$167+ 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 8/24. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — SJU
Aug 27 — Sep 31
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 28, 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 28, 2026.
This American Airlines deal was found by Cheapflights users on 7/24. Clicking the “Pick Dates” 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
Sat 8/2912:55 am
SJU
- MKE
1 stop7h 54m
American Airlines
Deal found 7/24![American Airlines logo]()
$341
This American Airlines deal was found by Cheapflights users on 7/26. Clicking the “Pick Dates” 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 10/156:27 pm
MKE
- SJU
2 stops16h 04m
American Airlines
Tue 10/206:20 am
SJU
- MKE
2 stops11h 37m
American Airlines
Deal found 7/26![American Airlines logo]()
$346
This American Airlines deal was found by Cheapflights users on 7/28. Clicking the “Pick Dates” 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 10/73:09 pm
MKE
- SJU
2 stops17h 37m
American Airlines
Tue 10/206:20 am
SJU
- MKE
2 stops11h 37m
American Airlines
Deal found 7/28![American Airlines logo]()
$351
This American Airlines deal was found by Cheapflights users on 7/26. Clicking the “Pick Dates” 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
2 stops14h 19m
American Airlines
Fri 10/3012:13 pm
SJU
- MKE
2 stops12h 05m
American Airlines
Deal found 7/26![American Airlines logo]()
$353
This United Airlines deal was found by Cheapflights users on 7/27. Clicking the “Pick Dates” 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 11/712:03 pm
MKE
- SJU
1 stop6h 57m
United Airlines
Fri 11/132:05 am
SJU
- MKE
2 stops13h 43m
United Airlines
Deal found 7/27![United Airlines logo]()
$356
This American Airlines deal was found by Cheapflights users on 7/24. Clicking the “Pick Dates” 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 9/162:02 pm
MKE
- SJU
2 stops18h 22m
American Airlines
Sun 9/2011:51 am
SJU
- MKE
2 stops11h 03m
American Airlines
Deal found 7/24![American Airlines logo]()
$359
This American 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/96:50 pm
MKE
- SJU
2 stops13h 45m
American Airlines
Wed 12/163:47 pm
SJU
- MKE
1 stop8h 55m
American Airlines
Deal found 7/23![American Airlines logo]()
$360
This Southwest deal was found by Cheapflights users on 7/24. Clicking the “Pick Dates” 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 9/241:55 pm
MKE
- SJU
1 stop7h 20m
Southwest
Mon 9/286:30 am
SJU
- MKE
2 stops9h 55m
Southwest
Deal found 7/24![Southwest logo]()
$361
This Southwest deal was found by Cheapflights users on 7/27. Clicking the “Pick Dates” 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 11/67:55 pm
MKE
- SJU
1 stop13h 25m
Southwest
Fri 11/134:00 pm
SJU
- MKE
2 stops9h 55m
Southwest
Deal found 7/27![Southwest logo]()
$366
This Kiwi.com deal was found by Cheapflights users on 7/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/1812:10 pm
MKE
- SJU
1 stop13h 05m
Frontier
Mon 8/248:57 pm
SJU
- MKE
1 stop15h 16m
Frontier
Deal found 7/26![Frontier logo]()
$369
This American Airlines deal was found by Cheapflights users on 7/26. Clicking the “Pick Dates” 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 8/2911:32 am
MKE
- SJU
1 stop10h 22m
American Airlines
Thu 9/312:55 am
SJU
- MKE
1 stop12h 52m
American Airlines
Deal found 7/26![American Airlines logo]()
$371
This Delta deal was found by Cheapflights users on 7/25. Clicking the “Pick Dates” 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 11/105:30 am
MKE
- MBJ
1 stop10h 05m
Delta
Wed 11/183:40 pm
MBJ
- MKE
1 stop9h 14m
Delta
Deal found 7/25![Delta 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 28, 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 28, 2026.
