$182+ Cheap flights from Madison (MSN) to Jamaica
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 9/7. Fares are subject to change and may not be available on all flights or dates of travel.
MSN — MBJ
Sep 24 — Oct 11
Round-trip
1 adult, Economy
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Find cheap flights from Madison to Jamaica with Cheapflights
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Cheapest
Best
Last-minute
One-way
Cheapest flights from Madison to JamaicaExplore 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 August 25, 2026.
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 August 25, 2026.
This United Airlines deal was found by Cheapflights users on 8/21. 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 10/265:00 am -
1 stop7h 48m
Mon 11/231:25 pm -
1 stop11h 12m
Deal found 8/21![United Airlines logo]()
$412
This American Airlines deal was found by Cheapflights users on 8/21. 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 12/46:38 pm -
2 stops14h 37m
Thu 12/101:02 pm -
1 stop11h 57m
Deal found 8/21![American Airlines logo]()
$417
This American Airlines deal was found by Cheapflights users on 8/21. 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 11/118:42 pm -
1 stop17h 15m
Wed 11/1811:05 am -
2 stops13h 06m
Deal found 8/21![American Airlines logo]()
$422
This American Airlines deal was found by Cheapflights users on 8/21. 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.
Sun 9/138:05 pm -
2 stops17h 04m
Sat 9/1912:05 pm -
1 stop22h 46m
Deal found 8/21![American Airlines logo]()
$425
This United Airlines deal was found by Cheapflights users on 8/23. 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 11/37:00 pm -
2 stops16h 13m
Tue 11/103:20 pm -
2 stops19h 30m
Deal found 8/23![United Airlines logo]()
$449
This American Airlines deal was found by Cheapflights users on 8/21. 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 9/55:46 pm -
2 stops20h 03m
Sat 9/121:54 pm -
2 stops20h 57m
Deal found 8/21![American Airlines logo]()
$476
This American Airlines deal was found by Cheapflights users on 8/24. 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.
Sun 10/48:05 pm -
2 stops17h 03m
Sun 10/115:13 pm -
2 stops19h 31m
Deal found 8/24![American Airlines logo]()
$513
This United Airlines deal was found by Cheapflights users on 8/20. 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 10/265:00 am -
1 stop7h 48m
Fri 10/3012:25 pm -
1 stop11h 12m
Deal found 8/20![United Airlines logo]()
$532
Best flights from Madison to JamaicaDiscover carefully curated flight deals from Madison to Jamaica that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 25, 2026.
Discover carefully curated flight deals from Madison to Jamaica that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 25, 2026.
This American Airlines deal was found by Cheapflights users on 8/20. 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 12/46:38 pm -
2 stops14h 37m
Thu 12/1011:05 am -
2 stops14h 08m
Deal found 8/20![American Airlines logo]()
$417
This United Airlines deal was found by Cheapflights users on 8/23. 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 11/37:00 pm -
2 stops16h 13m
Tue 11/103:20 pm -
2 stops19h 30m
Deal found 8/23![United Airlines logo]()
$449
This American Airlines deal was found by Cheapflights users on 8/22. 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.
Sun 9/138:05 pm -
2 stops17h 04m
Sat 9/1912:05 pm -
1 stop22h 46m
Deal found 8/22![American Airlines logo]()
$425
This United Airlines deal was found by Cheapflights users on 8/20. 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 10/267:15 pm -
2 stops17h 59m
Fri 10/302:01 pm -
1 stop7h 04m
Deal found 8/20![United Airlines logo]()
$537
This United Airlines deal was found by Cheapflights users on 8/24. 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 2/17:15 pm -
1 stop17h 31m
Fri 2/52:48 pm -
1 stop9h 05m
Deal found 8/24![United Airlines logo]()
$539
Last-minute flights from Madison to JamaicaDiscover last-minute flight deals from Madison to Jamaica. Data last updated August 25, 2026 and is based on user searches.
Discover last-minute flight deals from Madison to Jamaica. Data last updated August 25, 2026 and is based on user searches.
This American Airlines deal was found by Cheapflights users on 8/24. 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 8/295:00 am -
1 stop8h 12m
Sat 9/52:12 pm -
1 stop8h 06m
Deal found 8/24![American Airlines logo]()
$566
This American Airlines deal was found by Cheapflights users on 8/21. 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 9/55:46 pm -
2 stops20h 03m
Sat 9/121:54 pm -
2 stops20h 57m
Deal found 8/21![American Airlines logo]()
$476
This American Airlines deal was found by Cheapflights users on 8/24. 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.
Sun 9/138:05 pm -
2 stops17h 04m
Sat 9/195:16 pm -
2 stops19h 40m
Deal found 8/24![American Airlines logo]()
$417
One-way flights from Madison to JamaicaSearch for one-way flight options from Madison to Jamaica. Find affordable one-way fares based on user searches. Data last updated August 25, 2026.
Search for one-way flight options from Madison to Jamaica. Find affordable one-way fares based on user searches. Data last updated August 25, 2026.
This Delta deal was found by Cheapflights users on 8/23. 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.
Mon 9/75:43 am -
1 stop9h 51m
Deal found 8/23![Delta logo]()
$182
This American Airlines deal was found by Cheapflights users on 8/22. 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 9/115:50 pm -
2 stops19h 03m
Deal found 8/22![American Airlines logo]()
$188
This American Airlines deal was found by Cheapflights users on 8/24. 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 12/58:22 pm -
1 stop17h 30m
Deal found 8/24![American Airlines logo]()
$194
This American Airlines deal was found by Cheapflights users on 8/23. 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 9/127:17 am -
1 stop8h 59m
Deal found 8/23![American Airlines logo]()
$241
This American Airlines deal was found by Cheapflights users on 8/23. 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.
