$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 10/17. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — SJU
Jul 27 — Aug 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 June 27, 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 June 27, 2026.
This deal was found by Cheapflights users on 6/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/188:10 pm
MKE
- SJU
1 stop10h 48m
Frontier
Fri 10/309:03 am
SJU
- MKE
1 stop11h 05m
Frontier
Deal found 6/22![Frontier logo]()
$198
This Delta deal was found by Cheapflights users on 6/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/175:45 am
MKE
- SJU
1 stop9h 48m
Delta
Sat 10/315:43 pm
SJU
- MKE
1 stop7h 06m
Delta
Deal found 6/22![Delta logo]()
$226
This American Airlines deal was found by Cheapflights users on 6/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/165:11 pm
MKE
- SJU
2 stops15h 13m
American Airlines
Tue 9/222:58 pm
SJU
- MKE
2 stops18h 03m
American Airlines
Deal found 6/22![American Airlines logo]()
$231
This United Airlines deal was found by Cheapflights users on 6/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/116:00 am
MKE
- SJU
2 stops13h 38m
United Airlines
Mon 9/142:20 pm
SJU
- MKE
1 stop9h 19m
United Airlines
Deal found 6/23![United Airlines logo]()
$244
This United Airlines deal was found by Cheapflights users on 6/24. 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.
Thu 9/106:00 am
MKE
- SJU
2 stops13h 38m
United Airlines
Mon 9/142:20 pm
SJU
- MKE
1 stop9h 19m
United Airlines
Deal found 6/24![United Airlines logo]()
$248
This deal was found by Cheapflights users on 6/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/158:10 pm
MKE
- SJU
1 stop10h 48m
Frontier
Mon 11/210:03 am
SJU
- MKE
1 stop11h 05m
Frontier
Deal found 6/22![Frontier logo]()
$253
This United Airlines deal was found by Cheapflights users on 6/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/196:00 am
MKE
- SJU
2 stops13h 38m
United Airlines
Sun 10/43:56 pm
SJU
- MKE
1 stop8h 03m
United Airlines
Deal found 6/23![United Airlines logo]()
$259
This Delta deal was found by Cheapflights users on 6/24. 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.
Tue 10/202:45 pm
MKE
- SJU
1 stop6h 14m
Delta
Tue 11/36:43 pm
SJU
- MKE
1 stop7h 06m
Delta
Deal found 6/24![Delta logo]()
$265
This Delta deal was found by Cheapflights users on 6/23. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/66:45 am
MKE
- SJU
1 stop8h 48m
Delta
Wed 9/97:00 am
SJU
- MKE
1 stop11h 32m
Delta
Deal found 6/23![Delta logo]()
$276
This American Airlines deal was found by Cheapflights users on 6/24. 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 8/266:28 am
MKE
- SJU
2 stops14h 27m
American Airlines
Thu 9/104:38 pm
SJU
- MKE
2 stops16h 23m
American Airlines
Deal found 6/24![American Airlines logo]()
$281
This Delta deal was found by Cheapflights users on 6/24. 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.
Thu 9/1712:44 pm
MKE
- SJU
1 stop8h 35m
Delta
Sat 10/35:59 pm
SJU
- MKE
1 stop6h 49m
Delta
Deal found 6/24![Delta logo]()
$295
This American Airlines deal was found by Cheapflights users on 6/23. 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.
Tue 8/252:49 pm
MKE
- SJU
1 stop8h 10m
American Airlines
Tue 9/1511:51 am
SJU
- MKE
2 stops25h 59m
American Airlines
Deal found 6/23![American Airlines logo]()
$296
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 June 27, 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 June 27, 2026.
This Delta deal was found by Cheapflights users on 6/23. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/255:34 am
MKE
- SJU
1 stop10h 04m
Delta
Tue 9/15:49 pm
SJU
- MKE
1 stop7h 04m
Delta
Deal found 6/23![Delta logo]()
$226
This United Airlines deal was found by Cheapflights users on 6/25. 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.
