$182+ Cheap flights from Milwaukee (MKE) 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 10/5. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — MBJ
Oct 17 — Oct 241
Round-trip
1 adult, Economy
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Cheapest flights from Milwaukee to JamaicaExplore the most affordable flight options available from Milwaukee to Jamaica. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 17, 2026.
Explore the most affordable flight options available from Milwaukee to Jamaica. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 17, 2026.
This American Airlines deal was found by Cheapflights users on 9/14. 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 10/317:19 pm -
2 stops16h 43m
Fri 11/61:02 pm -
1 stop11h 54m
Deal found 9/14![American Airlines logo]()
$357
This American Airlines deal was found by Cheapflights users on 9/14. 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 10/307:14 am -
1 stop8h 58m
Fri 11/61:21 pm -
1 stop9h 35m
Deal found 9/14![American Airlines logo]()
$382
This American Airlines deal was found by Cheapflights users on 9/17. 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 12/52:55 pm -
2 stops18h 20m
Sat 12/126:09 pm -
2 stops17h 59m
Deal found 9/17![American Airlines logo]()
$387
This American Airlines deal was found by Cheapflights users on 9/16. 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 10/315:47 pm -
1 stop23h 22m
Sat 11/71:21 pm -
1 stop9h 39m
Deal found 9/16![American Airlines logo]()
$389
This Delta deal was found by Cheapflights users on 9/16. 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.
Tue 10/275:55 pm -
1 stop17h 35m
Fri 11/63:26 pm -
1 stop6h 31m
Deal found 9/16![Delta logo]()
$412
This Delta deal was found by Cheapflights users on 9/16. 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.
Tue 10/273:20 pm -
2 stops20h 10m
Sat 11/75:50 pm -
1 stop16h 21m
Deal found 9/16![Delta logo]()
$417
This American Airlines deal was found by Cheapflights users on 9/13. 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 10/287:19 pm -
2 stops17h 49m
Wed 11/43:22 pm -
2 stops9h 33m
Deal found 9/13![American Airlines logo]()
$442
This American Airlines deal was found by Cheapflights users on 9/14. 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 12/117:00 am -
1 stop6h 28m
Wed 12/161:22 pm -
1 stop9h 38m
Deal found 9/14![American Airlines logo]()
$447
This United Airlines deal was found by Cheapflights users on 9/16. 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.
Sun 10/259:33 am -
1 stop27h 15m
Thu 10/292:20 pm -
1 stop8h 44m
Deal found 9/16![United Airlines logo]()
$478
This United Airlines deal was found by Cheapflights users on 9/13. 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.
Wed 10/286:18 pm -
3 stops19h 37m
Wed 11/42:58 pm -
2 stops20h 15m
Deal found 9/13![United Airlines logo]()
$757
This United Airlines deal was found by Cheapflights users on 9/15. 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 10/156:32 pm -
3 stops19h 23m
Wed 10/212:57 pm -
3 stops19h 10m
Deal found 9/15![United Airlines logo]()
$761
This United Airlines deal was found by Cheapflights users on 9/13. 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 9/248:00 am -
2 stops29h 51m
Mon 9/282:57 pm -
2 stops55h 48m
Deal found 9/13![United Airlines logo]()
$846
Best flights from Milwaukee to JamaicaDiscover carefully curated flight deals from Milwaukee to Jamaica that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 17, 2026.
Discover carefully curated flight deals from Milwaukee to Jamaica that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 17, 2026.
This American Airlines deal was found by Cheapflights users on 9/14. 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 10/307:14 am -
1 stop8h 58m
Fri 11/63:28 pm -
2 stops9h 27m
Deal found 9/14![American Airlines logo]()
$387
This United Airlines deal was found by Cheapflights users on 9/13. 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.
Wed 10/286:47 am -
1 stop6h 01m
Wed 11/42:54 pm -
1 stop6h 56m
Deal found 9/13![United Airlines logo]()
$412
This American Airlines deal was found by Cheapflights users on 9/17. 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 12/52:55 pm -
2 stops18h 20m
Sat 12/1211:59 am -
1 stop25h 05m
Deal found 9/17![American Airlines logo]()
$394
This United Airlines deal was found by Cheapflights users on 9/16. 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.
