$101+ Cheap flights from Milwaukee (MKE) to Caribbean Islands
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 2/18. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — SJU
Mar 6 — Mar 131
1 adult, Economy
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Find cheap flights from Milwaukee to Caribbean Islands with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
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Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from Milwaukee to Caribbean Islands
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Cheapest flights from Milwaukee to Caribbean IslandsExplore the most affordable flight options available from Milwaukee to Caribbean Islands. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 4, 2026.
Explore the most affordable flight options available from Milwaukee to Caribbean Islands. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 4, 2026.
This Frontier deal was found by Cheapflights users on 2/2. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/198:39 am
MKE
- SJU
1 stop13h 14m
Frontier
Tue 2/243:53 am
SJU
- MKE
1 stop13h 51m
Frontier
Deal found 2/2![Frontier logo]()
$244
This Priceline deal was found by Cheapflights users on 2/3. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/174:39 pm
MKE
- SJU
1 stop8h 09m
Frontier
Thu 2/193:53 am
SJU
- MKE
1 stop7h 50m
Frontier
Deal found 2/3![Frontier logo]()
$247
This Delta deal was found by Cheapflights users on 2/4. Clicking the “Pick Dates” 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 2/251:35 pm
MKE
- SJU
1 stop8h 23m
Delta
Wed 3/116:15 am
SJU
- MKE
1 stop6h 58m
Delta
Deal found 2/4![Delta logo]()
$256
This Frontier deal was found by Cheapflights users on 2/2. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/184:39 pm
MKE
- SJU
1 stop8h 14m
Frontier
Thu 2/2610:57 am
SJU
- MKE
1 stop9h 45m
Frontier
Deal found 2/2![Frontier logo]()
$258
This Priceline deal was found by Cheapflights users on 2/3. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/106:35 pm
MKE
- SJU
1 stop6h 28m
Frontier
Sat 3/142:59 pm
SJU
- MKE
1 stop17h 31m
Frontier
Deal found 2/3![Frontier logo]()
$261
This Priceline deal was found by Cheapflights users on 2/4. Clicking the “Pick Dates” 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 2/114:39 pm
MKE
- SJU
1 stop8h 14m
Frontier
Tue 2/243:53 am
SJU
- MKE
1 stop13h 51m
Frontier
Deal found 2/4![Frontier logo]()
$274
This Frontier deal was found by Cheapflights users on 2/4. Clicking the “Pick Dates” 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 3/34:39 pm
MKE
- SJU
1 stop8h 14m
Frontier
Thu 3/123:08 am
SJU
- MKE
1 stop9h 28m
Frontier
Deal found 2/4![Frontier logo]()
$277
This CheapOair deal was found by Cheapflights users on 2/2. 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.
Sat 4/114:00 pm
MKE
- SJU
1 stop7h 51m
Frontier
Sat 4/183:19 pm
SJU
- MKE
1 stop20h 49m
Frontier
Deal found 2/2![Frontier logo]()
$279
This Frontier deal was found by Cheapflights users on 2/4. Clicking the “Pick Dates” 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 3/34:39 pm
MKE
- SJU
1 stop8h 14m
Frontier
Thu 3/1212:07 pm
SJU
- MKE
1 stop8h 59m
Frontier
Deal found 2/4![Frontier logo]()
$280
This CheapOair deal was found by Cheapflights users on 2/3. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/712:03 pm
MKE
- SJU
1 stop9h 45m
Multiple Airlines
Mon 5/116:30 pm
SJU
- MKE
2 stops22h 09m
Multiple Airlines
Deal found 2/3![Multiple Airlines logo]()
$281
This Southwest deal was found by Cheapflights users on 2/3. 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.
Tue 5/55:40 am
MKE
- SJU
1 stop11h 30m
Southwest
Tue 5/123:15 pm
SJU
- MKE
1 stop7h 40m
Southwest
Deal found 2/3![Southwest logo]()
$285
This Frontier deal was found by Cheapflights users on 2/3. 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.