Wed 10/216:15 am
MKE
- SJU
2 stops13h 23m
United Airlines
Wed 10/283:55 pm
SJU
- MKE
1 stop7h 50m
United Airlines
Deal found 6/25![United Airlines logo]()
$226
This Southwest deal was found by Cheapflights users on 6/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/1610:30 am
MKE
- SJU
1 stop6h 40m
Southwest
Tue 9/228:20 am
SJU
- MKE
1 stop9h 00m
Southwest
Deal found 6/22![Southwest logo]()
$276
This American Airlines deal was found by Cheapflights users on 6/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/38:14 pm
MKE
- MBJ
2 stops16h 39m
American Airlines
Tue 10/135:00 pm
MBJ
- MKE
2 stops19h 02m
American Airlines
Deal found 6/22![American Airlines logo]()
$377
This Delta deal was found by Cheapflights users on 6/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/237:05 am
MKE
- SJU
1 stop8h 44m
Delta
Fri 10/25:59 pm
SJU
- MKE
1 stop6h 49m
Delta
Deal found 6/22![Delta logo]()
$226
This Delta deal was found by Cheapflights users on 6/25. 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.
Mon 8/1712:51 pm
MKE
- SJU
1 stop8h 38m
Delta
Tue 9/15:49 pm
SJU
- MKE
1 stop7h 04m
Delta
Deal found 6/25![Delta logo]()
$226
This Delta deal was found by Cheapflights users on 6/23. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/245:34 am
MKE
- SJU
1 stop10h 04m
Delta
Tue 9/151:21 pm
SJU
- MKE
1 stop8h 15m
Delta
Deal found 6/23![Delta logo]()
$226
This Justfly.com deal was found by Cheapflights users on 6/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/299:36 am
MKE
- PUJ
1 stop23h 30m
JetBlue
Fri 9/46:51 pm
PUJ
- MKE
1 stop14h 53m
JetBlue
Deal found 6/22![JetBlue logo]()
$581
This United Airlines deal was found by Cheapflights users on 6/25. 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.
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 6/25![United Airlines logo]()
$316
This United Airlines deal was found by Cheapflights users on 6/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/176:00 am
MKE
- SJU
1 stop7h 44m
United Airlines
Thu 10/13:56 pm
SJU
- MKE
1 stop8h 03m
United Airlines
Deal found 6/23![United Airlines logo]()
$316
This Copa Airlines deal was found by Cheapflights users on 6/24. 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 Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/65:00 am
MKE
- AUA
2 stops30h 09m
Copa Airlines
Mon 8/107:37 pm
AUA
- MKE
2 stops36h 30m
Copa Airlines
Deal found 6/24![Copa Airlines logo]()
$721
This American Airlines deal was found by Cheapflights users on 6/25. 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 9/197:00 am
MKE
- MBJ
1 stop9h 16m
American Airlines
Sat 9/265:16 pm
MBJ
- MKE
2 stops18h 11m
American Airlines
Deal found 6/25![American Airlines logo]()
$377
This Delta deal was found by Cheapflights users on 6/25. 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.
Wed 10/212:45 pm
MKE
- SJU
1 stop6h 14m
Delta
Wed 10/285:43 pm
SJU
- MKE
1 stop7h 06m
Delta
Deal found 6/25![Delta logo]()
$295
This United Airlines deal was found by Cheapflights users on 6/26. 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 9/268:30 am
MKE
- SJU
2 stops14h 20m
United Airlines
Sat 10/107:00 am
SJU
- MKE
1 stop11h 13m
United Airlines
Deal found 6/26![United Airlines logo]()
$326
This American Airlines deal was found by Cheapflights users on 6/24. 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 12/127:19 pm
MKE
- MBJ
1 stop17h 01m
American Airlines
Thu 12/173:45 pm
MBJ
- MKE
1 stop20h 18m
American Airlines
Deal found 6/24![American Airlines logo]()
$380
This United Airlines deal was found by Cheapflights users on 6/26. 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 9/265:00 am
MKE
- SJU
2 stops14h 38m
United Airlines
Tue 10/131:00 am
SJU
- MKE
2 stops11h 30m
United Airlines
Deal found 6/26![United Airlines logo]()
$326
This American Airlines deal was found by Cheapflights users on 6/27. 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 8/115:50 pm
MKE
- GCM
2 stops19h 20m
American Airlines
Tue 8/182:10 pm
GCM
- MKE
2 stops17h 39m
American Airlines
Deal found 6/27![American Airlines logo]()
$424
This American Airlines deal was found by Cheapflights users on 6/26. 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 12/16:48 pm
MKE
- STT
2 stops20h 10m
American Airlines
Tue 12/86:17 pm
STT
- MKE
2 stops16h 03m
American Airlines
Deal found 6/26![American Airlines logo]()
$430
This Southwest deal was found by Cheapflights users on 6/27. 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.