Sun 10/259:33 am -
1 stop27h 15m
Thu 10/292:20 pm -
1 stop8h 44m
Deal found 9/16![United Airlines logo]()
$478
This United Airlines deal was found by Cheapflights users on 9/12. 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 10/277:03 pm -
1 stop16h 10m
Tue 11/32:54 pm -
1 stop6h 58m
Deal found 9/12![United Airlines logo]()
$512
This Air Canada deal was found by Cheapflights users on 9/15. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/2012:05 pm -
2 stops25h 50m
Fri 10/233:05 pm -
2 stops28h 04m
Deal found 9/15![Air Canada logo]()
$1,739
This United Airlines deal was found by Cheapflights users on 9/13. 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.
Wed 10/288:00 am -
2 stops29h 55m
Wed 11/42:58 pm -
2 stops27h 45m
Deal found 9/13![United Airlines logo]()
$757
This United Airlines deal was found by Cheapflights users on 9/15. 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 10/156:32 pm -
3 stops19h 23m
Wed 10/212:57 pm -
2 stops16h 10m
Deal found 9/15![United Airlines logo]()
$757
This United Airlines deal was found by Cheapflights users on 9/16. 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 10/206:00 am -
2 stops31h 55m
Fri 10/232:57 pm -
2 stops20h 33m
Deal found 9/16![United Airlines logo]()
$1,082
Last-minute flights from Milwaukee to JamaicaDiscover last-minute flight deals from Milwaukee to Jamaica. Data last updated September 17, 2026 and is based on user searches.
Discover last-minute flight deals from Milwaukee to Jamaica. Data last updated September 17, 2026 and is based on user searches.
This United Airlines deal was found by Cheapflights users on 9/13. 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 9/248:00 am -
2 stops29h 51m
Mon 9/282:57 pm -
2 stops55h 48m
Deal found 9/13![United Airlines logo]()
$846
This United Airlines deal was found by Cheapflights users on 9/15. 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 10/156:32 pm -
3 stops19h 23m
Wed 10/212:57 pm -
3 stops19h 10m
Deal found 9/15![United Airlines logo]()
$761
This United Airlines deal was found by Cheapflights users on 9/16. 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.
Sun 10/259:33 am -
1 stop27h 15m
Thu 10/292:20 pm -
1 stop8h 44m
Deal found 9/16![United Airlines logo]()
$478
This Delta deal was found by Cheapflights users on 9/16. 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.
Tue 10/275:55 pm -
1 stop17h 35m
Fri 11/63:26 pm -
1 stop6h 31m
Deal found 9/16![Delta logo]()
$412
This Delta deal was found by Cheapflights users on 9/16. 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.
Tue 10/273:20 pm -
2 stops20h 10m
Sat 11/75:50 pm -
1 stop16h 21m
Deal found 9/16![Delta logo]()
$417
This American Airlines deal was found by Cheapflights users on 9/13. 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 10/287:19 pm -
2 stops17h 49m
Wed 11/43:22 pm -
2 stops9h 33m
Deal found 9/13![American Airlines logo]()
$442
This Delta deal was found by Cheapflights users on 9/16. 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.
Wed 10/285:30 am -
1 stop6h 21m
Sat 11/75:50 pm -
1 stop16h 21m
Deal found 9/16![Delta logo]()
$499
This United Airlines deal was found by Cheapflights users on 9/13. 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.
Wed 10/286:18 pm -
3 stops19h 37m
Wed 11/42:58 pm -
2 stops20h 15m
Deal found 9/13![United Airlines logo]()
$757
This Delta deal was found by Cheapflights users on 9/13. 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.
