$163+ 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 6/30. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — SJU
Jun 19 — Jun 261
Round-trip
1 adult, Economy
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Find cheap flights from Milwaukee to Caribbean with Cheapflights
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Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
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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 20, 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 20, 2026.
This American Airlines deal was found by Cheapflights users on 5/20. Clicking the “Pick Dates” 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
1 stop7h 18m
American Airlines
Tue 8/181:38 pm
SJU
- MKE
2 stops10h 21m
American Airlines
Deal found 5/20![American Airlines logo]()
$331
This American Airlines deal was found by Cheapflights users on 5/20. Clicking the “Pick Dates” 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 5/20![American Airlines logo]()
$332
This American Airlines deal was found by Cheapflights users on 5/17. Clicking the “Pick Dates” 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 8/226:16 am
MKE
- SJU
2 stops11h 04m
American Airlines
Mon 8/316:51 am
SJU
- MKE
1 stop17h 32m
American Airlines
Deal found 5/17![American Airlines logo]()
$336
This United Airlines deal was found by Cheapflights users on 5/19. Clicking the “Pick Dates” 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 12/146:00 am
MKE
- MBJ
1 stop6h 46m
United Airlines
Fri 12/182:48 pm
MBJ
- MKE
1 stop10h 21m
United Airlines
Deal found 5/19![United Airlines logo]()
$352
This American Airlines deal was found by Cheapflights users on 5/18. Clicking the “Pick Dates” 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 6/55:17 pm
MBJ
- MKE
2 stops18h 47m
American Airlines
Deal found 5/18![American Airlines logo]()
$357
This American Airlines deal was found by Cheapflights users on 5/19. Clicking the “Pick Dates” 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 12/77:19 pm
MKE
- MBJ
1 stop17h 01m
American Airlines
Fri 12/112:30 pm
MBJ
- MKE
1 stop18h 50m
American Airlines
Deal found 5/19![American Airlines logo]()
$358
This United Airlines deal was found by Cheapflights users on 5/15. 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 9/1210:43 am
MKE
- SJU
1 stop8h 55m
United Airlines
Fri 9/181:00 am
SJU
- MKE
2 stops10h 00m
United Airlines
Deal found 5/15![United Airlines logo]()
$358
This American Airlines deal was found by Cheapflights users on 5/16. 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 6/86:17 pm
MKE
- MBJ
1 stop19h 14m
American Airlines
Wed 6/1712:31 pm
MBJ
- MKE
1 stop11h 28m
American Airlines
Deal found 5/16![American Airlines logo]()
$359
This Southwest deal was found by Cheapflights users on 5/15. 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.
Sat 9/261:15 pm
MKE
- SJU
1 stop6h 40m
Southwest
Sun 9/275:30 am
SJU
- MKE
1 stop10h 55m
Southwest
Deal found 5/15![Southwest logo]()
$360
This American Airlines deal was found by Cheapflights users on 5/18. Clicking the “Pick Dates” 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 8/196:01 pm
MKE
- MBJ
2 stops19h 33m
American Airlines
Mon 8/245:13 pm
MBJ
- MKE
2 stops18h 24m
American Airlines
Deal found 5/18![American Airlines logo]()
$362
This American Airlines deal was found by Cheapflights users on 5/18. Clicking the “Pick Dates” 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 6/296:17 pm
MKE
- MBJ
2 stops18h 51m
American Airlines
Sat 7/43:02 pm
MBJ
- MKE
1 stop26h 15m
American Airlines
Deal found 5/18![American Airlines logo]()
$364
This United Airlines deal was found by Cheapflights users on 5/19. Clicking the “Pick Dates” 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 6/295:56 pm
MKE
- MBJ
1 stop19h 34m
United Airlines
Sat 7/42:40 pm
MBJ
- MKE
1 stop8h 05m
United Airlines
Deal found 5/19![United Airlines logo]()
$365
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 20, 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 20, 2026.