Mon 3/28:11 pm
MKE
- SJU
1 stop11h 43m
Frontier
Tue 3/33:53 am
SJU
- MKE
1 stop13h 51m
Frontier
Deal found 2/3![Frontier logo]()
$288
Best flights from Milwaukee to Caribbean IslandsDiscover carefully curated flight deals from Milwaukee to Caribbean Islands that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated February 4, 2026.
Discover carefully curated flight deals from Milwaukee to Caribbean Islands that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated February 4, 2026.
This United Airlines deal was found by Cheapflights users on 2/3. 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.
Sat 4/2510:45 am
MKE
- SJU
1 stop8h 49m
United Airlines
Tue 4/281:00 am
SJU
- MKE
1 stop10h 10m
United Airlines
Deal found 2/3![United Airlines logo]()
$256
This Southwest deal was found by Cheapflights users on 2/1. 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.
Wed 3/118:50 am
MKE
- SJU
1 stop13h 10m
Southwest
Wed 3/185:15 am
SJU
- MKE
1 stop7h 20m
Southwest
Deal found 2/1![Southwest logo]()
$256
This Kiwi.com deal was found by Cheapflights users on 2/2. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/16:39 pm
MKE
- STT
1 stop17h 52m
Multiple Airlines
Sun 3/82:36 pm
STT
- MKE
2 stops20h 27m
Multiple Airlines
Deal found 2/2![Multiple Airlines logo]()
$338
This Delta deal was found by Cheapflights users on 2/4. Clicking the “Pick Dates” 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 2/2212:20 pm
MKE
- SJU
1 stop9h 38m
Delta
Fri 2/276:15 am
SJU
- MKE
1 stop6h 58m
Delta
Deal found 2/4![Delta logo]()
$338
This American Airlines deal was found by Cheapflights users on 2/1. 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 3/74:47 pm
MKE
- PLS
2 stops17h 13m
American Airlines
Wed 3/111:00 pm
PLS
- MKE
1 stop11h 45m
American Airlines
Deal found 2/1![American Airlines logo]()
$368
This United Airlines deal was found by Cheapflights users on 2/3. 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.
Sat 4/119:43 am
MKE
- SJU
2 stops10h 41m
United Airlines
Fri 4/171:00 am
SJU
- MKE
1 stop10h 15m
United Airlines
Deal found 2/3![United Airlines logo]()
$256
This United Airlines deal was found by Cheapflights users on 2/3. 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.
Tue 5/56:49 am
MKE
- SJU
1 stop6h 55m
United Airlines
Tue 5/127:20 am
SJU
- MKE
2 stops14h 28m
United Airlines
Deal found 2/3![United Airlines logo]()
$256
This United Airlines deal was found by Cheapflights users on 2/1. 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 4/259:43 am
MKE
- SJU
2 stops10h 41m
United Airlines
Fri 5/11:00 am
SJU
- MKE
2 stops9h 45m
United Airlines
Deal found 2/1![United Airlines logo]()
$256
This Southwest deal was found by Cheapflights users on 2/4. Clicking the “Pick Dates” 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 4/1012:40 pm
MKE
- SJU
1 stop10h 15m
Southwest
Tue 4/145:35 am
SJU
- MKE
1 stop10h 40m
Southwest
Deal found 2/4![Southwest logo]()
$310
This Delta deal was found by Cheapflights users on 2/4. Clicking the “Pick Dates” 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 4/205:21 am
MKE
- PLS
1 stop6h 19m
Delta
Fri 4/242:05 pm
PLS
- MKE
1 stop7h 30m
Delta
Deal found 2/4![Delta logo]()
$363
This American Airlines deal was found by Cheapflights users on 2/1. 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 2/283:11 pm
MKE
- PLS
2 stops20h 07m
American Airlines
Fri 3/61:20 pm
PLS
- MKE
2 stops11h 04m
American Airlines
Deal found 2/1![American Airlines logo]()
$370
This American Airlines deal was found by Cheapflights users on 2/1. 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 2/284:47 pm
MKE
- PLS
2 stops18h 31m
American Airlines
Tue 3/31:20 pm
PLS
- MKE
1 stop10h 54m
American Airlines
Deal found 2/1![American Airlines logo]()
$370
This Kiwi.com deal was found by Cheapflights users on 2/2. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/246:35 pm
MKE
- STT
1 stop17h 51m
Multiple Airlines
Mon 3/302:36 pm
STT
- MKE
2 stops23h 26m
Multiple Airlines
Deal found 2/2![Multiple Airlines logo]()
$438
This American Airlines deal was found by Cheapflights users on 2/2. 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.
