$152+ Cheap flights from Milwaukee (MKE) 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 4/27. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — MBJ
Apr 17 — Apr 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 March 18, 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 March 18, 2026.
This United Airlines deal was found by Cheapflights users on 3/14. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/286:50 am
MKE
- MBJ
2 stops8h 20m
United Airlines
Tue 5/52:40 pm
MBJ
- MKE
1 stop8h 19m
United Airlines
Deal found 3/14![United Airlines logo]()
$352
This American Airlines deal was found by Cheapflights users on 3/13. 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.
Mon 6/16:45 pm
MKE
- MBJ
2 stops18h 23m
American Airlines
Fri 6/55:17 pm
MBJ
- MKE
2 stops18h 47m
American Airlines
Deal found 3/13![American Airlines logo]()
$357
This American Airlines deal was found by Cheapflights users on 3/13. 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 4/295:06 am
MKE
- MBJ
2 stops8h 19m
American Airlines
Mon 5/44:37 pm
MBJ
- MKE
2 stops17h 32m
American Airlines
Deal found 3/13![American Airlines logo]()
$362
This American Airlines deal was found by Cheapflights users on 3/16. 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 8/277:10 am
MKE
- MBJ
1 stop26h 15m
American Airlines
Mon 8/313:20 pm
MBJ
- MKE
2 stops20h 12m
American Airlines
Deal found 3/16![American Airlines logo]()
$364
This United Airlines deal was found by Cheapflights users on 3/17. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/228:45 pm
MKE
- MBJ
2 stops18h 25m
United Airlines
Fri 7/34:12 pm
MBJ
- MKE
2 stops17h 46m
United Airlines
Deal found 3/17![United Airlines logo]()
$377
This Delta deal was found by Cheapflights users on 3/14. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/267:00 am
MKE
- MBJ
1 stop5h 54m
Delta
Fri 5/14:32 pm
MBJ
- MKE
1 stop16h 33m
Delta
Deal found 3/14![Delta logo]()
$402
This Delta deal was found by Cheapflights users on 3/14. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/252:50 pm
MKE
- MBJ
2 stops20h 37m
Delta
Tue 5/54:32 pm
MBJ
- MKE
1 stop16h 33m
Delta
Deal found 3/14![Delta logo]()
$407
This United Airlines deal was found by Cheapflights users on 3/16. 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 6/18:45 pm
MKE
- MBJ
2 stops16h 45m
United Airlines
Sat 6/61:52 pm
MBJ
- MKE
1 stop8h 32m
United Airlines
Deal found 3/16![United Airlines logo]()
$412
This United Airlines deal was found by Cheapflights users on 3/16. 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 4/216:50 am
MKE
- MBJ
2 stops8h 20m
United Airlines
Fri 4/244:12 pm
MBJ
- MKE
2 stops17h 48m
United Airlines
Deal found 3/16![United Airlines logo]()
$418
This American Airlines deal was found by Cheapflights users on 3/14. 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 4/246:41 pm
MKE
- MBJ
1 stop16h 48m
American Airlines
Fri 5/12:29 pm
MBJ
- MKE
1 stop8h 28m
American Airlines
Deal found 3/14![American Airlines logo]()
$422
This United Airlines deal was found by Cheapflights users on 3/16. 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 6/305:29 pm
MKE
- MBJ
2 stops20h 01m
United Airlines
Wed 7/82:40 pm
MBJ
- MKE
1 stop8h 05m
United Airlines
Deal found 3/16![United Airlines logo]()
$425
This United Airlines deal was found by Cheapflights users on 3/15. 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 5/36:00 am
MKE
- KIN
2 stops31h 54m
United Airlines
Thu 5/72:59 pm
KIN
- MKE
2 stops43h 39m
United Airlines
Deal found 3/15![United Airlines logo]()
$707
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 March 18, 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 March 18, 2026.
