$158+ 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 11/19. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — SJU
Jun 28 — Jul 51
Round-trip
1 adult, Economy
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Cheapest flights from Milwaukee to CaribbeanExplore the most affordable flight options available from Milwaukee to Caribbean. Find the lowest fares from popular airlines and budget airlines, with prices last updated on May 29, 2026.
Explore the most affordable flight options available from Milwaukee to Caribbean. Find the lowest fares from popular airlines and budget airlines, with prices last updated on May 29, 2026.
This American Airlines deal was found by Cheapflights users on 5/28. 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 8/126:28 am
MKE
- SJU
2 stops14h 27m
American Airlines
Tue 8/183:47 pm
SJU
- MKE
1 stop8h 12m
American Airlines
Deal found 5/28![American Airlines logo]()
$331
This American Airlines deal was found by Cheapflights users on 5/29. Clicking the “Pick Dates” 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 10/57:24 am
MKE
- SJU
1 stop15h 26m
American Airlines
Fri 10/303:25 pm
SJU
- MKE
1 stop6h 53m
American Airlines
Deal found 5/29![American Airlines logo]()
$332
This American Airlines deal was found by Cheapflights users on 5/24. 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 8/226:20 am
MKE
- SJU
1 stop15h 04m
American Airlines
Sat 8/2910:33 am
SJU
- MKE
2 stops13h 26m
American Airlines
Deal found 5/24![American Airlines logo]()
$335
This Southwest deal was found by Cheapflights users on 5/29. Clicking the “Pick Dates” 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
Mon 8/3111:35 am
SJU
- MKE
2 stops10h 05m
Southwest
Deal found 5/29![Southwest logo]()
$351
This United Airlines deal was found by Cheapflights users on 5/28. 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.
Sat 11/75:00 am
MKE
- MBJ
2 stops10h 12m
United Airlines
Thu 11/121:25 pm
MBJ
- MKE
1 stop11h 02m
United Airlines
Deal found 5/28![United Airlines logo]()
$352
This United Airlines deal was found by Cheapflights users on 5/26. 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.
Sat 10/248:30 am
MKE
- SJU
2 stops11h 08m
United Airlines
Wed 10/287:30 am
SJU
- MKE
2 stops10h 43m
United Airlines
Deal found 5/26![United Airlines logo]()
$355
This American Airlines deal was found by Cheapflights users on 5/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/274:25 pm
MKE
- MBJ
2 stops19h 17m
American Airlines
Mon 8/315:08 pm
MBJ
- MKE
2 stops18h 29m
American Airlines
Deal found 5/29![American Airlines logo]()
$357
This American Airlines deal was found by Cheapflights users on 5/28. 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.
Mon 12/76:14 am
MKE
- MBJ
1 stop8h 39m
American Airlines
Fri 12/112:30 pm
MBJ
- MKE
1 stop18h 50m
American Airlines
Deal found 5/28![American Airlines logo]()
$358
This United Airlines deal was found by Cheapflights users on 5/24. 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.
Tue 10/65:00 am
MKE
- SJU
1 stop8h 44m
United Airlines
Tue 10/133:56 pm
SJU
- MKE
1 stop8h 03m
United Airlines
Deal found 5/24![United Airlines logo]()
$358
This Southwest deal was found by Cheapflights users on 5/29. Clicking the “Pick Dates” 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 9/2512:30 pm
MKE
- SJU
1 stop9h 20m
Southwest
Mon 10/510:10 am
SJU
- MKE
2 stops9h 50m
Southwest
Deal found 5/29![Southwest logo]()
$365
This American Airlines deal was found by Cheapflights users on 5/29. Clicking the “Pick Dates” 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 10/312:22 pm
MKE
- SJU
1 stop8h 28m
American Airlines
Sat 11/76:44 am
SJU
- MKE
1 stop16h 47m
American Airlines
Deal found 5/29![American Airlines logo]()
$366
This American Airlines deal was found by Cheapflights users on 5/29. Clicking the “Pick Dates” 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 9/165:53 pm
MKE
- MBJ
2 stops19h 00m
American Airlines
Sun 9/205:16 pm
MBJ
- MKE
2 stops19h 25m
American Airlines
Deal found 5/29![American Airlines logo]()
$367
Best flights from Milwaukee to CaribbeanDiscover carefully curated flight deals from Milwaukee to Caribbean that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated May 29, 2026.
Discover carefully curated flight deals from Milwaukee to Caribbean that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated May 29, 2026.
