$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 5/3. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — SJU
May 16 — May 231
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 16, 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 16, 2026.
This FlightHub deal was found by Cheapflights users on 4/13. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/15:13 pm
MKE
- PUJ
1 stop19h 41m
Frontier
Thu 5/73:35 pm
PUJ
- MKE
1 stop20h 39m
Frontier
Deal found 4/13![Frontier logo]()
$284
This CheapOair deal was found by Cheapflights users on 4/14. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/172:47 pm
MKE
- SJU
1 stop7h 42m
Frontier
Sat 4/258:00 am
SJU
- MKE
1 stop25h 38m
Frontier
Deal found 4/14![Frontier logo]()
$285
This CheapOair deal was found by Cheapflights users on 4/13. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 6/148:43 am
MKE
- SJU
1 stop13h 46m
Frontier
Wed 6/176:05 pm
SJU
- MKE
1 stop14h 53m
Frontier
Deal found 4/13![Frontier logo]()
$286
This Priceline deal was found by Cheapflights users on 4/15. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/59:56 am
MKE
- SJU
1 stop15h 12m
Frontier
Mon 5/113:03 am
SJU
- MKE
1 stop6h 58m
Frontier
Deal found 4/15![Frontier logo]()
$291
This Priceline deal was found by Cheapflights users on 4/12. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/109:56 am
MKE
- SJU
1 stop15h 12m
Frontier
Sat 5/163:03 am
SJU
- MKE
1 stop6h 58m
Frontier
Deal found 4/12![Frontier logo]()
$295
This FlightHub deal was found by Cheapflights users on 4/13. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/412:21 pm
MKE
- PUJ
2 stops30h 58m
Frontier
Sun 5/103:35 pm
PUJ
- MKE
1 stop20h 39m
Frontier
Deal found 4/13![Frontier logo]()
$304
This Priceline deal was found by Cheapflights users on 4/12. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/48:46 am
MKE
- SJU
1 stop7h 26m
Frontier
Wed 6/174:05 pm
SJU
- MKE
1 stop16h 53m
Frontier
Deal found 4/12![Frontier logo]()
$311
This Kiwi.com deal was found by Cheapflights users on 4/11. 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 5/412:21 pm
MKE
- SJU
1 stop20h 57m
Multiple Airlines
Sun 5/105:15 pm
SJU
- MKE
2 stops40h 46m
Multiple Airlines
Deal found 4/11![Multiple Airlines logo]()
$313
This Priceline deal was found by Cheapflights users on 4/13. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/138:43 am
MKE
- SJU
1 stop22h 26m
Frontier
Mon 8/174:05 pm
SJU
- MKE
1 stop16h 53m
Frontier
Deal found 4/13![Frontier logo]()
$321
This Delta deal was found by Cheapflights users on 4/11. 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 5/1612:40 pm
MKE
- SJU
1 stop9h 55m
Delta
Tue 5/191:13 pm
SJU
- MKE
1 stop9h 39m
Delta
Deal found 4/11![Delta logo]()
$326
This CheapOair deal was found by Cheapflights users on 4/13. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/288:46 am
MKE
- SJU
1 stop16h 22m
Frontier
Sat 6/68:13 pm
SJU
- MKE
1 stop12h 48m
Frontier
Deal found 4/13![Frontier logo]()
$329
This Priceline deal was found by Cheapflights users on 4/11. 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 stop12h 40m
Frontier
Sat 5/93:03 am
SJU
- MKE
1 stop6h 58m
Frontier
Deal found 4/11![Frontier logo]()
$330
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 16, 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 16, 2026.
This Southwest deal was found by Cheapflights users on 4/13. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/1810:30 am
MKE
- SJU
1 stop9h 35m
Southwest
Mon 8/3111:35 am
SJU
- MKE
1 stop10h 10m
Southwest
Deal found 4/13![Southwest logo]()
$326
This Delta deal was found by Cheapflights users on 4/15. 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.
Wed 7/110:08 am
MKE
- SJU
1 stop11h 19m
Delta
Wed 7/85:56 pm
SJU
- MKE
1 stop7h 00m
Delta
Deal found 4/15![Delta logo]()
$326
This American Airlines deal was found by Cheapflights users on 4/12. 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.
