$163+ 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 6/28. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — SJU
Jul 4 — Jul 111
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 4, 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 4, 2026.
This American Airlines deal was found by Cheapflights users on 6/3. Clicking the “Pick Dates” 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 8/122:49 pm
MKE
- SJU
1 stop8h 10m
American Airlines
Tue 8/1810:33 am
SJU
- MKE
2 stops13h 26m
American Airlines
Deal found 6/3![American Airlines logo]()
$331
This American Airlines deal was found by Cheapflights users on 6/3. Clicking the “Pick Dates” 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 10/58:16 pm
MKE
- SJU
1 stop16h 29m
American Airlines
Fri 10/303:50 pm
SJU
- MKE
1 stop9h 21m
American Airlines
Deal found 6/3![American Airlines logo]()
$332
This American Airlines deal was found by Cheapflights users on 5/31. Clicking the “Pick Dates” 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 9/86:28 am
MKE
- SJU
2 stops14h 27m
American Airlines
Tue 9/156:27 am
SJU
- MKE
2 stops16h 21m
American Airlines
Deal found 5/31![American Airlines logo]()
$351
This United Airlines deal was found by Cheapflights users on 6/1. Clicking the “Pick Dates” 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 9/45:00 am
MKE
- SJU
1 stop8h 44m
United Airlines
Sat 9/191:00 am
SJU
- MKE
2 stops10h 00m
United Airlines
Deal found 6/1![United Airlines logo]()
$355
This United Airlines deal was found by Cheapflights users on 5/30. Clicking the “Pick Dates” 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 9/1212:05 pm
MKE
- SJU
2 stops10h 45m
United Airlines
Fri 9/251:00 am
SJU
- MKE
2 stops10h 00m
United Airlines
Deal found 5/30![United Airlines logo]()
$356
This Southwest deal was found by Cheapflights users on 6/3. Clicking the “Pick Dates” 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 9/107:00 am
MKE
- SJU
2 stops8h 55m
Southwest
Mon 9/146:30 am
SJU
- MKE
1 stop10h 50m
Southwest
Deal found 6/3![Southwest logo]()
$365
This American Airlines deal was found by Cheapflights users on 6/3. Clicking the “Pick Dates” 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 10/3112:37 pm
MKE
- SJU
1 stop10h 28m
American Airlines
Sat 11/76:44 am
SJU
- MKE
1 stop16h 47m
American Airlines
Deal found 6/3![American Airlines logo]()
$366
This American Airlines deal was found by Cheapflights users on 6/3. Clicking the “Pick Dates” 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 9/25:00 am
MKE
- SJU
1 stop17h 15m
American Airlines
Mon 9/77:00 am
SJU
- MKE
1 stop15h 06m
American Airlines
Deal found 6/3![American Airlines logo]()
$371
This American Airlines deal was found by Cheapflights users on 6/2. Clicking the “Pick Dates” 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 9/36:28 am
MKE
- SJU
1 stop16h 31m
American Airlines
Mon 9/77:00 am
SJU
- MKE
1 stop15h 06m
American Airlines
Deal found 6/2![American Airlines logo]()
$373
This Delta deal was found by Cheapflights users on 5/31. Clicking the “Pick Dates” 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 9/175:30 am
MKE
- SJU
1 stop6h 46m
Delta
Mon 9/282:26 pm
SJU
- MKE
1 stop7h 26m
Delta
Deal found 5/31![Delta logo]()
$380
This Expedia deal was found by Cheapflights users on 6/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/28:53 am
MKE
- SJU
1 stop13h 36m
Frontier
Wed 7/88:37 pm
SJU
- MKE
1 stop12h 21m
Frontier
Deal found 6/1![Frontier logo]()
$396
This American Airlines deal was found by Cheapflights users on 6/3. Clicking the “Pick Dates” 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 12/82:49 pm
STT
- MKE
2 stops10h 41m
American Airlines
Deal found 6/3![American Airlines logo]()
$420
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 4, 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 4, 2026.