This United Airlines deal was found by Cheapflights users on 5/28. 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.
Sat 11/75:00 am
MKE
- MBJ
2 stops10h 12m
United Airlines
Thu 11/121:25 pm
MBJ
- MKE
1 stop11h 02m
United Airlines
Deal found 5/28![United Airlines logo]()
$352
This American Airlines deal was found by Cheapflights users on 5/28. 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 11/76:48 pm
MKE
- MBJ
2 stops18h 26m
American Airlines
Thu 11/123:50 pm
MBJ
- MKE
2 stops18h 48m
American Airlines
Deal found 5/28![American Airlines logo]()
$357
This Delta deal was found by Cheapflights users on 5/29. Clicking the “Pick Dates” 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 9/255:30 am
MKE
- SJU
1 stop6h 46m
Delta
Wed 10/77:30 am
SJU
- MKE
1 stop8h 34m
Delta
Deal found 5/29![Delta logo]()
$380
This Justfly.com deal was found by Cheapflights users on 5/26. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/98:41 am
MKE
- SDQ
1 stop14h 03m
JetBlue
Sat 6/205:01 am
SDQ
- MKE
1 stop28h 45m
JetBlue
Deal found 5/26![JetBlue logo]()
$578
This Southwest deal was found by Cheapflights users on 5/27. 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 9/186:20 pm
MKE
- STT
2 stops18h 00m
Southwest
Fri 9/252:35 pm
STT
- MKE
1 stop7h 10m
Southwest
Deal found 5/27![Southwest logo]()
$590
This American Airlines deal was found by Cheapflights users on 5/25. 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.
Sat 9/56:48 pm
MKE
- MBJ
2 stops16h 46m
American Airlines
Thu 9/101:54 pm
MBJ
- MKE
2 stops18h 07m
American Airlines
Deal found 5/25![American Airlines logo]()
$357
This United Airlines deal was found by Cheapflights users on 5/24. 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.
Tue 10/65:00 am
MKE
- SJU
1 stop8h 44m
United Airlines
Tue 10/133:56 pm
SJU
- MKE
1 stop8h 03m
United Airlines
Deal found 5/24![United Airlines logo]()
$358
This Delta deal was found by Cheapflights users on 5/28. 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.
Wed 9/210:22 am
MKE
- SJU
1 stop11h 07m
Delta
Mon 9/75:49 pm
SJU
- MKE
1 stop7h 04m
Delta
Deal found 5/28![Delta logo]()
$380
This American Airlines deal was found by Cheapflights users on 5/27. 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 9/165:10 pm
MKE
- MBJ
2 stops19h 43m
American Airlines
Sun 9/205:16 pm
MBJ
- MKE
2 stops19h 34m
American Airlines
Deal found 5/27![American Airlines logo]()
$367
This United Airlines deal was found by Cheapflights users on 5/26. 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.
Sun 9/66:15 am
MKE
- SJU
2 stops13h 23m
United Airlines
Sat 9/191:00 am
SJU
- MKE
2 stops10h 00m
United Airlines
Deal found 5/26![United Airlines logo]()
$416
This Delta deal was found by Cheapflights users on 5/26. 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 9/277:05 am
MKE
- SJU
1 stop8h 26m
Delta
Mon 10/55:41 pm
SJU
- MKE
1 stop7h 11m
Delta
Deal found 5/26![Delta logo]()
$426
This United Airlines deal was found by Cheapflights users on 5/28. 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
2 stops14h 38m
United Airlines
Sat 9/191:00 am
SJU
- MKE
2 stops10h 00m
United Airlines
Deal found 5/28![United Airlines logo]()
$416
This American Airlines deal was found by Cheapflights users on 5/29. Clicking the “Pick Dates” 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 11/86:48 pm
MKE
- STT
2 stops20h 07m
American Airlines
Wed 11/186:17 pm
STT
- MKE
2 stops19h 23m
American Airlines
Deal found 5/29![American Airlines logo]()
$420
This Delta deal was found by Cheapflights users on 5/26. 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 9/1610:11 am
MKE
- SJU
1 stop10h 49m
Delta
Sun 9/202:26 pm
SJU
- MKE
1 stop7h 26m
Delta
Deal found 5/26![Delta logo]()
$426
This American Airlines deal was found by Cheapflights users on 5/28. 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.