This American Airlines deal was found by Cheapflights users on 5/18. Clicking the “Pick Dates” 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 5/18![American Airlines logo]()
$357
This Delta deal was found by Cheapflights users on 5/19. Clicking the “Pick Dates” 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 8/1812:51 pm
MKE
- SJU
1 stop8h 38m
Delta
Mon 8/242:59 pm
SJU
- MKE
1 stop6h 54m
Delta
Deal found 5/19![Delta logo]()
$401
This Southwest deal was found by Cheapflights users on 5/18. Clicking the “Pick Dates” 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 8/57:40 am
MKE
- SJU
2 stops10h 20m
Southwest
Sun 8/99:25 pm
SJU
- MKE
1 stop12h 30m
Southwest
Deal found 5/18![Southwest logo]()
$491
This United Airlines deal was found by Cheapflights users on 5/18. Clicking the “Pick Dates” 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 5/18![United Airlines logo]()
$493
This Justfly.com deal was found by Cheapflights users on 5/18. Clicking the “Pick Dates” 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 5/18![JetBlue logo]()
$625
This American Airlines deal was found by Cheapflights users on 5/16. 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 6/86:17 pm
MKE
- MBJ
2 stops17h 27m
American Airlines
Wed 6/1712:31 pm
MBJ
- MKE
2 stops19h 11m
American Airlines
Deal found 5/16![American Airlines logo]()
$357
This American Airlines deal was found by Cheapflights users on 5/18. Clicking the “Pick Dates” 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 8/196:01 pm
MKE
- MBJ
2 stops19h 33m
American Airlines
Mon 8/245:13 pm
MBJ
- MKE
2 stops18h 24m
American Airlines
Deal found 5/18![American Airlines logo]()
$362
This Delta deal was found by Cheapflights users on 5/19. Clicking the “Pick Dates” 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 7/2812:58 pm
MKE
- SJU
1 stop8h 32m
Delta
Mon 8/32:11 pm
SJU
- MKE
1 stop7h 07m
Delta
Deal found 5/19![Delta logo]()
$403
This Delta deal was found by Cheapflights users on 5/17. Clicking the “Pick Dates” 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 6/3012:56 pm
MKE
- SJU
1 stop8h 33m
Delta
Tue 7/75:56 pm
SJU
- MKE
1 stop7h 00m
Delta
Deal found 5/17![Delta logo]()
$403
This Delta deal was found by Cheapflights users on 5/17. Clicking the “Pick Dates” 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 8/47:03 am
MKE
- SJU
1 stop8h 34m
Delta
Tue 8/116:48 am
SJU
- MKE
1 stop8h 05m
Delta
Deal found 5/17![Delta logo]()
$403
This Southwest deal was found by Cheapflights users on 5/17. Clicking the “Pick Dates” 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 7/46:00 am
MKE
- SJU
2 stops10h 25m
Southwest
Sun 7/126:05 am
SJU
- MKE
1 stop12h 40m
Southwest
Deal found 5/17![Southwest logo]()
$527
This Delta deal was found by Cheapflights users on 5/17. Clicking the “Pick Dates” 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 8/310:22 am
MKE
- SJU
1 stop11h 07m
Delta
Tue 8/116:48 am
SJU
- MKE
1 stop8h 05m
Delta
Deal found 5/17![Delta logo]()
$403
This American Airlines deal was found by Cheapflights users on 5/16. 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.
Wed 9/164:33 pm
MKE
- MBJ
2 stops18h 17m
American Airlines
Sun 9/203:15 pm
MBJ
- MKE
2 stops20h 17m
American Airlines
Deal found 5/16![American Airlines logo]()
$449
This United Airlines deal was found by Cheapflights users on 5/15. 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.
Tue 10/277:00 am
MKE
- PUJ
2 stops8h 25m
United Airlines
Mon 11/22:55 pm
PUJ
- MKE
1 stop9h 44m
United Airlines
Deal found 5/15![United Airlines logo]()
$578
This Southwest deal was found by Cheapflights users on 5/19. Clicking the “Pick Dates” 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 6/83:15 pm
MKE
- SJU
1 stop7h 20m
Southwest
Sat 6/136:30 am
SJU
- MKE
1 stop10h 30m
Southwest
Deal found 5/19![Southwest logo]()
$527
This Delta deal was found by Cheapflights users on 5/16. 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.