Sat 7/255:00 am
MKE
- SXM
1 stop9h 05m
Southwest
Wed 7/293:00 pm
SXM
- MKE
1 stop8h 50m
Southwest
Deal found 6/27![Southwest logo]()
$573
This Delta deal was found by Cheapflights users on 6/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/195:30 am
MKE
- MBJ
1 stop10h 04m
Delta
Sat 9/264:59 pm
MBJ
- MKE
1 stop6h 49m
Delta
Deal found 6/22![Delta logo]()
$432
This United Airlines deal was found by Cheapflights users on 6/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/65:00 am
MKE
- MBJ
1 stop7h 46m
United Airlines
Thu 12/102:48 pm
MBJ
- MKE
1 stop8h 51m
United Airlines
Deal found 6/23![United Airlines logo]()
$432
This Justfly.com deal was found by Cheapflights users on 6/27. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/1211:25 am
MKE
- AUA
1 stop27h 15m
JetBlue
Sat 9/194:30 pm
AUA
- MKE
1 stop19h 05m
JetBlue
Deal found 6/27![JetBlue logo]()
$645
This Southwest deal was found by Cheapflights users on 6/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/35:50 am
MKE
- SXM
1 stop6h 55m
Southwest
Sat 10/102:45 pm
SXM
- MKE
1 stop8h 10m
Southwest
Deal found 6/23![Southwest logo]()
$601
This American Airlines deal was found by Cheapflights users on 6/25. 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.
Wed 11/115:00 am
MKE
- PLS
2 stops8h 35m
American Airlines
Tue 11/173:36 pm
PLS
- MKE
1 stop9h 23m
American Airlines
Deal found 6/25![American Airlines logo]()
$473
This United Airlines deal was found by Cheapflights users on 6/24. 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 9/197:05 pm
MKE
- MBJ
1 stop16h 38m
United Airlines
Sat 9/262:40 pm
MBJ
- MKE
1 stop8h 05m
United Airlines
Deal found 6/24![United Airlines logo]()
$432
This Delta deal was found by Cheapflights users on 6/24. 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 11/76:40 pm
MKE
- MBJ
2 stops16h 45m
Delta
Mon 11/91:50 pm
MBJ
- MKE
2 stops20h 32m
Delta
Deal found 6/24![Delta logo]()
$447
This American Airlines deal was found by Cheapflights users on 6/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/54:26 pm
MKE
- MBJ
1 stop16h 39m
American Airlines
Sat 10/1010:50 am
MBJ
- MKE
1 stop13h 21m
American Airlines
Deal found 6/22![American Airlines logo]()
$476
This Southwest deal was found by Cheapflights users on 6/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/75:35 am
MKE
- PUJ
1 stop7h 05m
Southwest
Sat 9/121:25 pm
PUJ
- MKE
1 stop8h 10m
Southwest
Deal found 6/22![Southwest logo]()
$644
This American Airlines deal was found by Cheapflights users on 6/23. 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.
Fri 11/272:53 pm
MKE
- STT
2 stops19h 14m
American Airlines
Sat 12/56:17 pm
STT
- MKE
2 stops18h 29m
American Airlines
Deal found 6/23![American Airlines logo]()
$485
This Delta deal was found by Cheapflights users on 6/27. 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.
Tue 8/115:34 am
MKE
- GCM
1 stop6h 05m
Delta
Tue 8/181:04 pm
GCM
- MKE
1 stop10h 49m
Delta
Deal found 6/27![Delta logo]()
$501
Last-minute flights from Milwaukee to CaribbeanDiscover last-minute flight deals from Milwaukee to Caribbean. Data last updated June 27, 2026 and is based on user searches.
Discover last-minute flight deals from Milwaukee to Caribbean. Data last updated June 27, 2026 and is based on user searches.