This American Airlines deal was found by Cheapflights users on 3/12. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/65:06 am
MKE
- MBJ
1 stop7h 07m
American Airlines
Mon 5/114:37 pm
MBJ
- MKE
2 stops17h 32m
American Airlines
Deal found 3/12![American Airlines logo]()
$362
This Delta deal was found by Cheapflights users on 3/14. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/115:45 am
MKE
- MBJ
1 stop9h 48m
Delta
Thu 4/162:10 pm
MBJ
- MKE
1 stop9h 47m
Delta
Deal found 3/14![Delta logo]()
$402
This United Airlines deal was found by Cheapflights users on 3/12. 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 5/51:46 pm
MKE
- MBJ
2 stops23h 44m
United Airlines
Thu 5/72:40 pm
MBJ
- MKE
2 stops19h 05m
United Airlines
Deal found 3/12![United Airlines logo]()
$467
This United Airlines deal was found by Cheapflights users on 3/16. 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.
Wed 5/66:49 am
MKE
- MBJ
2 stops8h 21m
United Airlines
Mon 5/112:40 pm
MBJ
- MKE
2 stops23h 47m
United Airlines
Deal found 3/16![United Airlines logo]()
$467
This United Airlines deal was found by Cheapflights users on 3/15. 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 5/36:00 am
MKE
- KIN
2 stops31h 54m
United Airlines
Thu 5/72:59 pm
KIN
- MKE
2 stops43h 39m
United Airlines
Deal found 3/15![United Airlines logo]()
$707
This Delta deal was found by Cheapflights users on 3/15. 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 5/310:11 am
MKE
- KIN
1 stop9h 49m
Delta
Thu 5/79:00 am
KIN
- MKE
1 stop14h 53m
Delta
Deal found 3/15![Delta logo]()
$794
This United Airlines deal was found by Cheapflights users on 3/12. 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.
Mon 4/276:40 pm
MKE
- KIN
2 stops19h 12m
United Airlines
Fri 5/12:59 pm
KIN
- MKE
2 stops19h 05m
United Airlines
Deal found 3/12![United Airlines logo]()
$712
This Delta deal was found by Cheapflights users on 3/13. 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.
Sun 4/55:45 am
MKE
- KIN
1 stop14h 15m
Delta
Thu 4/99:00 am
KIN
- MKE
1 stop8h 41m
Delta
Deal found 3/13![Delta logo]()
$874
This American Airlines deal was found by Cheapflights users on 3/13. 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.
Sun 4/56:38 am
MKE
- KIN
1 stop12h 34m
American Airlines
Thu 4/97:00 am
KIN
- MKE
2 stops15h 27m
American Airlines
Deal found 3/13![American Airlines logo]()
$1,009
This American Airlines deal was found by Cheapflights users on 3/13. 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.
Fri 4/36:38 am
MKE
- KIN
1 stop6h 51m
American Airlines
Thu 4/97:00 am
KIN
- MKE
2 stops16h 29m
American Airlines
Deal found 3/13![American Airlines logo]()
$1,009
Last-minute flights from Milwaukee to JamaicaDiscover last-minute flight deals from Milwaukee to Jamaica. Data last updated March 18, 2026 and is based on user searches.
Discover last-minute flight deals from Milwaukee to Jamaica. Data last updated March 18, 2026 and is based on user searches.
This Delta deal was found by Cheapflights users on 3/13. 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.
Fri 4/312:11 pm
MKE
- KIN
1 stop7h 49m
Delta
Thu 4/99:00 am
KIN
- MKE
1 stop14h 58m
Delta
Deal found 3/13![Delta logo]()
$874
This American Airlines deal was found by Cheapflights users on 3/14. 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.
