$113+ 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 8/15. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — SJU
Aug 9 — Aug 161
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 10, 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 10, 2026.
This American Airlines deal was found by Cheapflights users on 7/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/116:50 pm
MKE
- SJU
2 stops13h 45m
American Airlines
Wed 12/167:00 am
SJU
- MKE
1 stop12h 02m
American Airlines
Deal found 7/7![American Airlines logo]()
$226
This American Airlines deal was found by Cheapflights users on 7/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/126:28 am
MKE
- SJU
2 stops11h 05m
American Airlines
Mon 8/1712:55 am
SJU
- MKE
1 stop7h 54m
American Airlines
Deal found 7/7![American Airlines logo]()
$231
This American Airlines deal was found by Cheapflights users on 7/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/2710:21 am
MKE
- SJU
1 stop11h 03m
American Airlines
Tue 9/83:47 pm
SJU
- MKE
1 stop7h 07m
American Airlines
Deal found 7/7![American Airlines logo]()
$316
This Delta deal was found by Cheapflights users on 7/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/2210:24 am
MKE
- SJU
1 stop11h 05m
Delta
Wed 9/97:00 am
SJU
- MKE
1 stop7h 50m
Delta
Deal found 7/6![Delta logo]()
$326
This American Airlines deal was found by Cheapflights users on 7/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/26:28 am
MKE
- SJU
1 stop16h 31m
American Airlines
Sat 9/512:55 am
SJU
- MKE
1 stop7h 54m
American Airlines
Deal found 7/10![American Airlines logo]()
$331
This American Airlines deal was found by Cheapflights users on 7/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/56:27 pm
MKE
- SJU
2 stops16h 04m
American Airlines
Fri 10/3012:13 pm
SJU
- MKE
2 stops12h 05m
American Airlines
Deal found 7/6![American Airlines logo]()
$332
This American Airlines deal was found by Cheapflights users on 7/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/146:20 am
MKE
- SJU
2 stops11h 13m
American Airlines
Sat 8/222:33 pm
SJU
- MKE
1 stop9h 41m
American Airlines
Deal found 7/10![American Airlines logo]()
$334
This American Airlines deal was found by Cheapflights users on 7/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/245:53 pm
MKE
- STT
2 stops17h 58m
American Airlines
Mon 9/281:41 pm
STT
- MKE
2 stops24h 07m
American Airlines
Deal found 7/9![American Airlines logo]()
$336
This American Airlines deal was found by Cheapflights users on 7/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/147:19 pm
MKE
- SJU
1 stop17h 43m
American Airlines
Sat 11/213:53 pm
SJU
- MKE
1 stop18h 14m
American Airlines
Deal found 7/9![American Airlines logo]()
$342
This Southwest deal was found by Cheapflights users on 7/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/110:15 am
MKE
- SJU
1 stop12h 30m
Southwest
Mon 8/315:30 am
SJU
- MKE
1 stop7h 25m
Southwest
Deal found 7/9![Southwest logo]()
$348
This Southwest deal was found by Cheapflights users on 7/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/410:30 am
MKE
- SJU
1 stop6h 40m
Southwest
Thu 8/206:00 am
SJU
- MKE
1 stop11h 10m
Southwest
Deal found 7/8![Southwest logo]()
$349
This Southwest deal was found by Cheapflights users on 7/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/1012:30 pm
MKE
- SJU
2 stops9h 35m
Southwest
Sun 9/136:00 am
SJU
- MKE
1 stop8h 35m
Southwest
Deal found 7/6![Southwest logo]()
$351
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 10, 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 10, 2026.