Sun 3/85:00 am
MKE
- PLS
1 stop7h 21m
American Airlines
Mon 3/303:30 pm
PLS
- MKE
1 stop9h 15m
American Airlines
Deal found 2/2![American Airlines logo]()
$374
This Delta deal was found by Cheapflights users on 2/3. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/275:55 pm
MKE
- GCM
1 stop18h 06m
Delta
Wed 3/41:54 pm
GCM
- MKE
1 stop10h 53m
Delta
Deal found 2/3![Delta logo]()
$424
This Delta deal was found by Cheapflights users on 2/3. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/286:15 am
MKE
- GCM
1 stop7h 16m
Delta
Wed 3/41:54 pm
GCM
- MKE
1 stop10h 53m
Delta
Deal found 2/3![Delta logo]()
$424
This American Airlines deal was found by Cheapflights users on 2/3. 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 2/284:47 pm
MKE
- GCM
1 stop20h 48m
American Airlines
Tue 3/33:35 pm
GCM
- MKE
1 stop8h 22m
American Airlines
Deal found 2/3![American Airlines logo]()
$400
This United Airlines deal was found by Cheapflights users on 2/3. 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.
Thu 2/196:00 am
MKE
- NAS
1 stop8h 22m
United Airlines
Mon 2/233:35 pm
NAS
- MKE
1 stop6h 20m
United Airlines
Deal found 2/3![United Airlines logo]()
$404
This Delta deal was found by Cheapflights users on 2/3. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/185:23 am
MKE
- NAS
1 stop5h 27m
Delta
Mon 2/236:27 pm
NAS
- MKE
1 stop6h 20m
Delta
Deal found 2/3![Delta logo]()
$434
This American Airlines deal was found by Cheapflights users on 2/2. 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 3/74:47 pm
MKE
- GCM
1 stop19h 57m
American Airlines
Sun 3/152:44 pm
GCM
- MKE
1 stop17h 05m
American Airlines
Deal found 2/2![American Airlines logo]()
$436
This Delta deal was found by Cheapflights users on 2/2. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/205:21 am
MKE
- PUJ
1 stop7h 00m
Delta
Thu 4/231:00 pm
PUJ
- MKE
1 stop8h 35m
Delta
Deal found 2/2![Delta logo]()
$439
This United Airlines deal was found by Cheapflights users on 2/2. 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.
Mon 4/205:10 am
MKE
- PUJ
2 stops10h 20m
United Airlines
Thu 4/232:20 pm
PUJ
- MKE
1 stop9h 35m
United Airlines
Deal found 2/2![United Airlines logo]()
$439
This Southwest deal was found by Cheapflights users on 2/2. 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.
Mon 5/47:05 pm
MKE
- SXM
2 stops17h 35m
Southwest
Fri 5/82:35 pm
SXM
- MKE
1 stop9h 15m
Southwest
Deal found 2/2![Southwest logo]()
$610
This American Airlines deal was found by Cheapflights users on 2/3. 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 4/215:29 pm
MKE
- PUJ
1 stop16h 16m
American Airlines
Tue 4/2811:45 am
PUJ
- MKE
1 stop11h 12m
American Airlines
Deal found 2/3![American Airlines logo]()
$439
This United Airlines deal was found by Cheapflights users on 2/3. 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.
