$88+ Cheap flights from Milwaukee (MKE) to Caribbean
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 5/19. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — SJU
May 30 — Jun 61
Round-trip
1 adult, Economy
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Find cheap flights from Milwaukee to Caribbean with Cheapflights
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Cheapest flights from Milwaukee to CaribbeanExplore the most affordable flight options available from Milwaukee to Caribbean. Find the lowest fares from popular airlines and budget airlines, with prices last updated on April 30, 2026.
Explore the most affordable flight options available from Milwaukee to Caribbean. Find the lowest fares from popular airlines and budget airlines, with prices last updated on April 30, 2026.
This CheapOair deal was found by Cheapflights users on 4/25. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/238:43 am
MKE
- SJU
1 stop22h 14m
Frontier
Mon 8/36:31 pm
SJU
- MKE
1 stop14h 27m
Frontier
Deal found 4/25![Frontier logo]()
$315
This Frontier deal was found by Cheapflights users on 4/28. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/288:46 am
MKE
- SJU
1 stop13h 36m
Frontier
Sat 6/68:13 pm
SJU
- MKE
1 stop12h 48m
Frontier
Deal found 4/28![Frontier logo]()
$318
This CheapOair deal was found by Cheapflights users on 4/28. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/199:56 am
MKE
- SJU
1 stop15h 12m
Frontier
Sun 5/243:03 am
SJU
- MKE
1 stop29h 58m
Frontier
Deal found 4/28![Frontier logo]()
$321
This American Airlines deal was found by Cheapflights users on 4/29. 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 8/224:12 pm
MKE
- SJU
1 stop7h 03m
American Airlines
Mon 8/316:51 am
SJU
- MKE
1 stop17h 32m
American Airlines
Deal found 4/29![American Airlines logo]()
$326
This CheapOair deal was found by Cheapflights users on 4/28. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/179:56 am
MKE
- SJU
1 stop21h 08m
Frontier
Sat 5/233:58 pm
SJU
- MKE
1 stop17h 03m
Frontier
Deal found 4/28![Frontier logo]()
$329
This American Airlines deal was found by Cheapflights users on 4/29. 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 8/126:16 am
MKE
- SJU
2 stops11h 08m
American Airlines
Tue 8/186:51 am
SJU
- MKE
1 stop17h 32m
American Airlines
Deal found 4/29![American Airlines logo]()
$331
This American Airlines deal was found by Cheapflights users on 4/29. 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 6/16:00 am
MKE
- SJU
1 stop16h 01m
American Airlines
Sat 6/66:21 am
SJU
- MKE
1 stop18h 26m
American Airlines
Deal found 4/29![American Airlines logo]()
$333
This Frontier deal was found by Cheapflights users on 4/27. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/79:46 am
MKE
- SJU
1 stop6h 28m
Frontier
Mon 5/113:03 am
SJU
- MKE
1 stop6h 58m
Frontier
Deal found 4/27![Frontier logo]()
$335
This Priceline deal was found by Cheapflights users on 4/29. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/412:21 pm
MKE
- SJU
1 stop23h 54m
Frontier
Sat 5/93:03 am
SJU
- MKE
1 stop6h 58m
Frontier
Deal found 4/29![Frontier logo]()
$336
This American Airlines deal was found by Cheapflights users on 4/27. 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.
Wed 5/2712:34 pm
MKE
- SJU
1 stop9h 27m
American Airlines
Fri 6/57:00 am
SJU
- MKE
1 stop11h 37m
American Airlines
Deal found 4/27![American Airlines logo]()
$340
This CheapOair deal was found by Cheapflights users on 4/26. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/308:43 am
MKE
- SJU
1 stop22h 14m
Frontier
Mon 8/106:31 pm
SJU
- MKE
1 stop14h 27m
Frontier
Deal found 4/26![Frontier logo]()
$341
This Priceline deal was found by Cheapflights users on 4/28. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/28:46 am
MKE
- SJU
1 stop13h 36m
Frontier
Wed 6/104:05 pm
SJU
- MKE
1 stop16h 53m
Frontier
Deal found 4/28![Frontier logo]()
$345
Best flights from Milwaukee to CaribbeanDiscover carefully curated flight deals from Milwaukee to Caribbean that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated April 30, 2026.
Discover carefully curated flight deals from Milwaukee to Caribbean that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated April 30, 2026.