This Southwest deal was found by Cheapflights users on 6/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/2011:00 am
MKE
- SJU
1 stop11h 05m
Southwest
Mon 8/246:30 am
SJU
- MKE
2 stops9h 55m
Southwest
Deal found 6/3![Southwest logo]()
$365
This Delta deal was found by Cheapflights users on 5/30. Clicking the “Pick Dates” 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 9/135:55 am
MKE
- SJU
1 stop6h 21m
Delta
Sun 9/2712:58 pm
SJU
- MKE
1 stop8h 54m
Delta
Deal found 5/30![Delta logo]()
$380
This United Airlines deal was found by Cheapflights users on 6/2. Clicking the “Pick Dates” 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 9/226:00 am
MKE
- SJU
2 stops13h 38m
United Airlines
Sat 9/261:00 am
SJU
- MKE
2 stops10h 00m
United Airlines
Deal found 6/2![United Airlines logo]()
$401
This American Airlines deal was found by Cheapflights users on 6/3. Clicking the “Pick Dates” 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 7/216:00 am
MKE
- SJU
1 stop15h 57m
American Airlines
Wed 7/297:00 am
SJU
- MKE
1 stop17h 44m
American Airlines
Deal found 6/3![American Airlines logo]()
$406
This Priceline deal was found by Cheapflights users on 6/2. Clicking the “Pick Dates” 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.
Wed 8/129:36 am
MKE
- AUA
1 stop28h 54m
JetBlue
Wed 8/192:25 pm
AUA
- MKE
1 stop19h 20m
JetBlue
Deal found 6/2![JetBlue logo]()
$595
This Southwest deal was found by Cheapflights users on 6/3. Clicking the “Pick Dates” 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 10/1510:20 am
MKE
- SJU
1 stop13h 15m
Southwest
Mon 10/199:45 pm
SJU
- MKE
1 stop12h 10m
Southwest
Deal found 6/3![Southwest logo]()
$365
This United Airlines deal was found by Cheapflights users on 5/31. Clicking the “Pick Dates” 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 9/166:00 am
MKE
- SJU
2 stops13h 38m
United Airlines
Sat 9/191:00 am
SJU
- MKE
2 stops10h 00m
United Airlines
Deal found 5/31![United Airlines logo]()
$416
This American Airlines deal was found by Cheapflights users on 6/2. Clicking the “Pick Dates” 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 12/82:49 pm
STT
- MKE
2 stops10h 41m
American Airlines
Deal found 6/2![American Airlines logo]()
$420
This Delta deal was found by Cheapflights users on 5/31. Clicking the “Pick Dates” 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 8/145:34 am
MKE
- STT
1 stop7h 00m
Delta
Thu 8/202:49 pm
STT
- MKE
1 stop10h 04m
Delta
Deal found 5/31![Delta logo]()
$420
This Southwest deal was found by Cheapflights users on 6/1. Clicking the “Pick Dates” 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
2 stops9h 35m
Southwest
Sat 10/36:25 am
SJU
- MKE
2 stops9h 40m
Southwest
Deal found 6/1![Southwest logo]()
$404
This Southwest deal was found by Cheapflights users on 6/1. Clicking the “Pick Dates” 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 10/127:45 pm
MKE
- SJU
1 stop12h 20m
Southwest
Sat 10/175:30 am
SJU
- MKE
1 stop7h 10m
Southwest
Deal found 6/1![Southwest logo]()
$404
This Delta deal was found by Cheapflights users on 5/31. Clicking the “Pick Dates” 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 7/36:49 pm
MKE
- SXM
1 stop18h 26m
Delta
Sat 7/113:20 pm
SXM
- MKE
1 stop9h 23m
Delta
Deal found 5/31![Delta logo]()
$476
This American Airlines deal was found by Cheapflights users on 5/30. Clicking the “Pick Dates” 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 8/155:50 pm
MKE
- STT
2 stops20h 12m
American Airlines
Sat 8/223:43 pm
STT
- MKE
1 stop8h 16m
American Airlines
Deal found 5/30![American Airlines logo]()
$485
This United Airlines deal was found by Cheapflights users on 6/2. Clicking the “Pick Dates” 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 10/172:20 pm
MKE
- GCM
2 stops22h 10m
United Airlines
Sat 10/241:35 pm
GCM
- MKE
1 stop9h 06m
United Airlines
Deal found 6/2![United Airlines logo]()
$499
This Delta deal was found by Cheapflights users on 5/30. Clicking the “Pick Dates” 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 8/86:00 am
