$172+ 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 1/30. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — MBJ
Sep 3 — Sep 101
Round-trip
1 adult, Economy
We work with more than 300 partners to bring you better travel deals
Find cheap flights from Milwaukee to Jamaica 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
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
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 Milwaukee to Jamaica
Cheapest
Best
Last-minute
One-way
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 August 4, 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 August 4, 2026.
This United Airlines deal was found by Cheapflights users on 8/3. 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 11/147:03 pm -
1 stop16h 10m
Fri 11/201:25 pm -
1 stop10h 22m
Deal found 8/3![United Airlines logo]()
$392
This American Airlines deal was found by Cheapflights users on 8/3. 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 11/147:24 pm -
2 stops15h 55m
Fri 11/206:22 pm -
2 stops16h 42m
Deal found 8/3![American Airlines logo]()
$397
This American Airlines deal was found by Cheapflights users on 8/4. 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 11/1411:38 am -
1 stop26h 19m
Thu 11/1911:05 am -
1 stop13h 46m
Deal found 8/4![American Airlines logo]()
$398
This United Airlines deal was found by Cheapflights users on 8/2. 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 9/1211:45 am -
1 stop23h 58m
Sat 9/192:40 pm -
1 stop7h 59m
Deal found 8/2![United Airlines logo]()
$400
This American Airlines deal was found by Cheapflights users on 8/3. 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 -
2 stops19h 10m
Tue 10/131:34 pm -
2 stops20h 40m
Deal found 8/3![American Airlines logo]()
$412
This United Airlines deal was found by Cheapflights users on 8/3. 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 9/147:05 pm -
1 stop16h 38m
Sat 9/192:40 pm -
1 stop7h 59m
Deal found 8/3![United Airlines logo]()
$417
This American Airlines deal was found by Cheapflights users on 8/2. 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 10/106:27 pm -
1 stop16h 41m
Sat 10/1712:26 pm -
1 stop11h 31m
Deal found 8/2![American Airlines logo]()
$465
This American Airlines deal was found by Cheapflights users on 8/1. 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 10/96:02 pm -
1 stop20h 00m
Wed 10/1412:18 pm -
1 stop9h 34m
Deal found 8/1![American Airlines logo]()
$474
This American Airlines deal was found by Cheapflights users on 8/1. 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 12/26:50 pm -
2 stops18h 22m
Wed 12/92:02 pm -
2 stops10h 59m
Deal found 8/1![American Airlines logo]()
$475
This American Airlines deal was found by Cheapflights users on 8/1. 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 8/275:50 pm -
1 stop22h 18m
Mon 8/315:08 pm -
2 stops17h 49m
Deal found 8/1![American Airlines logo]()
$477
This Delta deal was found by Cheapflights users on 7/31. 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 11/185:30 am -
1 stop10h 05m
Wed 11/256:00 pm -
1 stop16h 11m
Deal found 7/31![Delta logo]()
$487
This United Airlines deal was found by Cheapflights users on 8/3. 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 9/13:15 pm -
3 stops22h 36m
Mon 9/72:57 pm -
2 stops19h 03m
Deal found 8/3![United Airlines logo]()
$737
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 August 4, 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 August 4, 2026.
