$118+ 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 8/19. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — SJU
Jul 16 — Jul 231
Round-trip
1 adult, Economy
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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 June 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 June 16, 2026.
This deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/138:10 pm
MKE
- SJU
1 stop10h 48m
Frontier
Sun 10/49:03 am
SJU
- MKE
1 stop11h 12m
Frontier
Deal found 6/16![Frontier logo]()
$187
This deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/178:10 pm
MKE
- SJU
1 stop10h 48m
Frontier
Thu 10/89:03 am
SJU
- MKE
1 stop11h 12m
Frontier
Deal found 6/16![Frontier logo]()
$205
This American Airlines deal was found by Cheapflights users on 6/12. 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.
Sun 8/234:25 pm
MKE
- SJU
1 stop6h 50m
American Airlines
Thu 8/271:38 pm
SJU
- MKE
2 stops9h 09m
American Airlines
Deal found 6/12![American Airlines logo]()
$226
This Southwest deal was found by Cheapflights users on 6/11. 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.
Sat 9/59:05 am
MKE
- SJU
1 stop8h 00m
Southwest
Wed 9/91:45 pm
SJU
- MKE
1 stop8h 20m
Southwest
Deal found 6/11![Southwest logo]()
$276
This United Airlines deal was found by Cheapflights users on 6/11. 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.
Fri 10/236:15 am
MKE
- SJU
1 stop7h 29m
United Airlines
Wed 10/281:05 am
SJU
- MKE
1 stop9h 41m
United Airlines
Deal found 6/11![United Airlines logo]()
$305
This American Airlines deal was found by Cheapflights users on 6/11. 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 8/226:20 am
MKE
- SJU
1 stop15h 04m
American Airlines
Tue 8/2510:33 am
SJU
- MKE
2 stops13h 26m
American Airlines
Deal found 6/11![American Airlines logo]()
$316
This Southwest deal was found by Cheapflights users on 6/13. 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 9/110:50 am
MKE
- SJU
1 stop7h 10m
Southwest
Wed 9/26:00 am
SJU
- MKE
1 stop7h 00m
Southwest
Deal found 6/13![Southwest logo]()
$321
This Delta deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/155:30 am
MKE
- SJU
1 stop10h 01m
Delta
Mon 10/512:58 pm
SJU
- MKE
1 stop8h 54m
Delta
Deal found 6/16![Delta logo]()
$326
This American Airlines deal was found by Cheapflights users on 6/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/26:28 am
MKE
- SJU
2 stops14h 27m
American Airlines
Sat 9/512:55 am
SJU
- MKE
1 stop14h 31m
American Airlines
Deal found 6/12![American Airlines logo]()
$331
This American Airlines deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/58:16 pm
MKE
- SJU
1 stop16h 29m
American Airlines
Fri 10/303:50 pm
SJU
- MKE
1 stop9h 21m
American Airlines
Deal found 6/16![American Airlines logo]()
$332
This Southwest deal was found by Cheapflights users on 6/15. 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.
Sun 8/97:00 pm
MKE
- SJU
1 stop13h 10m
Southwest
Wed 8/122:25 pm
SJU
- MKE
1 stop7h 30m
Southwest
Deal found 6/15![Southwest logo]()
$336
This American Airlines deal was found by Cheapflights users on 6/11. 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 10/38:14 pm
MKE
- MBJ
2 stops16h 39m
American Airlines
Tue 10/135:00 pm
MBJ
- MKE
2 stops19h 02m
American Airlines
Deal found 6/11![American Airlines logo]()
$357
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 June 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 June 16, 2026.
This Southwest deal was found by Cheapflights users on 6/13. 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.