MKE
- SXM
1 stop6h 53m
Delta
Sat 8/153:18 pm
SXM
- MKE
1 stop9h 35m
Delta
Deal found 5/30![Delta logo]()
$483
This American Airlines deal was found by Cheapflights users on 6/1. Clicking the “Pick Dates” 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 8/297:00 am
MKE
- GCM
1 stop7h 17m
American Airlines
Sat 9/53:17 pm
GCM
- MKE
1 stop7h 40m
American Airlines
Deal found 6/1![American Airlines logo]()
$499
This Delta deal was found by Cheapflights users on 5/30. Clicking the “Pick Dates” 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 8/95:34 am
MKE
- SXM
1 stop7h 19m
Delta
Sun 8/163:18 pm
SXM
- MKE
1 stop9h 35m
Delta
Deal found 5/30![Delta logo]()
$483
This American Airlines deal was found by Cheapflights users on 6/2. Clicking the “Pick Dates” 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 8/112:49 pm
MKE
- GCM
2 stops20h 11m
American Airlines
Tue 8/1812:30 pm
GCM
- MKE
1 stop10h 29m
American Airlines
Deal found 6/2![American Airlines logo]()
$504
This American Airlines deal was found by Cheapflights users on 5/31. Clicking the “Pick Dates” 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 8/164:25 pm
MKE
- GCM
2 stops18h 35m
American Airlines
Fri 8/2112:00 pm
GCM
- MKE
2 stops11h 56m
American Airlines
Deal found 5/31![American Airlines logo]()
$504
This United Airlines deal was found by Cheapflights users on 6/3. Clicking the “Pick Dates” 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 7/245:00 am
MKE
- PUJ
1 stop8h 27m
United Airlines
Tue 7/281:50 pm
PUJ
- MKE
1 stop8h 06m
United Airlines
Deal found 6/3![United Airlines logo]()
$611
This Delta deal was found by Cheapflights users on 5/31. Clicking the “Pick Dates” 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 8/125:34 am
MKE
- STT
1 stop7h 00m
Delta
Thu 8/202:49 pm
STT
- MKE
1 stop10h 04m
Delta
Deal found 5/31![Delta logo]()
$535
This Southwest deal was found by Cheapflights users on 5/31. Clicking the “Pick Dates” 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 7/36:35 pm
MKE
- SXM
2 stops19h 30m
Southwest
Sat 7/112:15 pm
SXM
- MKE
2 stops10h 20m
Southwest
Deal found 5/31![Southwest logo]()
$590
This United Airlines deal was found by Cheapflights users on 6/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/77:00 pm
MKE
- AUA
2 stops16h 40m
United Airlines
Thu 11/124:10 pm
AUA
- MKE
1 stop9h 17m
United Airlines
Deal found 6/1![United Airlines logo]()
$632
This American Airlines deal was found by Cheapflights users on 5/31. Clicking the “Pick Dates” 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 9/54:12 pm
MKE
- GCM
2 stops20h 58m
American Airlines
Sat 9/1211:55 am
GCM
- MKE
2 stops24h 56m
American Airlines
Deal found 5/31![American Airlines logo]()
$523
This Delta deal was found by Cheapflights users on 5/31. Clicking the “Pick Dates” 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 8/156:00 am
MKE
- STT
1 stop8h 02m
Delta
Tue 8/252:49 pm
STT
- MKE
1 stop7h 20m
Delta
Deal found 5/31![Delta logo]()
$535
This FlightHub deal was found by Cheapflights users on 6/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/119:36 am
MKE
- ANU
2 stops27h 45m
JetBlue
Tue 8/183:30 pm
ANU
- MKE
2 stops18h 15m
JetBlue
Deal found 6/3![JetBlue logo]()
$914
This United Airlines deal was found by Cheapflights users on 5/31. Clicking the “Pick Dates” 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 10/236:32 pm
MKE
- AUA
2 stops20h 08m
United Airlines
Wed 10/281:50 pm
AUA
- MKE
2 stops11h 19m
United Airlines
Deal found 5/31![United Airlines logo]()
$632
This American Airlines deal was found by Cheapflights users on 6/2. Clicking the “Pick Dates” 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 8/17:01 am
MKE
- GCM
1 stop8h 02m
American Airlines
Tue 8/112:10 pm
GCM
- MKE
2 stops20h 52m
American Airlines
Deal found 6/2![American Airlines logo]()
$525
This Delta deal was found by Cheapflights users on 5/31. Clicking the “Pick Dates” 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 8/175:34 am
MKE
- STT
1 stop7h 00m
Delta
Fri 8/212:49 pm