Thu 4/306:41 pm
MKE
- MBJ
1 stop14h 32m
American Airlines
Thu 5/710:17 am
MBJ
- MKE
1 stop7h 34m
American Airlines
Deal found 4/12![American Airlines logo]()
$354
This United Airlines deal was found by Cheapflights users on 4/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/296:05 am
MKE
- MBJ
2 stops9h 05m
United Airlines
Fri 6/54:12 pm
MBJ
- MKE
2 stops20h 36m
United Airlines
Deal found 4/13![United Airlines logo]()
$357
This Orbitz deal was found by Cheapflights users on 4/14. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/44:56 pm
MKE
- PUJ
1 stop17h 19m
Multiple Airlines
Sun 5/103:35 pm
PUJ
- MKE
1 stop20h 39m
Multiple Airlines
Deal found 4/14![Multiple Airlines logo]()
$451
This Delta deal was found by Cheapflights users on 4/11. 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 5/177:09 am
MKE
- SJU
1 stop8h 24m
Delta
Wed 5/202:48 pm
SJU
- MKE
1 stop10h 05m
Delta
Deal found 4/11![Delta logo]()
$326
This FlightHub deal was found by Cheapflights users on 4/13. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/44:56 pm
MKE
- AUA
1 stop22h 44m
JetBlue
Mon 5/115:35 pm
AUA
- MKE
2 stops23h 28m
JetBlue
Deal found 4/13![JetBlue logo]()
$657
This American Airlines deal was found by Cheapflights users on 4/13. 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 5/295:53 pm
MKE
- MBJ
2 stops17h 26m
American Airlines
Fri 6/53:00 pm
MBJ
- MKE
1 stop8h 47m
American Airlines
Deal found 4/13![American Airlines logo]()
$357
This Delta deal was found by Cheapflights users on 4/11. 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 5/1612:40 pm
MKE
- SJU
1 stop9h 55m
Delta
Tue 5/191:13 pm
SJU
- MKE
1 stop9h 39m
Delta
Deal found 4/11![Delta logo]()
$326
This Southwest deal was found by Cheapflights users on 4/12. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/206:25 am
MKE
- SJU
2 stops9h 30m
Southwest
Tue 8/2511:50 am
SJU
- MKE
2 stops10h 35m
Southwest
Deal found 4/12![Southwest logo]()
$365
This American Airlines deal was found by Cheapflights users on 4/15. 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.
Thu 8/277:37 pm
MKE
- MBJ
2 stops17h 51m
American Airlines
Mon 8/315:13 pm
MBJ
- MKE
2 stops18h 24m
American Airlines
Deal found 4/15![American Airlines logo]()
$357
This Delta deal was found by Cheapflights users on 4/15. 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.
Thu 7/166:50 am
MKE
- SJU
1 stop8h 55m
Delta
Thu 7/232:42 pm
SJU
- MKE
1 stop7h 12m
Delta
Deal found 4/15![Delta logo]()
$326
This Southwest deal was found by Cheapflights users on 4/15. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/238:15 pm
MKE
- SJU
1 stop11h 45m
Southwest
Mon 8/35:15 pm
SJU
- MKE
1 stop7h 35m
Southwest
Deal found 4/15![Southwest logo]()
$365
This American Airlines deal was found by Cheapflights users on 4/11. 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 6/16:34 pm
MKE
- MBJ
2 stops17h 11m
American Airlines
Fri 6/52:55 pm
MBJ
- MKE
1 stop8h 52m
American Airlines
Deal found 4/11![American Airlines logo]()
$357
This Delta deal was found by Cheapflights users on 4/11. 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 6/305:40 am
MKE
- SJU
1 stop10h 06m
Delta
Fri 7/106:00 am
SJU
- MKE
1 stop6h 51m
Delta
Deal found 4/11![Delta logo]()
$326
This United Airlines deal was found by Cheapflights users on 4/12. 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.
Sat 5/26:49 am
MKE
- MBJ
2 stops8h 21m
United Airlines
Wed 5/64:12 pm
MBJ
- MKE
2 stops20h 59m
United Airlines
Deal found 4/12![United Airlines logo]()
$467
This Delta deal was found by Cheapflights users on 4/15. 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.
Mon 6/2910:08 am
MKE
- SJU
1 stop11h 19m
Delta
Fri 7/36:00 am
SJU
- MKE
1 stop6h 51m
Delta
Deal found 4/15![Delta logo]()
$326
This American Airlines deal was found by Cheapflights users on 4/11. 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
2 stops9h 37m
American Airlines
Mon 5/44:37 pm
MBJ
- MKE
2 stops17h 32m
American Airlines
Deal found 4/11![American Airlines logo]()
$362
This United Airlines deal was found by Cheapflights users on 4/12. 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 5/125:56 pm
MKE
- MBJ
2 stops19h 34m
United Airlines
Sat 5/162:40 pm
MBJ
- MKE
2 stops17h 09m
United Airlines
Deal found 4/12![United Airlines logo]()
$467
This Delta deal was found by Cheapflights users on 4/15. 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.
