$101+ 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 3/17. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — SJU
Apr 2 — Apr 91
1 adult, Economy
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Find cheap flights from Milwaukee to Caribbean 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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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 March 3, 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 March 3, 2026.
This American Airlines deal was found by Cheapflights users on 2/26. 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.
Sat 5/26:00 am
MKE
- SJU
1 stop15h 05m
American Airlines
Tue 5/55:45 am
SJU
- MKE
2 stops11h 11m
American Airlines
Deal found 2/26![American Airlines logo]()
$270
This Southwest deal was found by Cheapflights users on 3/1. 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.
Sat 5/92:15 pm
MKE
- SJU
1 stop8h 00m
Southwest
Tue 5/125:05 am
SJU
- MKE
1 stop7h 50m
Southwest
Deal found 3/1![Southwest logo]()
$277
This Priceline deal was found by Cheapflights users on 2/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/238:20 pm
MKE
- SJU
1 stop12h 37m
Frontier
Thu 3/2612:04 pm
SJU
- MKE
1 stop9h 02m
Frontier
Deal found 2/27![Frontier logo]()
$278
This Priceline deal was found by Cheapflights users on 3/2. 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.
Fri 4/177:34 pm
MKE
- SJU
1 stop29h 27m
Frontier
Mon 4/207:15 am
SJU
- MKE
1 stop7h 37m
Frontier
Deal found 3/2![Frontier logo]()
$279
This Frontier deal was found by Cheapflights users on 2/26. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/3012:21 pm
MKE
- SJU
1 stop9h 35m
Frontier
Sat 5/93:08 am
SJU
- MKE
1 stop9h 00m
Frontier
Deal found 2/26![Frontier logo]()
$280
This Priceline deal was found by Cheapflights users on 2/25. 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 Priceline 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
Wed 3/116:30 am
SJU
- MKE
1 stop12h 20m
Frontier
Deal found 2/25![Frontier logo]()
$284
This United Airlines deal was found by Cheapflights users on 2/27. 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.
Tue 4/2110:45 am
MKE
- SJU
2 stops9h 39m
United Airlines
Tue 5/51:00 am
SJU
- MKE
2 stops9h 45m
United Airlines
Deal found 2/27![United Airlines logo]()
$290
This Expedia deal was found by Cheapflights users on 3/1. 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.
Mon 3/912:36 pm
MKE
- SJU
1 stop12h 22m
Frontier
Wed 3/116:30 am
SJU
- MKE
1 stop12h 20m
Frontier
Deal found 3/1![Frontier logo]()
$295
This United Airlines deal was found by Cheapflights users on 3/1. 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.
Tue 4/1410:45 am
MKE
- SJU
2 stops9h 39m
United Airlines
Sat 4/257:40 am
SJU
- MKE
1 stop7h 07m
United Airlines
Deal found 3/1![United Airlines logo]()
$299
This United Airlines deal was found by Cheapflights users on 2/26. 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 5/28:33 am
MKE
- SJU
2 stops14h 17m
United Airlines
Fri 5/81:00 am
SJU
- MKE
2 stops14h 27m
United Airlines
Deal found 2/26![United Airlines logo]()
$300
This CheapOair deal was found by Cheapflights users on 3/1. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/114:15 pm
MKE
- SJU
1 stop7h 36m
Frontier
Wed 4/1510:54 am
SJU
- MKE
1 stop25h 32m
Frontier
Deal found 3/1![Frontier logo]()
$301
This American Airlines deal was found by Cheapflights users on 2/27. 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.
Sat 4/256:40 pm
MKE
- MBJ
1 stop17h 33m
American Airlines
Sat 5/22:10 pm
MBJ
- MKE
1 stop8h 17m
American Airlines
Deal found 2/27![American Airlines logo]()
$312
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 March 3, 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 March 3, 2026.
This United Airlines deal was found by Cheapflights users on 2/27. 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.