Thu 8/274:25 pm
MKE
- MBJ
2 stops19h 17m
American Airlines
Mon 8/3112:47 pm
MBJ
- MKE
1 stop10h 10m
American Airlines
Deal found 5/28![American Airlines logo]()
$439
This United Airlines deal was found by Cheapflights users on 5/25. 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.
Sat 7/46:14 am
MKE
- SXM
1 stop7h 29m
United Airlines
Thu 7/93:50 pm
SXM
- MKE
2 stops16h 10m
United Airlines
Deal found 5/25![United Airlines logo]()
$514
This American Airlines deal was found by Cheapflights users on 5/27. 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.
Fri 9/185:53 pm
MKE
- STT
2 stops17h 58m
American Airlines
Fri 9/251:41 pm
STT
- MKE
2 stops21h 05m
American Airlines
Deal found 5/27![American Airlines logo]()
$485
This Delta deal was found by Cheapflights users on 5/26. 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.
Fri 7/176:50 am
MKE
- STT
1 stop7h 30m
Delta
Thu 7/231:21 pm
STT
- MKE
1 stop8h 33m
Delta
Deal found 5/26![Delta logo]()
$535
This Delta deal was found by Cheapflights users on 5/28. 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.
Wed 6/245:40 am
MKE
- GCM
1 stop5h 54m
Delta
Thu 6/2512:59 pm
GCM
- MKE
1 stop7h 50m
Delta
Deal found 5/28![Delta logo]()
$551
This American Airlines deal was found by Cheapflights users on 5/27. 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 8/166:48 pm
MKE
- GCM
2 stops16h 39m
American Airlines
Fri 8/2112:30 pm
GCM
- MKE
1 stop10h 29m
American Airlines
Deal found 5/27![American Airlines logo]()
$504
This United Airlines deal was found by Cheapflights users on 5/27. 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 6/277:24 pm
MKE
- SXM
2 stops16h 09m
United Airlines
Thu 7/23:50 pm
SXM
- MKE
2 stops19h 03m
United Airlines
Deal found 5/27![United Airlines logo]()
$559
This Delta deal was found by Cheapflights users on 5/27. 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.
Fri 9/185:30 am
MKE
- STT
1 stop7h 14m
Delta
Fri 9/252:54 pm
STT
- MKE
1 stop6h 58m
Delta
Deal found 5/27![Delta logo]()
$572
This American Airlines deal was found by Cheapflights users on 5/28. 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 7/115:58 pm
MKE
- MBJ
1 stop20h 04m
American Airlines
Wed 7/152:36 pm
MBJ
- MKE
1 stop17h 26m
American Airlines
Deal found 5/28![American Airlines logo]()
$525
This United Airlines deal was found by Cheapflights users on 5/28. 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.
Sat 11/75:00 am
MKE
- PUJ
1 stop8h 19m
United Airlines
Thu 11/122:55 pm
PUJ
- MKE
1 stop9h 44m
United Airlines
Deal found 5/28![United Airlines logo]()
$588
This Delta deal was found by Cheapflights users on 5/28. 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.
Fri 7/316:50 am
MKE
- MBJ
1 stop8h 44m
Delta
Mon 8/101:09 pm
MBJ
- MKE
1 stop7h 44m
Delta
Deal found 5/28![Delta logo]()
$573
This American Airlines deal was found by Cheapflights users on 5/25. 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.
Sat 9/53:00 pm
MKE
- PLS
1 stop22h 20m
American Airlines
Thu 9/103:19 pm
PLS
- MKE
2 stops19h 27m
American Airlines
Deal found 5/25![American Airlines logo]()
$527
This United Airlines deal was found by Cheapflights users on 5/28. 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.
Sun 9/206:00 am
MKE
- PUJ
1 stop8h 30m
United Airlines
Sun 9/271:50 pm
PUJ
- MKE
1 stop8h 45m
United Airlines
Deal found 5/28![United Airlines logo]()
$588
This Delta deal was found by Cheapflights users on 5/26. 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.
Fri 7/106:50 am
MKE
- PLS
1 stop6h 40m
Delta
Fri 7/173:45 pm
PLS
- MKE
1 stop9h 11m
Delta
Deal found 5/26![Delta logo]()
$588
This American Airlines deal was found by Cheapflights users on 5/27. 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 6/236:17 pm
MKE
- GCM
1 stop17h 13m
American Airlines
Sat 6/2711:22 am
GCM
- MKE
1 stop12h 12m
American Airlines
Deal found 5/27![American Airlines logo]()
$541
This United Airlines deal was found by Cheapflights users on 5/28. 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 7/247:23 pm
MKE
- PLS
2 stops15h 16m
United Airlines
Tue 7/283:30 pm
PLS
- MKE
2 stops16h 30m
United Airlines
Deal found 5/28![United Airlines logo]()
$598
Last-minute flights from Milwaukee to CaribbeanDiscover last-minute flight deals from Milwaukee to Caribbean. Data last updated May 29, 2026 and is based on user searches.