STT
- MKE
1 stop10h 04m
Delta
Deal found 5/31![Delta logo]()
$535
This Southwest deal was found by Cheapflights users on 6/3. Clicking the “Pick Dates” 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 6/286:25 pm
MKE
- PUJ
2 stops17h 00m
Southwest
Sun 7/53:35 pm
PUJ
- MKE
1 stop8h 40m
Southwest
Deal found 6/3![Southwest logo]()
$689
Last-minute flights from Milwaukee to CaribbeanDiscover last-minute flight deals from Milwaukee to Caribbean. Data last updated June 4, 2026 and is based on user searches.
Discover last-minute flight deals from Milwaukee to Caribbean. Data last updated June 4, 2026 and is based on user searches.
This Delta deal was found by Cheapflights users on 5/30. Clicking the “Pick Dates” 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 6/126:40 pm
MKE
- GCM
1 stop16h 54m
Delta
Wed 6/1712:59 pm
GCM
- MKE
1 stop11h 00m
Delta
Deal found 5/30![Delta logo]()
$541
This CheapOair deal was found by Cheapflights users on 6/2. Clicking the “Pick Dates” 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 7/1512:13 pm
SJU
- MKE
1 stop20h 45m
Frontier
Deal found 6/2![Frontier logo]()
$417
This American Airlines deal was found by Cheapflights users on 5/31. Clicking the “Pick Dates” 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
Tue 6/307:00 am
SJU
- MKE
2 stops12h 20m
American Airlines
Deal found 5/31![American Airlines logo]()
$416
This Delta deal was found by Cheapflights users on 6/1. Clicking the “Pick Dates” 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 6/2912:56 pm
MKE
- SJU
1 stop6h 47m
Delta
Fri 7/35:56 pm
SJU
- MKE
1 stop7h 03m
Delta
Deal found 6/1![Delta logo]()
$380
This American Airlines deal was found by Cheapflights users on 6/3. Clicking the “Pick Dates” 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 6/306:00 am
MKE
- SJU
2 stops11h 25m
American Airlines
Fri 7/106:00 am
SJU
- MKE
2 stops12h 31m
American Airlines
Deal found 6/3![American Airlines logo]()
$409
This American Airlines deal was found by Cheapflights users on 5/30. Clicking the “Pick Dates” 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 7/17:00 am
MKE
- SJU
1 stop14h 45m
American Airlines
Wed 7/87:25 am
SJU
- MKE
1 stop15h 29m
American Airlines
Deal found 5/30![American Airlines logo]()
$371
This Expedia deal was found by Cheapflights users on 6/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/28:53 am
MKE
- SJU
1 stop13h 36m
Frontier
Wed 7/88:37 pm
SJU
- MKE
1 stop12h 21m
Frontier
Deal found 6/1![Frontier logo]()
$396
This Delta deal was found by Cheapflights users on 5/31. Clicking the “Pick Dates” 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 7/36:49 pm
MKE
- SXM
1 stop18h 26m
Delta
Sat 7/113:20 pm
SXM
- MKE
1 stop9h 23m
Delta
Deal found 5/31![Delta logo]()
$476
This American Airlines deal was found by Cheapflights users on 5/31. Clicking the “Pick Dates” 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 7/78:43 am
MKE
- SJU
2 stops13h 16m
American Airlines
Tue 7/147:25 am
SJU
- MKE
1 stop15h 29m
American Airlines
Deal found 5/31![American Airlines logo]()
$398
This American Airlines deal was found by Cheapflights users on 6/3. Clicking the “Pick Dates” 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 7/216:00 am
MKE
- SJU
2 stops11h 24m
American Airlines
Wed 7/297:00 am
SJU
- MKE
1 stop17h 44m
American Airlines
Deal found 6/3![American Airlines logo]()
$406
This Southwest deal was found by Cheapflights users on 5/30. Clicking the “Pick Dates” 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 7/303:15 pm
MKE
- SJU
1 stop7h 25m
Southwest
Tue 8/410:30 am
SJU
- MKE
1 stop6h 50m
Southwest
Deal found 5/30![Southwest logo]()
$365
This American Airlines deal was found by Cheapflights users on 6/3. Clicking the “Pick Dates” 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 7/306:00 am
MKE
- SJU
1 stop15h 57m
American Airlines
Thu 8/67:00 am
SJU
- MKE
1 stop17h 14m
American Airlines
Deal found 6/3![American Airlines logo]()
$366
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 4, 2026.