Tue 4/75:10 am
MKE
- PUJ
2 stops10h 20m
United Airlines
Tue 4/142:20 pm
PUJ
- MKE
1 stop9h 39m
United Airlines
Deal found 2/3![United Airlines logo]()
$439
This Delta deal was found by Cheapflights users on 2/1. 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.
Tue 4/76:59 pm
MKE
- PUJ
1 stop17h 06m
Delta
Wed 4/151:00 pm
PUJ
- MKE
1 stop11h 57m
Delta
Deal found 2/1![Delta logo]()
$439
This Southwest deal was found by Cheapflights users on 2/1. 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 6/155:00 am
MKE
- SXM
1 stop8h 00m
Southwest
Sun 6/213:35 pm
SXM
- MKE
1 stop9h 00m
Southwest
Deal found 2/1![Southwest logo]()
$625
This American Airlines deal was found by Cheapflights users on 2/3. 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 4/77:08 am
MKE
- PUJ
1 stop8h 17m
American Airlines
Tue 4/1411:45 am
PUJ
- MKE
1 stop11h 12m
American Airlines
Deal found 2/3![American Airlines logo]()
$439
This Delta deal was found by Cheapflights users on 2/1. 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.
Tue 4/77:00 am
MKE
- PUJ
1 stop7h 17m
Delta
Tue 4/142:20 pm
PUJ
- MKE
2 stops19h 30m
Delta
Deal found 2/1![Delta logo]()
$443
This United Airlines deal was found by Cheapflights users on 2/2. 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.
Mon 2/235:00 am
MKE
- NAS
2 stops8h 32m
United Airlines
Mon 3/23:35 pm
NAS
- MKE
1 stop6h 20m
United Airlines
Deal found 2/2![United Airlines logo]()
$452
Last-minute flights from Milwaukee to Caribbean IslandsDiscover last-minute flight deals from Milwaukee to Caribbean Islands. Data last updated February 4, 2026 and is based on user searches.
Discover last-minute flight deals from Milwaukee to Caribbean Islands. Data last updated February 4, 2026 and is based on user searches.
This CheapOair deal was found by Cheapflights users on 2/3. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/711:12 am
MKE
- SJU
1 stop10h 47m
Frontier
Fri 2/133:53 am
SJU
- MKE
1 stop16h 59m
Frontier
Deal found 2/3![Frontier logo]()
$290
This Priceline deal was found by Cheapflights users on 2/4. Clicking the “Pick Dates” 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 2/114:39 pm
MKE
- SJU
1 stop8h 14m
Frontier
Tue 2/243:53 am
SJU
- MKE
1 stop13h 51m
Frontier
Deal found 2/4![Frontier logo]()
$274
This Priceline deal was found by Cheapflights users on 2/3. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/174:39 pm
MKE
- SJU
1 stop8h 09m
Frontier
Thu 2/193:53 am
SJU
- MKE
1 stop7h 50m
Frontier
Deal found 2/3![Frontier logo]()
$247
This Frontier deal was found by Cheapflights users on 2/2. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/184:39 pm
MKE
- SJU
1 stop8h 14m
Frontier
Thu 2/2610:57 am
SJU
- MKE
1 stop9h 45m
Frontier
Deal found 2/2![Frontier logo]()
$258
This Frontier deal was found by Cheapflights users on 2/2. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/198:39 am
MKE
- SJU
1 stop13h 14m
Frontier
Tue 2/243:53 am
SJU
- MKE
1 stop13h 51m
Frontier
Deal found 2/2![Frontier logo]()
$244
This eDestinos deal was found by Cheapflights users on 2/3. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/235:30 pm
MKE
- SJU
2 stops31h 23m
Frontier
Thu 2/264:11 pm
SJU
- MKE
1 stop27h 14m
Frontier
Deal found 2/3![Frontier logo]()
$289
This Delta deal was found by Cheapflights users on 2/4. Clicking the “Pick Dates” 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 2/251:35 pm
MKE
- SJU
1 stop8h 23m
Delta
Wed 3/116:15 am
SJU
- MKE
1 stop6h 58m
Delta
Deal found 2/4![Delta logo]()
$256
This Frontier deal was found by Cheapflights users on 2/4. Clicking the “Pick Dates” 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.
