$173+ 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 8/11. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — SJU
Aug 22 — Aug 291
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 July 23, 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 July 23, 2026.
This United Airlines deal was found by Cheapflights users on 7/21. Clicking the “Pick Dates” 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 9/55:00 am
MKE
- SJU
1 stop8h 44m
United Airlines
Sat 9/51:00 am
SJU
- MKE
1 stop10h 34m
United Airlines
Deal found 7/21![United Airlines logo]()
$341
This American Airlines deal was found by Cheapflights users on 7/19. 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.
Sat 8/222:42 pm
MKE
- SJU
1 stop7h 12m
American Airlines
Sat 8/2912:55 am
SJU
- MKE
1 stop7h 54m
American Airlines
Deal found 7/19![American Airlines logo]()
$346
This American Airlines deal was found by Cheapflights users on 7/22. Clicking the “Pick Dates” 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 12/26:50 pm
MKE
- SJU
2 stops13h 45m
American Airlines
Wed 12/94:41 pm
SJU
- MKE
1 stop9h 20m
American Airlines
Deal found 7/22![American Airlines logo]()
$351
This American Airlines deal was found by Cheapflights users on 7/19. 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 10/56:27 pm
MKE
- SJU
1 stop16h 42m
American Airlines
Fri 10/3012:13 pm
SJU
- MKE
1 stop12h 44m
American Airlines
Deal found 7/19![American Airlines logo]()
$353
This American Airlines deal was found by Cheapflights users on 7/20. 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 9/302:02 pm
MKE
- SJU
2 stops18h 22m
American Airlines
Sun 10/117:30 am
SJU
- MKE
1 stop16h 44m
American Airlines
Deal found 7/20![American Airlines logo]()
$358
This Southwest deal was found by Cheapflights users on 7/22. Clicking the “Pick Dates” 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 9/241:50 pm
MKE
- SJU
2 stops9h 00m
Southwest
Tue 9/295:15 am
SJU
- MKE
1 stop6h 40m
Southwest
Deal found 7/22![Southwest logo]()
$361
This American Airlines deal was found by Cheapflights users on 7/19. 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.
Sat 8/296:20 am
MKE
- SJU
2 stops11h 10m
American Airlines
Fri 9/41:38 pm
SJU
- MKE
2 stops10h 21m
American Airlines
Deal found 7/19![American Airlines logo]()
$371
This Southwest deal was found by Cheapflights users on 7/22. Clicking the “Pick Dates” 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 8/157:30 am
MKE
- SJU
1 stop13h 25m
Southwest
Wed 8/1911:50 am
SJU
- MKE
1 stop10h 15m
Southwest
Deal found 7/22![Southwest logo]()
$373
This Southwest deal was found by Cheapflights users on 7/20. 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 8/1910:50 am
MKE
- SJU
1 stop7h 10m
Southwest
Sat 8/226:25 am
SJU
- MKE
1 stop9h 45m
Southwest
Deal found 7/20![Southwest logo]()
$374
This United Airlines deal was found by Cheapflights users on 7/23. Clicking the “Pick Dates” 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 8/1511:18 am
MKE
- SJU
2 stops11h 32m
United Airlines
Wed 8/191:00 am
SJU
- MKE
2 stops12h 38m
United Airlines
Deal found 7/23![United Airlines logo]()
$375
This Southwest deal was found by Cheapflights users on 7/19. 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.
Thu 8/2712:30 pm
MKE
- SJU
2 stops9h 35m
Southwest
Mon 8/316:30 am
SJU
- MKE
2 stops9h 55m
Southwest
Deal found 7/19![Southwest logo]()
$376
This United Airlines deal was found by Cheapflights users on 7/22. Clicking the “Pick Dates” 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 10/306:30 am
MKE
- MBJ
1 stop6h 18m
United Airlines
Mon 11/23:20 pm
MBJ
- MKE
1 stop9h 07m
United Airlines
Deal found 7/22![United Airlines logo]()
$392
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 July 23, 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 July 23, 2026.