Fri 8/146:45 am
MKE
- SJU
1 stop8h 48m
Delta
Sun 8/1612:56 pm
SJU
- MKE
1 stop8h 09m
Delta
Deal found 5/16![Delta logo]()
$403
This United Airlines deal was found by Cheapflights users on 5/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/175:17 pm
MKE
- PUJ
2 stops18h 23m
United Airlines
Sat 8/222:20 pm
PUJ
- MKE
1 stop9h 19m
United Airlines
Deal found 5/18![United Airlines logo]()
$578
This Justfly.com deal was found by Cheapflights users on 5/20. Clicking the “Pick Dates” 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 6/68:41 am
MKE
- AUA
1 stop30h 59m
JetBlue
Sat 6/1312:20 pm
AUA
- MKE
1 stop21h 26m
JetBlue
Deal found 5/20![JetBlue logo]()
$642
This American Airlines deal was found by Cheapflights users on 5/16. 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.
Thu 7/96:17 pm
MKE
- MBJ
1 stop19h 14m
American Airlines
Wed 7/152:36 pm
MBJ
- MKE
1 stop17h 26m
American Airlines
Deal found 5/16![American Airlines logo]()
$491
This Delta deal was found by Cheapflights users on 5/19. Clicking the “Pick Dates” 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 8/117:03 am
MKE
- MBJ
1 stop8h 31m
Delta
Sat 8/151:09 pm
MBJ
- MKE
1 stop6h 56m
Delta
Deal found 5/19![Delta logo]()
$422
This United Airlines deal was found by Cheapflights users on 5/15. 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 6/66:09 am
MKE
- PUJ
1 stop7h 39m
United Airlines
Tue 6/96:45 pm
PUJ
- MKE
2 stops19h 10m
United Airlines
Deal found 5/15![United Airlines logo]()
$583
This American Airlines deal was found by Cheapflights users on 5/20. Clicking the “Pick Dates” 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 8/166:46 pm
MKE
- GCM
2 stops18h 24m
American Airlines
Fri 8/2112:00 pm
GCM
- MKE
2 stops19h 49m
American Airlines
Deal found 5/20![American Airlines logo]()
$504
This United Airlines deal was found by Cheapflights users on 5/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/126:00 am
MKE
- PUJ
1 stop7h 27m
United Airlines
Fri 9/183:35 pm
PUJ
- MKE
2 stops19h 25m
United Airlines
Deal found 5/19![United Airlines logo]()
$583
This Delta deal was found by Cheapflights users on 5/15. 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 7/165:40 am
MKE
- SJU
1 stop6h 52m
Delta
Mon 7/202:21 pm
SJU
- MKE
1 stop6h 59m
Delta
Deal found 5/15![Delta logo]()
$480
This American Airlines deal was found by Cheapflights users on 5/19. Clicking the “Pick Dates” 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 8/72:46 pm
MKE
- GCM
1 stop24h 22m
American Airlines
Thu 8/1312:30 pm
GCM
- MKE
1 stop11h 27m
American Airlines
Deal found 5/19![American Airlines logo]()
$530
This United Airlines deal was found by Cheapflights users on 5/19. Clicking the “Pick Dates” 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 11/138:45 pm
MKE
- NAS
2 stops16h 03m
United Airlines
Tue 11/172:35 pm
NAS
- MKE
1 stop9h 11m
United Airlines
Deal found 5/19![United Airlines logo]()
$601
This Delta deal was found by Cheapflights users on 5/18. Clicking the “Pick Dates” 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 8/125:34 am
MKE
- SXM
1 stop7h 19m
Delta
Thu 8/203:18 pm
SXM
- MKE
1 stop9h 35m
Delta
Deal found 5/18![Delta logo]()
$483
This American Airlines deal was found by Cheapflights users on 5/16. 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.