This Delta deal was found by Cheapflights users on 4/29. 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 6/27:15 am
MKE
- SJU
1 stop8h 14m
Delta
Tue 6/92:04 pm
SJU
- MKE
1 stop7h 18m
Delta
Deal found 4/29![Delta logo]()
$326
This United Airlines deal was found by Cheapflights users on 4/27. 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.
Sat 9/265:21 pm
MKE
- MBJ
2 stops18h 22m
United Airlines
Sat 10/32:40 pm
MBJ
- MKE
1 stop8h 01m
United Airlines
Deal found 4/27![United Airlines logo]()
$352
This American Airlines deal was found by Cheapflights users on 4/30. 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.
Mon 6/16:08 am
MKE
- MBJ
1 stop7h 22m
American Airlines
Fri 6/53:00 pm
MBJ
- MKE
1 stop8h 47m
American Airlines
Deal found 4/30![American Airlines logo]()
$352
This Southwest deal was found by Cheapflights users on 4/28. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/183:30 pm
MKE
- SJU
1 stop7h 10m
Southwest
Sat 5/234:25 pm
SJU
- MKE
1 stop7h 30m
Southwest
Deal found 4/28![Southwest logo]()
$444
This Justfly.com deal was found by Cheapflights users on 4/25. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/2112:08 pm
MKE
- PUJ
1 stop25h 21m
Frontier
Sat 8/295:30 pm
PUJ
- MKE
1 stop15h 28m
Frontier
Deal found 4/25![Frontier logo]()
$508
This Kiwi.com deal was found by Cheapflights users on 4/25. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/2312:29 pm
MKE
- STT
2 stops24h 47m
Multiple Airlines
Sat 5/303:21 pm
STT
- MKE
1 stop17h 40m
Multiple Airlines
Deal found 4/25![Multiple Airlines logo]()
$682
This American Airlines deal was found by Cheapflights users on 4/30. 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.
Thu 8/274:25 pm
MKE
- MBJ
2 stops19h 17m
American Airlines
Mon 8/315:13 pm
MBJ
- MKE
2 stops18h 24m
American Airlines
Deal found 4/30![American Airlines logo]()
$357
This Delta deal was found by Cheapflights users on 4/28. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/2312:58 pm
MKE
- SJU
1 stop6h 47m
Delta
Tue 8/412:56 pm
SJU
- MKE
1 stop7h 19m
Delta
Deal found 4/28![Delta logo]()
$398
This American Airlines deal was found by Cheapflights users on 4/25. 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.
Wed 9/165:51 pm
MKE
- MBJ
2 stops16h 59m
American Airlines
Sun 9/203:15 pm
MBJ
- MKE
2 stops18h 46m
American Airlines
Deal found 4/25![American Airlines logo]()
$367
This United Airlines deal was found by Cheapflights users on 4/26. 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.
Mon 8/106:05 am
MKE
- MBJ
2 stops9h 05m
United Airlines
Sat 8/154:12 pm
MBJ
- MKE
2 stops17h 48m
United Airlines
Deal found 4/26![United Airlines logo]()
$410
This United Airlines deal was found by Cheapflights users on 4/29. 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 6/96:05 am
MKE
- MBJ
2 stops9h 05m
United Airlines
Fri 6/124:12 pm
MBJ
- MKE
2 stops18h 56m
United Airlines
Deal found 4/29![United Airlines logo]()
$410
This Delta deal was found by Cheapflights users on 4/27. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/175:23 am
MKE
- SJU
1 stop10h 10m
Delta
Sun 5/247:30 am
SJU
- MKE
1 stop8h 27m
Delta
Deal found 4/27![Delta logo]()
$444
This Southwest deal was found by Cheapflights users on 4/28. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/145:35 am
MKE
- NAS
1 stop5h 40m
Southwest
Mon 9/211:10 pm
NAS
- MKE
1 stop8h 35m
Southwest
Deal found 4/28![Southwest logo]()
$499
This Delta deal was found by Cheapflights users on 4/27. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/212:56 pm
MKE
- SJU
1 stop6h 47m
Delta
Sun 7/52:04 pm
SJU
- MKE
1 stop7h 18m
Delta
Deal found 4/27![Delta logo]()
$444
This American Airlines deal was found by Cheapflights users on 4/25. 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 9/196:26 pm
MKE
- PUJ
1 stop15h 19m
American Airlines
Wed 9/233:10 pm
PUJ
- MKE
1 stop10h 00m
American Airlines
Deal found 4/25![American Airlines logo]()
$456
This United Airlines deal was found by Cheapflights users on 4/27. 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.