Discover last-minute flight deals from Milwaukee to Caribbean. Data last updated May 29, 2026 and is based on user searches.
This American Airlines deal was found by Cheapflights users on 5/25. 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.
Mon 6/16:17 pm
MKE
- MBJ
2 stops18h 51m
American Airlines
Fri 6/52:08 pm
MBJ
- MKE
2 stops17h 34m
American Airlines
Deal found 5/25![American Airlines logo]()
$435
This American Airlines deal was found by Cheapflights users on 5/29. Clicking the “Pick Dates” 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 6/126:00 am
MKE
- SJU
2 stops11h 25m
American Airlines
Fri 6/193:39 pm
SJU
- MKE
1 stop9h 20m
American Airlines
Deal found 5/29![American Airlines logo]()
$418
This Priceline deal was found by Cheapflights users on 5/27. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/1312:08 pm
MKE
- SJU
1 stop7h 24m
Frontier
Tue 6/233:06 am
SJU
- MKE
1 stop29h 52m
Frontier
Deal found 5/27![Frontier logo]()
$416
This Priceline deal was found by Cheapflights users on 5/28. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/1312:08 pm
MKE
- SJU
1 stop7h 24m
Frontier
Fri 6/193:06 am
SJU
- MKE
1 stop29h 52m
Frontier
Deal found 5/28![Frontier logo]()
$436
This Priceline deal was found by Cheapflights users on 5/28. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/2012:08 pm
MKE
- SJU
1 stop7h 24m
Frontier
Tue 6/233:06 am
SJU
- MKE
1 stop29h 52m
Frontier
Deal found 5/28![Frontier logo]()
$396
This American Airlines deal was found by Cheapflights users on 5/25. 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.
Sat 6/206:05 am
MKE
- SJU
1 stop17h 06m
American Airlines
Thu 6/256:21 am
SJU
- MKE
1 stop18h 26m
American Airlines
Deal found 5/25![American Airlines logo]()
$409
This Delta deal was found by Cheapflights users on 5/28. 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 6/2012:56 pm
MKE
- SJU
1 stop6h 47m
Delta
Thu 6/2512:54 pm
SJU
- MKE
1 stop8h 55m
Delta
Deal found 5/28![Delta logo]()
$434
This Southwest deal was found by Cheapflights users on 5/26. 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.
Sun 6/211:35 pm
MKE
- SJU
1 stop9h 50m
Southwest
Thu 6/255:30 am
SJU
- MKE
1 stop7h 20m
Southwest
Deal found 5/26![Southwest logo]()
$448
This American Airlines deal was found by Cheapflights users on 5/27. 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.
Thu 6/256:00 am
MKE
- SJU
1 stop16h 00m
American Airlines
Mon 7/67:25 am
SJU
- MKE
1 stop11h 06m
American Airlines
Deal found 5/27![American Airlines logo]()
$406
This CheapOair deal was found by Cheapflights users on 5/26. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/258:53 am
MKE
- SJU
1 stop16h 16m
Frontier
Wed 7/156:26 pm
SJU
- MKE
1 stop14h 32m
Frontier
Deal found 5/26![Frontier logo]()
$426
This CheapOair deal was found by Cheapflights users on 5/28. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/258:53 am
MKE
- SJU
1 stop16h 16m
Frontier
Mon 7/610:48 pm
SJU
- MKE
1 stop10h 10m
Frontier
Deal found 5/28![Frontier logo]()
$446
This American Airlines deal was found by Cheapflights users on 5/28. 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.
Tue 6/306:13 am
MKE
- SJU
1 stop16h 46m
American Airlines
Tue 7/711:54 am
SJU
- MKE
2 stops12h 14m
American Airlines
Deal found 5/28![American Airlines logo]()
$449
One-way flights from Milwaukee to CaribbeanSearch for one-way flight options from Milwaukee to Caribbean. Find affordable one-way fares based on user searches. Data last updated May 29, 2026.
