$182+ Cheap flights from Madison (MSN) to Montego Bay (MBJ)
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 12/5. Fares are subject to change and may not be available on all flights or dates of travel.
MSN — MBJ
Sep 27 — Oct 41
Round-trip
1 adult, Economy
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Find cheap flights from Madison to Montego Bay with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
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Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from Madison to Montego Bay
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Cheapest flights from Madison to Montego BayExplore the most affordable flight options available from Madison to Montego Bay. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 28, 2026.
Explore the most affordable flight options available from Madison to Montego Bay. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 28, 2026.
This United Airlines deal was found by Cheapflights users on 8/25. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/246:39 pm -
2 stops18h 35m
Wed 10/282:01 pm -
1 stop9h 06m
Deal found 8/25![United Airlines logo]()
$412
This American Airlines deal was found by Cheapflights users on 8/26. 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 12/46:38 pm -
2 stops14h 37m
Thu 12/101:02 pm -
1 stop11h 57m
Deal found 8/26![American Airlines logo]()
$417
This American Airlines deal was found by Cheapflights users on 8/26. 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 10/297:05 pm -
2 stops16h 03m
Sun 11/13:56 pm -
1 stop17h 14m
Deal found 8/26![American Airlines logo]()
$422
This American Airlines deal was found by Cheapflights users on 8/25. 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 11/55:18 pm -
1 stop18h 54m
Sun 11/86:09 pm -
2 stops17h 37m
Deal found 8/25![American Airlines logo]()
$430
This American Airlines deal was found by Cheapflights users on 8/28. 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 9/51:25 pm -
1 stop24h 58m
Sat 9/125:16 pm -
2 stops19h 40m
Deal found 8/28![American Airlines logo]()
$485
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 American Airlines deal was found by Cheapflights users on 8/25. 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.
Sat 9/268:05 pm -
2 stops16h 48m
Wed 9/301:00 pm -
2 stops21h 51m
Deal found 8/25![American Airlines logo]()
$530
Best flights from Madison to Montego BayDiscover carefully curated flight deals from Madison to Montego Bay that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 28, 2026.
Discover carefully curated flight deals from Madison to Montego Bay that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 28, 2026.
This United Airlines deal was found by Cheapflights users on 8/25. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/246:39 pm -
2 stops18h 35m
Wed 10/282:01 pm -
1 stop9h 06m
Deal found 8/25![United Airlines logo]()
$412
This American Airlines deal was found by Cheapflights users on 8/25. 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.
Fri 12/46:38 pm -
2 stops14h 37m
Thu 12/1011:05 am -
2 stops13h 54m
Deal found 8/25![American Airlines logo]()
$417
This United Airlines deal was found by Cheapflights users on 8/26. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/297:15 pm -
2 stops15h 58m
Sun 11/13:45 pm -
2 stops19h 05m
Deal found 8/26![United Airlines logo]()
$417
This American Airlines deal was found by Cheapflights users on 8/28. 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 9/137:17 am -
1 stop8h 59m
Sat 9/1912:17 pm -
1 stop9h 26m
Deal found 8/28![American Airlines logo]()
$471
This United Airlines deal was found by Cheapflights users on 8/27. 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 2/15:00 am -
1 stop7h 46m
Fri 2/52:48 pm -
1 stop7h 01m
Deal found 8/27![United Airlines logo]()
$533
Last-minute flights from Madison to Montego BayDiscover last-minute flight deals from Madison to Montego Bay. Data last updated August 28, 2026 and is based on user searches.
Discover last-minute flight deals from Madison to Montego Bay. Data last updated August 28, 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 8/28. 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 9/51:25 pm -
1 stop24h 58m
Sat 9/125:16 pm -
2 stops19h 40m
Deal found 8/28![American Airlines logo]()
$485
This American Airlines deal was found by Cheapflights users on 8/27. 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 9/135:50 pm -
2 stops19h 03m
Sat 9/195:16 pm -
2 stops19h 40m
Deal found 8/27![American Airlines logo]()
$417
This American Airlines deal was found by Cheapflights users on 8/25. 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.
Sat 9/268:05 pm -
2 stops16h 48m
Wed 9/301:00 pm -
2 stops21h 51m
Deal found 8/25![American Airlines logo]()
$530
One-way flights from Madison to Montego BaySearch for one-way flight options from Madison to Montego Bay. Find affordable one-way fares based on user searches. Data last updated August 28, 2026.
Search for one-way flight options from Madison to Montego Bay. Find affordable one-way fares based on user searches. Data last updated August 28, 2026.
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.
Sat 12/56:30 am -
2 stops8h 49m
Deal found 8/24![United Airlines logo]()
$182
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 8/26. 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 2/187:05 pm -
2 stops18h 20m
Deal found 8/26![American Airlines logo]()
$247
This United Airlines deal was found by Cheapflights users on 8/26. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/188:20 am -
1 stop28h 26m
Deal found 8/26![United Airlines logo]()
$254
This American Airlines deal was found by Cheapflights users on 8/25. 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 9/35:47 pm -
2 stops17h 55m
Deal found 8/25![American Airlines logo]()
$283
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.
