$138+ 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 7/21. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — SJU
Jun 10 — Jun 171
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 May 11, 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 May 11, 2026.
This American Airlines deal was found by Cheapflights users on 5/11. 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 9/55:00 am
MKE
- SJU
1 stop16h 52m
American Airlines
Wed 9/96:30 am
SJU
- MKE
2 stops16h 24m
American Airlines
Deal found 5/11![American Airlines logo]()
$351
This United Airlines deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/128:45 pm
MKE
- MBJ
1 stop16h 01m
United Airlines
Tue 11/172:48 pm
MBJ
- MKE
1 stop10h 21m
United Airlines
Deal found 5/6![United Airlines logo]()
$352
This American Airlines deal was found by Cheapflights users on 5/11. 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 6/15:53 pm
MKE
- MBJ
2 stops17h 26m
American Airlines
Fri 6/55:17 pm
MBJ
- MKE
2 stops18h 47m
American Airlines
Deal found 5/11![American Airlines logo]()
$357
This American Airlines deal was found by Cheapflights users on 5/9. Clicking the “Pick Dates” 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 11/96:48 pm
MKE
- MBJ
1 stop14h 20m
American Airlines
Mon 11/162:19 pm
MBJ
- MKE
1 stop18h 41m
American Airlines
Deal found 5/9![American Airlines logo]()
$358
This Priceline deal was found by Cheapflights users on 5/10. Clicking the “Pick Dates” 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 stop16h 28m
Frontier
Mon 7/204:05 pm
SJU
- MKE
1 stop16h 53m
Frontier
Deal found 5/10![Frontier logo]()
$361
This Delta deal was found by Cheapflights users on 5/7. Clicking the “Pick Dates” 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 7/296:50 am
MKE
- MBJ
1 stop8h 44m
Delta
Wed 8/51:09 pm
MBJ
- MKE
1 stop10h 44m
Delta
Deal found 5/7![Delta logo]()
$362
This American Airlines deal was found by Cheapflights users on 5/7. Clicking the “Pick Dates” 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 6/296:50 pm
MKE
- MBJ
2 stops18h 18m
American Airlines
Sat 7/43:02 pm
MBJ
- MKE
1 stop26h 15m
American Airlines
Deal found 5/7![American Airlines logo]()
$364
This Southwest deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” 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 7/299:25 am
MKE
- SJU
1 stop13h 20m
Southwest
Wed 8/55:15 am
SJU
- MKE
1 stop6h 40m
Southwest
Deal found 5/6![Southwest logo]()
$365
This American Airlines deal was found by Cheapflights users on 5/10. Clicking the “Pick Dates” 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 8/178:20 am
MKE
- SJU
1 stop13h 47m
American Airlines
Fri 8/211:38 pm
SJU
- MKE
2 stops10h 21m
American Airlines
Deal found 5/10![American Airlines logo]()
$366
This American Airlines deal was found by Cheapflights users on 5/11. 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 8/126:33 am
MKE
- SJU
2 stops13h 41m
American Airlines
Tue 8/186:51 am
SJU
- MKE
1 stop17h 32m
American Airlines
Deal found 5/11![American Airlines logo]()
$371
This American Airlines deal was found by Cheapflights users on 5/11. 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 9/36:16 am
MKE
- SJU
2 stops11h 08m
American Airlines
Tue 9/82:33 pm
SJU
- MKE
1 stop7h 35m
American Airlines
Deal found 5/11![American Airlines logo]()
$376
This Southwest deal was found by Cheapflights users on 5/7. Clicking the “Pick Dates” 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 9/210:00 am
MKE
- SJU
2 stops11h 00m
Southwest
Sun 9/66:00 am
SJU
- MKE
1 stop7h 40m
Southwest
Deal found 5/7![Southwest logo]()
$387
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 May 11, 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 May 11, 2026.