Search for one-way flight options from Milwaukee to Caribbean. Find affordable one-way fares based on user searches. Data last updated May 29, 2026.
This American Airlines deal was found by Cheapflights users on 5/25. 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 11/196:48 pm
MKE
- MBJ
2 stops18h 26m
American Airlines
Deal found 5/25![American Airlines logo]()
$158
This Delta deal was found by Cheapflights users on 5/28. 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.
Wed 8/195:34 am
MKE
- SJU
1 stop7h 08m
Delta
Deal found 5/28![Delta logo]()
$163
This American Airlines deal was found by Cheapflights users on 5/28. 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 8/196:28 am
MKE
- SJU
2 stops14h 27m
American Airlines
Deal found 5/28![American Airlines logo]()
$168
This American Airlines deal was found by Cheapflights users on 5/29. Clicking the “Pick Dates” 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 stops18h 26m
American Airlines
Deal found 5/29![American Airlines logo]()
$169
This American Airlines deal was found by Cheapflights users on 5/27. 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 8/56:33 am
MKE
- SJU
1 stop16h 26m
American Airlines
Deal found 5/27![American Airlines logo]()
$172
This Travelocity deal was found by Cheapflights users on 5/27. 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/308:43 am
MKE
- SJU
1 stop13h 46m
Frontier
Deal found 5/27![Frontier logo]()
$188
This United Airlines deal was found by Cheapflights users on 5/27. 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 6/285:56 pm
MKE
- SJU
1 stop10h 33m
United Airlines
Deal found 5/27![United Airlines logo]()
$195
This Southwest deal was found by Cheapflights users on 5/24. 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 10/110:20 am
MKE
- SJU
1 stop13h 15m
Southwest
Deal found 5/24![Southwest logo]()
$202
This American Airlines deal was found by Cheapflights users on 5/28. 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 6/276:00 am
MKE
- SJU
1 stop16h 00m
American Airlines
Deal found 5/28![American Airlines logo]()
$203
This American Airlines deal was found by Cheapflights users on 5/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/35:02 am
MKE
- SJU
1 stop17h 46m
American Airlines
Deal found 5/29![American Airlines logo]()
$207
This Frontier deal was found by Cheapflights users on 5/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/238:43 am
MKE
- SJU
1 stop9h 49m
Frontier
Deal found 5/29![Frontier logo]()
$208
This Delta deal was found by Cheapflights users on 5/28. 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 6/285:40 am
MKE
- GCM
1 stop5h 54m
Delta
Deal found 5/28![Delta logo]()
$218
Find flight deals from Milwaukee to Caribbean
Keep the following information in mind while searching for Milwaukee to Caribbean flight deals. Data was last updated May 29, 2026.
Round-trip from | $331 (American Airlines) |
|---|---|
One-way from | $158 (American Airlines) |
Popular in | December |
Cheapest in | September |
Average price | $416 |
Cheapflights Fare Finder
Customize your flight search to find flights from Milwaukee to Caribbean that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated May 29, 2026.
Use the filters below to find and compare flights from Milwaukee to Caribbean that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
MilwaukeeMontego Bay
MKE - MBJ
MKEMBJ
Milwaukee-Mitchell
Sat 11/7
5:00 am-4:12 pm
2 stops10h 12m
Montego Bay Sangster Intl
Thu 11/12
1:25 pm-11:27 pm
1 stop11h 02m
$352
MilwaukeeMontego Bay
MKE - MBJ
MKEMBJ
Milwaukee-Mitchell
Sat 11/7
6:48 pm-2:14 pm
2 stops18h 26m
Montego Bay Sangster Intl
Thu 11/12
3:50 pm-9:38 am
2 stops18h 48m
$357
MilwaukeeMontego Bay
MKE - MBJ
MKEMBJ
Milwaukee-Mitchell
Sat 9/5
6:48 pm-11:34 am
2 stops16h 46m
Montego Bay Sangster Intl
Thu 9/10
1:54 pm-8:01 am
2 stops18h 07m
$357
MilwaukeeSan Juan
MKE - SJU
MKESJU
Milwaukee-Mitchell
Tue 10/6
5:00 am-2:44 pm
1 stop8h 44m
San Juan Luis Munoz Marin Intl
Tue 10/13
3:56 pm-10:59 pm
1 stop8h 03m
$358
MilwaukeeMontego Bay
MKE - MBJ
MKEMBJ
Milwaukee-Mitchell
Wed 9/16
5:10 pm-12:53 pm
2 stops19h 43m