Mon 3/28:11 pm
MKE
- SJU
1 stop11h 43m
Frontier
Wed 3/1110:04 am
SJU
- MKE
1 stop8h 46m
Frontier
Deal found 2/4![Frontier logo]()
$288
This Frontier deal was found by Cheapflights users on 2/4. Clicking the “Pick Dates” 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.
Mon 3/28:11 pm
MKE
- SJU
1 stop11h 43m
Frontier
Thu 3/123:08 am
SJU
- MKE
1 stop9h 28m
Frontier
Deal found 2/4![Frontier logo]()
$291
This Frontier deal was found by Cheapflights users on 2/4. Clicking the “Pick Dates” 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 3/34:39 pm
MKE
- SJU
1 stop8h 14m
Frontier
Thu 3/123:08 am
SJU
- MKE
1 stop9h 28m
Frontier
Deal found 2/4![Frontier logo]()
$277
This Frontier deal was found by Cheapflights users on 2/4. Clicking the “Pick Dates” 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 3/34:39 pm
MKE
- SJU
1 stop8h 14m
Frontier
Thu 3/1212:07 pm
SJU
- MKE
1 stop8h 59m
Frontier
Deal found 2/4![Frontier logo]()
$280
This Priceline deal was found by Cheapflights users on 2/3. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/106:35 pm
MKE
- SJU
1 stop6h 28m
Frontier
Sat 3/142:59 pm
SJU
- MKE
1 stop17h 31m
Frontier
Deal found 2/3![Frontier logo]()
$261
One-way flights from Milwaukee to Caribbean IslandsSearch for one-way flight options from Milwaukee to Caribbean Islands. Find affordable one-way fares based on user searches. Data last updated February 4, 2026.
Search for one-way flight options from Milwaukee to Caribbean Islands. Find affordable one-way fares based on user searches. Data last updated February 4, 2026.
This Priceline deal was found by Cheapflights users on 2/1. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/28:11 pm
MKE
- SJU
1 stop11h 43m
Frontier
Deal found 2/1![Frontier logo]()
$101
This Priceline deal was found by Cheapflights users on 2/1. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/217:47 pm
MKE
- SJU
1 stop29h 06m
Frontier
Deal found 2/1![Frontier logo]()
$107
This Frontier deal was found by Cheapflights users on 2/2. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/238:20 pm
MKE
- SJU
1 stop12h 37m
Frontier
Deal found 2/2![Frontier logo]()
$120
This Priceline deal was found by Cheapflights users on 2/2. 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.
Mon 2/97:01 pm
MKE
- SJU
1 stop15h 56m
Frontier
Deal found 2/2![Frontier logo]()
$122
This Priceline deal was found by Cheapflights users on 2/1. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/168:20 pm
MKE
- SJU
1 stop28h 43m
Frontier
Deal found 2/1![Frontier logo]()
$126
This Delta deal was found by Cheapflights users on 2/1. 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.