This Delta deal was found by Cheapflights users on 7/22. Clicking the “Pick Dates” 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 10/55:30 am
MKE
- SJU
1 stop7h 15m
Delta
Fri 10/305:43 pm
SJU
- MKE
1 stop7h 10m
Delta
Deal found 7/22![Delta logo]()
$346
This Southwest deal was found by Cheapflights users on 7/23. Clicking the “Pick Dates” 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 8/299:05 am
MKE
- SJU
1 stop6h 35m
Southwest
Fri 9/46:00 am
SJU
- MKE
1 stop11h 10m
Southwest
Deal found 7/23![Southwest logo]()
$346
This United Airlines deal was found by Cheapflights users on 7/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/238:30 am
MKE
- SJU
2 stops11h 08m
United Airlines
Fri 9/251:00 am
SJU
- MKE
2 stops13h 43m
United Airlines
Deal found 7/23![United Airlines logo]()
$346
This American Airlines deal was found by Cheapflights users on 7/22. Clicking the “Pick Dates” 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 1/96:40 am
MKE
- MBJ
1 stop7h 36m
American Airlines
Sat 1/164:27 pm
MBJ
- MKE
1 stop19h 50m
American Airlines
Deal found 7/22![American Airlines logo]()
$400
This Southwest deal was found by Cheapflights users on 7/19. 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.
Sun 8/167:00 pm
MKE
- SJU
1 stop13h 10m
Southwest
Sun 8/239:25 pm
SJU
- MKE
1 stop12h 30m
Southwest
Deal found 7/19![Southwest logo]()
$346
This United Airlines deal was found by Cheapflights users on 7/22. Clicking the “Pick Dates” 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 10/2910:37 am
MKE
- SJU
1 stop8h 23m
United Airlines
Thu 11/53:46 pm
SJU
- MKE
1 stop9h 04m
United Airlines
Deal found 7/22![United Airlines logo]()
$346
This Southwest deal was found by Cheapflights users on 7/18. 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.
Sat 8/157:30 am
MKE
- SJU
1 stop13h 25m
Southwest
Sat 8/2210:25 am
SJU
- MKE
1 stop7h 05m
Southwest
Deal found 7/18![Southwest logo]()
$346
This United Airlines deal was found by Cheapflights users on 7/23. Clicking the “Pick Dates” 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 8/296:15 am
MKE
- SJU
2 stops13h 23m
United Airlines
Fri 9/42:55 pm
SJU
- MKE
1 stop9h 42m
United Airlines
Deal found 7/23![United Airlines logo]()
$346
This Delta deal was found by Cheapflights users on 7/20. 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 8/247:03 am
MKE
- MBJ
1 stop8h 31m
Delta
Thu 8/274:59 pm
MBJ
- MKE
1 stop6h 54m
Delta
Deal found 7/20![Delta logo]()
$392
This Southwest deal was found by Cheapflights users on 7/20. 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.
Thu 9/247:00 pm
MKE
- SJU
1 stop13h 10m
Southwest
Fri 11/136:35 am
SJU
- MKE
1 stop12h 40m
Southwest
Deal found 7/20![Southwest logo]()
$346
This American Airlines deal was found by Cheapflights users on 7/21. Clicking the “Pick Dates” 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 1/126:13 am
MKE
- PLS
1 stop7h 19m
American Airlines
Sat 1/233:25 pm
PLS
- MKE
1 stop8h 17m
American Airlines
Deal found 7/21![American Airlines logo]()
$423
This Southwest deal was found by Cheapflights users on 7/21. Clicking the “Pick Dates” 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 8/232:10 pm
MKE
- SJU
1 stop8h 15m
Southwest
Thu 8/272:35 pm
SJU
- MKE
1 stop7h 10m
Southwest
Deal found 7/21![Southwest logo]()
$346
This American Airlines deal was found by Cheapflights users on 7/20. 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 8/182:49 pm
MKE
- GCM
2 stops20h 11m
American Airlines
Mon 8/2412:30 pm
GCM
- MKE
1 stop10h 29m
American Airlines
Deal found 7/20![American Airlines logo]()
$430
This United Airlines deal was found by Cheapflights users on 7/22. Clicking the “Pick Dates” 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 11/35:00 am
MKE
- MBJ
1 stop7h 48m
United Airlines
Tue 11/103:20 pm
MBJ
- MKE
2 stops18h 31m
United Airlines
Deal found 7/22![United Airlines logo]()
$392
This Delta deal was found by Cheapflights users on 7/19. 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.