This American Airlines deal was found by Cheapflights users on 5/11. 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 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 5/11![American Airlines logo]()
$357
This Delta deal was found by Cheapflights users on 5/7. Clicking the “Pick Dates” 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 7/296:50 am
MKE
- MBJ
1 stop8h 44m
Delta
Wed 8/51:09 pm
MBJ
- MKE
1 stop10h 44m
Delta
Deal found 5/7![Delta logo]()
$362
This United Airlines deal was found by Cheapflights users on 5/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/296:20 am
MKE
- MBJ
2 stops8h 50m
United Airlines
Sat 7/42:40 pm
MBJ
- MKE
2 stops16h 20m
United Airlines
Deal found 5/7![United Airlines logo]()
$391
This Southwest deal was found by Cheapflights users on 5/10. Clicking the “Pick Dates” 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 7/313:15 pm
MKE
- SJU
1 stop7h 20m
Southwest
Tue 8/410:30 am
SJU
- MKE
1 stop6h 50m
Southwest
Deal found 5/10![Southwest logo]()
$404
This Gotogate deal was found by Cheapflights users on 5/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/812:09 pm
MKE
- PUJ
2 stops21h 23m
Frontier
Fri 6/123:35 pm
PUJ
- MKE
1 stop20h 38m
Frontier
Deal found 5/8![Frontier logo]()
$537
This SmartFares deal was found by Cheapflights users on 5/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/278:41 am
MKE
- SDQ
1 stop16h 03m
JetBlue
Wed 6/105:01 am
SDQ
- MKE
1 stop28h 45m
JetBlue
Deal found 5/7![JetBlue logo]()
$554
This American Airlines deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” 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 6/151:30 pm
MKE
- SJU
1 stop8h 15m
American Airlines
Mon 6/227:00 am
SJU
- MKE
1 stop17h 59m
American Airlines
Deal found 5/6![American Airlines logo]()
$406
This Southwest deal was found by Cheapflights users on 5/8. Clicking the “Pick Dates” 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 8/26:15 am
MKE
- SJU
2 stops16h 40m
Southwest
Sun 8/169:25 pm
SJU
- MKE
1 stop12h 30m
Southwest
Deal found 5/8![Southwest logo]()
$448
This United Airlines deal was found by Cheapflights users on 5/7. Clicking the “Pick Dates” 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 6/277:23 pm
MKE
- MBJ
2 stops18h 07m
United Airlines
Sat 7/42:40 pm
MBJ
- MKE
2 stops16h 20m
United Airlines
Deal found 5/7![United Airlines logo]()
$467
This American Airlines deal was found by Cheapflights users on 5/11. 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 6/16:17 pm
MKE
- MBJ
1 stop17h 02m
American Airlines
Fri 6/53:00 pm
MBJ
- MKE
1 stop8h 47m
American Airlines
Deal found 5/11![American Airlines logo]()
$434
This Delta deal was found by Cheapflights users on 5/9. Clicking the “Pick Dates” 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 8/312:51 pm
MKE
- SJU
1 stop8h 38m
Delta
Mon 8/1012:56 pm
SJU
- MKE
1 stop8h 57m
Delta
Deal found 5/9![Delta logo]()
$480
This Southwest deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” 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 6/2912:25 pm
MKE
- SJU
1 stop10h 50m
Southwest
Fri 7/310:20 pm
SJU
- MKE
1 stop12h 00m
Southwest
Deal found 5/6![Southwest logo]()
$466
This American Airlines deal was found by Cheapflights users on 5/10. Clicking the “Pick Dates” 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 6/16:17 pm
MKE
- MBJ
2 stops18h 51m
American Airlines
Sat 6/63:00 pm
MBJ
- MKE
1 stop8h 47m
American Airlines
Deal found 5/10![American Airlines logo]()
$439
This Southwest deal was found by Cheapflights users on 5/11. 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.