Tue 3/1710:09 am
MKE
- SJU
1 stop9h 09m
Delta
Deal found 2/1![Delta logo]()
$128
This CheapOair deal was found by Cheapflights users on 2/3. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/147:47 pm
MKE
- SJU
1 stop27h 07m
Frontier
Deal found 2/3![Frontier logo]()
$143
This Orbitz deal was found by Cheapflights users on 2/3. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/167:52 pm
MKE
- SJU
1 stop12h 02m
Frontier
Deal found 2/3![Frontier logo]()
$146
This Kiwi.com deal was found by Cheapflights users on 2/1. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/25:30 pm
MKE
- SJU
3 stops20h 01m
Multiple Airlines
Deal found 2/1![Multiple Airlines logo]()
$147
This Southwest deal was found by Cheapflights users on 2/1. 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.
Sun 3/151:00 pm
MKE
- SJU
1 stop9h 20m
Southwest
Deal found 2/1![Southwest logo]()
$157
This Priceline deal was found by Cheapflights users on 2/3. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/44:00 pm
MKE
- SJU
1 stop7h 51m
Frontier
Deal found 2/3![Frontier logo]()
$160
This Kiwi.com deal was found by Cheapflights users on 2/3. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/308:20 pm
MKE
- AUA
2 stops17h 15m
Multiple Airlines
Deal found 2/3![Multiple Airlines logo]()
$182
Find flight deals from Milwaukee to Caribbean Islands
Keep the following information in mind while searching for Milwaukee to Caribbean Islands flight deals. Data was last updated February 4, 2026.
Round-trip from | $244 (Frontier) |
|---|---|
One-way from | $101 (Priceline) |
Popular in | December |
Cheapest in | September |
Average price | $420 |
Cheapflights Fare Finder
Customize your flight search to find flights from Milwaukee to Caribbean Islands 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 February 4, 2026.
Use the filters below to find and compare flights from Milwaukee to Caribbean Islands that are best for you.
Fly from
Milwaukee
Fly to
Caribbean Islands
Route
Depart
Return
Price
MilwaukeeSan Juan
MKE - SJU
MKESJU
Milwaukee-Mitchell
Sat 4/25
10:45 am-8:34 pm
1 stop8h 49m
San Juan Luis Munoz Marin Intl
Tue 4/28
1:00 am-10:10 am
1 stop10h 10m
$256
MilwaukeeSan Juan
MKE - SJU
MKESJU
Milwaukee-Mitchell
Wed 3/11
8:50 am-11:00 pm
1 stop13h 10m
San Juan Luis Munoz Marin Intl
Wed 3/18
5:15 am-11:35 am
1 stop7h 20m
$256
MilwaukeeSan Juan
MKE - SJU
MKESJU
Milwaukee-Mitchell
Sat 4/11
9:43 am-9:24 pm
2 stops10h 41m
San Juan Luis Munoz Marin Intl
Fri 4/17
1:00 am-10:15 am
1 stop10h 15m
$256
MilwaukeeSan Juan
MKE - SJU
MKESJU
Milwaukee-Mitchell
Tue 5/5
6:49 am-2:44 pm
1 stop6h 55m
San Juan Luis Munoz Marin Intl
Tue 5/12
7:20 am-8:48 pm
2 stops14h 28m
$256
MilwaukeeSan Juan
MKE - SJU
MKESJU
Milwaukee-Mitchell
Sat 4/25
9:43 am-9:24 pm
2 stops10h 41m
San Juan Luis Munoz Marin Intl
Fri 5/1
1:00 am-9:45 am
2 stops9h 45m
$256
MilwaukeeSan Juan
MKE - SJU
MKESJU
Milwaukee-Mitchell
Fri 4/10
12:40 pm-11:55 pm
1 stop10h 15m
San Juan Luis Munoz Marin Intl
Tue 4/14
5:35 am-3:15 pm
1 stop10h 40m
$310
MilwaukeeSaint Thomas Island
MKE - STT
MKESTT
Milwaukee-Mitchell
Sun 3/1
6:39 pm-2:31 pm
1 stop17h 52m
Saint Thomas Island Cyril E King
Sun 3/8
2:36 pm-10:03 am
2 stops20h 27m
$338
MilwaukeeSan Juan
MKE - SJU
MKESJU
Milwaukee-Mitchell
Sun 2/22
12:20 pm-11:58 pm
1 stop9h 38m
San Juan Luis Munoz Marin Intl
Fri 2/27
6:15 am-11:13 am
1 stop6h 58m
$338
MilwaukeeProvidenciales
MKE - PLS
MKEPLS
Milwaukee-Mitchell
Mon 4/20
5:21 am-12:40 pm
1 stop6h 19m
Providenciales
Fri 4/24
2:05 pm-8:35 pm
1 stop7h 30m
$363
MilwaukeeProvidenciales
MKE - PLS
MKEPLS
Milwaukee-Mitchell
Sat 3/7
4:47 pm-11:00 am
2 stops17h 13m
Providenciales
Wed 3/11
1:00 pm-11:45 pm
1 stop11h 45m
$368
Showing 1-10 of 60 results
Best time to book a flight from Milwaukee to Caribbean Islands
Have a flexible travel schedule? Discover the best time to fly to Caribbean Islands from Milwaukee with our price prediction graph.