Search for one-way flight options from Milwaukee to Caribbean. Find affordable one-way fares based on user searches. Data last updated June 4, 2026.
This American Airlines deal was found by Cheapflights users on 6/3. Clicking the “Pick Dates” 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 6/287:00 am
MKE
- SJU
1 stop14h 45m
American Airlines
Deal found 6/3![American Airlines logo]()
$163
This American Airlines deal was found by Cheapflights users on 5/31. Clicking the “Pick Dates” 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
2 stops11h 12m
American Airlines
Deal found 5/31![American Airlines logo]()
$166
This American Airlines deal was found by Cheapflights users on 5/30. Clicking the “Pick Dates” 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 8/47:01 am
MKE
- SJU
2 stops13h 58m
American Airlines
Deal found 5/30![American Airlines logo]()
$167
This American Airlines deal was found by Cheapflights users on 6/3. Clicking the “Pick Dates” 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 8/1912:28 pm
MKE
- SJU
2 stops10h 31m
American Airlines
Deal found 6/3![American Airlines logo]()
$168
This American Airlines deal was found by Cheapflights users on 6/2. Clicking the “Pick Dates” 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 6/2![American Airlines logo]()
$169
This American Airlines deal was found by Cheapflights users on 6/1. Clicking the “Pick Dates” 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 7/46:00 am
MKE
- SJU
2 stops11h 24m
American Airlines
Deal found 6/1![American Airlines logo]()
$188
This Expedia deal was found by Cheapflights users on 5/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/48:43 am
MKE
- SJU
1 stop29h 20m
Frontier
Deal found 5/30![Frontier logo]()
$194
This Southwest deal was found by Cheapflights users on 6/2. Clicking the “Pick Dates” 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 8/211:25 am
MKE
- SJU
1 stop10h 15m
Southwest
Deal found 6/2![Southwest logo]()
$202
This American Airlines deal was found by Cheapflights users on 6/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/106:20 am
MKE
- SJU
2 stops11h 14m
American Airlines
Deal found 6/3![American Airlines logo]()
$203
This American Airlines deal was found by Cheapflights users on 6/2. Clicking the “Pick Dates” 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 7/36:08 am
MKE
- SJU
1 stop16h 40m
American Airlines
Deal found 6/2![American Airlines logo]()
$207
This United Airlines deal was found by Cheapflights users on 6/2. Clicking the “Pick Dates” 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 7/186:20 am
MKE
- STT
2 stops9h 40m
United Airlines
Deal found 6/2![United Airlines logo]()
$208
This Frontier deal was found by Cheapflights users on 6/3. Clicking the “Pick Dates” 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 6/3![Frontier logo]()
$208
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 4, 2026.