Sat 9/55:50 pm
MKE
- GCM
2 stops17h 40m
American Airlines
Sat 9/121:20 pm
GCM
- MKE
2 stops22h 56m
American Airlines
Deal found 5/16![American Airlines logo]()
$545
This United Airlines deal was found by Cheapflights users on 5/16. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/67:33 am
MKE
- SXM
2 stops28h 00m
United Airlines
Fri 6/121:35 pm
SXM
- MKE
1 stop10h 59m
United Airlines
Deal found 5/16![United Airlines logo]()
$608
This Delta deal was found by Cheapflights users on 5/18. Clicking the “Pick Dates” 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 8/135:34 am
MKE
- SXM
1 stop7h 19m
Delta
Thu 8/203:18 pm
SXM
- MKE
1 stop9h 35m
Delta
Deal found 5/18![Delta logo]()
$483
Last-minute flights from Milwaukee to CaribbeanDiscover last-minute flight deals from Milwaukee to Caribbean. Data last updated May 20, 2026 and is based on user searches.
Discover last-minute flight deals from Milwaukee to Caribbean. Data last updated May 20, 2026 and is based on user searches.
This Priceline deal was found by Cheapflights users on 5/18. Clicking the “Pick Dates” 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 5/288:46 am
MKE
- SJU
1 stop13h 36m
Frontier
Mon 6/16:00 am
SJU
- MKE
1 stop27h 01m
Frontier
Deal found 5/18![Frontier logo]()
$446
This CheapOair deal was found by Cheapflights users on 5/16. 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 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 6/66:00 am
SJU
- MKE
1 stop27h 01m
Frontier
Deal found 5/16![Frontier logo]()
$447
This American Airlines deal was found by Cheapflights users on 5/18. Clicking the “Pick Dates” 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 6/55:17 pm
MBJ
- MKE
2 stops18h 47m
American Airlines
Deal found 5/18![American Airlines logo]()
$357
This American Airlines deal was found by Cheapflights users on 5/18. Clicking the “Pick Dates” 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 6/67:00 am
MKE
- SJU
1 stop14h 45m
American Airlines
Wed 6/101:47 pm
SJU
- MKE
1 stop11h 00m
American Airlines
Deal found 5/18![American Airlines logo]()
$418
This American Airlines deal was found by Cheapflights users on 5/16. 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 6/86:17 pm
MKE
- MBJ
1 stop19h 14m
American Airlines
Wed 6/1712:31 pm
MBJ
- MKE
1 stop11h 28m
American Airlines
Deal found 5/16![American Airlines logo]()
$359
This American Airlines deal was found by Cheapflights users on 5/18. Clicking the “Pick Dates” 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 6/147:00 am
MKE
- SJU
1 stop14h 45m
American Airlines
Thu 6/186:21 am
SJU
- MKE
1 stop18h 26m
American Airlines
Deal found 5/18![American Airlines logo]()
$409
This American Airlines deal was found by Cheapflights users on 5/17. Clicking the “Pick Dates” 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 6/157:00 am
MKE
- SJU
1 stop14h 45m
American Airlines
Thu 6/186:21 am
SJU
- MKE
1 stop18h 26m
American Airlines
Deal found 5/17![American Airlines logo]()
$419
This American Airlines deal was found by Cheapflights users on 5/15. 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 6/166:00 am
MKE
- SJU
2 stops11h 25m
American Airlines
Thu 6/256:21 am
SJU
- MKE
1 stop18h 26m
American Airlines
Deal found 5/15![American Airlines logo]()
$376
This American Airlines deal was found by Cheapflights users on 5/18. Clicking the “Pick Dates” 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 6/296:17 pm
MKE
- MBJ
2 stops18h 51m
American Airlines
Sat 7/43:02 pm
MBJ
- MKE
1 stop26h 15m
American Airlines
Deal found 5/18![American Airlines logo]()
$364
This United Airlines deal was found by Cheapflights users on 5/19. Clicking the “Pick Dates” 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 6/295:56 pm
MKE
- MBJ
1 stop19h 34m
United Airlines
Sat 7/42:40 pm
MBJ
- MKE
1 stop8h 05m
United Airlines
Deal found 5/19![United Airlines logo]()
$365
This Delta deal was found by Cheapflights users on 5/17. Clicking the “Pick Dates” 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 6/3012:56 pm
MKE
- SJU
1 stop8h 33m
Delta
Tue 7/75:56 pm
SJU
- MKE
1 stop7h 00m
Delta
Deal found 5/17![Delta logo]()
$403
This American Airlines deal was found by Cheapflights users on 5/20. Clicking the “Pick Dates” 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 6/301:30 pm
MKE
- SJU
1 stop8h 15m
American Airlines
Fri 7/107:25 am
SJU
- MKE
1 stop11h 06m
American Airlines
Deal found 5/20![American Airlines logo]()
$449
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 20, 2026.