MKE-SJU
MKE-AUA
MKE-MBJ
MKE-NAS
MKE-PUJ
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 Islands
MKE-zzEPX
MKE-SJU
MKE-AUA
MKE-MBJ
MKE-NAS
What is the cheapest month to book a flight from Milwaukee to Caribbean Islands?
Currently, April is the cheapest month in which you can book a flight from Milwaukee to Caribbean Islands (average of $91). Flying from Milwaukee to Caribbean Islands in December is currently the most expensive (average of $195). 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.
What is the cheapest time of day to fly from MKE to EPX?
Find hourly flight availability from Milwaukee to Caribbean Islands. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated February 4, 2026.
When flying from Milwaukee to Caribbean Islands, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.
Reviews of airlines servicing Caribbean Islands
Get insights into the airlines that provide service to Caribbean Islands. 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 Islands. Reviews last updated February 4, 2026.
Peruse reviews from past customers who have flown with Southwest, Delta, and United Airlines from Milwaukee to Caribbean Islands to help guide your decision. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Entertainment
7.5
Boarding
8.1
Food
7.0
Comfort
8.0
Crew
8.6
Overall
8.0
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Entertainment
7.5
Boarding
8.1
Food
7.0
Comfort
8.0
Crew
8.6
Overall
8.0
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Entertainment
7.5
Boarding
8.1
Food
7.0
Comfort
8.0
Crew
8.6
Overall
8.0
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Entertainment
7.5
Boarding
8.1
Food
7.0
Comfort
8.0
Crew
8.6
Overall
8.0
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Entertainment
7.5
Boarding
8.1
Food
7.0
Comfort
8.0
Crew
8.6
Overall
8.0
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Entertainment
7.5
Boarding
8.1
Food
7.0
Comfort
8.0
Crew
8.6
Overall
8.0
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Related info for your journey
Find useful and relevant information for your journey from Milwaukee to Caribbean Islands. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
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Alternative routes for Milwaukee to Caribbean Islands
See prices for flight routes from nearby airports that may be better suited for you.
Complete your trip
Complete your trip to Caribbean Islands by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Milwaukee to Caribbean Islands by cabin class
Find flights from Milwaukee to Caribbean Islands, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Milwaukee and Caribbean Islands flights
Browse other Milwaukee and Caribbean Islands flight options. Last updated on February 4, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Milwaukee to Caribbean Islands flights
Consider these flights traveling from Milwaukee to Caribbean Islands.
Top 7 airlines flying from Milwaukee to Caribbean Islands
Discover the top 7 airlines that operate flights from Milwaukee to Caribbean Islands. 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 February 4, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$85 | Average$297 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$118 | Average$614 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$182 | Average$562 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$208 | Average$402 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$266 | Average$670 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$315 | Average$755 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$497 | Average$652 | FlexibilityNo cancel fee | On-time83% |