entertainment

7.9

Overall

8.0

Crew

8.5

Boarding

8.2

Comfort

7.9

Food

7.3

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
American Airlines
7.2
Good
11,042 reviews
Delta
8.0
Very good
7,969 reviews

Entertainment

7.9

Overall

8.0

Crew

8.5

Boarding

8.2

Comfort

7.9

Food

7.3

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!

Related info for your journey

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

    If you book a flight to Jamaica from Madison, you will be flying from Truax Field, which is the city’s only airport. Madison Truax Field (MSN) is located 5.4 mi from the center of Madison.

  • How long is the flight from Madison to Jamaica?

    For as low as $539, Delta can have you in Jamaica from Madison in 7h 25m. The distance from Madison to Jamaica is about 1826 mi. This flight may include one or multiple stops.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Madison to Jamaica 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 Madison to Jamaica?

    Currently, October is the cheapest month in which you can book a flight from Madison to Jamaica (average of $312). Flying from Madison to Jamaica in July is currently the most expensive (average of $595). 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

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Alternative routes for Madison to Jamaica

See prices for flight routes from nearby airports that may be better suited for you.
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Top 3 airlines flying from Madison to Jamaica

Discover the top 3 airlines that operate flights from Madison to Jamaica. 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 October 8, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$521Average$680FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$523Average$626FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$529Average$689FlexibilityNo cancel feeOn-time69%

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