Montego Bay Sangster Intl
Sun 9/20
5:16 pm-12:50 pm
2 stops19h 34m
$367
MilwaukeeSan Juan
MKE - SJU
MKESJU
Milwaukee-Mitchell
Fri 9/25
5:30 am-1:16 pm
1 stop6h 46m
San Juan Luis Munoz Marin Intl
Wed 10/7
7:30 am-3:04 pm
1 stop8h 34m
$380
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
Mon 9/7
5:49 pm-11:53 pm
1 stop7h 04m
$380
MilwaukeeSan Juan
MKE - SJU
MKESJU
Milwaukee-Mitchell
Sun 9/6
6:15 am-8:38 pm
2 stops13h 23m
San Juan Luis Munoz Marin Intl
Sat 9/19
1:00 am-10:00 am
2 stops10h 00m
$416
MilwaukeeSan Juan
MKE - SJU
MKESJU
Milwaukee-Mitchell
Wed 9/16
5:00 am-8:38 pm
2 stops14h 38m
San Juan Luis Munoz Marin Intl
Sat 9/19
1:00 am-10:00 am
2 stops10h 00m
$416
MilwaukeeSaint Thomas Island
MKE - STT
MKESTT
Milwaukee-Mitchell
Sun 11/8
6:48 pm-4:55 pm
2 stops20h 07m
Saint Thomas Island Cyril E King
Wed 11/18
6:17 pm-11:40 am
2 stops19h 23m
$420
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-MBJ
MKE-SJU
MKE-SDQ
MKE-GCM
MKE-SXM
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-MBJ
MKE-SJU
MKE-SDQ
MKE-GCM
What is the cheapest month to book a flight from Milwaukee to Caribbean?
Currently, October is the cheapest month in which you can book a flight from Milwaukee to Caribbean (average of $108). Flying from Milwaukee to Caribbean in March is currently the most expensive (average of $992). 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 90 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.
Reviews of airlines servicing Caribbean
Get insights into the airlines that provide service to Caribbean. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Caribbean. Reviews last updated May 29, 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.
Boarding
8.1
Overall
8.0
Crew
8.6
Food
7.0
Comfort
8.0
Entertainment
7.5
Reviews
1 / 20
10.0
ExcellentWalter,May 2026
LAS - BUR
Boarding
8.1
Overall
8.0
Crew
8.6
Food
7.0
Comfort
8.0
Entertainment
7.5
Reviews
1 / 20
10.0
ExcellentWalter,May 2026
LAS - BUR
Boarding
8.1
Overall
8.0
Crew
8.6
Food
7.0
Comfort
8.0
Entertainment
7.5
Reviews
1 / 20
10.0
ExcellentWalter,May 2026
LAS - BUR
Boarding
8.1
Overall
8.0
Crew
8.6
Food
7.0
Comfort
8.0
Entertainment
7.5
Reviews
1 / 20
10.0
ExcellentWalter,May 2026
LAS - BUR
Boarding
8.1
Overall
8.0
Crew
8.6
Food
7.0
Comfort
8.0
Entertainment
7.5
Reviews
1 / 20
10.0
ExcellentWalter,May 2026
LAS - BUR
Boarding
8.1
Overall
8.0
Crew
8.6
Food
7.0
Comfort
8.0
Entertainment
7.5
Reviews
1 / 20
10.0
ExcellentWalter,May 2026
LAS - BUR
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.
Browse thousands of different options on Cheapflights for your next trip
Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
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Alternative routes for Milwaukee to Caribbean
See prices for flight routes from nearby airports that may be better suited for you.
Complete your trip
Complete your trip to Caribbean by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Milwaukee to Caribbean by cabin class
Find flights from Milwaukee to Caribbean, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Milwaukee and Caribbean flights
Browse other Milwaukee and Caribbean flight options. Last updated on May 29, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Fly to Caribbean countries
Consider these flights traveling to countries located in Caribbean.
Milwaukee to Caribbean flights
Consider these flights traveling from Milwaukee to Caribbean.
Top 7 airlines flying from Milwaukee to Caribbean
Discover the top 7 airlines that operate flights from Milwaukee to Caribbean. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated May 29, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$112 | Average$570 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$156 | Average$360 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$219 | Average$366 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$225 | Average$564 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$256 | Average$665 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$315 | Average$734 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$547 | Average$841 | FlexibilityNo cancel fee | On-time83% |