This Southwest deal was found by Cheapflights users on 7/24. Clicking the “Pick Dates” 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 11/95:10 am
MKE
- SJU
1 stop10h 40m
Southwest
Fri 11/1312:40 pm
SJU
- MKE
1 stop8h 35m
Southwest
Deal found 7/24![Southwest logo]()
$346
This United Airlines deal was found by Cheapflights users on 7/27. Clicking the “Pick Dates” 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 7/27![United Airlines logo]()
$356
This Delta deal was found by Cheapflights users on 7/24. Clicking the “Pick Dates” 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
- MBJ
1 stop7h 40m
Delta
Wed 10/282:45 pm
MBJ
- MKE
1 stop9h 08m
Delta
Deal found 7/24![Delta logo]()
$392
This American Airlines deal was found by Cheapflights users on 7/28. Clicking the “Pick Dates” 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 8/226:35 am
MKE
- PLS
1 stop6h 43m
American Airlines
Tue 8/251:27 pm
PLS
- MKE
1 stop10h 32m
American Airlines
Deal found 7/28![American Airlines logo]()
$423
This Southwest deal was found by Cheapflights users on 7/28. Clicking the “Pick Dates” 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 10/232:25 pm
MKE
- SJU
1 stop8h 55m
Southwest
Wed 11/47:40 am
SJU
- MKE
2 stops10h 15m
Southwest
Deal found 7/28![Southwest logo]()
$346
This United Airlines deal was found by Cheapflights users on 7/27. Clicking the “Pick Dates” 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 11/77:03 pm
MKE
- MBJ
1 stop16h 10m
United Airlines
Sat 11/143:20 pm
MBJ
- MKE
1 stop8h 27m
United Airlines
Deal found 7/27![United Airlines logo]()
$402
This Southwest deal was found by Cheapflights users on 7/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/1810:00 am
MKE
- SJU
2 stops11h 00m
Southwest
Sun 8/239:25 pm
SJU
- MKE
1 stop12h 30m
Southwest
Deal found 7/26![Southwest logo]()
$380
This Delta deal was found by Cheapflights users on 7/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/155:30 am
MKE
- PLS
1 stop6h 10m
Delta
Sun 9/202:05 pm
PLS
- MKE
1 stop8h 25m
Delta
Deal found 7/26![Delta logo]()
$423
This United Airlines deal was found by Cheapflights users on 7/24. Clicking the “Pick Dates” 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 8/297:18 am
MKE
- SJU
2 stops12h 20m
United Airlines
Sat 8/291:00 am
SJU
- MKE
2 stops10h 00m
United Airlines
Deal found 7/24![United Airlines logo]()
$402
This Delta deal was found by Cheapflights users on 7/26. Clicking the “Pick Dates” 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 8/255:34 am
MKE
- PLS
1 stop6h 06m
Delta
Tue 9/12:05 pm
PLS
- MKE
1 stop7h 22m
Delta
Deal found 7/26![Delta logo]()
$423
This American Airlines deal was found by Cheapflights users on 7/27. Clicking the “Pick Dates” 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 12/86:17 pm
STT
- MKE
2 stops18h 50m
American Airlines
Deal found 7/27![American Airlines logo]()
$489
This Southwest deal was found by Cheapflights users on 7/28. Clicking the “Pick Dates” 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 11/207:55 pm
MKE
- SJU
1 stop12h 15m
Southwest
Fri 12/46:45 am
SJU
- MKE
1 stop7h 15m
Southwest
Deal found 7/28![Southwest logo]()
$406
This United Airlines deal was found by Cheapflights users on 7/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/57:00 am
MKE
- MBJ
2 stops8h 24m
United Airlines
Sat 12/125:26 pm
MBJ
- MKE
2 stops17h 23m
United Airlines
Deal found 7/27![United Airlines logo]()
$407
This American Airlines deal was found by Cheapflights users on 7/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/77:24 pm
MKE
- AUA
2 stops19h 23m
American Airlines
Thu 11/123:33 pm
AUA
- MKE
1 stop10h 23m
American Airlines
Deal found 7/26![American Airlines logo]()
$490
This Southwest deal was found by Cheapflights users on 7/28. Clicking the “Pick Dates” 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 7/28![Southwest logo]()
$406
This United Airlines deal was found by Cheapflights users on 7/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/66:00 am
MKE
- MBJ
1 stop29h 43m
United Airlines
Sat 9/122:40 pm
MBJ
- MKE
1 stop7h 59m
United Airlines