This United Airlines deal was found by Cheapflights users on 7/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/26:15 am
MKE
- SJU
2 stops13h 23m
United Airlines
Sat 9/51:00 am
SJU
- MKE
2 stops10h 00m
United Airlines
Deal found 7/6![United Airlines logo]()
$326
This Delta deal was found by Cheapflights users on 7/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/256:45 am
MKE
- SJU
1 stop8h 48m
Delta
Fri 9/42:59 pm
SJU
- MKE
1 stop9h 54m
Delta
Deal found 7/7![Delta logo]()
$326
This Southwest deal was found by Cheapflights users on 7/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/2610:30 am
MKE
- SJU
1 stop6h 40m
Southwest
Sun 8/309:25 pm
SJU
- MKE
1 stop12h 30m
Southwest
Deal found 7/6![Southwest logo]()
$326
This American Airlines deal was found by Cheapflights users on 7/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/38:14 pm
MKE
- MBJ
2 stops16h 39m
American Airlines
Tue 10/135:13 pm
MBJ
- MKE
2 stops18h 55m
American Airlines
Deal found 7/10![American Airlines logo]()
$357
This Delta deal was found by Cheapflights users on 7/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/210:22 am
MKE
- SJU
1 stop11h 07m
Delta
Sun 9/65:49 pm
SJU
- MKE
1 stop7h 04m
Delta
Deal found 7/6![Delta logo]()
$326
This United Airlines deal was found by Cheapflights users on 7/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/266:15 am
MKE
- SJU
2 stops13h 23m
United Airlines
Wed 9/302:55 pm
SJU
- MKE
1 stop8h 50m
United Airlines
Deal found 7/10![United Airlines logo]()
$366
This American Airlines deal was found by Cheapflights users on 7/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/16:48 pm
MKE
- STT
2 stops17h 04m
American Airlines
Tue 12/86:17 pm
STT
- MKE
2 stops18h 50m
American Airlines
Deal found 7/9![American Airlines logo]()
$383
This United Airlines deal was found by Cheapflights users on 7/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/227:18 am
MKE
- SJU
2 stops12h 20m
United Airlines
Fri 9/43:56 pm
SJU
- MKE
1 stop7h 40m
United Airlines
Deal found 7/8![United Airlines logo]()
$366
This Southwest deal was found by Cheapflights users on 7/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/152:25 pm
MKE
- SJU
1 stop8h 55m
Southwest
Sun 10/183:05 pm
SJU
- MKE
1 stop9h 50m
Southwest
Deal found 7/9![Southwest logo]()
$413
This United Airlines deal was found by Cheapflights users on 7/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/256:15 am
MKE
- SJU
2 stops13h 23m
United Airlines
Fri 9/43:56 pm
SJU
- MKE
1 stop7h 40m
United Airlines
Deal found 7/8![United Airlines logo]()
$366
This Southwest deal was found by Cheapflights users on 7/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/2311:50 am
MKE
- SJU
2 stops9h 55m
Southwest
Mon 8/316:30 am
SJU
- MKE
2 stops9h 55m
Southwest
Deal found 7/10![Southwest logo]()
$413
This Delta deal was found by Cheapflights users on 7/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/2012:34 pm
MKE
- SJU
1 stop8h 25m
Delta
Sun 11/12:06 pm
SJU
- MKE
1 stop8h 02m
Delta
Deal found 7/8![Delta logo]()
$421
This Delta deal was found by Cheapflights users on 7/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/15:40 am
MKE
- PLS
1 stop6h 05m
Delta
Thu 11/52:05 pm
PLS
- MKE
1 stop10h 48m
Delta
Deal found 7/10![Delta logo]()
$431
This American Airlines deal was found by Cheapflights users on 7/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/76:48 pm
MKE
- NAS
1 stop16h 22m
American Airlines
Thu 11/123:00 pm
NAS
- MKE
1 stop9h 59m
American Airlines
Deal found 7/8![American Airlines logo]()
$478
This Southwest deal was found by Cheapflights users on 7/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/25:10 am
MKE
- PLS
1 stop7h 35m
Southwest
Fri 11/62:40 pm
PLS
- MKE
1 stop10h 05m
Southwest
Deal found 7/10![Southwest logo]()
$453
This United Airlines deal was found by Cheapflights users on 7/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/165:00 am