Wed 10/287:03 am -
1 stop13h 12m
Wed 11/49:15 am -
1 stop12h 07m
Deal found 9/13![Delta logo]()
$847
This American Airlines deal was found by Cheapflights users on 9/14. 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 10/307:14 am -
1 stop8h 58m
Fri 11/61:21 pm -
1 stop9h 35m
Deal found 9/14![American Airlines logo]()
$382
This American Airlines deal was found by Cheapflights users on 9/14. 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 10/317:19 pm -
2 stops16h 43m
Fri 11/61:02 pm -
1 stop11h 54m
Deal found 9/14![American Airlines logo]()
$357
This American Airlines deal was found by Cheapflights users on 9/16. 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 10/315:47 pm -
1 stop23h 22m
Sat 11/71:21 pm -
1 stop9h 39m
Deal found 9/16![American Airlines logo]()
$389
One-way flights from Milwaukee to JamaicaSearch for one-way flight options from Milwaukee to Jamaica. Find affordable one-way fares based on user searches. Data last updated September 17, 2026.
Search for one-way flight options from Milwaukee to Jamaica. Find affordable one-way fares based on user searches. Data last updated September 17, 2026.
This United Airlines deal was found by Cheapflights users on 9/16. 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 10/36:47 pm -
2 stops18h 43m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/16![United Airlines logo]()
$182
This American Airlines deal was found by Cheapflights users on 9/16. 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 10/46:43 pm -
2 stops18h 18m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/16![American Airlines logo]()
$188
This American Airlines deal was found by Cheapflights users on 9/16. 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 10/35:43 pm -
1 stop22h 33m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/16![American Airlines logo]()
$196
This American Airlines deal was found by Cheapflights users on 9/15. 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 10/25:53 pm -
2 stops19h 00m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/15![American Airlines logo]()
$247
This United Airlines deal was found by Cheapflights users on 9/16. 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 10/56:32 pm -
3 stops19h 23m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/16![United Airlines logo]()
$334
This United Airlines deal was found by Cheapflights users on 9/15. 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.
Sun 10/46:00 am -
2 stops31h 55m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/15![United Airlines logo]()
$413
This United Airlines deal was found by Cheapflights users on 9/15. 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.
Fri 10/26:38 pm -
1 stop17h 05m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/15![United Airlines logo]()
$463
This Delta deal was found by Cheapflights users on 9/15. 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.
Sun 10/47:05 am -
1 stop13h 05m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/15![Delta logo]()
$519
This American Airlines deal was found by Cheapflights users on 9/16. 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 12/246:49 pm -
2 stops16h 20m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/16![American Airlines logo]()
$586
This Kiwi.com deal was found by Cheapflights users on 9/15. 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.
Fri 10/26:47 pm -
3 stops23h 43m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/15![WestJet logo]()
$600
This Kiwi.com deal was found by Cheapflights users on 9/16. 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.
Sun 10/410:10 am -
3 stops25h 07m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/16![Multiple Airlines logo]()
$656
This American Airlines deal was found by Cheapflights users on 9/16. 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 12/2310:45 am -
2 stops24h 24m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/16![American Airlines logo]()
$657
Find flight deals from Milwaukee to Jamaica
Keep the following information in mind while searching for Milwaukee to Jamaica flight deals. Data was last updated September 17, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $357 (American Airlines) |
One-way from | $182 (United Airlines) |
Popular in | November |
Cheapest in | August |
Average price | $654 |
Cheapflights Fare Finder
Customize your flight search to find flights from Milwaukee 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 September 17, 2026.