Deal found 7/27![United Airlines logo]()
$410
This Air Canada deal was found by Cheapflights users on 7/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/212:23 pm
MKE
- CUR
2 stops23h 22m
Air Canada
Sat 11/284:20 pm
CUR
- MKE
2 stops31h 55m
Air Canada
Deal found 7/26![Air Canada logo]()
$1,092
This Delta deal was found by Cheapflights users on 7/28. Clicking the “Pick Dates” 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 1/35:45 am
MKE
- STT
1 stop7h 20m
Delta
Fri 1/151:50 pm
STT
- MKE
1 stop9h 18m
Delta
Deal found 7/28![Delta logo]()
$469
This American Airlines deal was found by Cheapflights users on 7/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/1710:54 am
MKE
- AUA
1 stop27h 22m
American Airlines
Sat 10/244:55 pm
AUA
- MKE
2 stops19h 17m
American Airlines
Deal found 7/26![American Airlines logo]()
$498
This Southwest deal was found by Cheapflights users on 7/24. Clicking the “Pick Dates” 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 8/2112:30 pm
MKE
- SJU
2 stops9h 35m
Southwest
Sun 8/239:25 pm
SJU
- MKE
1 stop12h 30m
Southwest
Deal found 7/24![Southwest logo]()
$412
This United Airlines deal was found by Cheapflights users on 7/27. Clicking the “Pick Dates” 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 8/286:15 am
MKE
- SJU
2 stops13h 23m
United Airlines
Sat 8/291:00 am
SJU
- MKE
2 stops10h 00m
United Airlines
Deal found 7/27![United Airlines logo]()
$417
This Delta deal was found by Cheapflights users on 7/28. Clicking the “Pick Dates” 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 12/55:30 am
MKE
- NAS
1 stop9h 00m
Delta
Fri 12/111:00 pm
NAS
- MKE
1 stop8h 40m
Delta
Deal found 7/28![Delta logo]()
$470
This United Airlines deal was found by Cheapflights users on 7/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/57:00 am
MKE
- PLS
2 stops8h 00m
United Airlines
Sat 12/122:23 pm
PLS
- MKE
1 stop9h 16m
United Airlines
Deal found 7/27![United Airlines logo]()
$423
This Delta deal was found by Cheapflights users on 7/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/102:55 pm
MKE
- NAS
2 stops19h 46m
Delta
Mon 9/143:18 pm
NAS
- MKE
1 stop7h 12m
Delta
Deal found 7/27![Delta logo]()
$474
This American Airlines deal was found by Cheapflights users on 7/27. Clicking the “Pick Dates” 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 9/57:45 am
MKE
- NAS
2 stops10h 26m
American Airlines
Thu 9/1012:34 pm
NAS
- MKE
2 stops10h 20m
American Airlines
Deal found 7/27![American Airlines logo]()
$532
This United Airlines deal was found by Cheapflights users on 7/26. Clicking the “Pick Dates” 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 12/47:00 am
MKE
- PLS
2 stops8h 00m
United Airlines
Sat 12/122:23 pm
PLS
- MKE
1 stop7h 31m
United Airlines
Deal found 7/26![United Airlines logo]()
$423
This Delta deal was found by Cheapflights users on 7/27. Clicking the “Pick Dates” 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 9/97:05 am
MKE
- NAS
1 stop5h 48m
Delta
Tue 9/151:06 pm
NAS
- MKE
2 stops20h 42m
Delta
Deal found 7/27![Delta logo]()
$474
This American Airlines deal was found by Cheapflights users on 7/27. Clicking the “Pick Dates” 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 11/17:00 am
MKE
- PUJ
1 stop6h 57m
American Airlines
Fri 11/612:37 pm
PUJ
- MKE
2 stops12h 58m
American Airlines
Deal found 7/27![American Airlines logo]()
$541
This Delta deal was found by Cheapflights users on 7/27. Clicking the “Pick Dates” 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 9/96:37 pm
MKE
- NAS
2 stops16h 04m
Delta
Mon 9/143:18 pm
NAS
- MKE
1 stop7h 12m
Delta
Deal found 7/27![Delta logo]()
$474
This United Airlines deal was found by Cheapflights users on 7/28. Clicking the “Pick Dates” 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 9/165:00 am
MKE
- SJU
1 stop8h 44m
United Airlines
Sat 9/191:00 am
SJU
- MKE
2 stops11h 30m
United Airlines
Deal found 7/28![United Airlines logo]()
$436
Last-minute flights from Milwaukee to CaribbeanDiscover last-minute flight deals from Milwaukee to Caribbean. Data last updated July 28, 2026 and is based on user searches.