Thu 5/281:30 pm
MKE
- MBJ
2 stops25h 40m
United Airlines
Thu 6/112:40 pm
MBJ
- MKE
2 stops22h 08m
United Airlines
Deal found 4/27![United Airlines logo]()
$467
This Delta deal was found by Cheapflights users on 4/29. 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 8/145:55 am
MKE
- SXM
1 stop7h 01m
Delta
Wed 8/193:21 pm
SXM
- MKE
1 stop9h 04m
Delta
Deal found 4/29![Delta logo]()
$455
This Southwest deal was found by Cheapflights users on 4/27. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/275:40 am
MKE
- SXM
1 stop6h 50m
Southwest
Wed 6/32:25 pm
SXM
- MKE
1 stop9h 25m
Southwest
Deal found 4/27![Southwest logo]()
$554
This American Airlines deal was found by Cheapflights users on 4/29. 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 10/58:16 pm
MKE
- PUJ
2 stops17h 09m
American Airlines
Tue 10/135:20 pm
PUJ
- MKE
1 stop7h 51m
American Airlines
Deal found 4/29![American Airlines logo]()
$461
This United Airlines deal was found by Cheapflights users on 4/29. 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 5/36:49 am
MKE
- SJU
2 stops12h 49m
United Airlines
Tue 5/53:56 pm
SJU
- MKE
1 stop7h 09m
United Airlines
Deal found 4/29![United Airlines logo]()
$490
This Delta deal was found by Cheapflights users on 4/27. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/255:45 am
MKE
- PUJ
1 stop7h 46m
Delta
Thu 10/293:56 pm
PUJ
- MKE
1 stop8h 28m
Delta
Deal found 4/27![Delta logo]()
$456
This American Airlines deal was found by Cheapflights users on 4/25. 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.
Sun 10/258:16 pm
MKE
- PUJ
2 stops17h 09m
American Airlines
Thu 10/295:00 pm
PUJ
- MKE
1 stop19h 32m
American Airlines
Deal found 4/25![American Airlines logo]()
$461
This American Airlines deal was found by Cheapflights users on 4/30. 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.
Sun 6/76:17 pm
MKE
- GCM
2 stops16h 44m
American Airlines
Thu 6/1112:33 pm
GCM
- MKE
2 stops19h 09m
American Airlines
Deal found 4/30![American Airlines logo]()
$462
This Delta deal was found by Cheapflights users on 4/28. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/2410:11 am
MKE
- SJU
1 stop11h 18m
Delta
Mon 8/35:56 pm
SJU
- MKE
1 stop7h 00m
Delta
Deal found 4/28![Delta logo]()
$466
This Southwest deal was found by Cheapflights users on 4/28. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/166:00 am
MKE
- SXM
1 stop6h 40m
Southwest
Sun 5/243:20 pm
SXM
- MKE
1 stop8h 25m
Southwest
Deal found 4/28![Southwest logo]()
$644
This United Airlines deal was found by Cheapflights users on 4/29. 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 10/128:45 pm
MKE
- NAS
2 stops15h 48m
United Airlines
Mon 10/192:53 pm
NAS
- MKE
2 stops19h 56m
United Airlines
Deal found 4/29![United Airlines logo]()
$554
This American Airlines deal was found by Cheapflights users on 4/27. 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 6/146:50 pm
MKE
- NAS
1 stop15h 46m
American Airlines
Fri 6/1912:36 pm
NAS
- MKE
1 stop9h 29m
American Airlines
Deal found 4/27![American Airlines logo]()
$464
This Delta deal was found by Cheapflights users on 4/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/105:55 am
MKE
- SXM
1 stop7h 01m
Delta
Thu 8/203:21 pm
SXM
- MKE
1 stop9h 04m
Delta
Deal found 4/29![Delta logo]()
$483
This American Airlines deal was found by Cheapflights users on 4/28. 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 7/126:00 am
MKE
- NAS
2 stops8h 09m
American Airlines
Wed 7/1512:29 pm
NAS
- MKE
1 stop6h 49m
American Airlines
Deal found 4/28![American Airlines logo]()
$468
This Delta deal was found by Cheapflights users on 4/25. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/125:55 am
MKE
- SXM
1 stop6h 55m
Delta
Sat 9/193:20 pm
SXM
- MKE
1 stop7h 39m
Delta
Deal found 4/25![Delta logo]()
$483
Last-minute flights from Milwaukee to CaribbeanDiscover last-minute flight deals from Milwaukee to Caribbean. Data last updated April 30, 2026 and is based on user searches.