Round-trip from | $331 (American Airlines) |
|---|---|
One-way from | $163 (American Airlines) |
Popular in | December |
Cheapest in | October |
Average price | $475 |
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 4, 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
Thu 8/20
11:00 am-11:05 pm
1 stop11h 05m
San Juan Luis Munoz Marin Intl
Mon 8/24
6:30 am-3:25 pm
2 stops9h 55m
$365
MilwaukeeSan Juan
MKE - SJU
MKESJU
Milwaukee-Mitchell
Thu 10/15
10:20 am-12:35 am
1 stop13h 15m
San Juan Luis Munoz Marin Intl
Mon 10/19
9:45 pm-8:55 am
1 stop12h 10m
$365
MilwaukeeSan Juan
MKE - SJU
MKESJU
Milwaukee-Mitchell
Sun 9/13
5:55 am-1:16 pm
1 stop6h 21m
San Juan Luis Munoz Marin Intl
Sun 9/27
12:58 pm-8:52 pm
1 stop8h 54m
$380
MilwaukeeSan Juan
MKE - SJU
MKESJU
Milwaukee-Mitchell
Tue 9/22
6:00 am-8:38 pm
2 stops13h 38m
San Juan Luis Munoz Marin Intl
Sat 9/26
1:00 am-10:00 am
2 stops10h 00m
$401
MilwaukeeSan Juan
MKE - SJU
MKESJU
Milwaukee-Mitchell
Fri 9/25
12:30 pm-11:05 pm
2 stops9h 35m
San Juan Luis Munoz Marin Intl
Sat 10/3
6:25 am-3:05 pm
2 stops9h 40m
$404
MilwaukeeSan Juan
MKE - SJU
MKESJU
Milwaukee-Mitchell
Mon 10/12
7:45 pm-9:05 am
1 stop12h 20m
San Juan Luis Munoz Marin Intl
Sat 10/17
5:30 am-11:40 am
1 stop7h 10m
$404
MilwaukeeSan Juan
MKE - SJU
MKESJU
Milwaukee-Mitchell
Tue 7/21
6:00 am-10:57 pm
1 stop15h 57m
San Juan Luis Munoz Marin Intl
Wed 7/29
7:00 am-11:44 pm
1 stop17h 44m
$406
MilwaukeeSan Juan
MKE - SJU
MKESJU
Milwaukee-Mitchell
Wed 9/16
6:00 am-8:38 pm
2 stops13h 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
Tue 12/1
6:48 pm-4:58 pm
2 stops20h 10m
Saint Thomas Island Cyril E King
Tue 12/8
2:49 pm-11:30 pm
2 stops10h 41m
$420
MilwaukeeSaint Thomas Island
MKE - STT
MKESTT
Milwaukee-Mitchell
Fri 8/14
5:34 am-1:34 pm
1 stop7h 00m
Saint Thomas Island Cyril E King
Thu 8/20
2:49 pm-11:53 pm
1 stop10h 04m
$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-SJU
MKE-STT
MKE-SXM
MKE-GCM
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-STT
MKE-SXM
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 $1,003). 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 4, 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
Crew
8.6
Comfort
8.0
Entertainment
7.5
Boarding
8.1
Overall
8.0
Reviews
1 / 20
10.0
ExcellentWalter,May 2026
LAS - BUR
Food
7.0
Crew
8.6
Comfort
8.0
Entertainment
7.5
Boarding
8.1
Overall
8.0
Reviews
1 / 20
10.0
ExcellentWalter,May 2026
LAS - BUR
Food
7.0
Crew
8.6
Comfort
8.0
Entertainment
7.5
Boarding
8.1
Overall
8.0
Reviews
1 / 20
10.0
ExcellentWalter,May 2026
LAS - BUR
Food
7.0
Crew
8.6
Comfort
8.0
Entertainment
7.5
Boarding
8.1
Overall
8.0
Reviews
1 / 20
10.0
ExcellentWalter,May 2026
LAS - BUR
Food
7.0
Crew
8.6
Comfort
8.0
Entertainment
7.5
Boarding
8.1
Overall
8.0
Reviews
1 / 20
10.0
ExcellentWalter,May 2026
LAS - BUR
Food
7.0
Crew
8.6
Comfort
8.0
Entertainment
7.5
Boarding
8.1
Overall
8.0
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 June 4, 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 4, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$112 | Average$573 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$156 | Average$360 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$225 | Average$554 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$256 | Average$667 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$315 | Average$734 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$547 | Average$841 | FlexibilityNo cancel fee | On-time83% |