Discover last-minute flight deals from Milwaukee to Caribbean. Data last updated July 28, 2026 and is based on user searches.
This American Airlines deal was found by Cheapflights users on 7/26. Clicking the “Pick Dates” 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 8/172:49 pm
MKE
- SJU
1 stop8h 10m
American Airlines
Thu 8/2012:55 am
SJU
- MKE
1 stop7h 54m
American Airlines
Deal found 7/26![American Airlines logo]()
$373
This Kiwi.com deal was found by Cheapflights users on 7/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/1812:10 pm
MKE
- SJU
1 stop13h 05m
Frontier
Mon 8/248:57 pm
SJU
- MKE
1 stop15h 16m
Frontier
Deal found 7/26![Frontier logo]()
$369
This Southwest deal was found by Cheapflights users on 7/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/1810:00 am
MKE
- SJU
2 stops11h 00m
Southwest
Sun 8/239:25 pm
SJU
- MKE
1 stop12h 30m
Southwest
Deal found 7/26![Southwest logo]()
$380
This FlightHub deal was found by Cheapflights users on 7/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/1812:10 pm
MKE
- SJU
1 stop6h 42m
Frontier
Sat 8/228:57 pm
SJU
- MKE
1 stop15h 16m
Frontier
Deal found 7/26![Frontier logo]()
$389
This Southwest deal was found by Cheapflights users on 7/28. Clicking the “Pick Dates” 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 8/196:40 am
MKE
- SJU
2 stops10h 30m
Southwest
Sun 8/239:25 pm
SJU
- MKE
1 stop12h 30m
Southwest
Deal found 7/28![Southwest logo]()
$388
This Southwest deal was found by Cheapflights users on 7/24. Clicking the “Pick Dates” 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 8/217:00 pm
MKE
- SJU
1 stop13h 25m
Southwest
Sun 8/239:25 pm
SJU
- MKE
1 stop12h 30m
Southwest
Deal found 7/24![Southwest logo]()
$384
This American Airlines deal was found by Cheapflights users on 7/26. Clicking the “Pick Dates” 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 8/225:00 am
MKE
- SJU
2 stops8h 51m
American Airlines
Sun 8/3012:55 am
SJU
- MKE
1 stop7h 54m
American Airlines
Deal found 7/26![American Airlines logo]()
$386
This American Airlines deal was found by Cheapflights users on 7/26. Clicking the “Pick Dates” 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 8/276:20 am
MKE
- SJU
1 stop15h 04m
American Airlines
Mon 8/312:33 pm
SJU
- MKE
1 stop9h 41m
American Airlines
Deal found 7/26![American Airlines logo]()
$346
This American Airlines deal was found by Cheapflights users on 7/25. Clicking the “Pick Dates” 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 8/276:20 am
MKE
- SJU
1 stop15h 04m
American Airlines
Tue 9/87:03 am
SJU
- MKE
1 stop15h 03m
American Airlines
Deal found 7/25![American Airlines logo]()
$353
This American Airlines deal was found by Cheapflights users on 7/24. Clicking the “Pick Dates” 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
Sat 8/2912:55 am
SJU
- MKE
1 stop7h 54m
American Airlines
Deal found 7/24![American Airlines logo]()
$341
This United Airlines deal was found by Cheapflights users on 7/27. Clicking the “Pick Dates” 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 7/27![United Airlines logo]()
$356
This American Airlines deal was found by Cheapflights users on 7/26. Clicking the “Pick Dates” 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 8/2911:32 am
MKE
- SJU
1 stop10h 22m
American Airlines
Thu 9/312:55 am
SJU
- MKE
1 stop12h 52m
American Airlines
Deal found 7/26![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 28, 2026.