Mon 1/186:40 pm
MKE
- PLS
2 stops16h 20m
Delta
Sat 1/233:50 pm
PLS
- MKE
1 stop8h 59m
Delta
Deal found 7/19![Delta logo]()
$438
This American Airlines deal was found by Cheapflights users on 7/19. 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.
Tue 12/16:31 pm
MKE
- STT
2 stops17h 21m
American Airlines
Tue 12/82:49 pm
STT
- MKE
2 stops10h 41m
American Airlines
Deal found 7/19![American Airlines logo]()
$450
This Delta deal was found by Cheapflights users on 7/20. 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.
Sun 10/45:30 am
MKE
- GCM
1 stop6h 10m
Delta
Sat 10/1012:55 pm
GCM
- MKE
1 stop8h 07m
Delta
Deal found 7/20![Delta logo]()
$451
This Southwest deal was found by Cheapflights users on 7/19. 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.
Fri 8/2812:30 pm
MKE
- SJU
2 stops9h 35m
Southwest
Mon 8/316:30 am
SJU
- MKE
2 stops9h 55m
Southwest
Deal found 7/19![Southwest logo]()
$376
This United Airlines deal was found by Cheapflights users on 7/20. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/146:30 am
MKE
- MBJ
2 stops8h 49m
United Airlines
Sat 11/216:00 pm
MBJ
- MKE
2 stops17h 01m
United Airlines
Deal found 7/20![United Airlines logo]()
$417
This American Airlines deal was found by Cheapflights users on 7/18. 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 1/137:19 pm
MKE
- STT
2 stops19h 46m
American Airlines
Fri 1/226:39 pm
STT
- MKE
2 stops18h 38m
American Airlines
Deal found 7/18![American Airlines logo]()
$455
This Delta deal was found by Cheapflights users on 7/21. Clicking the “Pick Dates” 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
- SXM
1 stop7h 23m
Delta
Wed 9/233:18 pm
SXM
- MKE
1 stop9h 30m
Delta
Deal found 7/21![Delta logo]()
$465
This Southwest deal was found by Cheapflights users on 7/20. 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.
Fri 12/47:20 pm
MKE
- SJU
1 stop12h 40m
Southwest
Sat 12/126:45 am
SJU
- MKE
1 stop7h 20m
Southwest
Deal found 7/20![Southwest logo]()
$389
This United Airlines deal was found by Cheapflights users on 7/22. Clicking the “Pick Dates” 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 10/246:38 pm
MKE
- GCM
1 stop17h 37m
United Airlines
Sat 10/311:25 pm
GCM
- MKE
1 stop10h 02m
United Airlines
Deal found 7/22![United Airlines logo]()
$431
This Delta deal was found by Cheapflights users on 7/20. 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.
Wed 10/75:40 am
MKE
- STT
1 stop6h 59m
Delta
Mon 10/122:49 pm
STT
- MKE
1 stop7h 13m
Delta
Deal found 7/20![Delta logo]()
$469
This American Airlines deal was found by Cheapflights users on 7/18. 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 1/153:49 pm
MKE
- PLS
2 stops17h 35m
American Airlines
Wed 1/201:18 pm
PLS
- MKE
2 stops10h 24m
American Airlines
Deal found 7/18![American Airlines logo]()
$478
This Southwest deal was found by Cheapflights users on 7/20. 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.
Sat 8/298:35 am
MKE
- SJU
2 stops8h 30m
Southwest
Mon 8/316:30 am
SJU
- MKE
2 stops9h 55m
Southwest
Deal found 7/20![Southwest logo]()
$401
This United Airlines deal was found by Cheapflights users on 7/19. 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 10/242:20 pm
MKE
- AUA
2 stops21h 20m
United Airlines
Sat 10/312:00 pm
AUA
- MKE
1 stop7h 55m
United Airlines
Deal found 7/19![United Airlines logo]()
$485
This American Airlines deal was found by Cheapflights users on 7/18. 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 1/136:13 am
MKE
- AUA
1 stop8h 46m
American Airlines
Fri 1/223:46 pm
AUA
- MKE
1 stop8h 56m
American Airlines
Deal found 7/18![American Airlines logo]()
$490
This Delta deal was found by Cheapflights users on 7/20. 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.