Sun 8/2311:50 am
MKE
- SJU
1 stop11h 00m
Southwest
Thu 8/2711:35 am
SJU
- MKE
2 stops9h 15m
Southwest
Deal found 6/13![Southwest logo]()
$326
This Delta deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/237:03 am
MKE
- SJU
1 stop8h 35m
Delta
Tue 8/255:49 pm
SJU
- MKE
1 stop7h 04m
Delta
Deal found 6/16![Delta logo]()
$326
This American Airlines deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/286:48 pm
MKE
- MBJ
2 stops18h 33m
American Airlines
Tue 9/12:37 pm
MBJ
- MKE
2 stops17h 07m
American Airlines
Deal found 6/16![American Airlines logo]()
$367
This United Airlines deal was found by Cheapflights users on 6/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/65:00 am
MKE
- SJU
2 stops14h 38m
United Airlines
Wed 9/94:20 pm
SJU
- MKE
1 stop8h 17m
United Airlines
Deal found 6/15![United Airlines logo]()
$416
This FlightHub deal was found by Cheapflights users on 6/12. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/299:36 am
MKE
- STT
1 stop27h 27m
JetBlue
Fri 7/102:49 pm
STT
- MKE
2 stops18h 56m
JetBlue
Deal found 6/12![JetBlue logo]()
$576
This Delta deal was found by Cheapflights users on 6/12. 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.
Wed 8/1212:51 pm
MKE
- SJU
1 stop8h 38m
Delta
Tue 8/185:49 pm
SJU
- MKE
1 stop7h 04m
Delta
Deal found 6/12![Delta logo]()
$326
This Delta deal was found by Cheapflights users on 6/15. 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 8/227:03 am
MKE
- SJU
1 stop8h 35m
Delta
Mon 8/315:49 pm
SJU
- MKE
1 stop7h 04m
Delta
Deal found 6/15![Delta logo]()
$326
This American Airlines deal was found by Cheapflights users on 6/11. 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 9/195:43 pm
MKE
- MBJ
1 stop22h 33m
American Airlines
Sat 9/265:16 pm
MBJ
- MKE
2 stops17h 51m
American Airlines
Deal found 6/11![American Airlines logo]()
$369
This Delta deal was found by Cheapflights users on 6/12. 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.
Mon 9/145:30 am
MKE
- SJU
1 stop10h 01m
Delta
Fri 10/25:41 pm
SJU
- MKE
1 stop7h 11m
Delta
Deal found 6/12![Delta logo]()
$326
This Southwest deal was found by Cheapflights users on 6/15. 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 8/2012:30 pm
MKE
- SJU
2 stops9h 35m
Southwest
Sun 8/236:00 am
SJU
- MKE
1 stop8h 35m
Southwest
Deal found 6/15![Southwest logo]()
$401
This United Airlines deal was found by Cheapflights users on 6/12. 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 6/3010:28 am
MKE
- SJU
1 stop9h 06m
United Airlines
Tue 7/71:00 am
SJU
- MKE
2 stops9h 53m
United Airlines
Deal found 6/12![United Airlines logo]()
$447
This American Airlines deal was found by Cheapflights users on 6/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/106:28 am
MKE
- STT
1 stop7h 31m
American Airlines
Fri 8/214:42 pm
STT
- MKE
2 stops19h 20m
American Airlines
Deal found 6/14![American Airlines logo]()
$469
This Delta deal was found by Cheapflights users on 6/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/106:45 am
MKE
- SJU
1 stop8h 48m
Delta
Sat 8/155:49 pm
SJU
- MKE
1 stop7h 04m
Delta
Deal found 6/14![Delta logo]()
$401
This Southwest deal was found by Cheapflights users on 6/11. 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.
Fri 7/173:15 pm
MKE
- SJU
1 stop7h 25m
Southwest
Sat 7/256:30 am
SJU
- MKE
1 stop10h 30m
Southwest
Deal found 6/11![Southwest logo]()
$490
This American Airlines deal was found by Cheapflights users on 6/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/511:57 am
MKE
- MBJ
1 stop25h 58m
American Airlines
Sat 12/121:55 pm
MBJ
- MKE
1 stop11h 06m
American Airlines
Deal found 6/15![American Airlines logo]()
$474
This Southwest deal was found by Cheapflights users on 6/12. 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 7/238:15 pm
MKE
- SJU
1 stop11h 45m
Southwest
Sun 7/266:05 am
SJU
- MKE
1 stop12h 40m
Southwest
Deal found 6/12![Southwest logo]()
$492
This United Airlines deal was found by Cheapflights users on 6/13. 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.