Discover last-minute flight deals from Milwaukee to Caribbean. Data last updated April 30, 2026 and is based on user searches.
This Priceline deal was found by Cheapflights users on 4/29. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/412:21 pm
MKE
- SJU
1 stop23h 54m
Frontier
Sat 5/93:03 am
SJU
- MKE
1 stop6h 58m
Frontier
Deal found 4/29![Frontier logo]()
$336
This American Airlines deal was found by Cheapflights users on 4/25. 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.
Wed 5/66:00 am
MKE
- MBJ
1 stop8h 15m
American Airlines
Mon 5/114:37 pm
MBJ
- MKE
2 stops17h 32m
American Airlines
Deal found 4/25![American Airlines logo]()
$393
This Frontier deal was found by Cheapflights users on 4/27. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/79:46 am
MKE
- SJU
1 stop6h 28m
Frontier
Mon 5/113:03 am
SJU
- MKE
1 stop6h 58m
Frontier
Deal found 4/27![Frontier logo]()
$335
This CheapOair deal was found by Cheapflights users on 4/29. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/129:56 am
MKE
- SJU
1 stop15h 12m
Frontier
Sat 5/163:33 pm
SJU
- MKE
1 stop18h 28m
Frontier
Deal found 4/29![Frontier logo]()
$347
This American Airlines deal was found by Cheapflights users on 4/27. 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.
Thu 5/146:42 pm
MKE
- MBJ
2 stops17h 09m
American Airlines
Tue 5/194:37 pm
MBJ
- MKE
2 stops18h 22m
American Airlines
Deal found 4/27![American Airlines logo]()
$359
This CheapOair deal was found by Cheapflights users on 4/28. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/179:56 am
MKE
- SJU
1 stop21h 08m
Frontier
Sat 5/233:58 pm
SJU
- MKE
1 stop17h 03m
Frontier
Deal found 4/28![Frontier logo]()
$329
This CheapOair deal was found by Cheapflights users on 4/25. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/179:56 am
MKE
- SJU
1 stop15h 12m
Multiple Airlines
Fri 5/223:25 pm
SJU
- MKE
1 stop17h 26m
Multiple Airlines
Deal found 4/25![Multiple Airlines logo]()
$361
This CheapOair deal was found by Cheapflights users on 4/28. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/199:56 am
MKE
- SJU
1 stop15h 12m
Frontier
Sun 5/243:03 am
SJU
- MKE
1 stop29h 58m
Frontier
Deal found 4/28![Frontier logo]()
$321
This American Airlines deal was found by Cheapflights users on 4/27. 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.
Wed 5/2712:34 pm
MKE
- SJU
1 stop9h 27m
American Airlines
Fri 6/57:00 am
SJU
- MKE
1 stop11h 37m
American Airlines
Deal found 4/27![American Airlines logo]()
$340
This Frontier deal was found by Cheapflights users on 4/28. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/288:46 am
MKE
- SJU
1 stop13h 36m
Frontier
Sat 6/68:13 pm
SJU
- MKE
1 stop12h 48m
Frontier
Deal found 4/28![Frontier logo]()
$318
This American Airlines deal was found by Cheapflights users on 4/27. 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.
Thu 5/286:00 am
MKE
- SJU
1 stop16h 01m
American Airlines
Sat 6/66:21 am
SJU
- MKE
1 stop18h 26m
American Airlines
Deal found 4/27![American Airlines logo]()
$326
This Delta deal was found by Cheapflights users on 4/27. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/301:08 pm
MKE
- MBJ
2 stops22h 18m
Delta
Wed 6/104:59 pm
MBJ
- MKE
1 stop7h 00m
Delta
Deal found 4/27![Delta logo]()
$367
One-way flights from Milwaukee to CaribbeanSearch for one-way flight options from Milwaukee to Caribbean. Find affordable one-way fares based on user searches. Data last updated April 30, 2026.
Search for one-way flight options from Milwaukee to Caribbean. Find affordable one-way fares based on user searches. Data last updated April 30, 2026.