MKE
- SJU
1 stop8h 44m
United Airlines
Sat 9/191:00 am
SJU
- MKE
2 stops10h 00m
United Airlines
Deal found 7/7![United Airlines logo]()
$416
This Delta deal was found by Cheapflights users on 7/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/284:46 pm
MKE
- MBJ
2 stops18h 48m
Delta
Sat 10/104:49 pm
MBJ
- MKE
1 stop7h 04m
Delta
Deal found 7/6![Delta logo]()
$447
This American Airlines deal was found by Cheapflights users on 7/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/176:02 pm
MKE
- PUJ
2 stops17h 37m
American Airlines
Sat 10/244:04 pm
PUJ
- MKE
2 stops19h 10m
American Airlines
Deal found 7/9![American Airlines logo]()
$492
This United Airlines deal was found by Cheapflights users on 7/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/257:18 am
MKE
- SJU
2 stops12h 20m
United Airlines
Tue 9/84:20 pm
SJU
- MKE
1 stop8h 17m
United Airlines
Deal found 7/7![United Airlines logo]()
$416
This Southwest deal was found by Cheapflights users on 7/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/25:10 am
MKE
- GCM
1 stop6h 25m
Southwest
Sat 11/71:55 pm
GCM
- MKE
1 stop6h 30m
Southwest
Deal found 7/10![Southwest logo]()
$479
This Delta deal was found by Cheapflights users on 7/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/286:37 pm
MKE
- MBJ
2 stops16h 57m
Delta
Sun 10/44:59 pm
MBJ
- MKE
1 stop6h 49m
Delta
Deal found 7/6![Delta logo]()
$447
This American Airlines deal was found by Cheapflights users on 7/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/26:48 pm
MKE
- GCM
2 stops18h 29m
American Airlines
Sat 11/71:00 pm
GCM
- MKE
2 stops11h 59m
American Airlines
Deal found 7/10![American Airlines logo]()
$504
This United Airlines deal was found by Cheapflights users on 7/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/26:30 am
MKE
- MBJ
1 stop6h 18m
United Airlines
Sat 11/72:54 pm
MBJ
- MKE
1 stop7h 01m
United Airlines
Deal found 7/8![United Airlines logo]()
$427
This Southwest deal was found by Cheapflights users on 7/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/113:35 pm
MKE
- GCM
2 stops20h 00m
Southwest
Tue 11/171:30 pm
GCM
- MKE
2 stops9h 40m
Southwest
Deal found 7/7![Southwest logo]()
$495
This American Airlines deal was found by Cheapflights users on 7/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/215:50 pm
MKE
- STT
2 stops18h 03m
American Airlines
Mon 8/314:42 pm
STT
- MKE
2 stops19h 15m
American Airlines
Deal found 7/6![American Airlines logo]()
$515
This United Airlines deal was found by Cheapflights users on 7/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/146:30 am
MKE
- MBJ
2 stops8h 49m
United Airlines
Sat 11/213:45 pm
MBJ
- MKE
2 stops18h 06m
United Airlines
Deal found 7/8![United Airlines logo]()
$427
This Delta deal was found by Cheapflights users on 7/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/295:30 am
MKE
- NAS
1 stop5h 21m
Delta
Wed 9/303:18 pm
NAS
- MKE
1 stop6h 37m
Delta
Deal found 7/9![Delta logo]()
$478
This American Airlines deal was found by Cheapflights users on 7/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/146:48 pm
MKE
- PLS
2 stops16h 24m
American Airlines
Thu 11/191:12 pm
PLS
- MKE
2 stops19h 55m
American Airlines
Deal found 7/10![American Airlines logo]()
$522
This Delta deal was found by Cheapflights users on 7/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/75:34 am
MKE
- SXM
1 stop7h 19m
Delta
Thu 8/133:18 pm
SXM
- MKE
1 stop9h 35m
Delta
Deal found 7/9![Delta logo]()
$503
This United Airlines deal was found by Cheapflights users on 7/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/98:00 am
MKE
- GCM
1 stop7h 30m
United Airlines
Tue 12/155:45 pm
GCM
- MKE
2 stops18h 49m
United Airlines
Deal found 7/7![United Airlines logo]()
$464
Last-minute flights from Milwaukee to CaribbeanDiscover last-minute flight deals from Milwaukee to Caribbean. Data last updated July 10, 2026 and is based on user searches.