This United Airlines deal was found by Cheapflights users on 8/3. 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 11/77:03 pm -
1 stop16h 10m
Sat 11/143:20 pm -
1 stop8h 27m
Deal found 8/3![United Airlines logo]()
$392
This Delta deal was found by Cheapflights users on 8/3. 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 10/177:00 am -
1 stop8h 35m
Sat 10/244:50 pm -
1 stop7h 03m
Deal found 8/3![Delta logo]()
$392
This American Airlines deal was found by Cheapflights users on 8/3. 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 1/267:19 pm -
2 stops17h 54m
Tue 2/92:19 pm -
1 stop9h 39m
Deal found 8/3![American Airlines logo]()
$397
This United Airlines deal was found by Cheapflights users on 8/3. 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 11/147:03 pm -
1 stop16h 10m
Fri 11/201:25 pm -
1 stop10h 22m
Deal found 8/3![United Airlines logo]()
$392
This United Airlines deal was found by Cheapflights users on 8/1. 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 12/26:00 am -
1 stop6h 46m
Wed 12/93:36 pm -
1 stop8h 51m
Deal found 8/1![United Airlines logo]()
$392
This Delta deal was found by Cheapflights users on 8/4. 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 12/15:30 am -
1 stop10h 05m
Wed 12/96:00 pm -
1 stop6h 54m
Deal found 8/4![Delta logo]()
$487
This Delta deal was found by Cheapflights users on 7/31. 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 11/186:41 pm -
2 stops16h 44m
Wed 11/256:00 pm -
1 stop6h 54m
Deal found 7/31![Delta logo]()
$492
This United Airlines deal was found by Cheapflights users on 8/3. 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 10/276:47 am -
1 stop6h 01m
Thu 10/292:20 pm -
1 stop8h 27m
Deal found 8/3![United Airlines logo]()
$492
This United Airlines deal was found by Cheapflights users on 8/2. 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 9/13:15 pm -
3 stops22h 36m
Mon 9/72:57 pm -
2 stops19h 03m
Deal found 8/2![United Airlines logo]()
$737
This Delta deal was found by Cheapflights users on 7/31. 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.
Thu 11/1910:16 am -
1 stop7h 44m
Wed 11/259:00 am -
1 stop15h 54m
Deal found 7/31![Delta logo]()
$825
This United Airlines deal was found by Cheapflights users on 7/31. 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 11/189:33 am -
2 stops27h 19m
Tue 11/242:58 pm -
2 stops32h 49m
Deal found 7/31![United Airlines logo]()
$737
This Delta deal was found by Cheapflights users on 7/31. 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.
Thu 11/1910:16 am -
1 stop7h 44m
Tue 11/249:00 am -
1 stop9h 36m
Deal found 7/31![Delta logo]()
$825
This United Airlines deal was found by Cheapflights users on 7/31. 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 11/199:33 am -
2 stops27h 19m
Wed 11/252:58 pm -
2 stops20h 15m
Deal found 7/31![United Airlines logo]()
$737
This Delta deal was found by Cheapflights users on 8/1. 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.
Thu 9/2410:11 am -
1 stop9h 59m
Mon 9/289:10 am -
1 stop11h 44m
Deal found 8/1![Delta logo]()
$836
This United Airlines deal was found by Cheapflights users on 7/31. 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 10/266:18 pm -
2 stops43h 40m
Fri 10/302:58 pm -
2 stops26h 40m
Deal found 7/31![United Airlines logo]()
$742
This United Airlines deal was found by Cheapflights users on 8/2. 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 9/122:20 pm -
2 stops47h 31m
Sat 9/192:57 pm -
3 stops20h 33m
Deal found 8/2![United Airlines logo]()
$747
This Delta deal was found by Cheapflights users on 8/2. 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 9/110:22 am -
1 stop9h 51m
Mon 9/79:13 am -
1 stop12h 11m
Deal found 8/2![Delta logo]()
$925
Last-minute flights from Milwaukee to JamaicaDiscover last-minute flight deals from Milwaukee to Jamaica. Data last updated August 4, 2026 and is based on user searches.
Discover last-minute flight deals from Milwaukee to Jamaica. Data last updated August 4, 2026 and is based on user searches.