Thu 7/168:15 pm
MKE
- SJU
1 stop11h 45m
Southwest
Tue 7/218:35 pm
SJU
- MKE
1 stop13h 15m
Southwest
Deal found 5/11![Southwest logo]()
$470
This American Airlines deal was found by Cheapflights users on 5/7. Clicking the “Pick Dates” 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 7/296:17 pm
MKE
- MBJ
2 stops18h 52m
American Airlines
Wed 8/512:38 pm
MBJ
- MKE
2 stops11h 12m
American Airlines
Deal found 5/7![American Airlines logo]()
$444
This Booking.com deal was found by Cheapflights users on 5/11. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/2312:29 pm
MKE
- PUJ
1 stop24h 55m
Frontier
Tue 5/2611:45 am
PUJ
- MKE
2 stops24h 29m
Frontier
Deal found 5/11![Frontier logo]()
$593
This Delta deal was found by Cheapflights users on 5/10. Clicking the “Pick Dates” 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 6/127:00 am
MKE
- STI
1 stop17h 59m
Delta
Mon 6/228:59 pm
STI
- MKE
2 stops16h 36m
Delta
Deal found 5/10![Delta logo]()
$543
This United Airlines deal was found by Cheapflights users on 5/7. Clicking the “Pick Dates” 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 9/258:45 pm
MKE
- PUJ
2 stops17h 45m
United Airlines
Sat 10/32:20 pm
PUJ
- MKE
1 stop9h 21m
United Airlines
Deal found 5/7![United Airlines logo]()
$568
This Justfly.com deal was found by Cheapflights users on 5/7. Clicking the “Pick Dates” 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.
Tue 6/98:41 am
MKE
- SDQ
1 stop14h 03m
JetBlue
Sat 6/205:17 pm
SDQ
- MKE
1 stop16h 29m
JetBlue
Deal found 5/7![JetBlue logo]()
$630
This American Airlines deal was found by Cheapflights users on 5/7. Clicking the “Pick Dates” 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
- MBJ
1 stop17h 42m
American Airlines
Sat 7/43:02 pm
MBJ
- MKE
1 stop26h 15m
American Airlines
Deal found 5/7![American Airlines logo]()
$447
This Delta deal was found by Cheapflights users on 5/7. Clicking the “Pick Dates” 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 6/107:00 am
MKE
- STI
1 stop17h 59m
Delta
Mon 6/228:59 pm
STI
- MKE
2 stops16h 36m
Delta
Deal found 5/7![Delta logo]()
$543
This American Airlines deal was found by Cheapflights users on 5/9. Clicking the “Pick Dates” 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 9/164:33 pm
MKE
- MBJ
2 stops18h 17m
American Airlines
Sun 9/203:15 pm
MBJ
- MKE
2 stops20h 47m
American Airlines
Deal found 5/9![American Airlines logo]()
$449
This Southwest deal was found by Cheapflights users on 5/11. 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 6/109:25 am
MKE
- SJU
1 stop13h 20m
Southwest
Wed 6/175:00 am
SJU
- MKE
1 stop7h 50m
Southwest
Deal found 5/11![Southwest logo]()
$550
This United Airlines deal was found by Cheapflights users on 5/7. Clicking the “Pick Dates” 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 6/67:00 pm
MKE
- SXM
2 stops16h 33m
United Airlines
Fri 6/123:50 pm
SXM
- MKE
2 stops23h 46m
United Airlines
Deal found 5/7![United Airlines logo]()
$608
This Delta deal was found by Cheapflights users on 5/10. Clicking the “Pick Dates” 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 8/95:34 am
MKE
- PUJ
1 stop8h 05m
Delta
Fri 8/141:10 pm
PUJ
- MKE
1 stop8h 43m
Delta
Deal found 5/10![Delta logo]()
$568
This United Airlines deal was found by Cheapflights users on 5/8. Clicking the “Pick Dates” 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 10/37:00 pm
MKE
- STI
2 stops16h 57m
United Airlines
Tue 10/66:00 am
STI
- MKE
2 stops19h 09m
United Airlines
Deal found 5/8![United Airlines logo]()
$613
This Delta deal was found by Cheapflights users on 5/10. Clicking the “Pick Dates” 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 8/296:00 am
MKE
- PUJ
1 stop7h 39m
Delta
Fri 9/44:16 pm
PUJ
- MKE
1 stop8h 09m
Delta
Deal found 5/10![Delta logo]()
$568
This Southwest deal was found by Cheapflights users on 5/10. Clicking the “Pick Dates” 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 6/297:30 am
MKE
- NAS
1 stop10h 00m
Southwest
Thu 7/22:10 pm
NAS
- MKE
2 stops10h 45m
Southwest
Deal found 5/10![Southwest logo]()
$586
This United Airlines deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” 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 10/177:00 am