Sat 5/912:40 pm
MKE
- SJU
1 stop9h 55m
Delta
Sat 5/166:15 am
SJU
- MKE
1 stop8h 31m
Delta
Deal found 4/15![Delta logo]()
$326
This Southwest deal was found by Cheapflights users on 4/11. 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 9/236:05 am
MKE
- NAS
1 stop5h 10m
Southwest
Wed 9/301:10 pm
NAS
- MKE
1 stop8h 55m
Southwest
Deal found 4/11![Southwest logo]()
$520
This United Airlines deal was found by Cheapflights users on 4/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/138:33 am
MKE
- NAS
1 stop5h 24m
United Airlines
Wed 5/2012:35 pm
NAS
- MKE
2 stops12h 24m
United Airlines
Deal found 4/13![United Airlines logo]()
$524
This Delta deal was found by Cheapflights users on 4/11. 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 5/265:23 am
MKE
- MBJ
1 stop10h 11m
Delta
Tue 6/212:51 pm
MBJ
- MKE
1 stop9h 01m
Delta
Deal found 4/11![Delta logo]()
$362
This Justfly.com deal was found by Cheapflights users on 4/14. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/74:58 pm
MKE
- SDQ
1 stop7h 56m
JetBlue
Mon 5/114:20 pm
SDQ
- MKE
1 stop24h 43m
JetBlue
Deal found 4/14![JetBlue logo]()
$660
This United Airlines deal was found by Cheapflights users on 4/11. 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 5/75:55 am
MKE
- PUJ
1 stop8h 17m
United Airlines
Wed 5/132:20 pm
PUJ
- MKE
1 stop9h 39m
United Airlines
Deal found 4/11![United Airlines logo]()
$530
This Delta deal was found by Cheapflights users on 4/12. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/125:23 am
MKE
- MBJ
1 stop10h 11m
Delta
Fri 5/1512:51 pm
MBJ
- MKE
2 stops19h 58m
Delta
Deal found 4/12![Delta logo]()
$367
This American Airlines deal was found by Cheapflights users on 4/11. 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 9/54:24 pm
MKE
- GCM
1 stop19h 01m
American Airlines
Sat 9/121:20 pm
GCM
- MKE
2 stops19h 38m
American Airlines
Deal found 4/11![American Airlines logo]()
$510
This FlightHub deal was found by Cheapflights users on 4/11. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/54:56 pm
MKE
- AUA
1 stop18h 34m
JetBlue
Mon 5/115:00 pm
AUA
- MKE
1 stop24h 03m
JetBlue
Deal found 4/11![JetBlue logo]()
$682
This Southwest deal was found by Cheapflights users on 4/13. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/117:10 am
MKE
- NAS
2 stops10h 20m
Southwest
Mon 5/182:10 pm
NAS
- MKE
2 stops10h 00m
Southwest
Deal found 4/13![Southwest logo]()
$582
This Delta deal was found by Cheapflights users on 4/12. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/312:20 pm
MKE
- SJU
1 stop9h 03m
Delta
Sun 9/65:45 pm
SJU
- MKE
1 stop6h 40m
Delta
Deal found 4/12![Delta logo]()
$387
Last-minute flights from Milwaukee to CaribbeanDiscover last-minute flight deals from Milwaukee to Caribbean. Data last updated April 16, 2026 and is based on user searches.
Discover last-minute flight deals from Milwaukee to Caribbean. Data last updated April 16, 2026 and is based on user searches.