Sat 12/57:00 am
MKE
- GCM
1 stop5h 45m
United Airlines
Mon 12/145:45 pm
GCM
- MKE
2 stops17h 04m
United Airlines
Deal found 6/13![United Airlines logo]()
$556
This Delta deal was found by Cheapflights users on 6/11. 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 9/195:30 am
MKE
- MBJ
1 stop10h 04m
Delta
Sat 9/261:25 pm
MBJ
- MKE
1 stop7h 27m
Delta
Deal found 6/11![Delta logo]()
$422
This Justfly.com deal was found by Cheapflights users on 6/12. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/1211:25 am
MKE
- AUA
1 stop27h 15m
JetBlue
Sat 9/194:30 pm
AUA
- MKE
1 stop19h 05m
JetBlue
Deal found 6/12![JetBlue logo]()
$646
This American Airlines deal was found by Cheapflights users on 6/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/112:49 pm
MKE
- GCM
2 stops20h 11m
American Airlines
Tue 8/182:10 pm
GCM
- MKE
2 stops8h 49m
American Airlines
Deal found 6/14![American Airlines logo]()
$504
This United Airlines deal was found by Cheapflights users on 6/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/187:23 pm
MKE
- SXM
2 stops16h 10m
United Airlines
Sat 7/253:50 pm
SXM
- MKE
2 stops19h 03m
United Airlines
Deal found 6/15![United Airlines logo]()
$564
This Delta deal was found by Cheapflights users on 6/12. 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.
Sat 9/193:59 pm
MKE
- MBJ
2 stops19h 26m
Delta
Fri 9/254:59 pm
MBJ
- MKE
1 stop6h 53m
Delta
Deal found 6/12![Delta logo]()
$427
This United Airlines deal was found by Cheapflights users on 6/11. 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.
Mon 12/76:00 am
MKE
- PUJ
1 stop8h 02m
United Airlines
Thu 12/102:55 pm
PUJ
- MKE
1 stop9h 44m
United Airlines
Deal found 6/11![United Airlines logo]()
$564
This American Airlines deal was found by Cheapflights users on 6/11. 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 12/126:50 pm
MKE
- NAS
1 stop16h 23m
American Airlines
Thu 12/172:00 pm
NAS
- MKE
1 stop6h 28m
American Airlines
Deal found 6/11![American Airlines logo]()
$514
This Delta deal was found by Cheapflights users on 6/12. 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.
Fri 9/184:36 pm
MKE
- MBJ
2 stops18h 49m
Delta
Sat 9/264:59 pm
MBJ
- MKE
1 stop16h 07m
Delta
Deal found 6/12![Delta logo]()
$427
This Southwest deal was found by Cheapflights users on 6/15. 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.
Sun 11/85:10 am
MKE
- NAS
1 stop6h 05m
Southwest
Sat 11/141:55 pm
NAS
- MKE
2 stops8h 40m
Southwest
Deal found 6/15![Southwest logo]()
$580
This American Airlines deal was found by Cheapflights users on 6/11. 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 11/77:03 pm
MKE
- PUJ
1 stop17h 49m
American Airlines
Sat 11/145:52 pm
PUJ
- MKE
1 stop17h 46m
American Airlines
Deal found 6/11![American Airlines logo]()
$521
This United Airlines deal was found by Cheapflights users on 6/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/305:00 am
MKE
- NAS
1 stop8h 57m
United Airlines
Thu 8/63:59 pm
NAS
- MKE
1 stop7h 30m
United Airlines
Deal found 6/15![United Airlines logo]()
$576
This United Airlines deal was found by Cheapflights users on 6/13. 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.