This American Airlines deal was found by Cheapflights users on 7/31. 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 8/276:00 pm -
2 stops17h 42m
Mon 8/315:08 pm -
2 stops18h 29m
Deal found 7/31![American Airlines logo]()
$470
This United Airlines deal was found by Cheapflights users on 8/3. 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 9/13:15 pm -
3 stops22h 36m
Mon 9/72:57 pm -
2 stops19h 03m
Deal found 8/3![United Airlines logo]()
$737
This Delta deal was found by Cheapflights users on 8/2. 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 9/110:22 am -
1 stop9h 51m
Mon 9/79:13 am -
1 stop12h 11m
Deal found 8/2![Delta logo]()
$925
This American Airlines deal was found by Cheapflights users on 7/31. 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 9/65:50 pm -
2 stops17h 52m
Sat 9/125:16 pm -
2 stops18h 11m
Deal found 7/31![American Airlines logo]()
$397
This United Airlines deal was found by Cheapflights users on 7/31. 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 9/66:00 am -
1 stop29h 43m
Sat 9/122:40 pm -
1 stop7h 59m
Deal found 7/31![United Airlines logo]()
$501
This United Airlines deal was found by Cheapflights users on 8/2. 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 9/123:52 pm -
2 stops19h 51m
Sat 9/192:40 pm -
1 stop7h 59m
Deal found 8/2![United Airlines logo]()
$392
This United Airlines deal was found by Cheapflights users on 8/2. 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 9/122:20 pm -
2 stops47h 31m
Sat 9/192:57 pm -
2 stops19h 03m
Deal found 8/2![United Airlines logo]()
$742
This Delta deal was found by Cheapflights users on 8/2. 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 9/1210:03 am -
1 stop10h 07m
Sat 9/199:10 am -
1 stop12h 20m
Deal found 8/2![Delta logo]()
$926
This United Airlines deal was found by Cheapflights users on 8/3. 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 9/147:05 pm -
1 stop16h 38m
Sat 9/192:40 pm -
1 stop7h 59m
Deal found 8/3![United Airlines logo]()
$417
This American Airlines deal was found by Cheapflights users on 7/31. 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 9/145:53 pm -
2 stops18h 03m
Mon 9/215:16 pm -
2 stops17h 51m
Deal found 7/31![American Airlines logo]()
$492
This Delta deal was found by Cheapflights users on 8/1. 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.
Thu 9/2410:11 am -
1 stop9h 59m
Mon 9/289:10 am -
1 stop11h 44m
Deal found 8/1![Delta logo]()
$836
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 August 4, 2026.
Search for one-way flight options from Milwaukee to Jamaica. Find affordable one-way fares based on user searches. Data last updated August 4, 2026.
This American Airlines deal was found by Cheapflights users on 7/31. 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 1/306:40 am -
1 stop7h 36m
Deal found 7/31![American Airlines logo]()
$172
This American Airlines deal was found by Cheapflights users on 7/30. 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 9/54:12 pm -
2 stops19h 30m
Deal found 7/30![American Airlines logo]()
$178
This American Airlines deal was found by Cheapflights users on 7/31. 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 8/152:49 pm -
1 stop22h 45m
Deal found 7/31![American Airlines logo]()
$186
This American Airlines deal was found by Cheapflights users on 8/2. 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 8/146:28 am -
1 stop7h 00m
Deal found 8/2![American Airlines logo]()
$231
This United Airlines deal was found by Cheapflights users on 7/30. 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 9/51:19 pm -
2 stops46h 24m
Deal found 7/30![United Airlines logo]()
$248
This American Airlines deal was found by Cheapflights users on 8/2. 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 -
1 stop19h 16m
Deal found 8/2![American Airlines logo]()
$261
This American Airlines deal was found by Cheapflights users on 7/31. 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 9/15:00 am -
1 stop8h 12m
Deal found 7/31![American Airlines logo]()
$267
This American Airlines deal was found by Cheapflights users on 7/31. 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 9/25:00 am -
1 stop8h 12m
Deal found 7/31![American Airlines logo]()
$319
This United Airlines deal was found by Cheapflights users on 7/31. 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 9/13:15 pm -
3 stops22h 36m
Deal found 7/31![United Airlines logo]()