Discover last-minute flight deals from Milwaukee to Caribbean. Data last updated July 10, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 7/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/110:15 am
MKE
- SJU
1 stop12h 30m
Southwest
Mon 8/315:30 am
SJU
- MKE
1 stop7h 25m
Southwest
Deal found 7/9![Southwest logo]()
$348
This Southwest deal was found by Cheapflights users on 7/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/410:30 am
MKE
- SJU
1 stop6h 40m
Southwest
Thu 8/206:00 am
SJU
- MKE
1 stop11h 10m
Southwest
Deal found 7/8![Southwest logo]()
$349
This American Airlines deal was found by Cheapflights users on 7/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/126:28 am
MKE
- SJU
2 stops11h 05m
American Airlines
Mon 8/1712:55 am
SJU
- MKE
1 stop7h 54m
American Airlines
Deal found 7/7![American Airlines logo]()
$231
This American Airlines deal was found by Cheapflights users on 7/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/146:20 am
MKE
- SJU
2 stops11h 13m
American Airlines
Sat 8/222:33 pm
SJU
- MKE
1 stop9h 41m
American Airlines
Deal found 7/10![American Airlines logo]()
$334
This American Airlines deal was found by Cheapflights users on 7/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/191:17 pm
MKE
- SJU
1 stop8h 58m
American Airlines
Tue 9/86:00 am
SJU
- MKE
2 stops16h 54m
American Airlines
Deal found 7/8![American Airlines logo]()
$363
This American Airlines deal was found by Cheapflights users on 7/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/2112:58 pm
MKE
- SJU
1 stop8h 26m
American Airlines
Mon 8/247:03 am
SJU
- MKE
1 stop17h 11m
American Airlines
Deal found 7/9![American Airlines logo]()
$356
This Delta deal was found by Cheapflights users on 7/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/2210:24 am
MKE
- SJU
1 stop11h 05m
Delta
Thu 9/35:49 pm
SJU
- MKE
1 stop7h 04m
Delta
Deal found 7/6![Delta logo]()
$326
This American Airlines deal was found by Cheapflights users on 7/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/227:00 pm
MKE
- MBJ
2 stops18h 34m
American Airlines
Sat 8/292:21 pm
MBJ
- MKE
2 stops17h 28m
American Airlines
Deal found 7/8![American Airlines logo]()
$367
This American Airlines deal was found by Cheapflights users on 7/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/225:00 am
MKE
- MBJ
1 stop8h 12m
American Airlines
Fri 8/2812:47 pm
MBJ
- MKE
1 stop10h 10m
American Airlines
Deal found 7/6![American Airlines logo]()
$372
This American Airlines deal was found by Cheapflights users on 7/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/234:25 pm
MKE
- SJU
1 stop6h 50m
American Airlines
Sat 9/512:55 am
SJU
- MKE
1 stop7h 54m
American Airlines
Deal found 7/8![American Airlines logo]()
$358
This Southwest deal was found by Cheapflights users on 7/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/245:45 am
MKE
- SJU
2 stops10h 10m
Southwest
Mon 8/316:30 am
SJU
- MKE
2 stops9h 55m
Southwest
Deal found 7/7![Southwest logo]()
$351
This American Airlines deal was found by Cheapflights users on 7/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/275:00 am
MKE
- SJU
2 stops8h 51m
American Airlines
Tue 9/86:00 am
SJU
- MKE
2 stops12h 00m
American Airlines
Deal found 7/7![American Airlines logo]()
$316
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 10, 2026.