This Expedia deal was found by Cheapflights users on 4/26. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/199:56 am
MKE
- SJU
1 stop15h 12m
Frontier
Deal found 4/26![Frontier logo]()
$88
This Orbitz deal was found by Cheapflights users on 4/25. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/129:56 am
MKE
- SJU
1 stop15h 12m
Frontier
Deal found 4/25![Frontier logo]()
$98
This Priceline deal was found by Cheapflights users on 4/30. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/168:43 am
MKE
- SJU
1 stop7h 53m
Frontier
Deal found 4/30![Frontier logo]()
$138
This CheapOair deal was found by Cheapflights users on 4/27. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/238:43 am
MKE
- SJU
1 stop22h 14m
Frontier
Deal found 4/27![Frontier logo]()
$159
This American Airlines deal was found by Cheapflights users on 4/29. 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 7/116:00 am
MKE
- SJU
1 stop16h 21m
American Airlines
Deal found 4/29![American Airlines logo]()
$163
This American Airlines deal was found by Cheapflights users on 4/28. 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.
Tue 6/26:00 am
MKE
- SJU
1 stop16h 01m
American Airlines
Deal found 4/28![American Airlines logo]()
$167
This American Airlines deal was found by Cheapflights users on 4/29. 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 5/277:00 am
MKE
- SJU
1 stop14h 45m
American Airlines
Deal found 4/29![American Airlines logo]()
$168
This American Airlines deal was found by Cheapflights users on 4/29. 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 8/154:12 pm
MKE
- SXM
2 stops20h 10m
American Airlines
Deal found 4/29![American Airlines logo]()
$169
This CheapOair deal was found by Cheapflights users on 4/28. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/218:10 pm
MKE
- SJU
1 stop16h 06m
Frontier
Deal found 4/28![Frontier logo]()
$176
This Delta deal was found by Cheapflights users on 4/28. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/135:45 am
MKE
- GCM
1 stop5h 46m
Delta
Deal found 4/28![Delta logo]()
$176
This Kiwi.com deal was found by Cheapflights users on 4/29. 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 5/288:46 am
MKE
- SJU
2 stops42h 15m
Frontier
Deal found 4/29![Frontier logo]()
$177
This American Airlines deal was found by Cheapflights users on 4/28. 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 6/277:49 pm
MKE
- GCM
2 stops15h 41m
American Airlines
Deal found 4/28![American Airlines logo]()
$182
Find flight deals from Milwaukee to Caribbean
Keep the following information in mind while searching for Milwaukee to Caribbean flight deals. Data was last updated April 30, 2026.
Round-trip from | $315 (CheapOair) |
|---|---|
One-way from | $88 (Expedia) |
Popular in | December |
Cheapest in | September |
Average price | $379 |
Cheapflights Fare Finder
Customize your flight search to find flights from Milwaukee to Caribbean 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 April 30, 2026.
Use the filters below to find and compare flights from Milwaukee to Caribbean that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
MilwaukeeSan Juan
MKE - SJU
MKESJU
Milwaukee-Mitchell
Tue 6/2
7:15 am-4:29 pm
1 stop8h 14m
San Juan Luis Munoz Marin Intl
Tue 6/9
2:04 pm-8:22 pm
1 stop7h 18m
$326
MilwaukeeMontego Bay
MKE - MBJ
MKEMBJ
Milwaukee-Mitchell
Sat 9/26
5:21 pm-11:43 am
2 stops18h 22m
Montego Bay Sangster Intl
Sat 10/3
2:40 pm-10:41 pm
1 stop8h 01m
$352
MilwaukeeMontego Bay
MKE - MBJ
MKEMBJ
Milwaukee-Mitchell
Mon 6/1
6:08 am-1:30 pm
1 stop7h 22m
Montego Bay Sangster Intl
Fri 6/5
3:00 pm-11:47 pm
1 stop8h 47m
$352
MilwaukeeMontego Bay
MKE - MBJ
MKEMBJ
Milwaukee-Mitchell
Thu 8/27
4:25 pm-11:42 am
2 stops19h 17m
Montego Bay Sangster Intl
Mon 8/31
5:13 pm-11:37 am
2 stops18h 24m
$357
MilwaukeeMontego Bay
MKE - MBJ
MKEMBJ
Milwaukee-Mitchell
Wed 9/16
5:51 pm-10:50 am
2 stops16h 59m
Montego Bay Sangster Intl
Sun 9/20
3:15 pm-10:01 am
2 stops18h 46m
$367
MilwaukeeSan Juan
MKE - SJU
MKESJU
Milwaukee-Mitchell
Thu 7/23
12:58 pm-8:45 pm
1 stop6h 47m
San Juan Luis Munoz Marin Intl
Tue 8/4
12:56 pm-7:15 pm
1 stop7h 19m
$398
MilwaukeeMontego Bay
MKE - MBJ
MKEMBJ
Milwaukee-Mitchell
Mon 8/10
6:05 am-3:10 pm
2 stops9h 05m