Sat 8/15:00 am
MKE
- NAS
2 stops9h 56m
United Airlines
Fri 8/73:59 pm
NAS
- MKE
1 stop7h 30m
United Airlines
Deal found 6/13![United Airlines logo]()
$576
This American Airlines deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/242:49 pm
MKE
- GCM
1 stop20h 38m
American Airlines
Sat 8/293:17 pm
GCM
- MKE
1 stop7h 40m
American Airlines
Deal found 6/16![American Airlines logo]()
$530
Last-minute flights from Milwaukee to CaribbeanDiscover last-minute flight deals from Milwaukee to Caribbean. Data last updated June 16, 2026 and is based on user searches.
Discover last-minute flight deals from Milwaukee to Caribbean. Data last updated June 16, 2026 and is based on user searches.
This Priceline deal was found by Cheapflights users on 6/12. 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.
Tue 6/308:43 am
MKE
- SJU
1 stop16h 26m
Frontier
Wed 7/86:26 pm
SJU
- MKE
1 stop14h 32m
Frontier
Deal found 6/12![Frontier logo]()
$416
This Priceline deal was found by Cheapflights users on 6/14. 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 7/58:43 am
MKE
- SJU
1 stop25h 33m
Frontier
Wed 7/154:08 pm
SJU
- MKE
1 stop16h 50m
Frontier
Deal found 6/14![Frontier logo]()
$436
This American Airlines deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/77:01 am
MKE
- SJU
1 stop14h 58m
American Airlines
Thu 7/167:00 am
SJU
- MKE
1 stop11h 17m
American Airlines
Deal found 6/16![American Airlines logo]()
$434
This Southwest deal was found by Cheapflights users on 6/13. 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.
Sat 7/119:50 am
MKE
- SJU
1 stop12h 15m
Southwest
Thu 7/167:00 am
SJU
- MKE
1 stop12h 50m
Southwest
Deal found 6/13![Southwest logo]()
$420
This American Airlines deal was found by Cheapflights users on 6/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/151:25 pm
MKE
- SJU
1 stop8h 34m
American Airlines
Wed 7/227:00 am
SJU
- MKE
1 stop11h 17m
American Airlines
Deal found 6/14![American Airlines logo]()
$414
This American Airlines deal was found by Cheapflights users on 6/12. 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.
Tue 7/216:00 am
MKE
- SJU
1 stop15h 57m
American Airlines
Wed 7/297:00 am
SJU
- MKE
1 stop17h 44m
American Airlines
Deal found 6/12![American Airlines logo]()
$366
This Frontier deal was found by Cheapflights users on 6/15. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/218:43 am
MKE
- SJU
1 stop7h 48m
Frontier
Wed 7/298:37 pm
SJU
- MKE
1 stop12h 21m
Frontier
Deal found 6/15![Frontier logo]()
$376
This Priceline deal was found by Cheapflights users on 6/13. 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 7/238:43 am
MKE
- SJU
1 stop25h 33m
Frontier
Wed 7/298:37 pm
SJU
- MKE
1 stop12h 21m
Frontier
Deal found 6/13![Frontier logo]()
$446
This Frontier deal was found by Cheapflights users on 6/14. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/288:43 am
MKE
- SJU
1 stop7h 48m
Frontier
Mon 8/38:37 pm
SJU
- MKE
1 stop12h 21m
Frontier
Deal found 6/14![Frontier logo]()
$396
This American Airlines deal was found by Cheapflights users on 6/15. 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.
Tue 7/287:01 am
MKE
- SJU
1 stop14h 58m
American Airlines
Mon 8/37:25 am
SJU
- MKE
1 stop15h 29m
American Airlines
Deal found 6/15![American Airlines logo]()
$406
This American Airlines deal was found by Cheapflights users on 6/11. 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.
Thu 7/306:00 am
MKE
- SJU
2 stops11h 24m
American Airlines
Thu 8/67:00 am
SJU
- MKE
1 stop17h 14m
American Airlines
Deal found 6/11![American Airlines logo]()
$409
This Delta deal was found by Cheapflights users on 6/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/3012:58 pm
MKE
- SJU
1 stop6h 47m
Delta
Tue 8/115:49 pm
SJU
- MKE
1 stop7h 04m
Delta
Deal found 6/14![Delta logo]()
$418
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 June 16, 2026.