MKE
- SDQ
2 stops14h 46m
United Airlines
Sat 10/243:20 pm
SDQ
- MKE
1 stop9h 16m
United Airlines
Deal found 5/6![United Airlines logo]()
$635
This Delta deal was found by Cheapflights users on 5/10. Clicking the “Pick Dates” 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 6/306:50 am
MKE
- NAS
1 stop8h 47m
Delta
Wed 7/16:02 pm
NAS
- MKE
1 stop16h 01m
Delta
Deal found 5/10![Delta logo]()
$586
Last-minute flights from Milwaukee to CaribbeanDiscover last-minute flight deals from Milwaukee to Caribbean. Data last updated May 11, 2026 and is based on user searches.
Discover last-minute flight deals from Milwaukee to Caribbean. Data last updated May 11, 2026 and is based on user searches.
This American Airlines deal was found by Cheapflights users on 5/8. Clicking the “Pick Dates” 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 5/267:00 am
MKE
- SJU
2 stops13h 59m
American Airlines
Wed 6/36:20 am
SJU
- MKE
1 stop18h 27m
American Airlines
Deal found 5/8![American Airlines logo]()
$418
This American Airlines deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” 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 5/6![American Airlines logo]()
$406
This American Airlines deal was found by Cheapflights users on 5/10. Clicking the “Pick Dates” 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 5/316:00 am
MKE
- SJU
1 stop16h 01m
American Airlines
Wed 6/106:21 am
SJU
- MKE
1 stop18h 26m
American Airlines
Deal found 5/10![American Airlines logo]()
$420
This American Airlines deal was found by Cheapflights users on 5/11. 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 6/16:17 pm
MKE
- MBJ
2 stops18h 51m
American Airlines
Fri 6/53:00 pm
MBJ
- MKE
1 stop8h 47m
American Airlines
Deal found 5/11![American Airlines logo]()
$357
This American Airlines deal was found by Cheapflights users on 5/7. Clicking the “Pick Dates” 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
Tue 6/96:21 am
SJU
- MKE
1 stop17h 49m
American Airlines
Deal found 5/7![American Airlines logo]()
$366
This Delta deal was found by Cheapflights users on 5/10. Clicking the “Pick Dates” 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 6/12:55 pm
MKE
- SJU
1 stop6h 22m
Delta
Fri 6/56:15 am
SJU
- MKE
1 stop9h 57m
Delta
Deal found 5/10![Delta logo]()
$403
This American Airlines deal was found by Cheapflights users on 5/7. Clicking the “Pick Dates” 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 6/36:00 am
MKE
- SJU
1 stop16h 01m
American Airlines
Tue 6/96:21 am
SJU
- MKE
1 stop12h 02m
American Airlines
Deal found 5/7![American Airlines logo]()
$411
This American Airlines deal was found by Cheapflights users on 5/7. Clicking the “Pick Dates” 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 6/36:01 am
MKE
- SJU
2 stops11h 24m
American Airlines
Mon 6/86:21 am
SJU
- MKE
1 stop18h 26m
American Airlines
Deal found 5/7![American Airlines logo]()
$423
This American Airlines deal was found by Cheapflights users on 5/8. Clicking the “Pick Dates” 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 6/46:00 am
MKE
- SJU
1 stop16h 00m
American Airlines
Wed 6/106:21 am
SJU
- MKE
1 stop18h 26m
American Airlines
Deal found 5/8![American Airlines logo]()
$409
This American Airlines deal was found by Cheapflights users on 5/7. Clicking the “Pick Dates” 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 6/296:50 pm
MKE
- MBJ
2 stops18h 18m
American Airlines
Sat 7/43:02 pm
MBJ
- MKE
1 stop26h 15m
American Airlines
Deal found 5/7![American Airlines logo]()
$364
This United Airlines deal was found by Cheapflights users on 5/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/296:20 am
MKE
- MBJ
2 stops8h 50m
United Airlines
Sat 7/42:40 pm
MBJ
- MKE
2 stops16h 20m
United Airlines
Deal found 5/7![United Airlines logo]()
$391
This Priceline deal was found by Cheapflights users on 5/7. Clicking the “Pick Dates” 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 6/2912:08 pm
MKE
- PUJ
1 stop25h 38m
Frontier
Thu 7/93:59 pm
PUJ
- MKE
1 stop20h 16m
Frontier
Deal found 5/7![Frontier logo]()
$426
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 May 11, 2026.