Search for one-way flight options from Milwaukee to Caribbean. Find affordable one-way fares based on user searches. Data last updated July 28, 2026.
This Delta deal was found by Cheapflights users on 7/27. Clicking the “Pick Dates” 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 8/245:34 am
MKE
- PLS
1 stop6h 06m
Delta
Deal found 7/27![Delta logo]()
$167
This Delta deal was found by Cheapflights users on 7/26. Clicking the “Pick Dates” 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 9/137:05 am
MKE
- MBJ
1 stop8h 30m
Delta
Deal found 7/26![Delta logo]()
$172
This Delta deal was found by Cheapflights users on 7/28. Clicking the “Pick Dates” 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 9/212:55 pm
MKE
- SJU
1 stop6h 24m
Delta
Deal found 7/28![Delta logo]()
$173
This American Airlines deal was found by Cheapflights users on 7/25. Clicking the “Pick Dates” 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 8/216:00 pm
MKE
- PLS
2 stops15h 32m
American Airlines
Deal found 7/25![American Airlines logo]()
$177
This United Airlines deal was found by Cheapflights users on 7/25. Clicking the “Pick Dates” 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 9/146:47 pm
MKE
- MBJ
2 stops16h 56m
United Airlines
Deal found 7/25![United Airlines logo]()
$177
This American Airlines deal was found by Cheapflights users on 7/26. Clicking the “Pick Dates” 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 7/26![American Airlines logo]()
$177
This American Airlines deal was found by Cheapflights users on 7/26. Clicking the “Pick Dates” 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 7/26![American Airlines logo]()
$178
This American Airlines deal was found by Cheapflights users on 7/24. Clicking the “Pick Dates” 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 10/226:27 pm
MKE
- SJU
2 stops16h 04m
American Airlines
Deal found 7/24![American Airlines logo]()
$179
This Delta deal was found by Cheapflights users on 7/26. Clicking the “Pick Dates” 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 9/95:30 am
MKE
- NAS
1 stop5h 21m
Delta
Deal found 7/26![Delta logo]()
$181
This American Airlines deal was found by Cheapflights users on 7/27. Clicking the “Pick Dates” 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 12/96:50 pm
MKE
- SJU
2 stops13h 45m
American Airlines
Deal found 7/27![American Airlines logo]()
$182
This United Airlines deal was found by Cheapflights users on 7/28. Clicking the “Pick Dates” 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 8/146:00 pm
MKE
- MBJ
1 stop19h 30m
United Airlines
Deal found 7/28![United Airlines logo]()
$186
This American Airlines deal was found by Cheapflights users on 7/26. Clicking the “Pick Dates” 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 9/95:03 am
MKE
- NAS
2 stops11h 52m
American Airlines
Deal found 7/26![American Airlines logo]()
$186
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 28, 2026.