Search for one-way flight options from Milwaukee to Caribbean. Find affordable one-way fares based on user searches. Data last updated June 16, 2026.
This American Airlines deal was found by Cheapflights users on 6/11. 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 8/1912:58 pm
MKE
- SJU
1 stop8h 26m
American Airlines
Deal found 6/11![American Airlines logo]()
$118
This American Airlines deal was found by Cheapflights users on 6/15. 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.
Mon 8/246:20 am
MKE
- MBJ
1 stop8h 03m
American Airlines
Deal found 6/15![American Airlines logo]()
$157
This American Airlines deal was found by Cheapflights users on 6/12. 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.
Sat 7/115:58 pm
MKE
- MBJ
2 stops19h 11m
American Airlines
Deal found 6/12![American Airlines logo]()
$163
This Delta deal was found by Cheapflights users on 6/12. 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.
Mon 8/106:45 am
MKE
- SJU
1 stop8h 48m
Delta
Deal found 6/12![Delta logo]()
$163
This American Airlines deal was found by Cheapflights users on 6/11. 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.
Fri 8/76:28 am
MKE
- SJU
1 stop16h 31m
American Airlines
Deal found 6/11![American Airlines logo]()
$166
This Delta deal was found by Cheapflights users on 6/15. 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 8/227:03 am
MKE
- MBJ
1 stop8h 31m
Delta
Deal found 6/15![Delta logo]()
$187
This American Airlines deal was found by Cheapflights users on 6/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/76:01 am
MKE
- SJU
1 stop16h 47m
American Airlines
Deal found 6/14![American Airlines logo]()
$188
This American Airlines deal was found by Cheapflights users on 6/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/222:49 pm
MKE
- MBJ
2 stops20h 53m
American Airlines
Deal found 6/15![American Airlines logo]()
$192
This United Airlines deal was found by Cheapflights users on 6/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/87:50 am
MKE
- SJU
2 stops12h 34m
United Airlines
Deal found 6/15![United Airlines logo]()
$192
This Delta deal was found by Cheapflights users on 6/15. 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.
Tue 8/253:01 pm
MKE
- MBJ
2 stops20h 33m
Delta
Deal found 6/15![Delta logo]()
$193
This American Airlines deal was found by Cheapflights users on 6/15. 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.
Wed 8/265:00 am
MKE
- MBJ
1 stop8h 12m
American Airlines
Deal found 6/15![American Airlines logo]()
$197
This American Airlines deal was found by Cheapflights users on 6/15. 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.
Sun 8/236:48 pm
MKE
- MBJ
2 stops18h 40m
American Airlines
Deal found 6/15![American Airlines logo]()
$198
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 June 16, 2026.
Round-trip from | $187 |
|---|---|
One-way from | $118 (American Airlines) |
Popular in | December |
Cheapest in | October |
Average price | $475 |
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 June 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
Sun 8/23
11:50 am-11:50 pm
1 stop11h 00m
San Juan Luis Munoz Marin Intl
Thu 8/27
11:35 am-7:50 pm
2 stops9h 15m
$326
MilwaukeeSan Juan
MKE - SJU
MKESJU
Milwaukee-Mitchell
Sun 8/23
7:03 am-4:38 pm
1 stop8h 35m
San Juan Luis Munoz Marin Intl
Tue 8/25
5:49 pm-11:53 pm
1 stop7h 04m
$326
MilwaukeeSan Juan
MKE - SJU
MKESJU
Milwaukee-Mitchell
Wed 8/12
12:51 pm-10:29 pm
1 stop8h 38m
San Juan Luis Munoz Marin Intl
Tue 8/18
5:49 pm-11:53 pm