Mon 9/75:46 pm -
2 stops17h 51m
Deal found 8/23![American Airlines logo]()
$247
This Kiwi.com deal was found by Cheapflights users on 8/23. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/1210:33 am -
3 stops27h 54m
Deal found 8/23![Multiple Airlines logo]()
$259
This American Airlines deal was found by Cheapflights users on 8/23. 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 9/86:00 am -
1 stop8h 23m
Deal found 8/23![American Airlines logo]()
$277
This American Airlines deal was found by Cheapflights users on 8/21. 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 9/35:47 pm -
2 stops17h 55m
Deal found 8/21![American Airlines logo]()
$283
Find flight deals from Madison to Jamaica
Keep the following information in mind while searching for Madison to Jamaica flight deals. Data was last updated August 25, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $412 (United Airlines) |
One-way from | $182 (Delta) |
Popular in | June |
Cheapest in | January |
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 7,457,451 searches. Data last updated August 25, 2026.
Use the filters below to find and compare flights from Madison to Jamaica that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
MadisonMontego Bay
MSN Madison Truax Field - MBJ Montego Bay Sangster Intl
MSNMBJ
Madison Truax Field
Fri 12/4
6:38 pm-10:15 am
2 stops14h 37m
Montego Bay Sangster Intl
Thu 12/10
11:05 am-12:13 am
2 stops14h 08m
$417
MadisonMontego Bay
MSN Madison Truax Field - MBJ Montego Bay Sangster Intl
MSNMBJ
Madison Truax Field
Sun 9/13
8:05 pm-1:09 pm
2 stops17h 04m
Montego Bay Sangster Intl
Sat 9/19
12:05 pm-10:51 am
1 stop22h 46m
$425
MadisonMontego Bay
MSN Madison Truax Field - MBJ Montego Bay Sangster Intl
MSNMBJ
Madison Truax Field
Tue 11/3
7:00 pm-12:13 pm
2 stops16h 13m
Montego Bay Sangster Intl
Tue 11/10
3:20 pm-9:50 am
2 stops19h 30m
$449
Quickest round-trip
MadisonMontego Bay
MSN Madison Truax Field - MBJ Montego Bay Sangster Intl
MSNMBJ
Madison Truax Field
Mon 10/26
7:15 pm-1:14 pm
2 stops17h 59m
Montego Bay Sangster Intl
Fri 10/30
2:01 pm-9:05 pm
1 stop7h 04m
$537
MadisonMontego Bay
MSN Madison Truax Field - MBJ Montego Bay Sangster Intl
MSNMBJ
Madison Truax Field
Mon 2/1
7:15 pm-1:46 pm
1 stop17h 31m
Montego Bay Sangster Intl
Fri 2/5
2:48 pm-10:53 pm
1 stop9h 05m
$539
Cheapest one-way
Quickest one-way
MadisonMontego Bay
MSN Madison Truax Field - MBJ Montego Bay Sangster Intl
MSNMBJ
Madison Truax Field
Mon 9/7
6:30 am-1:28 pm
1 stop6h 58m
$182
MadisonMontego Bay
MSN Madison Truax Field - MBJ Montego Bay Sangster Intl
MSNMBJ
Madison Truax Field
Mon 9/7
5:43 am-3:34 pm
1 stop9h 51m
$182
MadisonMontego Bay
MSN Madison Truax Field - MBJ Montego Bay Sangster Intl
MSNMBJ
Madison Truax Field
Sat 12/5
6:30 am-4:19 pm
2 stops8h 49m
$182
MadisonMontego Bay
MSN Madison Truax Field - MBJ Montego Bay Sangster Intl
MSNMBJ
Madison Truax Field
Sat 9/12
8:05 pm-1:08 pm
2 stops17h 03m
$247
MadisonMontego Bay
MSN Madison Truax Field - MBJ Montego Bay Sangster Intl
MSNMBJ
Madison Truax Field
Thu 9/3
5:47 pm-11:42 am
2 stops17h 55m
$283
Showing 1-10 of 12 resultsSorted by cheapest first
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.
MSN-MBJ
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
MSN-JM0
MSN-MBJ
No data available for this route at this time. Please check back soon.
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 August 25, 2026.
Get a feel of what it's like to fly with 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.
Food
6.7
Overall
7.4
Boarding
7.7
Entertainment
7.1
Comfort
7.3
Crew
8.1
Reviews
1 / 20
4.0
OkayChris,Aug 2026
MIA - ORD
Food
6.7
Overall
7.4
Boarding
7.7
Entertainment
7.1
Comfort
7.3
Crew
8.1
Reviews
1 / 20
4.0
OkayChris,Aug 2026
MIA - ORD
Food
6.7
Overall
7.4
Boarding
7.7
Entertainment
7.1
Comfort
7.3
Crew
8.1
Reviews
1 / 20
4.0
OkayChris,Aug 2026
MIA - ORD
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.
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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.
Complete your trip
Complete your trip to Jamaica by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Madison to Jamaica by cabin class
Find flights from Madison to Jamaica, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Madison and Jamaica flights
Browse other Madison and Jamaica flight options. Last updated on August 25, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top 2 airlines flying from Madison to Jamaica
Discover the top 2 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 7,457,451 searches. Data last updated August 25, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$390 | Average$665 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$406 | Average$604 | FlexibilityNo cancel fee | On-time71% |