Tue 4/2110:45 am
MKE
- SJU
2 stops9h 39m
United Airlines
Tue 5/51:00 am
SJU
- MKE
2 stops9h 45m
United Airlines
Deal found 2/27![United Airlines logo]()
$290
This American Airlines deal was found by Cheapflights users on 2/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/66:42 pm
MKE
- MBJ
1 stop14h 31m
American Airlines
Mon 5/1110:17 am
MBJ
- MKE
1 stop7h 34m
American Airlines
Deal found 2/27![American Airlines logo]()
$312
This Delta deal was found by Cheapflights users on 2/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/245:45 am
MKE
- MBJ
1 stop9h 43m
Delta
Thu 3/264:49 pm
MBJ
- MKE
1 stop16h 15m
Delta
Deal found 2/28![Delta logo]()
$362
This Southwest deal was found by Cheapflights users on 3/2. 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.
Wed 6/39:15 am
MKE
- SJU
1 stop12h 25m
Southwest
Mon 6/810:20 pm
SJU
- MKE
1 stop11h 30m
Southwest
Deal found 3/2![Southwest logo]()
$366
This Faresmojo deal was found by Cheapflights users on 2/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Faresmojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/187:10 am
MKE
- STI
1 stop11h 23m
JetBlue
Sun 4/266:00 am
STI
- MKE
1 stop15h 25m
JetBlue
Deal found 2/28![JetBlue logo]()
$598
This United Airlines deal was found by Cheapflights users on 3/1. 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.
Tue 4/289:43 am
MKE
- SJU
1 stop9h 51m
United Airlines
Tue 5/51:00 am
SJU
- MKE
1 stop10h 04m
United Airlines
Deal found 3/1![United Airlines logo]()
$300
This American Airlines deal was found by Cheapflights users on 3/1. 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 4/256:32 pm
MKE
- MBJ
1 stop14h 41m
American Airlines
Sat 5/21:15 pm
MBJ
- MKE
1 stop10h 25m
American Airlines
Deal found 3/1![American Airlines logo]()
$312
This Sun Country Air deal was found by Cheapflights users on 2/25. 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 Sun Country Air is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/128:00 am
MKE
- PUJ
Nonstop4h 35m
Sun Country Air
Sun 3/152:35 pm
PUJ
- MKE
Nonstop5h 16m
Sun Country Air
Deal found 2/25![Sun Country Air logo]()
$638
This United Airlines deal was found by Cheapflights users on 2/26. 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 5/210:20 am
MKE
- SJU
2 stops12h 30m
United Airlines
Fri 5/81:00 am
SJU
- MKE
1 stop10h 04m
United Airlines
Deal found 2/26![United Airlines logo]()
$300
This American Airlines deal was found by Cheapflights users on 2/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/295:06 am
MKE
- MBJ
2 stops10h 31m
American Airlines
Mon 5/44:37 pm
MBJ
- MKE
2 stops17h 32m
American Airlines
Deal found 2/27![American Airlines logo]()
$326
This Delta deal was found by Cheapflights users on 3/2. 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.
Wed 4/85:49 pm
MKE
- PLS
1 stop17h 11m
Delta
Thu 4/162:05 pm
PLS
- MKE
1 stop10h 52m
Delta
Deal found 3/2![Delta logo]()
$363
This Southwest deal was found by Cheapflights users on 2/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/243:30 pm
MKE
- SJU
1 stop7h 10m
Southwest
Sun 5/39:45 pm
SJU
- MKE
1 stop12h 55m
Southwest
Deal found 2/28![Southwest logo]()
$388
This United Airlines deal was found by Cheapflights users on 2/26. 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.
Fri 5/15:55 am
MKE
- MBJ
2 stops9h 15m
United Airlines
Fri 5/82:40 pm
MBJ
- MKE
2 stops17h 09m
United Airlines
Deal found 2/26![United Airlines logo]()
$322
This Delta deal was found by Cheapflights users on 2/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/135:45 am
MKE
- STT
1 stop7h 02m
Delta
Thu 3/191:55 pm
STT
- MKE
1 stop11h 03m
Delta
Deal found 2/26![Delta logo]()
$400
This United Airlines deal was found by Cheapflights users on 2/27. 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.
Tue 5/58:33 am
MKE
- SJU
2 stops11h 05m
United Airlines
Sat 5/91:00 am
SJU
- MKE
2 stops9h 45m
United Airlines
Deal found 2/27![United Airlines logo]()
$333
This Southwest deal was found by Cheapflights users on 3/3. 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.