Search for one-way flight options from Milwaukee to Caribbean. Find affordable one-way fares based on user searches. Data last updated May 20, 2026.
This American Airlines deal was found by Cheapflights users on 5/20. Clicking the “Pick Dates” 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 7/117:00 am
MKE
- SJU
1 stop14h 33m
American Airlines
Deal found 5/20![American Airlines logo]()
$163
This Frontier deal was found by Cheapflights users on 5/17. Clicking the “Pick Dates” 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.
Sat 6/2012:08 pm
MKE
- SJU
1 stop7h 24m
Frontier
Deal found 5/17![Frontier logo]()
$188
This CheapOair deal was found by Cheapflights users on 5/16. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/238:43 am
MKE
- SJU
1 stop16h 28m
Frontier
Deal found 5/16![Frontier logo]()
$193
This Delta deal was found by Cheapflights users on 5/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/105:34 am
MKE
- SXM
1 stop7h 19m
Delta
Deal found 5/20![Delta logo]()
$197
This Trip.com deal was found by Cheapflights users on 5/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 7/58:43 am
MKE
- SJU
1 stop16h 28m
Frontier
Deal found 5/18![Frontier logo]()
$197
This Southwest deal was found by Cheapflights users on 5/20. Clicking the “Pick Dates” 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
Deal found 5/20![Southwest logo]()
$202
This American Airlines deal was found by Cheapflights users on 5/18. Clicking the “Pick Dates” 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 6/166:00 am
MKE
- SJU
2 stops11h 25m
American Airlines
Deal found 5/18![American Airlines logo]()
$203
This Priceline deal was found by Cheapflights users on 5/18. Clicking the “Pick Dates” 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 6/168:43 am
MKE
- SJU
1 stop16h 26m
Frontier
Deal found 5/18![Frontier logo]()
$208
This American Airlines deal was found by Cheapflights users on 5/18. Clicking the “Pick Dates” 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 7/35:02 am
MKE
- SJU
1 stop17h 46m
American Airlines
Deal found 5/18![American Airlines logo]()
$211
This Delta deal was found by Cheapflights users on 5/19. Clicking the “Pick Dates” 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 5/305:23 am
MKE
- GCM
1 stop6h 31m
Delta
Deal found 5/19![Delta logo]()
$218
This American Airlines deal was found by Cheapflights users on 5/19. Clicking the “Pick Dates” 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 7/96:03 pm
MKE
- PLS
2 stops17h 07m
American Airlines
Deal found 5/19![American Airlines logo]()
$252
This American Airlines deal was found by Cheapflights users on 5/20. Clicking the “Pick Dates” 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 8/106:01 pm
MKE
- SXM
2 stops18h 21m
American Airlines
Deal found 5/20![American Airlines logo]()
$268
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 20, 2026.