Thu 4/95:41 pm
MKE
- MBJ
2 stops19h 44m
American Airlines
Fri 4/1710:17 am
MBJ
- MKE
1 stop7h 34m
American Airlines
Deal found 3/14![American Airlines logo]()
$427
This American Airlines deal was found by Cheapflights users on 3/17. 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 4/116:32 pm
MKE
- MBJ
1 stop14h 41m
American Airlines
Sat 4/1810:13 am
MBJ
- MKE
1 stop12h 44m
American Airlines
Deal found 3/17![American Airlines logo]()
$434
This United Airlines deal was found by Cheapflights users on 3/16. 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 4/216:50 am
MKE
- MBJ
2 stops8h 20m
United Airlines
Fri 4/244:12 pm
MBJ
- MKE
2 stops17h 48m
United Airlines
Deal found 3/16![United Airlines logo]()
$418
This American Airlines deal was found by Cheapflights users on 3/14. 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 4/246:41 pm
MKE
- MBJ
1 stop16h 48m
American Airlines
Tue 5/512:25 pm
MBJ
- MKE
1 stop9h 32m
American Airlines
Deal found 3/14![American Airlines logo]()
$422
This Delta deal was found by Cheapflights users on 3/14. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/252:50 pm
MKE
- MBJ
2 stops20h 37m
Delta
Fri 5/12:10 pm
MBJ
- MKE
1 stop9h 47m
Delta
Deal found 3/14![Delta logo]()
$407
This American Airlines deal was found by Cheapflights users on 3/15. 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.
Sat 4/256:32 pm
MKE
- MBJ
1 stop16h 52m
American Airlines
Sat 5/22:10 pm
MBJ
- MKE
1 stop8h 17m
American Airlines
Deal found 3/15![American Airlines logo]()
$435
This Delta deal was found by Cheapflights users on 3/14. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/265:30 am
MKE
- MBJ
1 stop7h 24m
Delta
Wed 5/62:10 pm
MBJ
- MKE
1 stop9h 48m
Delta
Deal found 3/14![Delta logo]()
$402
This United Airlines deal was found by Cheapflights users on 3/12. 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.
Mon 4/276:40 pm
MKE
- KIN
2 stops19h 12m
United Airlines
Fri 5/12:59 pm
KIN
- MKE
2 stops19h 05m
United Airlines
Deal found 3/12![United Airlines logo]()
$712
This United Airlines deal was found by Cheapflights users on 3/14. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/286:50 am
MKE
- MBJ
2 stops8h 20m
United Airlines
Tue 5/52:40 pm
MBJ
- MKE
1 stop8h 19m
United Airlines
Deal found 3/14![United Airlines logo]()
$352
This American Airlines deal was found by Cheapflights users on 3/13. 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 4/296:00 am
MKE
- MBJ
1 stop8h 15m
American Airlines
Mon 5/410:17 am
MBJ
- MKE
1 stop12h 40m
American Airlines
Deal found 3/13![American Airlines logo]()
$357
This American Airlines deal was found by Cheapflights users on 3/14. 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.
Wed 4/297:00 am
MKE
- MBJ
1 stop6h 25m
American Airlines
Tue 5/52:19 pm
MBJ
- MKE
2 stops17h 22m
American Airlines
Deal found 3/14![American Airlines logo]()
$432
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 March 18, 2026.
Search for one-way flight options from Milwaukee to Jamaica. Find affordable one-way fares based on user searches. Data last updated March 18, 2026.
This United Airlines deal was found by Cheapflights users on 3/14. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/276:50 am
MKE
- MBJ
1 stop6h 00m
United Airlines
Deal found 3/14![United Airlines logo]()
$152
This Kiwi.com deal was found by Cheapflights users on 3/14. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/229:01 pm
MKE
- MBJ
2 stops14h 04m
Multiple Airlines
Deal found 3/14![Multiple Airlines logo]()
$255
This United Airlines deal was found by Cheapflights users on 3/14. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/228:00 am
MKE
- MBJ
1 stop29h 05m
United Airlines
Deal found 3/14![United Airlines logo]()
$304
This United Airlines deal was found by Cheapflights users on 3/14. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/215:10 pm