Fri 5/17:10 am
MKE
- SJU
2 stops11h 50m
Southwest
Tue 5/1211:25 am
SJU
- MKE
2 stops11h 30m
Southwest
Deal found 3/3![Southwest logo]()
$408
This American Airlines deal was found by Cheapflights users on 2/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/126:44 am
MKE
- STT
2 stops8h 45m
American Airlines
Mon 3/161:13 pm
STT
- MKE
1 stop8h 12m
American Airlines
Deal found 2/25![American Airlines logo]()
$400
This Delta deal was found by Cheapflights users on 2/25. 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.
Thu 3/125:45 am
MKE
- STT
1 stop7h 02m
Delta
Mon 3/161:55 pm
STT
- MKE
1 stop8h 00m
Delta
Deal found 2/25![Delta logo]()
$400
This Southwest deal was found by Cheapflights users on 2/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/276:25 am
MKE
- SJU
2 stops9h 30m
Southwest
Mon 8/312:35 pm
SJU
- MKE
1 stop7h 10m
Southwest
Deal found 2/28![Southwest logo]()
$412
This Delta deal was found by Cheapflights users on 2/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/125:45 am
MKE
- STT
1 stop7h 02m
Delta
Thu 3/191:55 pm
STT
- MKE
1 stop8h 00m
Delta
Deal found 2/26![Delta logo]()
$400
This United Airlines deal was found by Cheapflights users on 3/1. 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.
Tue 4/2810:45 am
MKE
- SJU
2 stops9h 39m
United Airlines
Wed 5/61:00 am
SJU
- MKE
2 stops14h 27m
United Airlines
Deal found 3/1![United Airlines logo]()
$367
This American Airlines deal was found by Cheapflights users on 2/27. 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.
Sat 4/116:40 pm
MKE
- MBJ
1 stop17h 33m
American Airlines
Sat 4/1810:13 am
MBJ
- MKE
1 stop12h 44m
American Airlines
Deal found 2/27![American Airlines logo]()
$415
This Southwest deal was found by Cheapflights users on 3/2. 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.
Thu 4/97:10 am
MKE
- SJU
2 stops11h 50m
Southwest
Tue 4/145:35 am
SJU
- MKE
1 stop10h 40m
Southwest
Deal found 3/2![Southwest logo]()
$426
This United Airlines deal was found by Cheapflights users on 2/26. 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 4/116:50 am
MKE
- MBJ
1 stop6h 00m
United Airlines
Sat 4/181:52 pm
MBJ
- MKE
1 stop7h 57m
United Airlines
Deal found 2/26![United Airlines logo]()
$378
This Delta deal was found by Cheapflights users on 2/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/2810:13 am
MKE
- SJU
1 stop11h 04m
Delta
Tue 6/26:15 am
SJU
- MKE
1 stop10h 57m
Delta
Deal found 2/26![Delta logo]()
$426
This United Airlines deal was found by Cheapflights users on 2/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/186:05 am
MKE
- MBJ
2 stops9h 05m
United Airlines
Sat 7/254:33 pm
MBJ
- MKE
1 stop17h 32m
United Airlines
Deal found 2/28![United Airlines logo]()
$385
This Delta deal was found by Cheapflights users on 3/2. 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.
Thu 4/97:00 am
MKE
- PLS
1 stop6h 30m
Delta
Wed 4/152:55 pm
PLS
- MKE
2 stops20h 18m
Delta
Deal found 3/2![Delta logo]()
$431
This Southwest deal was found by Cheapflights users on 3/1. 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 4/157:35 am
MKE
- NAS
2 stops9h 55m
Southwest
Wed 4/222:10 pm
NAS
- MKE
2 stops8h 35m
Southwest
Deal found 3/1![Southwest logo]()
$487
This American Airlines deal was found by Cheapflights users on 2/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/214:47 pm
MKE
- PLS
2 stops18h 31m
American Airlines
Thu 3/263:25 pm
PLS
- MKE
2 stops19h 36m
American Airlines
Deal found 2/28![American Airlines logo]()
$498
This United Airlines deal was found by Cheapflights users on 2/26. 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 4/259:43 am
MKE
- SJU
2 stops13h 07m
United Airlines
Fri 5/11:00 am
SJU
- MKE
2 stops14h 27m
United Airlines
Deal found 2/26![United Airlines logo]()
$401
Last-minute flights from Milwaukee to CaribbeanDiscover last-minute flight deals from Milwaukee to Caribbean. Data last updated March 3, 2026 and is based on user searches.