Round-trip from | $331 (American Airlines) |
|---|---|
One-way from | $163 (American Airlines) |
Popular in | December |
Cheapest in | September |
Average price | $416 |
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 20, 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
Mon 6/1
6:17 pm-1:08 pm
2 stops18h 51m
Montego Bay Sangster Intl
Fri 6/5
3:00 pm-11:47 pm
1 stop8h 47m
$357
MilwaukeeMontego Bay
MKE - MBJ
MKEMBJ
Milwaukee-Mitchell
Mon 6/8
6:17 pm-11:44 am
2 stops17h 27m
Montego Bay Sangster Intl
Wed 6/17
12:31 pm-7:42 am
2 stops19h 11m
$357
MilwaukeeMontego Bay
MKE - MBJ
MKEMBJ
Milwaukee-Mitchell
Wed 8/19
6:01 pm-1:34 pm
2 stops19h 33m
Montego Bay Sangster Intl
Mon 8/24
5:13 pm-11:37 am
2 stops18h 24m
$362
MilwaukeeSan Juan
MKE - SJU
MKESJU
Milwaukee-Mitchell
Tue 8/18
12:51 pm-10:29 pm
1 stop8h 38m
San Juan Luis Munoz Marin Intl
Mon 8/24
2:59 pm-8:53 pm
1 stop6h 54m
$401
MilwaukeeSan Juan
MKE - SJU
MKESJU
Milwaukee-Mitchell
Tue 7/28
12:58 pm-10:30 pm
1 stop8h 32m
San Juan Luis Munoz Marin Intl
Mon 8/3
2:11 pm-8:18 pm
1 stop7h 07m
$403
MilwaukeeSan Juan
MKE - SJU
MKESJU
Milwaukee-Mitchell
Tue 6/30
12:56 pm-10:29 pm
1 stop8h 33m
San Juan Luis Munoz Marin Intl
Tue 7/7
5:56 pm-11:56 pm
1 stop7h 00m
$403
MilwaukeeSan Juan
MKE - SJU
MKESJU
Milwaukee-Mitchell
Tue 8/4
7:03 am-4:37 pm
1 stop8h 34m
San Juan Luis Munoz Marin Intl
Tue 8/11
6:48 am-1:53 pm
1 stop8h 05m
$403
MilwaukeeSan Juan
MKE - SJU
MKESJU
Milwaukee-Mitchell
Mon 8/3
10:22 am-10:29 pm
1 stop11h 07m
San Juan Luis Munoz Marin Intl
Tue 8/11
6:48 am-1:53 pm
1 stop8h 05m
$403
MilwaukeeSan Juan
MKE - SJU
MKESJU
Milwaukee-Mitchell
Fri 8/14
6:45 am-4:33 pm
1 stop8h 48m
San Juan Luis Munoz Marin Intl
Sun 8/16
12:56 pm-8:05 pm
1 stop8h 09m
$403
MilwaukeeMontego Bay
MKE - MBJ
MKEMBJ
Milwaukee-Mitchell
Tue 8/11
7:03 am-3:34 pm
1 stop8h 31m
Montego Bay Sangster Intl
Sat 8/15
1:09 pm-8:05 pm
1 stop6h 56m
$422
Showing 1-10 of 60 resultsSorted by cheapest first
Best time to book a flight from Milwaukee to Caribbean
Have a flexible travel schedule? Discover the best time to fly to Caribbean from Milwaukee with our price prediction graph.
MKE-SJU
MKE-GCM
MKE-SDQ
MKE-SXM
MKE-PLS
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Milwaukee to Caribbean
MKE-0CB
MKE-SJU
MKE-GCM
MKE-SDQ
MKE-SXM
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 $990). 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 May 20, 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.
Food
7.0
Comfort
8.0
Overall
7.9
Entertainment
7.5
Boarding
8.1
Crew
8.6
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Food
7.0
Comfort
8.0
Overall
7.9
Entertainment
7.5
Boarding
8.1
Crew
8.6
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Food
7.0
Comfort
8.0
Overall
7.9
Entertainment
7.5
Boarding
8.1
Crew
8.6
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Food
7.0
Comfort
8.0
Overall
7.9
Entertainment
7.5
Boarding
8.1
Crew
8.6
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Food
7.0
Comfort
8.0
Overall
7.9
Entertainment
7.5
Boarding
8.1
Crew
8.6
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Food
7.0
Comfort
8.0
Overall
7.9
Entertainment
7.5
Boarding
8.1
Crew
8.6
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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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 20, 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 20, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$112 | Average$565 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$156 | Average$360 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$202 | Average$571 | 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$734 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$547 | Average$841 | FlexibilityNo cancel fee | On-time83% |