This United Airlines deal was found by Cheapflights users on 6/25. 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 6/296:20 am
MKE
- MBJ
2 stops8h 50m
United Airlines
Sat 7/44:33 pm
MBJ
- MKE
2 stops17h 20m
United Airlines
Deal found 6/25![United Airlines logo]()
$491
This American Airlines deal was found by Cheapflights users on 6/25. 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 6/296:50 pm
MKE
- MBJ
2 stops18h 18m
American Airlines
Sun 7/52:36 pm
MBJ
- MKE
1 stop17h 26m
American Airlines
Deal found 6/25![American Airlines logo]()
$496
This Delta deal was found by Cheapflights users on 6/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/156:45 am
MKE
- SJU
1 stop8h 53m
Delta
Wed 7/222:42 pm
SJU
- MKE
1 stop10h 14m
Delta
Deal found 6/22![Delta logo]()
$418
This CheapOair deal was found by Cheapflights users on 6/23. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/159:35 am
MKE
- SJU
2 stops33h 25m
Multiple Airlines
Mon 7/2010:48 pm
SJU
- MKE
1 stop10h 10m
Multiple Airlines
Deal found 6/23![Multiple Airlines logo]()
$443
This Priceline deal was found by Cheapflights users on 6/24. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/168:43 am
MKE
- SJU
1 stop9h 49m
Frontier
Wed 7/224:08 pm
SJU
- MKE
1 stop16h 50m
Frontier
Deal found 6/24![Frontier logo]()
$436
This Southwest deal was found by Cheapflights users on 6/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/203:15 pm
MKE
- SJU
1 stop7h 25m
Southwest
Fri 8/145:30 am
SJU
- MKE
1 stop11h 30m
Southwest
Deal found 6/22![Southwest logo]()
$366
This Frontier deal was found by Cheapflights users on 6/23. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/218:43 am
MKE
- SJU
1 stop9h 59m
Frontier
Wed 7/298:37 pm
SJU
- MKE
1 stop12h 21m
Frontier
Deal found 6/23![Frontier logo]()
$376
This CheapOair deal was found by Cheapflights users on 6/24. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/238:43 am
MKE
- SJU
1 stop16h 32m
Frontier
Wed 7/298:37 pm
SJU
- MKE
1 stop12h 21m
Frontier
Deal found 6/24![Frontier logo]()
$406
This Delta deal was found by Cheapflights users on 6/24. 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.
Thu 7/235:40 am
MKE
- SJU
1 stop6h 52m
Delta
Tue 8/42:59 pm
SJU
- MKE
1 stop9h 54m
Delta
Deal found 6/24![Delta logo]()
$423
This United Airlines deal was found by Cheapflights users on 6/27. 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 7/255:29 pm
MKE
- SXM
2 stops20h 14m
United Airlines
Wed 7/293:50 pm
SXM
- MKE
2 stops16h 10m
United Airlines
Deal found 6/27![United Airlines logo]()
$508
This Frontier deal was found by Cheapflights users on 6/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/288:43 am
MKE
- SJU
1 stop9h 59m
Frontier
Mon 8/38:37 pm
SJU
- MKE
1 stop12h 21m
Frontier
Deal found 6/22![Frontier logo]()
$396
This American Airlines deal was found by Cheapflights users on 6/26. 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 7/307:01 am
MKE
- SJU
1 stop14h 58m
American Airlines
Tue 8/117:03 am
SJU
- MKE
1 stop17h 11m
American Airlines
Deal found 6/26![American Airlines logo]()
$446
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 June 27, 2026.
Search for one-way flight options from Milwaukee to Caribbean. Find affordable one-way fares based on user searches. Data last updated June 27, 2026.
This Delta deal was found by Cheapflights users on 6/23. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/1910:22 am
MKE
- SJU
1 stop11h 07m
Delta
Deal found 6/23![Delta logo]()
$113
This American Airlines deal was found by Cheapflights users on 6/23. 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.
Tue 9/155:53 pm
MKE
- SJU
2 stops19h 01m
American Airlines
Deal found 6/23![American Airlines logo]()
$116
This American Airlines deal was found by Cheapflights users on 6/24. 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 8/195:00 am
MKE
- SJU
2 stops10h 11m
American Airlines
Deal found 6/24![American Airlines logo]()
$118
This American Airlines deal was found by Cheapflights users on 6/24. 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.
Mon 9/218:14 pm
MKE
- SJU
2 stops17h 36m
American Airlines
Deal found 6/24![American Airlines logo]()
$119
This American Airlines deal was found by Cheapflights users on 6/24. 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 9/26:28 am
MKE
- SJU
2 stops11h 05m
American Airlines
Deal found 6/24![American Airlines logo]()
$121
This United Airlines deal was found by Cheapflights users on 6/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/127:18 am
MKE
- SJU
2 stops12h 20m
United Airlines
Deal found 6/23![United Airlines logo]()
$144
This Delta deal was found by Cheapflights users on 6/25. 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.