Discover last-minute flight deals from Milwaukee to Caribbean. Data last updated March 3, 2026 and is based on user searches.
This Priceline deal was found by Cheapflights users on 2/25. 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 Priceline 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
Wed 3/116:30 am
SJU
- MKE
1 stop12h 20m
Frontier
Deal found 2/25![Frontier logo]()
$284
This Frontier deal was found by Cheapflights users on 2/25. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/44:39 pm
MKE
- SJU
1 stop8h 14m
Frontier
Thu 3/126:30 am
SJU
- MKE
1 stop14h 36m
Frontier
Deal found 2/25![Frontier logo]()
$270
This Expedia deal was found by Cheapflights users on 3/1. 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.
Mon 3/912:36 pm
MKE
- SJU
1 stop12h 22m
Frontier
Wed 3/116:30 am
SJU
- MKE
1 stop12h 20m
Frontier
Deal found 3/1![Frontier logo]()
$295
This Priceline deal was found by Cheapflights users on 2/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/238:20 pm
MKE
- SJU
1 stop12h 37m
Frontier
Thu 3/2612:04 pm
SJU
- MKE
1 stop9h 02m
Frontier
Deal found 2/27![Frontier logo]()
$278
This CheapOair deal was found by Cheapflights users on 3/1. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/114:15 pm
MKE
- SJU
1 stop7h 36m
Frontier
Wed 4/1510:54 am
SJU
- MKE
1 stop25h 32m
Frontier
Deal found 3/1![Frontier logo]()
$301
This United Airlines deal was found by Cheapflights users on 3/1. 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.
Tue 4/1410:45 am
MKE
- SJU
2 stops9h 39m
United Airlines
Sat 4/257:40 am
SJU
- MKE
1 stop7h 07m
United Airlines
Deal found 3/1![United Airlines logo]()
$299
This United Airlines deal was found by Cheapflights users on 3/1. 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.
Tue 4/1412:13 pm
MKE
- SJU
2 stops10h 37m
United Airlines
Wed 4/221:00 am
SJU
- MKE
2 stops11h 32m
United Airlines
Deal found 3/1![United Airlines logo]()
$300
This Priceline deal was found by Cheapflights users on 3/2. 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.
Fri 4/177:34 pm
MKE
- SJU
1 stop29h 27m
Frontier
Mon 4/207:15 am
SJU
- MKE
1 stop7h 37m
Frontier
Deal found 3/2![Frontier logo]()
$279
This United Airlines deal was found by Cheapflights users on 2/27. 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.
Tue 4/2110:45 am
MKE
- SJU
2 stops9h 39m
United Airlines
Tue 5/51:00 am
SJU
- MKE
2 stops9h 45m
United Airlines
Deal found 2/27![United Airlines logo]()
$290
This American Airlines deal was found by Cheapflights users on 2/27. 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.
Sat 4/256:40 pm
MKE
- MBJ
1 stop17h 33m
American Airlines
Sat 5/22:10 pm
MBJ
- MKE
1 stop8h 17m
American Airlines
Deal found 2/27![American Airlines logo]()
$312
This Southwest deal was found by Cheapflights users on 2/27. 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.
Tue 4/2811:30 am
MKE
- SJU
2 stops11h 10m
Southwest
Sat 5/26:25 am
SJU
- MKE
1 stop8h 55m
Southwest
Deal found 2/27![Southwest logo]()
$277
This Frontier deal was found by Cheapflights users on 2/26. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/3012:21 pm
MKE
- SJU
1 stop9h 35m
Frontier
Sat 5/93:08 am
SJU
- MKE
1 stop9h 00m
Frontier
Deal found 2/26![Frontier logo]()
$280
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 March 3, 2026.
Search for one-way flight options from Milwaukee to Caribbean. Find affordable one-way fares based on user searches. Data last updated March 3, 2026.