Use the filters below to find and compare flights from Milwaukee to Jamaica that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
Quickest round-trip
MilwaukeeMontego Bay
MKE Milwaukee-Mitchell - MBJ Montego Bay Sangster Intl
MKEMBJ
Milwaukee-Mitchell
Mon 10/5
5:30 am-1:01 pm
1 stop7h 31m
Montego Bay Sangster Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$182
MilwaukeeMontego Bay
MKE Milwaukee-Mitchell - MBJ Montego Bay Sangster Intl
MKEMBJ
Milwaukee-Mitchell
Sat 10/3
6:47 pm-1:30 pm
2 stops18h 43m
Montego Bay Sangster Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$182
MilwaukeeMontego Bay
MKE Milwaukee-Mitchell - MBJ Montego Bay Sangster Intl
MKEMBJ
Milwaukee-Mitchell
Mon 10/5
6:02 pm-11:08 am
2 stops17h 06m
Montego Bay Sangster Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$188
MilwaukeeMontego Bay
MKE Milwaukee-Mitchell - MBJ Montego Bay Sangster Intl
MKEMBJ
Milwaukee-Mitchell
Sun 10/4
7:01 am-4:16 pm
1 stop9h 15m
Montego Bay Sangster Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$241
MilwaukeeMontego Bay
MKE Milwaukee-Mitchell - MBJ Montego Bay Sangster Intl
MKEMBJ
Milwaukee-Mitchell
Fri 10/2
5:53 pm-12:53 pm
2 stops19h 00m
Montego Bay Sangster Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$247
MilwaukeeKingston
MKE Milwaukee-Mitchell - KIN Kingston Norman Manley
MKEKIN
Milwaukee-Mitchell
Mon 10/5
6:32 pm-1:55 pm
3 stops19h 23m
Kingston Norman Manley
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$334
MilwaukeeMontego Bay
MKE Milwaukee-Mitchell - MBJ Montego Bay Sangster Intl
MKEMBJ
Milwaukee-Mitchell
Fri 10/30
7:14 am-4:12 pm
1 stop8h 58m
Montego Bay Sangster Intl
Fri 11/6
3:28 pm-11:55 pm
2 stops9h 27m
$387
MilwaukeeMontego Bay
MKE Milwaukee-Mitchell - MBJ Montego Bay Sangster Intl
MKEMBJ
Milwaukee-Mitchell
Sat 12/5
2:55 pm-10:15 am
2 stops18h 20m
Montego Bay Sangster Intl
Sat 12/12
11:59 am-12:04 pm
1 stop25h 05m
$394
MilwaukeeMontego Bay
MKE Milwaukee-Mitchell - MBJ Montego Bay Sangster Intl
MKEMBJ
Milwaukee-Mitchell
Wed 10/28
6:47 am-12:48 pm
1 stop6h 01m
Montego Bay Sangster Intl
Wed 11/4
2:54 pm-8:50 pm
1 stop6h 56m
$412
MilwaukeeKingston
MKE Milwaukee-Mitchell - KIN Kingston Norman Manley
MKEKIN
Milwaukee-Mitchell
Sun 10/4
6:00 am-1:55 pm
2 stops31h 55m
Kingston Norman Manley
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$413
Showing 1-10 of 23 resultsSorted by cheapest first
Best time to book a flight from Milwaukee to Jamaica
Have a flexible travel schedule? Discover the best time to fly to Jamaica from Milwaukee with our price prediction graph.
MKE-MBJ
MKE-KIN
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 Milwaukee to Jamaica
MKE-JM0
MKE-MBJ
MKE-KIN
What is the cheapest month to book a flight from Milwaukee to Jamaica?
Currently, August is the cheapest month in which you can book a flight from Milwaukee to Jamaica (average of $432). Flying from Milwaukee to Jamaica in November is currently the most expensive (average of $764). 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.
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 September 17, 2026.
Get a feel of what it's like to fly with Southwest,Delta, andAmerican Airlines from Milwaukee 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
7.0
Comfort
8.0
Entertainment
7.5
Crew
8.6
Boarding
8.1
Overall
8.0
Reviews
1 / 20
4.0
OkaySteven,Sep 2026
OGG - HNL
Food
7.0
Comfort
8.0
Entertainment
7.5
Crew
8.6
Boarding
8.1
Overall
8.0
Reviews
1 / 20
4.0
OkaySteven,Sep 2026
OGG - HNL
Food
7.0
Comfort
8.0
Entertainment
7.5
Crew
8.6
Boarding
8.1
Overall
8.0
Reviews
1 / 20
4.0
OkaySteven,Sep 2026
OGG - HNL
Food
7.0
Comfort
8.0
Entertainment
7.5
Crew
8.6
Boarding
8.1
Overall
8.0
Reviews
1 / 20
4.0
OkaySteven,Sep 2026
OGG - HNL
Related info for your journey
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Top 3 airlines flying from Milwaukee to Jamaica
Discover the top 3 airlines that operate flights from Milwaukee 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 September 17, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$352 | Average$780 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$462 | Average$539 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$615 | Average$666 | FlexibilityNo cancel fee | On-time63% |