Round-trip from | $341 (American Airlines) |
|---|---|
One-way from | $167 (Delta) |
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 28, 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 11/9
5:10 am-5:50 pm
1 stop10h 40m
San Juan Luis Munoz Marin Intl
Fri 11/13
12:40 pm-7:15 pm
1 stop8h 35m
$346
MilwaukeeSan Juan
MKE - SJU
MKESJU
Milwaukee-Mitchell
Fri 10/23
2:25 pm-12:20 am
1 stop8h 55m
San Juan Luis Munoz Marin Intl
Wed 11/4
7:40 am-3:55 pm
2 stops10h 15m
$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
$356
MilwaukeeSan Juan
MKE - SJU
MKESJU
Milwaukee-Mitchell
Tue 8/18
10:00 am-10:00 pm
2 stops11h 00m
San Juan Luis Munoz Marin Intl
Sun 8/23
9:25 pm-8:55 am
1 stop12h 30m
$380
MilwaukeeMontego Bay
MKE - MBJ
MKEMBJ
Milwaukee-Mitchell
Sat 10/24
5:40 am-1:20 pm
1 stop7h 40m
Montego Bay Sangster Intl
Wed 10/28
2:45 pm-11:53 pm
1 stop9h 08m
$392
MilwaukeeMontego Bay
MKE - MBJ
MKEMBJ
Milwaukee-Mitchell
Sat 11/7
7:03 pm-12:13 pm
1 stop16h 10m
Montego Bay Sangster Intl
Sat 11/14
3:20 pm-10:47 pm
1 stop8h 27m
$402
MilwaukeeSan Juan
MKE - SJU
MKESJU
Milwaukee-Mitchell
Sat 8/29
7:18 am-8:38 pm
2 stops12h 20m
San Juan Luis Munoz Marin Intl
Sat 8/29
1:00 am-10:00 am
2 stops10h 00m
$402
MilwaukeeSan Juan
MKE - SJU
MKESJU
Milwaukee-Mitchell
Fri 11/20
7:55 pm-10:10 am
1 stop12h 15m
San Juan Luis Munoz Marin Intl
Fri 12/4
6:45 am-12:00 pm
1 stop7h 15m
$406
MilwaukeeSan Juan
MKE - SJU
MKESJU
Milwaukee-Mitchell
Sat 8/29
8:35 am-6:05 pm
2 stops8h 30m
San Juan Luis Munoz Marin Intl
Mon 8/31
6:30 am-3:25 pm
2 stops9h 55m
$406
MilwaukeeMontego Bay
MKE - MBJ
MKEMBJ
Milwaukee-Mitchell
Sat 12/5
7:00 am-4:24 pm
2 stops8h 24m
Montego Bay Sangster Intl
Sat 12/12
5:26 pm-9:49 am
2 stops17h 23m
$407
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-STT
MKE-AUA
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Milwaukee to Caribbean
MKE-0CB
MKE-SJU
MKE-MBJ
MKE-PLS
MKE-STT
What is the cheapest month to book a flight from Milwaukee to Caribbean?
Currently, August is the cheapest month in which you can book a flight from Milwaukee to Caribbean (average of $501). Flying from Milwaukee to Caribbean in December is currently the most expensive (average of $720). 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 28, 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.
Comfort
8.0
Food
7.0
Boarding
8.1
Crew
8.6
Overall
8.0
Entertainment
7.5
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Comfort
8.0
Food
7.0
Boarding
8.1
Crew
8.6
Overall
8.0
Entertainment
7.5
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Comfort
8.0
Food
7.0
Boarding
8.1
Crew
8.6
Overall
8.0
Entertainment
7.5
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Comfort
8.0
Food
7.0
Boarding
8.1
Crew
8.6
Overall
8.0
Entertainment
7.5
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Comfort
8.0
Food
7.0
Boarding
8.1
Crew
8.6
Overall
8.0
Entertainment
7.5
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Comfort
8.0
Food
7.0
Boarding
8.1
Crew
8.6
Overall
8.0
Entertainment
7.5
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 28, 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 July 28, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$143 | Average$590 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$156 | Average$360 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$235 | Average$562 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$256 | Average$618 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$317 | Average$723 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$465 | Average$567 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$547 | Average$853 | FlexibilityNo cancel fee | On-time83% |