Tue 9/86:00 am -
1 stop8h 23m
Deal found 8/24![American Airlines logo]()
$357
This American Airlines deal was found by Cheapflights users on 8/26. 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.
Wed 12/234:33 pm -
2 stops16h 39m
Deal found 8/26![American Airlines logo]()
$368
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/510:33 am -
3 stops25h 35m
Deal found 8/24![Multiple Airlines logo]()
$390
This Kiwi.com deal was found by Cheapflights users on 8/28. 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.
Thu 9/106:00 pm -
3 stops42h 02m
Deal found 8/28![Multiple Airlines logo]()
$431
Find flight deals from Madison to Montego Bay
Discover tips and strategies to find the most affordable flight options for your journey from Madison (MSN) to Montego Bay (MBJ). 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 August 28, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $412 (United Airlines) |
One-way from | $182 (United Airlines) |
Popular in | June |
Cheapest in | January |
Cheapflights Fare Finder
Customize your flight search to find flights from Madison to Montego Bay 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 28, 2026.
Use the filters below to find and compare flights from Madison to Montego Bay 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
Sat 10/24
6:39 pm-1:14 pm
2 stops18h 35m
Montego Bay Sangster Intl
Wed 10/28
2:01 pm-11:07 pm
1 stop9h 06m
$412
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-11:59 pm
2 stops13h 54m
$417
MadisonMontego Bay
MSN Madison Truax Field - MBJ Montego Bay Sangster Intl
MSNMBJ
Madison Truax Field
Thu 10/29
7:15 pm-11:13 am
2 stops15h 58m
Montego Bay Sangster Intl
Sun 11/1
3:45 pm-9:50 am
2 stops19h 05m
$417
MadisonMontego Bay
MSN Madison Truax Field - MBJ Montego Bay Sangster Intl
MSNMBJ
Madison Truax Field
Sun 9/13
7:17 am-4:16 pm
1 stop8h 59m
Montego Bay Sangster Intl
Sat 9/19
12:17 pm-9:43 pm
1 stop9h 26m
$471
Quickest round-trip
MadisonMontego Bay
MSN Madison Truax Field - MBJ Montego Bay Sangster Intl
MSNMBJ
Madison Truax Field
Mon 2/1
5:00 am-1:46 pm
1 stop7h 46m
Montego Bay Sangster Intl
Fri 2/5
2:48 pm-8:49 pm
1 stop7h 01m
$533
Cheapest one-way
Quickest one-way
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
Thu 2/18
7:05 pm-2:25 pm
2 stops18h 20m
$247
MadisonMontego Bay
MSN Madison Truax Field - MBJ Montego Bay Sangster Intl
MSNMBJ
Madison Truax Field
Thu 2/18
8:20 am-1:46 pm
1 stop28h 26m
$254
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
MadisonMontego Bay
MSN Madison Truax Field - MBJ Montego Bay Sangster Intl
MSNMBJ
Madison Truax Field
Tue 9/8
5:47 pm-1:09 pm
2 stops19h 22m
$283
Showing 1-10 of 13 resultsSorted by cheapest first
Compare providers for flights from Madison to Montego Bay
Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Madison to Montego Bay in August.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars |
- Most accurate provider: When it comes to deals on Madison-Montego Bay flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Madison-Montego Bay flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Madison-Montego Bay flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Madison-Montego Bay flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Madison-Montego Bay flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.
Best time to book a flight from Madison to Montego Bay
Have a flexible travel schedule? Discover the best time to fly to Montego Bay 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.
Reviews of airlines servicing Montego Bay
Get insights into the airlines that provide service to Montego Bay. 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 Montego Bay. Reviews last updated August 28, 2026.
Read reviews from past customers who have flown United Airlines and American Airlines from Madison to Montego Bay. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Food
6.7
Overall
7.4
Entertainment
7.1
Boarding
7.7
Comfort
7.3
Crew
8.1
Reviews
1 / 20
4.0
OkayChris,Aug 2026
MIA - ORD
Food
6.7
Overall
7.4
Entertainment
7.1
Boarding
7.7
Comfort
7.3
Crew
8.1
Reviews
1 / 20
4.0
OkayChris,Aug 2026
MIA - ORD
Food
6.7
Overall
7.4
Entertainment
7.1
Boarding
7.7
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 Montego Bay. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Traveling to a place near Montego Bay?
Book flights to Montego Bay if you plan to visit one of these locationsLucea
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Other flights to Montego Bay
Explore flights to Montego Bay departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on August 28, 2026.
Madison and Montego Bay flights
Browse other Madison and Montego Bay flight options. Last updated on August 28, 2026.
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Browse through other flights departing from Madison. Flights are based on user searches made on Cheapflights and were last updated on August 28, 2026.
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Check out other popular destinations found by fellow travelers in 2026
Top 2 airlines flying from Madison to Montego Bay
Discover the top 2 airlines that operate flights from Madison to Montego Bay. 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 28, 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% |