This CheapOair deal was found by Cheapflights users on 4/14. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/172:47 pm
MKE
- SJU
1 stop7h 42m
Frontier
Sat 4/258:00 am
SJU
- MKE
1 stop25h 38m
Frontier
Deal found 4/14![Frontier logo]()
$285
This FlightHub deal was found by Cheapflights users on 4/13. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/15:13 pm
MKE
- PUJ
1 stop19h 41m
Frontier
Thu 5/73:35 pm
PUJ
- MKE
1 stop20h 39m
Frontier
Deal found 4/13![Frontier logo]()
$284
This FlightHub deal was found by Cheapflights users on 4/13. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/412:21 pm
MKE
- PUJ
2 stops30h 58m
Frontier
Sun 5/103:35 pm
PUJ
- MKE
1 stop20h 39m
Frontier
Deal found 4/13![Frontier logo]()
$304
This Kiwi.com deal was found by Cheapflights users on 4/11. 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 5/412:21 pm
MKE
- SJU
1 stop20h 57m
Multiple Airlines
Sun 5/105:15 pm
SJU
- MKE
2 stops40h 46m
Multiple Airlines
Deal found 4/11![Multiple Airlines logo]()
$313
This Priceline deal was found by Cheapflights users on 4/11. 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 stop12h 40m
Frontier
Sat 5/93:03 am
SJU
- MKE
1 stop6h 58m
Frontier
Deal found 4/11![Frontier logo]()
$330
This Priceline deal was found by Cheapflights users on 4/15. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/59:56 am
MKE
- SJU
1 stop15h 12m
Frontier
Mon 5/113:03 am
SJU
- MKE
1 stop6h 58m
Frontier
Deal found 4/15![Frontier logo]()
$291
This Priceline deal was found by Cheapflights users on 4/12. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/109:56 am
MKE
- SJU
1 stop15h 12m
Frontier
Sat 5/163:03 am
SJU
- MKE
1 stop6h 58m
Frontier
Deal found 4/12![Frontier logo]()
$295
This Priceline deal was found by Cheapflights users on 4/13. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/129:56 am
MKE
- SJU
1 stop26h 19m
Frontier
Mon 5/183:33 pm
SJU
- MKE
1 stop18h 28m
Frontier
Deal found 4/13![Frontier logo]()
$334
This American Airlines deal was found by Cheapflights users on 4/13. 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 5/137:00 am
MKE
- SJU
1 stop12h 51m
American Airlines
Thu 5/213:39 pm
SJU
- MKE
1 stop9h 20m
American Airlines
Deal found 4/13![American Airlines logo]()
$331
This Delta deal was found by Cheapflights users on 4/11. 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 5/1612:40 pm
MKE
- SJU
1 stop9h 55m
Delta
Tue 5/191:13 pm
SJU
- MKE
1 stop9h 39m
Delta
Deal found 4/11![Delta logo]()
$326
This Kiwi.com deal was found by Cheapflights users on 4/11. 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 5/248:46 am
MKE
- SJU
1 stop24h 32m
Multiple Airlines
Wed 5/278:32 am
SJU
- MKE
2 stops24h 29m
Multiple Airlines
Deal found 4/11![Multiple Airlines logo]()
$333
This CheapOair deal was found by Cheapflights users on 4/13. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/288:46 am
MKE
- SJU
1 stop16h 22m
Frontier
Sat 6/68:13 pm
SJU
- MKE
1 stop12h 48m
Frontier
Deal found 4/13![Frontier logo]()
$329
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 16, 2026.
Search for one-way flight options from Milwaukee to Caribbean. Find affordable one-way fares based on user searches. Data last updated April 16, 2026.
This Priceline deal was found by Cheapflights users on 4/12. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/39:33 am
MKE
- SJU
1 stop15h 28m
Frontier
Deal found 4/12![Frontier logo]()
$88
This Priceline deal was found by Cheapflights users on 4/14. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/179:56 am
MKE
- SJU
1 stop26h 19m
Frontier
Deal found 4/14![Frontier logo]()
$94
This Frontier deal was found by Cheapflights users on 4/12. 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 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
Deal found 4/12![Frontier logo]()
$123
This Priceline deal was found by Cheapflights users on 4/14. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/2712:21 pm
MKE
- SJU
1 stop24h 45m
Frontier
Deal found 4/14![Frontier logo]()
$138
This CheapOair deal was found by Cheapflights users on 4/13. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 6/288:43 am
MKE
- SJU
1 stop16h 26m
Frontier
Deal found 4/13![Frontier logo]()
$144
This Kiwi.com deal was found by Cheapflights users on 4/12. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/59:56 am
MKE
- SJU
2 stops29h 03m
Frontier
Deal found 4/12![Frontier logo]()
$151
This United Airlines deal was found by Cheapflights users on 4/14. 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 5/58:15 am
MKE
- SJU
1 stop11h 23m
United Airlines
Deal found 4/14![United Airlines logo]()
$163
This Expedia deal was found by Cheapflights users on 4/14. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/610:11 am
MKE
- SJU
1 stop9h 15m
Delta
Deal found 4/14![Delta logo]()
$164
This Kiwi.com deal was found by Cheapflights users on 4/11. 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 5/248:46 am
MKE
- SJU
2 stops42h 15m
Frontier
Deal found 4/11![Frontier logo]()
$166
This Delta deal was found by Cheapflights users on 4/11. 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 8/155:55 am
MKE
- SXM
1 stop7h 01m
Delta
Deal found 4/11![Delta logo]()
$197
This Kiwi.com deal was found by Cheapflights users on 4/13. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/2712:21 pm
MKE
- PUJ
2 stops23h 11m
Frontier
Deal found 4/13![Frontier logo]()
$207
This American Airlines deal was found by Cheapflights users on 4/11. 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 8/154:24 pm
MKE
- SXM
2 stops20h 06m
American Airlines
Deal found 4/11![American Airlines logo]()
$213
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 16, 2026.