Search for one-way flight options from Milwaukee to Caribbean. Find affordable one-way fares based on user searches. Data last updated July 10, 2026.
This United Airlines deal was found by Cheapflights users on 7/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/1510:19 am
MKE
- SJU
2 stops12h 31m
United Airlines
Deal found 7/8![United Airlines logo]()
$113
This American Airlines deal was found by Cheapflights users on 7/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/76:00 am
MKE
- SJU
1 stop16h 15m
American Airlines
Deal found 7/9![American Airlines logo]()
$115
This American Airlines deal was found by Cheapflights users on 7/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/256:20 am
MKE
- SJU
2 stops11h 13m
American Airlines
Deal found 7/8![American Airlines logo]()
$116
This American Airlines deal was found by Cheapflights users on 7/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/21:17 pm
MKE
- SJU
1 stop8h 58m
American Airlines
Deal found 7/9![American Airlines logo]()
$118
This American Airlines deal was found by Cheapflights users on 7/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/218:14 pm
MKE
- SJU
2 stops17h 36m
American Airlines
Deal found 7/9![American Airlines logo]()
$119
This American Airlines deal was found by Cheapflights users on 7/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/126:28 am
MKE
- SJU
1 stop16h 31m
American Airlines
Deal found 7/8![American Airlines logo]()
$134
This United Airlines deal was found by Cheapflights users on 7/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/96:15 am
MKE
- SJU
1 stop7h 29m
United Airlines
Deal found 7/9![United Airlines logo]()
$139
This United Airlines deal was found by Cheapflights users on 7/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/178:30 am
MKE
- SJU
2 stops14h 20m
United Airlines
Deal found 7/9![United Airlines logo]()
$140
This American Airlines deal was found by Cheapflights users on 7/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/226:00 pm
MKE
- MBJ
2 stops17h 42m
American Airlines
Deal found 7/7![American Airlines logo]()
$152
This United Airlines deal was found by Cheapflights users on 7/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/27:18 am
MKE
- SJU
2 stops12h 20m
United Airlines
Deal found 7/10![United Airlines logo]()
$158
This American Airlines deal was found by Cheapflights users on 7/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/76:00 pm
MKE
- MBJ
2 stops17h 42m
American Airlines
Deal found 7/5![American Airlines logo]()
$162
This United Airlines deal was found by Cheapflights users on 7/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/107:18 am
MKE
- SJU
2 stops12h 20m
United Airlines
Deal found 7/9![United Airlines logo]()
$162
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 10, 2026.
Round-trip from | $226 (American Airlines) |
|---|---|
One-way from | $113 (United Airlines) |
Popular in | December |
Cheapest in | October |
Average price | $489 |
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 10, 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
Wed 9/2
6:15 am-8:38 pm
2 stops13h 23m
San Juan Luis Munoz Marin Intl
Sat 9/5
1:00 am-10:00 am
2 stops10h 00m
$326
MilwaukeeSan Juan
MKE - SJU
MKESJU
Milwaukee-Mitchell
Tue 8/25
6:45 am-4:33 pm
1 stop8h 48m
San Juan Luis Munoz Marin Intl
Fri 9/4
2:59 pm-11:53 pm
1 stop9h 54m
$326
MilwaukeeSan Juan
MKE - SJU
MKESJU
Milwaukee-Mitchell
Wed 8/26
10:30 am-6:10 pm
1 stop6h 40m