Sat 10/245:40 am
MKE
- SXM
1 stop7h 09m
Delta
Thu 10/293:14 pm
SXM
- MKE
1 stop9h 39m
Delta
Deal found 7/20![Delta logo]()
$505
This United Airlines deal was found by Cheapflights users on 7/22. Clicking the “Pick Dates” 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 11/86:30 am
MKE
- MBJ
1 stop6h 18m
United Airlines
Sat 11/143:45 pm
MBJ
- MKE
1 stop8h 05m
United Airlines
Deal found 7/22![United Airlines logo]()
$492
Last-minute flights from Milwaukee to CaribbeanDiscover last-minute flight deals from Milwaukee to Caribbean. Data last updated July 23, 2026 and is based on user searches.
Discover last-minute flight deals from Milwaukee to Caribbean. Data last updated July 23, 2026 and is based on user searches.
This American Airlines deal was found by Cheapflights users on 7/20. 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 8/106:20 am
MKE
- SJU
1 stop15h 04m
American Airlines
Mon 8/1012:55 am
SJU
- MKE
1 stop12h 52m
American Airlines
Deal found 7/20![American Airlines logo]()
$381
This Justfly.com deal was found by Cheapflights users on 7/19. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/118:43 am
MKE
- SJU
1 stop7h 48m
Frontier
Wed 8/198:57 pm
SJU
- MKE
1 stop15h 16m
Frontier
Deal found 7/19![Frontier logo]()
$383
This Southwest deal was found by Cheapflights users on 7/22. Clicking the “Pick Dates” 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 8/157:30 am
MKE
- SJU
1 stop13h 25m
Southwest
Wed 8/1911:50 am
SJU
- MKE
1 stop10h 15m
Southwest
Deal found 7/22![Southwest logo]()
$373
This United Airlines deal was found by Cheapflights users on 7/23. Clicking the “Pick Dates” 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 8/1511:18 am
MKE
- SJU
2 stops11h 32m
United Airlines
Wed 8/191:00 am
SJU
- MKE
2 stops12h 38m
United Airlines
Deal found 7/23![United Airlines logo]()
$375
This American Airlines deal was found by Cheapflights users on 7/19. 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 8/1710:21 am
MKE
- SJU
2 stops10h 34m
American Airlines
Fri 8/213:47 pm
SJU
- MKE
1 stop8h 12m
American Airlines
Deal found 7/19![American Airlines logo]()
$386
This American Airlines deal was found by Cheapflights users on 7/22. Clicking the “Pick Dates” 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 8/195:00 am
MKE
- SJU
2 stops8h 51m
American Airlines
Wed 8/263:47 pm
SJU
- MKE
2 stops9h 12m
American Airlines
Deal found 7/22![American Airlines logo]()
$351
This Southwest deal was found by Cheapflights users on 7/20. 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 8/1910:50 am
MKE
- SJU
1 stop7h 10m
Southwest
Sat 8/226:25 am
SJU
- MKE
1 stop9h 45m
Southwest
Deal found 7/20![Southwest logo]()
$374
This American Airlines deal was found by Cheapflights users on 7/19. 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.
Sat 8/222:42 pm
MKE
- SJU
1 stop7h 12m
American Airlines
Sat 8/2912:55 am
SJU
- MKE
1 stop7h 54m
American Airlines
Deal found 7/19![American Airlines logo]()
$346
This Southwest deal was found by Cheapflights users on 7/20. 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.
Mon 8/246:25 am
MKE
- SJU
2 stops9h 30m
Southwest
Thu 9/36:30 am
SJU
- MKE
2 stops9h 55m
Southwest
Deal found 7/20![Southwest logo]()
$361
This Delta deal was found by Cheapflights users on 7/20. 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 8/247:03 am
MKE
- MBJ
1 stop8h 31m
Delta
Thu 8/274:59 pm
MBJ
- MKE
1 stop6h 54m
Delta
Deal found 7/20![Delta logo]()
$392
This Southwest deal was found by Cheapflights users on 7/19. 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.