This Orbitz deal was found by Cheapflights users on 3/2. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/176:35 pm
MKE
- SJU
1 stop6h 28m
Frontier
Deal found 3/2![Frontier logo]()
$101
This American Airlines deal was found by Cheapflights users on 2/26. 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.
Wed 5/136:00 am
MKE
- SJU
1 stop15h 05m
American Airlines
Deal found 2/26![American Airlines logo]()
$105
This Travelocity deal was found by Cheapflights users on 2/26. 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/187:53 pm
MKE
- SJU
1 stop26h 36m
Frontier
Deal found 2/26![Frontier logo]()
$107
This Sun Country Air deal was found by Cheapflights users on 2/26. 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 Sun Country Air is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/48:00 am
MKE
- PUJ
Nonstop4h 35m
Sun Country Air
Deal found 2/26![Sun Country Air logo]()
$116
This Delta deal was found by Cheapflights users on 2/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/1512:33 pm
MKE
- SJU
1 stop9h 39m
Delta
Deal found 2/28![Delta logo]()
$118
This Frontier deal was found by Cheapflights users on 2/26. 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 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 2/26![Frontier logo]()
$120
This American Airlines deal was found by Cheapflights users on 3/1. 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.
Thu 4/96:41 pm
MKE
- MBJ
1 stop14h 32m
American Airlines
Deal found 3/1![American Airlines logo]()
$132
This Southwest deal was found by Cheapflights users on 2/27. 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.
Wed 5/139:15 am
MKE
- SJU
1 stop12h 25m
Southwest
Deal found 2/27![Southwest logo]()
$133
This American Airlines deal was found by Cheapflights users on 2/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/275:00 am
MKE
- SJU
2 stops12h 25m
American Airlines
Deal found 2/28![American Airlines logo]()
$136
This Priceline deal was found by Cheapflights users on 2/25. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/35:44 pm
MKE
- SJU
1 stop13h 08m
Frontier
Deal found 2/25![Frontier logo]()
$138
This United Airlines deal was found by Cheapflights users on 2/26. 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 4/189:43 am
MKE
- SJU
2 stops13h 07m
United Airlines
Deal found 2/26![United Airlines logo]()
$150
This Priceline deal was found by Cheapflights users on 3/1. 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 3/1![Frontier logo]()
$154
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 March 3, 2026.
Round-trip from | $270 (American Airlines) |
|---|---|
One-way from | $101 (Orbitz) |
Popular in | December |
Cheapest in | September |
Average price | $464 |
Good round-trip deal | $488 or less |
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 March 3, 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
MilwaukeeSan Juan
MKE - SJU
MKESJU
Milwaukee-Mitchell
Tue 4/21
10:45 am-9:24 pm
2 stops9h 39m
San Juan Luis Munoz Marin Intl
Tue 5/5
1:00 am-9:45 am
2 stops9h 45m
$290
MilwaukeeSan Juan
MKE - SJU
MKESJU
Milwaukee-Mitchell
Tue 4/28
9:43 am-8:34 pm
1 stop9h 51m
San Juan Luis Munoz Marin Intl
Tue 5/5
1:00 am-10:04 am
1 stop10h 04m
$300
MilwaukeeSan Juan
MKE - SJU
MKESJU
Milwaukee-Mitchell
Sat 5/2
10:20 am-11:50 pm
2 stops12h 30m
San Juan Luis Munoz Marin Intl
Fri 5/8
1:00 am-10:04 am
1 stop10h 04m
$300
MilwaukeeMontego Bay
MKE - MBJ
MKEMBJ
Milwaukee-Mitchell
Wed 5/6
6:42 pm-9:13 am
1 stop14h 31m
Montego Bay Sangster Intl
Mon 5/11
10:17 am-5:51 pm
1 stop7h 34m
$312
MilwaukeeMontego Bay
MKE - MBJ
MKEMBJ
Milwaukee-Mitchell
Sat 4/25
6:32 pm-9:13 am
1 stop14h 41m
Montego Bay Sangster Intl
Sat 5/2
1:15 pm-11:40 pm
1 stop10h 25m
$312
MilwaukeeMontego Bay
MKE - MBJ
MKEMBJ
Milwaukee-Mitchell
Fri 5/1
5:55 am-3:10 pm
2 stops9h 15m
Montego Bay Sangster Intl
Fri 5/8
2:40 pm-7:49 am
2 stops17h 09m