1 stop7h 04m
$326
MilwaukeeSan Juan
MKE - SJU
MKESJU
Milwaukee-Mitchell
Sat 8/22
7:03 am-4:38 pm
1 stop8h 35m
San Juan Luis Munoz Marin Intl
Mon 8/31
5:49 pm-11:53 pm
1 stop7h 04m
$326
MilwaukeeSan Juan
MKE - SJU
MKESJU
Milwaukee-Mitchell
Mon 9/14
5:30 am-4:31 pm
1 stop10h 01m
San Juan Luis Munoz Marin Intl
Fri 10/2
5:41 pm-11:52 pm
1 stop7h 11m
$326
MilwaukeeMontego Bay
MKE - MBJ
MKEMBJ
Milwaukee-Mitchell
Fri 8/28
6:48 pm-1:21 pm
2 stops18h 33m
Montego Bay Sangster Intl
Tue 9/1
2:37 pm-7:44 am
2 stops17h 07m
$367
MilwaukeeMontego Bay
MKE - MBJ
MKEMBJ
Milwaukee-Mitchell
Sat 9/19
5:43 pm-4:16 pm
1 stop22h 33m
Montego Bay Sangster Intl
Sat 9/26
5:16 pm-11:07 am
2 stops17h 51m
$369
MilwaukeeSan Juan
MKE - SJU
MKESJU
Milwaukee-Mitchell
Thu 8/20
12:30 pm-11:05 pm
2 stops9h 35m
San Juan Luis Munoz Marin Intl
Sun 8/23
6:00 am-1:35 pm
1 stop8h 35m
$401
MilwaukeeSan Juan
MKE - SJU
MKESJU
Milwaukee-Mitchell
Mon 8/10
6:45 am-4:33 pm
1 stop8h 48m
San Juan Luis Munoz Marin Intl
Sat 8/15
5:49 pm-11:53 pm
1 stop7h 04m
$401
MilwaukeeSan Juan
MKE - SJU
MKESJU
Milwaukee-Mitchell
Sun 9/6
5:00 am-8:38 pm
2 stops14h 38m
San Juan Luis Munoz Marin Intl
Wed 9/9
4:20 pm-11:37 pm
1 stop8h 17m
$416
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-STT
MKE-GCM
MKE-AUA
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-STT
MKE-GCM
What is the cheapest month to book a flight from Milwaukee to Caribbean?
Currently, October is the cheapest month in which you can book a flight from Milwaukee to Caribbean (average of $108). Flying from Milwaukee to Caribbean in March is currently the most expensive (average of $1,030). 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.
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.
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 June 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.
Crew
8.6
Overall
7.9
Comfort
8.0
Boarding
8.1
Entertainment
7.5
Food
7.0
Reviews
1 / 20
8.0
ExcellentLa Tracimeldamarcos,Jun 2026
LAX - SLC
Crew
8.6
Overall
7.9
Comfort
8.0
Boarding
8.1
Entertainment
7.5
Food
7.0
Reviews
1 / 20
8.0
ExcellentLa Tracimeldamarcos,Jun 2026
LAX - SLC
Crew
8.6
Overall
7.9
Comfort
8.0
Boarding
8.1
Entertainment
7.5
Food
7.0
Reviews
1 / 20
8.0
ExcellentLa Tracimeldamarcos,Jun 2026
LAX - SLC
Crew
8.6
Overall
7.9
Comfort
8.0
Boarding
8.1
Entertainment
7.5
Food
7.0
Reviews
1 / 20
8.0
ExcellentLa Tracimeldamarcos,Jun 2026
LAX - SLC
Crew
8.6
Overall
7.9
Comfort
8.0
Boarding
8.1
Entertainment
7.5
Food
7.0
Reviews
1 / 20
8.0
ExcellentLa Tracimeldamarcos,Jun 2026
LAX - SLC
Crew
8.6
Overall
7.9
Comfort
8.0
Boarding
8.1
Entertainment
7.5
Food
7.0
Reviews
1 / 20
8.0
ExcellentLa Tracimeldamarcos,Jun 2026
LAX - SLC
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.
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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 June 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 6 airlines flying from Milwaukee to Caribbean
Discover the top 6 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 June 16, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$118 | Average$576 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$156 | Average$360 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$235 | Average$556 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$256 | Average$671 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$316 | Average$738 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$547 | Average$841 | FlexibilityNo cancel fee | On-time83% |