Mon 9/215:30 am
MKE
- SJU
1 stop10h 19m
Delta
Deal found 6/25![Delta logo]()
$152
This United Airlines deal was found by Cheapflights users on 6/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/205:00 am
MKE
- SJU
2 stops14h 38m
United Airlines
Deal found 6/23![United Airlines logo]()
$158
This American Airlines deal was found by Cheapflights users on 6/26. 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 9/16:20 am
MKE
- MBJ
1 stop8h 03m
American Airlines
Deal found 6/26![American Airlines logo]()
$162
This Delta deal was found by Cheapflights users on 6/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/156:45 am
MKE
- SJU
1 stop8h 53m
Delta
Deal found 6/22![Delta logo]()
$163
This American Airlines deal was found by Cheapflights users on 6/24. 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 10/217:24 am
MKE
- SJU
1 stop15h 26m
American Airlines
Deal found 6/24![American Airlines logo]()
$168
This American Airlines deal was found by Cheapflights users on 6/24. 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 12/96:50 pm
MKE
- SJU
2 stops13h 45m
American Airlines
Deal found 6/24![American Airlines logo]()
$171
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 June 27, 2026.
Round-trip from | $198 |
|---|---|
One-way from | $113 (Delta) |
Popular in | December |
Cheapest in | October |
Average price | $504 |
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 June 27, 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
Tue 8/25
5:34 am-4:38 pm
1 stop10h 04m
San Juan Luis Munoz Marin Intl
Tue 9/1
5:49 pm-11:53 pm
1 stop7h 04m
$226
MilwaukeeSan Juan
MKE - SJU
MKESJU
Milwaukee-Mitchell
Wed 10/21
6:15 am-8:38 pm
2 stops13h 23m
San Juan Luis Munoz Marin Intl
Wed 10/28
3:55 pm-10:45 pm
1 stop7h 50m
$226
MilwaukeeSan Juan
MKE - SJU
MKESJU
Milwaukee-Mitchell
Wed 9/23
7:05 am-4:49 pm
1 stop8h 44m
San Juan Luis Munoz Marin Intl
Fri 10/2
5:59 pm-11:48 pm
1 stop6h 49m
$226
MilwaukeeSan Juan
MKE - SJU
MKESJU
Milwaukee-Mitchell
Mon 8/17
12:51 pm-10:29 pm
1 stop8h 38m
San Juan Luis Munoz Marin Intl
Tue 9/1
5:49 pm-11:53 pm
1 stop7h 04m
$226
MilwaukeeSan Juan
MKE - SJU
MKESJU
Milwaukee-Mitchell
Mon 8/24
5:34 am-4:38 pm
1 stop10h 04m
San Juan Luis Munoz Marin Intl
Tue 9/15
1:21 pm-8:36 pm
1 stop8h 15m
$226
MilwaukeeSan Juan
MKE - SJU
MKESJU
Milwaukee-Mitchell
Wed 9/16
10:30 am-6:10 pm
1 stop6h 40m
San Juan Luis Munoz Marin Intl
Tue 9/22
8:20 am-4:20 pm
1 stop9h 00m
$276
Quickest round-trip
MilwaukeeSan Juan
MKE - SJU
MKESJU
Milwaukee-Mitchell
Wed 10/21
2:45 pm-9:59 pm
1 stop6h 14m
San Juan Luis Munoz Marin Intl
Wed 10/28
5:43 pm-11:49 pm
1 stop7h 06m
$295
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
$316
MilwaukeeSan Juan
MKE - SJU
MKESJU
Milwaukee-Mitchell
Thu 9/17
6:00 am-2:44 pm
1 stop7h 44m
San Juan Luis Munoz Marin Intl
Thu 10/1
3:56 pm-10:59 pm
1 stop8h 03m
$316
MilwaukeeSan Juan
MKE - SJU
MKESJU
Milwaukee-Mitchell
Sat 9/26
8:30 am-11:50 pm
2 stops14h 20m
San Juan Luis Munoz Marin Intl
Sat 10/10
7:00 am-5:13 pm
1 stop11h 13m
$326
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-SXM
MKE-ANU
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-SXM
MKE-ANU
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 $1,063). 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 June 27, 2026.
Read through reviews of airlines operating flights from Milwaukee to Caribbean, such as Southwest,Delta, andUnited Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Food
7.0
Overall
7.9
Comfort
8.0
Boarding
8.1
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Food
7.0
Overall
7.9
Comfort
8.0
Boarding
8.1
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Food
7.0
Overall
7.9
Comfort
8.0
Boarding
8.1
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Food
7.0
Overall
7.9
Comfort
8.0
Boarding
8.1
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Food
7.0
Overall
7.9
Comfort
8.0
Boarding
8.1
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Food
7.0
Overall
7.9
Comfort
8.0
Boarding
8.1
Crew
8.6
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.
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 June 27, 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 June 27, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$118 | Average$580 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$156 | Average$360 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$235 | Average$556 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$256 | Average$676 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$316 | Average$729 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$547 | Average$866 | FlexibilityNo cancel fee | On-time83% |