Montego Bay Sangster Intl
Sat 8/15
4:12 pm-10:00 am
2 stops17h 48m
$410
MilwaukeeMontego Bay
MKE - MBJ
MKEMBJ
Milwaukee-Mitchell
Tue 6/9
6:05 am-3:10 pm
2 stops9h 05m
Montego Bay Sangster Intl
Fri 6/12
4:12 pm-11:08 am
2 stops18h 56m
$410
MilwaukeeSan Juan
MKE - SJU
MKESJU
Milwaukee-Mitchell
Mon 5/18
3:30 pm-11:40 pm
1 stop7h 10m
San Juan Luis Munoz Marin Intl
Sat 5/23
4:25 pm-10:55 pm
1 stop7h 30m
$444
MilwaukeeSan Juan
MKE - SJU
MKESJU
Milwaukee-Mitchell
Sun 5/17
5:23 am-4:33 pm
1 stop10h 10m
San Juan Luis Munoz Marin Intl
Sun 5/24
7:30 am-2:57 pm
1 stop8h 27m
$444
Showing 1-10 of 60 resultsSorted by cheapest first
Best time to book a flight from Milwaukee to Caribbean
Have a flexible travel schedule? Discover the best time to fly to Caribbean from Milwaukee with our price prediction graph.
MKE-SJU
MKE-GCM
MKE-PUJ
MKE-SXM
MKE-PLS
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 Caribbean
MKE-0CB
MKE-SJU
MKE-GCM
MKE-PUJ
MKE-SXM
How far ahead should I book a flight from Milwaukee to Caribbean?
The best time to book flights from Milwaukee to Caribbean is 42 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.
What is the cheapest month to book a flight from Milwaukee to Caribbean?
Currently, April is the cheapest month in which you can book a flight from Milwaukee to Caribbean (average of $101). Flying from Milwaukee to Caribbean in March is currently the most expensive (average of $968). 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 Caribbean
Get insights into the airlines that provide service to Caribbean. 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 Caribbean. Reviews last updated April 30, 2026.
Read through reviews of airlines operating flights from Milwaukee to Caribbean, such as Southwest,Delta, andUnited Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Boarding
8.1
Food
7.0
Overall
8.0
Crew
8.6
Entertainment
7.5
Comfort
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Boarding
8.1
Food
7.0
Overall
8.0
Crew
8.6
Entertainment
7.5
Comfort
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Boarding
8.1
Food
7.0
Overall
8.0
Crew
8.6
Entertainment
7.5
Comfort
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Boarding
8.1
Food
7.0
Overall
8.0
Crew
8.6
Entertainment
7.5
Comfort
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Boarding
8.1
Food
7.0
Overall
8.0
Crew
8.6
Entertainment
7.5
Comfort
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Boarding
8.1
Food
7.0
Overall
8.0
Crew
8.6
Entertainment
7.5
Comfort
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Related info for your journey
Find useful and relevant information for your journey from Milwaukee to Caribbean. 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.
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Alternative routes for Milwaukee to Caribbean
See prices for flight routes from nearby airports that may be better suited for you.
Complete your trip
Complete your trip to Caribbean by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Milwaukee to Caribbean by cabin class
Find flights from Milwaukee to Caribbean, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Milwaukee and Caribbean flights
Browse other Milwaukee and Caribbean flight options. Last updated on April 30, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Fly to Caribbean countries
Consider these flights traveling to countries located in Caribbean.
Milwaukee to Caribbean flights
Consider these flights traveling from Milwaukee to Caribbean.
Top 7 airlines flying from Milwaukee to Caribbean
Discover the top 7 airlines that operate flights from Milwaukee to Caribbean. 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 April 30, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$112 | Average$553 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$156 | Average$360 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$202 | Average$558 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$219 | Average$366 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$256 | Average$661 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$315 | Average$721 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$547 | Average$841 | FlexibilityNo cancel fee | On-time83% |