Thu 8/2712:30 pm
MKE
- SJU
2 stops9h 35m
Southwest
Mon 8/316:30 am
SJU
- MKE
2 stops9h 55m
Southwest
Deal found 7/19![Southwest logo]()
$376
This American Airlines deal was found by Cheapflights users on 7/19. 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.
Sat 8/296:20 am
MKE
- SJU
2 stops11h 10m
American Airlines
Fri 9/41:38 pm
SJU
- MKE
2 stops10h 21m
American Airlines
Deal found 7/19![American Airlines logo]()
$371
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 July 23, 2026.
Search for one-way flight options from Milwaukee to Caribbean. Find affordable one-way fares based on user searches. Data last updated July 23, 2026.
This Southwest deal was found by Cheapflights users on 7/20. 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.
Fri 8/1412:30 pm
MKE
- SJU
1 stop9h 20m
Southwest
Deal found 7/20![Southwest logo]()
$173
This United Airlines deal was found by Cheapflights users on 7/18. 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.
Sun 11/85:00 am
MKE
- PLS
2 stops10h 00m
United Airlines
Deal found 7/18![United Airlines logo]()
$177
This American Airlines deal was found by Cheapflights users on 7/19. 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.
Tue 8/256:20 am
MKE
- SJU
2 stops11h 13m
American Airlines
Deal found 7/19![American Airlines logo]()
$177
This American Airlines deal was found by Cheapflights users on 7/19. 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.
Wed 8/196:00 am
MKE
- SJU
1 stop16h 15m
American Airlines
Deal found 7/19![American Airlines logo]()
$178
This American Airlines deal was found by Cheapflights users on 7/20. 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.
Thu 8/65:50 pm
MKE
- MBJ
1 stop22h 18m
American Airlines
Deal found 7/20![American Airlines logo]()
$186
This American Airlines deal was found by Cheapflights users on 7/22. Clicking the “Pick Dates” 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 1/46:27 pm
MKE
- SXM
1 stop17h 32m
American Airlines
Deal found 7/22![American Airlines logo]()
$188
This deal was found by Cheapflights users on 7/20. 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/812:10 pm
MKE
- SJU
1 stop6h 42m
Frontier
Deal found 7/20![Frontier logo]()
$188
This American Airlines deal was found by Cheapflights users on 7/22. Clicking the “Pick Dates” 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 1/65:00 am
MKE
- SXM
2 stops9h 28m
American Airlines
Deal found 7/22![American Airlines logo]()
$193
This American Airlines deal was found by Cheapflights users on 7/20. 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 9/85:01 am
MKE
- SJU
2 stops12h 32m
American Airlines
Deal found 7/20![American Airlines logo]()
$198
This Kiwi.com deal was found by Cheapflights users on 7/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/312:10 pm
MKE
- SJU
1 stop13h 05m
Frontier
Deal found 7/22![Frontier logo]()
$200
This Kiwi.com deal was found by Cheapflights users on 7/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/98:43 am
MKE
- SJU
1 stop22h 14m
Frontier
Deal found 7/22![Frontier logo]()
$212
This Southwest deal was found by Cheapflights users on 7/21. Clicking the “Pick Dates” 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 9/137:20 pm
MKE
- STT
2 stops17h 30m
Southwest
Deal found 7/21![Southwest logo]()
$213
Find flight deals from Milwaukee to Caribbean
Keep the following information in mind while searching for Milwaukee to Caribbean flight deals. Data was last updated July 23, 2026.