Round-trip from | $284 (FlightHub) |
|---|---|
One-way from | $88 (Priceline) |
Popular in | December |
Cheapest in | September |
Average price | $382 |
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 16, 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 8/18
10:30 am-9:05 pm
1 stop9h 35m
San Juan Luis Munoz Marin Intl
Mon 8/31
11:35 am-8:45 pm
1 stop10h 10m
$326
MilwaukeeSan Juan
MKE - SJU
MKESJU
Milwaukee-Mitchell
Wed 7/1
10:08 am-10:27 pm
1 stop11h 19m
San Juan Luis Munoz Marin Intl
Wed 7/8
5:56 pm-11:56 pm
1 stop7h 00m
$326
MilwaukeeSan Juan
MKE - SJU
MKESJU
Milwaukee-Mitchell
Sun 5/17
7:09 am-4:33 pm
1 stop8h 24m
San Juan Luis Munoz Marin Intl
Wed 5/20
2:48 pm-11:53 pm
1 stop10h 05m
$326
MilwaukeeSan Juan
MKE - SJU
MKESJU
Milwaukee-Mitchell
Sat 5/16
12:40 pm-11:35 pm
1 stop9h 55m
San Juan Luis Munoz Marin Intl
Tue 5/19
1:13 pm-9:52 pm
1 stop9h 39m
$326
MilwaukeeSan Juan
MKE - SJU
MKESJU
Milwaukee-Mitchell
Thu 7/16
6:50 am-4:45 pm
1 stop8h 55m
San Juan Luis Munoz Marin Intl
Thu 7/23
2:42 pm-8:54 pm
1 stop7h 12m
$326
MilwaukeeSan Juan
MKE - SJU
MKESJU
Milwaukee-Mitchell
Tue 6/30
5:40 am-4:46 pm
1 stop10h 06m
San Juan Luis Munoz Marin Intl
Fri 7/10
6:00 am-11:51 am
1 stop6h 51m
$326
MilwaukeeSan Juan
MKE - SJU
MKESJU
Milwaukee-Mitchell
Mon 6/29
10:08 am-10:27 pm
1 stop11h 19m
San Juan Luis Munoz Marin Intl
Fri 7/3
6:00 am-11:51 am
1 stop6h 51m
$326
MilwaukeeSan Juan
MKE - SJU
MKESJU
Milwaukee-Mitchell
Sat 5/9
12:40 pm-11:35 pm
1 stop9h 55m
San Juan Luis Munoz Marin Intl
Sat 5/16
6:15 am-1:46 pm
1 stop8h 31m
$326
MilwaukeeMontego Bay
MKE - MBJ
MKEMBJ
Milwaukee-Mitchell
Thu 4/30
6:41 pm-9:13 am
1 stop14h 32m
Montego Bay Sangster Intl
Thu 5/7
10:17 am-5:51 pm
1 stop7h 34m
$354
MilwaukeeMontego Bay
MKE - MBJ
MKEMBJ
Milwaukee-Mitchell
Fri 5/29
6:05 am-3:10 pm
2 stops9h 05m
Montego Bay Sangster Intl
Fri 6/5
4:12 pm-12:48 pm
2 stops20h 36m
$357
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-MBJ
MKE-PUJ
MKE-AUA
MKE-NAS
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-MBJ
MKE-PUJ
MKE-AUA
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 $91). Flying from Milwaukee to Caribbean in December is currently the most expensive (average of $198). 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 16, 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.
Overall
8.0
Crew
8.6
Comfort
8.0
Boarding
8.1
Entertainment
7.5
Food
7.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Overall
8.0
Crew
8.6
Comfort
8.0
Boarding
8.1
Entertainment
7.5
Food
7.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Overall
8.0
Crew
8.6
Comfort
8.0
Boarding
8.1
Entertainment
7.5
Food
7.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Overall
8.0
Crew
8.6
Comfort
8.0
Boarding
8.1
Entertainment
7.5
Food
7.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Overall
8.0
Crew
8.6
Comfort
8.0
Boarding
8.1
Entertainment
7.5
Food
7.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Overall
8.0
Crew
8.6
Comfort
8.0
Boarding
8.1
Entertainment
7.5
Food
7.0
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 16, 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 16, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$112 | Average$606 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$156 | Average$368 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$202 | Average$557 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$219 | Average$367 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$256 | Average$655 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$315 | Average$725 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$547 | Average$841 | FlexibilityNo cancel fee | On-time83% |