MKE
- MBJ
1 stop19h 55m
United Airlines
Deal found 3/14![United Airlines logo]()
$329
This Kiwi.com deal was found by Cheapflights users on 3/14. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/219:01 pm
MKE
- MBJ
2 stops14h 04m
Multiple Airlines
Deal found 3/14![Multiple Airlines logo]()
$337
This Kiwi.com deal was found by Cheapflights users on 3/14. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/2712:21 pm
MKE
- MBJ
3 stops23h 55m
Multiple Airlines
Deal found 3/14![Multiple Airlines logo]()
$604
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 March 18, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $352 (United Airlines) |
One-way from | $152 (United Airlines) |
Popular in | June |
Cheapest in | May |
Average price | $701 |
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 2,558,603 searches. Data last updated March 18, 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
MilwaukeeMontego Bay
MKE - MBJ
MKEMBJ
Milwaukee-Mitchell
Wed 5/6
5:06 am-12:13 pm
1 stop7h 07m
Montego Bay Sangster Intl
Mon 5/11
4:37 pm-10:09 am
2 stops17h 32m
$362
Quickest round-trip
MilwaukeeMontego Bay
MKE - MBJ
MKEMBJ
Milwaukee-Mitchell
Sat 4/11
5:45 am-3:33 pm
1 stop9h 48m
Montego Bay Sangster Intl
Thu 4/16
2:10 pm-11:57 pm
1 stop9h 47m
$402
MilwaukeeMontego Bay
MKE - MBJ
MKEMBJ
Milwaukee-Mitchell
Tue 5/5
1:46 pm-1:30 pm
2 stops23h 44m
Montego Bay Sangster Intl
Thu 5/7
2:40 pm-9:45 am
2 stops19h 05m
$467
MilwaukeeMontego Bay
MKE - MBJ
MKEMBJ
Milwaukee-Mitchell
Wed 5/6
6:49 am-3:10 pm
2 stops8h 21m
Montego Bay Sangster Intl
Mon 5/11
2:40 pm-2:27 pm
2 stops23h 47m
$467
MilwaukeeKingston
MKE - KIN
MKEKIN
Milwaukee-Mitchell
Sun 5/3
6:00 am-1:54 pm
2 stops31h 54m
Kingston Norman Manley
Thu 5/7
2:59 pm-10:38 am
2 stops43h 39m
$707
MilwaukeeKingston
MKE - KIN
MKEKIN
Milwaukee-Mitchell
Mon 4/27
6:40 pm-1:52 pm
2 stops19h 12m
Kingston Norman Manley
Fri 5/1
2:59 pm-10:04 am
2 stops19h 05m
$712
MilwaukeeKingston
MKE - KIN
MKEKIN
Milwaukee-Mitchell
Sun 5/3
10:11 am-8:00 pm
1 stop9h 49m
Kingston Norman Manley
Thu 5/7
9:00 am-11:53 pm
1 stop14h 53m
$794
MilwaukeeKingston
MKE - KIN
MKEKIN
Milwaukee-Mitchell
Sun 4/5
5:45 am-8:00 pm
1 stop14h 15m
Kingston Norman Manley
Thu 4/9
9:00 am-5:41 pm
1 stop8h 41m
$874
MilwaukeeKingston
MKE - KIN
MKEKIN
Milwaukee-Mitchell
Sun 4/5
6:38 am-7:12 pm
1 stop12h 34m
Kingston Norman Manley
Thu 4/9
7:00 am-10:27 pm
2 stops15h 27m
$1,009
MilwaukeeKingston
MKE - KIN
MKEKIN
Milwaukee-Mitchell
Fri 4/3
6:38 am-1:29 pm
1 stop6h 51m
Kingston Norman Manley
Thu 4/9
7:00 am-11:29 pm
2 stops16h 29m
$1,009
Showing 1-10 of 15 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, January is the cheapest month in which you can book a flight from Milwaukee to Jamaica (average of $95). Flying from Milwaukee to Jamaica in August is currently the most expensive (average of $384). 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 March 18, 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
Crew
8.6
Boarding
8.1
Comfort
8.0
Entertainment
7.5
Overall
8.0
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
Food
7.0
Crew
8.6
Boarding
8.1
Comfort
8.0
Entertainment
7.5
Overall
8.0
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
Food
7.0
Crew
8.6
Boarding
8.1
Comfort
8.0
Entertainment
7.5
Overall
8.0
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
Food
7.0
Crew
8.6
Boarding
8.1
Comfort
8.0
Entertainment
7.5
Overall
8.0
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - 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 2,558,603 searches. Data last updated March 18, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$277 | Average$643 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$514 | Average$806 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$571 | Average$716 | FlexibilityNo cancel fee | On-time63% |