$322
MilwaukeeMontego Bay
MKE - MBJ
MKEMBJ
Milwaukee-Mitchell
Wed 4/29
5:06 am-3:37 pm
2 stops10h 31m
Montego Bay Sangster Intl
Mon 5/4
4:37 pm-10:09 am
2 stops17h 32m
$326
MilwaukeeSan Juan
MKE - SJU
MKESJU
Milwaukee-Mitchell
Tue 5/5
8:33 am-8:38 pm
2 stops11h 05m
San Juan Luis Munoz Marin Intl
Sat 5/9
1:00 am-9:45 am
2 stops9h 45m
$333
MilwaukeeMontego Bay
MKE - MBJ
MKEMBJ
Milwaukee-Mitchell
Tue 3/24
5:45 am-3:28 pm
1 stop9h 43m
Montego Bay Sangster Intl
Thu 3/26
4:49 pm-9:04 am
1 stop16h 15m
$362
MilwaukeeProvidenciales
MKE - PLS
MKEPLS
Milwaukee-Mitchell
Wed 4/8
5:49 pm-12:00 pm
1 stop17h 11m
Providenciales
Thu 4/16
2:05 pm-11:57 pm
1 stop10h 52m
$363
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-STI
MKE-PUJ
MKE-PLS
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-STI
MKE-PUJ
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 $91). Flying from Milwaukee to Caribbean 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 CB?
Find hourly flight availability from Milwaukee to Caribbean. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated March 3, 2026.
When flying from Milwaukee to Caribbean, 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
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 March 3, 2026.
Read through reviews of airlines operating flights from Milwaukee to Caribbean, such as Southwest, Delta, and United Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Crew
8.6
Entertainment
7.5
Boarding
8.1
Overall
8.0
Comfort
8.0
Food
7.0
Reviews
1 / 20
8.0
ExcellentAnonymous,Feb 2026
DEN - BDL
Crew
8.6
Entertainment
7.5
Boarding
8.1
Overall
8.0
Comfort
8.0
Food
7.0
Reviews
1 / 20
8.0
ExcellentAnonymous,Feb 2026
DEN - BDL
Crew
8.6
Entertainment
7.5
Boarding
8.1
Overall
8.0
Comfort
8.0
Food
7.0
Reviews
1 / 20
8.0
ExcellentAnonymous,Feb 2026
DEN - BDL
Crew
8.6
Entertainment
7.5
Boarding
8.1
Overall
8.0
Comfort
8.0
Food
7.0
Reviews
1 / 20
8.0
ExcellentAnonymous,Feb 2026
DEN - BDL
Crew
8.6
Entertainment
7.5
Boarding
8.1
Overall
8.0
Comfort
8.0
Food
7.0
Reviews
1 / 20
8.0
ExcellentAnonymous,Feb 2026
DEN - BDL
Crew
8.6
Entertainment
7.5
Boarding
8.1
Overall
8.0
Comfort
8.0
Food
7.0
Reviews
1 / 20
8.0
ExcellentAnonymous,Feb 2026
DEN - BDL
Related info for your journey
Find useful and relevant information for your journey from Milwaukee to Caribbean. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
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Alternative routes for Milwaukee to Caribbean
See prices for flight routes from nearby airports that may be better suited for you.
Complete your trip
Complete your trip to Caribbean by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Milwaukee to Caribbean by cabin class
Find flights from Milwaukee to Caribbean, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Milwaukee and Caribbean flights
Browse other Milwaukee and Caribbean flight options. Last updated on March 3, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Fly to Caribbean countries
Consider these flights traveling to countries located in Caribbean.
Milwaukee to Caribbean flights
Consider these flights traveling from Milwaukee to Caribbean.
Top 7 airlines flying from Milwaukee to Caribbean
Discover the top 7 airlines that operate flights from Milwaukee to Caribbean. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated March 3, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$101 | Average$333 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$112 | Average$589 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$158 | Average$556 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$208 | Average$368 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$256 | Average$668 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$315 | Average$723 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$497 | Average$828 | FlexibilityNo cancel fee | On-time83% |