San Juan Luis Munoz Marin Intl
Sun 8/30
9:25 pm-8:55 am
1 stop12h 30m
$326
MilwaukeeSan Juan
MKE - SJU
MKESJU
Milwaukee-Mitchell
Wed 9/2
10:22 am-10:29 pm
1 stop11h 07m
San Juan Luis Munoz Marin Intl
Sun 9/6
5:49 pm-11:53 pm
1 stop7h 04m
$326
MilwaukeeMontego Bay
MKE - MBJ
MKEMBJ
Milwaukee-Mitchell
Sat 10/3
8:14 pm-12:53 pm
2 stops16h 39m
Montego Bay Sangster Intl
Tue 10/13
5:13 pm-12:08 pm
2 stops18h 55m
$357
MilwaukeeSan Juan
MKE - SJU
MKESJU
Milwaukee-Mitchell
Sat 9/26
6:15 am-8:38 pm
2 stops13h 23m
San Juan Luis Munoz Marin Intl
Wed 9/30
2:55 pm-10:45 pm
1 stop8h 50m
$366
MilwaukeeSan Juan
MKE - SJU
MKESJU
Milwaukee-Mitchell
Sat 8/22
7:18 am-8:38 pm
2 stops12h 20m
San Juan Luis Munoz Marin Intl
Fri 9/4
3:56 pm-10:36 pm
1 stop7h 40m
$366
MilwaukeeSan Juan
MKE - SJU
MKESJU
Milwaukee-Mitchell
Tue 8/25
6:15 am-8:38 pm
2 stops13h 23m
San Juan Luis Munoz Marin Intl
Fri 9/4
3:56 pm-10:36 pm
1 stop7h 40m
$366
MilwaukeeSaint Thomas Island
MKE - STT
MKESTT
Milwaukee-Mitchell
Tue 12/1
6:48 pm-1:52 pm
2 stops17h 04m
Saint Thomas Island Cyril E King
Tue 12/8
6:17 pm-11:07 am
2 stops18h 50m
$383
MilwaukeeSan Juan
MKE - SJU
MKESJU
Milwaukee-Mitchell
Thu 10/15
2:25 pm-12:20 am
1 stop8h 55m
San Juan Luis Munoz Marin Intl
Sun 10/18
3:05 pm-11:55 pm
1 stop9h 50m
$413
Showing 1-10 of 60 resultsSorted by cheapest first
Best time to book a flight from Milwaukee to Caribbean
Have a flexible travel schedule? Discover the best time to fly to Caribbean from Milwaukee with our price prediction graph.
MKE-SJU
MKE-MBJ
MKE-STT
MKE-PLS
MKE-NAS
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Milwaukee to Caribbean
MKE-0CB
MKE-SJU
MKE-MBJ
MKE-STT
MKE-PLS
What is the cheapest month to book a flight from Milwaukee to Caribbean?
Currently, April is the cheapest month in which you can book a flight from Milwaukee to Caribbean (average of $101). Flying from Milwaukee to Caribbean in March is currently the most expensive (average of $1,053). 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 10, 2026.
Read through reviews of airlines operating flights from Milwaukee to Caribbean, such as Southwest,Delta, andUnited Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Crew
8.6
Overall
7.9
Food
7.0
Entertainment
7.5
Comfort
8.0
Boarding
8.1
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Crew
8.6
Overall
7.9
Food
7.0
Entertainment
7.5
Comfort
8.0
Boarding
8.1
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Crew
8.6
Overall
7.9
Food
7.0
Entertainment
7.5
Comfort
8.0
Boarding
8.1
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Crew
8.6
Overall
7.9
Food
7.0
Entertainment
7.5
Comfort
8.0
Boarding
8.1
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Crew
8.6
Overall
7.9
Food
7.0
Entertainment
7.5
Comfort
8.0
Boarding
8.1
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Crew
8.6
Overall
7.9
Food
7.0
Entertainment
7.5
Comfort
8.0
Boarding
8.1
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 10, 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 10, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$143 | Average$586 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$156 | Average$360 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$235 | Average$561 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$256 | Average$623 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$316 | Average$705 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$547 | Average$853 | FlexibilityNo cancel fee | On-time83% |