Search for one-way flight options from Milwaukee to Caribbean. Find affordable one-way fares based on user searches. Data last updated May 11, 2026.
This Priceline deal was found by Cheapflights users on 5/10. Clicking the “Pick Dates” 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 7/218:43 am
MKE
- SJU
1 stop16h 28m
Frontier
Deal found 5/10![Frontier logo]()
$138
This American Airlines deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/157:24 am
MKE
- MBJ
1 stop5h 43m
American Airlines
Deal found 5/6![American Airlines logo]()
$152
This American Airlines deal was found by Cheapflights users on 5/11. 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 7/116:00 am
MKE
- SJU
1 stop15h 57m
American Airlines
Deal found 5/11![American Airlines logo]()
$163
This American Airlines deal was found by Cheapflights users on 5/9. Clicking the “Pick Dates” 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 7/110:00 am
MKE
- SJU
1 stop12h 59m
American Airlines
Deal found 5/9![American Airlines logo]()
$168
This CheapOair deal was found by Cheapflights users on 5/10. Clicking the “Pick Dates” 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 5/149:46 am
MKE
- SJU
1 stop15h 22m
Frontier
Deal found 5/10![Frontier logo]()
$178
This Frontier deal was found by Cheapflights users on 5/9. Clicking the “Pick Dates” 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 7/238:43 am
MKE
- SJU
1 stop13h 46m
Frontier
Deal found 5/9![Frontier logo]()
$183
This Southwest deal was found by Cheapflights users on 5/10. Clicking the “Pick Dates” 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 7/313:15 pm
MKE
- SJU
1 stop7h 20m
Southwest
Deal found 5/10![Southwest logo]()
$202
This American Airlines deal was found by Cheapflights users on 5/9. Clicking the “Pick Dates” 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 6/17:00 am
MKE
- SJU
1 stop14h 45m
American Airlines
Deal found 5/9![American Airlines logo]()
$203
This American Airlines deal was found by Cheapflights users on 5/7. Clicking the “Pick Dates” 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 6/26:01 am
MKE
- SJU
2 stops11h 24m
American Airlines
Deal found 5/7![American Airlines logo]()
$209
This Frontier deal was found by Cheapflights users on 5/9. Clicking the “Pick Dates” 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.
Sun 6/288:43 am
MKE
- SJU
1 stop13h 46m
Frontier
Deal found 5/9![Frontier logo]()
$223
This Southwest deal was found by Cheapflights users on 5/6. Clicking the “Pick Dates” 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 6/211:35 pm
MKE
- SJU
1 stop9h 50m
Southwest
Deal found 5/6![Southwest logo]()
$224
This American Airlines deal was found by Cheapflights users on 5/10. Clicking the “Pick Dates” 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 6/287:00 am
MKE
- SJU
1 stop14h 45m
American Airlines
Deal found 5/10![American Airlines logo]()
$228
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 May 11, 2026.