Round-trip from | $341 (United Airlines) |
|---|---|
One-way from | $173 (American Airlines) |
Popular in | December |
Cheapest in | October |
Average price | $503 |
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 July 23, 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
Mon 10/5
5:30 am-1:45 pm
1 stop7h 15m
San Juan Luis Munoz Marin Intl
Fri 10/30
5:43 pm-11:53 pm
1 stop7h 10m
$346
MilwaukeeSan Juan
MKE - SJU
MKESJU
Milwaukee-Mitchell
Sat 8/29
9:05 am-4:40 pm
1 stop6h 35m
San Juan Luis Munoz Marin Intl
Fri 9/4
6:00 am-4:10 pm
1 stop11h 10m
$346
MilwaukeeSan Juan
MKE - SJU
MKESJU
Milwaukee-Mitchell
Wed 9/23
8:30 am-8:38 pm
2 stops11h 08m
San Juan Luis Munoz Marin Intl
Fri 9/25
1:00 am-1:43 pm
2 stops13h 43m
$346
MilwaukeeSan Juan
MKE - SJU
MKESJU
Milwaukee-Mitchell
Sun 8/16
7:00 pm-9:10 am
1 stop13h 10m
San Juan Luis Munoz Marin Intl
Sun 8/23
9:25 pm-8:55 am
1 stop12h 30m
$346
MilwaukeeSan Juan
MKE - SJU
MKESJU
Milwaukee-Mitchell
Thu 10/29
10:37 am-8:00 pm
1 stop8h 23m
San Juan Luis Munoz Marin Intl
Thu 11/5
3:46 pm-10:50 pm
1 stop9h 04m
$346
MilwaukeeSan Juan
MKE - SJU
MKESJU
Milwaukee-Mitchell
Sat 8/15
7:30 am-9:55 pm
1 stop13h 25m
San Juan Luis Munoz Marin Intl
Sat 8/22
10:25 am-4:30 pm
1 stop7h 05m
$346
MilwaukeeSan Juan
MKE - SJU
MKESJU
Milwaukee-Mitchell
Sat 8/29
6:15 am-8:38 pm
2 stops13h 23m
San Juan Luis Munoz Marin Intl
Fri 9/4
2:55 pm-11:37 pm
1 stop9h 42m
$346
MilwaukeeSan Juan
MKE - SJU
MKESJU
Milwaukee-Mitchell
Thu 9/24
7:00 pm-9:10 am
1 stop13h 10m
San Juan Luis Munoz Marin Intl
Fri 11/13
6:35 am-5:15 pm
1 stop12h 40m
$346
MilwaukeeSan Juan
MKE - SJU
MKESJU
Milwaukee-Mitchell
Sun 8/23
2:10 pm-11:25 pm
1 stop8h 15m
San Juan Luis Munoz Marin Intl
Thu 8/27
2:35 pm-8:45 pm
1 stop7h 10m
$346
MilwaukeeSan Juan
MKE - SJU
MKESJU
Milwaukee-Mitchell
Fri 8/28
12:30 pm-11:05 pm
2 stops9h 35m
San Juan Luis Munoz Marin Intl
Mon 8/31
6:30 am-3:25 pm
2 stops9h 55m
$376
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-PLS
MKE-SDQ
MKE-PUJ
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-PLS
MKE-SDQ
What is the cheapest month to book a flight from Milwaukee to Caribbean?
Currently, January is the cheapest month in which you can book a flight from Milwaukee to Caribbean (average of $510). Flying from Milwaukee to Caribbean in December is currently the most expensive (average of $706). 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 July 23, 2026.
Read through reviews of airlines operating flights from Milwaukee to Caribbean, such as Southwest,Delta, andUnited Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Overall
8.0
Boarding
8.1
Comfort
8.0
Entertainment
7.5
Crew
8.6
Food
7.0
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Overall
8.0
Boarding
8.1
Comfort
8.0
Entertainment
7.5
Crew
8.6
Food
7.0
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Overall
8.0
Boarding
8.1
Comfort
8.0
Entertainment
7.5
Crew
8.6
Food
7.0
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Overall
8.0
Boarding
8.1
Comfort
8.0
Entertainment
7.5
Crew
8.6
Food
7.0
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Overall
8.0
Boarding
8.1
Comfort
8.0
Entertainment
7.5
Crew
8.6
Food
7.0
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Overall
8.0
Boarding
8.1
Comfort
8.0
Entertainment
7.5
Crew
8.6
Food
7.0
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
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 July 23, 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 July 23, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$143 | Average$585 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$156 | Average$360 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$235 | Average$572 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$256 | Average$624 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$317 | Average$714 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$547 | Average$853 | FlexibilityNo cancel fee | On-time83% |