$324
This United Airlines deal was found by Cheapflights users on 7/30. 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 9/57:05 pm -
2 stops42h 46m
Deal found 7/30![United Airlines logo]()
$338
This United Airlines deal was found by Cheapflights users on 8/4. 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 9/63:15 pm -
3 stops22h 36m
Deal found 8/4![United Airlines logo]()
$364
This Delta deal was found by Cheapflights users on 7/31. 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 9/17:03 am -
1 stop13h 10m
Deal found 7/31![Delta logo]()
$469
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 August 4, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $392 (United Airlines) |
One-way from | $172 (American Airlines) |
Popular in | December |
Cheapest in | July |
Average price | $623 |
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 August 4, 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
Sat 11/7
7:03 pm-12:13 pm
1 stop16h 10m
Montego Bay Sangster Intl
Sat 11/14
3:20 pm-10:47 pm
1 stop8h 27m
$392
MilwaukeeMontego Bay
MKE - MBJ
MKEMBJ
Milwaukee-Mitchell
Sat 10/17
7:00 am-3:35 pm
1 stop8h 35m
Montego Bay Sangster Intl
Sat 10/24
4:50 pm-11:53 pm
1 stop7h 03m
$392
MilwaukeeMontego Bay
MKE - MBJ
MKEMBJ
Milwaukee-Mitchell
Sat 11/14
7:03 pm-12:13 pm
1 stop16h 10m
Montego Bay Sangster Intl
Fri 11/20
1:25 pm-10:47 pm
1 stop10h 22m
$392
MilwaukeeMontego Bay
MKE - MBJ
MKEMBJ
Milwaukee-Mitchell
Wed 12/2
6:00 am-1:46 pm
1 stop6h 46m
Montego Bay Sangster Intl
Wed 12/9
3:36 pm-11:27 pm
1 stop8h 51m
$392
MilwaukeeMontego Bay
MKE - MBJ
MKEMBJ
Milwaukee-Mitchell
Tue 1/26
7:19 pm-2:13 pm
2 stops17h 54m
Montego Bay Sangster Intl
Tue 2/9
2:19 pm-10:58 pm
1 stop9h 39m
$397
MilwaukeeMontego Bay
MKE - MBJ
MKEMBJ
Milwaukee-Mitchell
Tue 12/1
5:30 am-4:35 pm
1 stop10h 05m
Montego Bay Sangster Intl
Wed 12/9
6:00 pm-11:54 pm
1 stop6h 54m
$487
MilwaukeeMontego Bay
MKE - MBJ
MKEMBJ
Milwaukee-Mitchell
Wed 11/18
6:41 pm-12:25 pm
2 stops16h 44m
Montego Bay Sangster Intl
Wed 11/25
6:00 pm-11:54 pm
1 stop6h 54m
$492
Quickest round-trip
MilwaukeeMontego Bay
MKE - MBJ
MKEMBJ
Milwaukee-Mitchell
Tue 10/27
6:47 am-12:48 pm
1 stop6h 01m
Montego Bay Sangster Intl
Thu 10/29
2:20 pm-10:47 pm
1 stop8h 27m
$492
MilwaukeeKingston
MKE - KIN
MKEKIN
Milwaukee-Mitchell
Tue 9/1
3:15 pm-1:51 pm
3 stops22h 36m
Kingston Norman Manley
Mon 9/7
2:57 pm-10:00 am
2 stops19h 03m
$737
MilwaukeeKingston
MKE - KIN
MKEKIN
Milwaukee-Mitchell
Wed 11/18
9:33 am-1:52 pm
2 stops27h 19m
Kingston Norman Manley
Tue 11/24
2:58 pm-10:47 pm
2 stops32h 49m
$737
Showing 1-10 of 27 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 August 4, 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.
Overall
8.0
Boarding
8.1
Food
7.0
Entertainment
7.5
Comfort
8.0
Crew
8.6
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Overall
8.0
Boarding
8.1
Food
7.0
Entertainment
7.5
Comfort
8.0
Crew
8.6
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Overall
8.0
Boarding
8.1
Food
7.0
Entertainment
7.5
Comfort
8.0
Crew
8.6
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Overall
8.0
Boarding
8.1
Food
7.0
Entertainment
7.5
Comfort
8.0
Crew
8.6
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Related info for your journey
Find useful and relevant information for your journey from Milwaukee to Jamaica. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Browse thousands of different options on Cheapflights for your next trip
Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
Alternative routes
Complete your trip
Flights by cabin class
Other flight options
Popular flights
Top destinations
Alternative routes for Milwaukee 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 Milwaukee to Jamaica by cabin class
Find flights from Milwaukee to Jamaica, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Milwaukee and Jamaica flights
Browse other Milwaukee and Jamaica flight options. Last updated on August 4, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Milwaukee to Jamaica flights
Consider these flights traveling from Milwaukee to Jamaica.
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 August 4, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$352 | Average$788 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$462 | Average$539 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$615 | Average$749 | FlexibilityNo cancel fee | On-time63% |