Round-trip from | $326 (Delta) |
|---|---|
One-way from | $138 (Priceline) |
Popular in | December |
Cheapest in | September |
Average price | $415 |
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 May 11, 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
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 7/29
6:50 am-3:34 pm
1 stop8h 44m
Montego Bay Sangster Intl
Wed 8/5
1:09 pm-11:53 pm
1 stop10h 44m
$362
MilwaukeeMontego Bay
MKE - MBJ
MKEMBJ
Milwaukee-Mitchell
Mon 6/29
6:20 am-3:10 pm
2 stops8h 50m
Montego Bay Sangster Intl
Sat 7/4
2:40 pm-7:00 am
2 stops16h 20m
$391
Quickest round-trip
MilwaukeeSan Juan
MKE - SJU
MKESJU
Milwaukee-Mitchell
Fri 7/31
3:15 pm-11:35 pm
1 stop7h 20m
San Juan Luis Munoz Marin Intl
Tue 8/4
10:30 am-4:20 pm
1 stop6h 50m
$404
MilwaukeeSan Juan
MKE - SJU
MKESJU
Milwaukee-Mitchell
Mon 6/15
1:30 pm-10:45 pm
1 stop8h 15m
San Juan Luis Munoz Marin Intl
Mon 6/22
7:00 am-11:59 pm
1 stop17h 59m
$406
MilwaukeeMontego Bay
MKE - MBJ
MKEMBJ
Milwaukee-Mitchell
Mon 6/1
6:17 pm-11:19 am
1 stop17h 02m
Montego Bay Sangster Intl
Fri 6/5
3:00 pm-11:47 pm
1 stop8h 47m
$434
MilwaukeeMontego Bay
MKE - MBJ
MKEMBJ
Milwaukee-Mitchell
Mon 6/1
6:17 pm-1:08 pm
2 stops18h 51m
Montego Bay Sangster Intl
Sat 6/6
3:00 pm-11:47 pm
1 stop8h 47m
$439
MilwaukeeMontego Bay
MKE - MBJ
MKEMBJ
Milwaukee-Mitchell
Wed 7/29
6:17 pm-1:09 pm
2 stops18h 52m
Montego Bay Sangster Intl
Wed 8/5
12:38 pm-11:50 pm
2 stops11h 12m
$444
MilwaukeeMontego Bay
MKE - MBJ
MKEMBJ
Milwaukee-Mitchell
Sat 6/27
7:49 pm-1:31 pm
1 stop17h 42m
Montego Bay Sangster Intl
Sat 7/4
3:02 pm-5:17 pm
1 stop26h 15m
$447
MilwaukeeSan Juan
MKE - SJU
MKESJU
Milwaukee-Mitchell
Sun 8/2
6:15 am-11:55 pm
2 stops16h 40m
San Juan Luis Munoz Marin Intl
Sun 8/16
9:25 pm-8:55 am
1 stop12h 30m
$448
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-SDQ
MKE-STI
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-SDQ
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 May 11, 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.
Entertainment
7.5
Crew
8.6
Comfort
8.0
Boarding
8.1
Overall
8.0
Food
7.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Entertainment
7.5
Crew
8.6
Comfort
8.0
Boarding
8.1
Overall
8.0
Food
7.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Entertainment
7.5
Crew
8.6
Comfort
8.0
Boarding
8.1
Overall
8.0
Food
7.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Entertainment
7.5
Crew
8.6
Comfort
8.0
Boarding
8.1
Overall
8.0
Food
7.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Entertainment
7.5
Crew
8.6
Comfort
8.0
Boarding
8.1
Overall
8.0
Food
7.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Entertainment
7.5
Crew
8.6
Comfort
8.0
Boarding
8.1
Overall
8.0
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.
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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 May 11, 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 May 11, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$112 | Average$562 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$156 | Average$360 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$202 | Average$560 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$219 | Average$367 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$256 | Average$664 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$315 | Average$714 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$547 | Average$841 | FlexibilityNo cancel fee | On-time83% |