$101+ Cheap flights from Caribbean to Milwaukee (MKE)
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 2/24. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — MKE
Mar 14 — Mar 211
1 adult, Economy
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Find cheap flights from Caribbean to Milwaukee with Cheapflights
1. Tell us where you want to go
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Cheapest flights from Caribbean to MilwaukeeExplore the most affordable flight options available from Caribbean to Milwaukee. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 12, 2026.
Explore the most affordable flight options available from Caribbean to Milwaukee. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 12, 2026.
This Expedia deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” 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.
Wed 4/293:08 am
SJU
- MKE
1 stop9h 00m
Frontier
Sat 5/167:42 pm
MKE
- SJU
1 stop18h 00m
Frontier
Deal found 2/9![Frontier logo]()
$223
This Travelocity deal was found by Cheapflights users on 2/11. Clicking the “Pick Dates” 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.
Thu 2/193:53 am
SJU
- MKE
1 stop7h 50m
Frontier
Sun 2/226:37 pm
MKE
- SJU
1 stop13h 17m
Frontier
Deal found 2/11![Frontier logo]()
$244
This Delta deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” 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 5/1812:50 pm
SJU
- MKE
1 stop9h 12m
Delta
Sat 5/302:55 pm
MKE
- SJU
1 stop6h 22m
Delta
Deal found 2/9![Delta logo]()
$256
This CheapOair deal was found by Cheapflights users on 2/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/43:53 am
SJU
- MKE
1 stop16h 49m
Frontier
Sun 3/89:01 pm
MKE
- SJU
1 stop10h 53m
Frontier
Deal found 2/11![Frontier logo]()
$259
This American Airlines deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” 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 4/153:19 pm
SJU
- MKE
1 stop7h 22m
American Airlines
Wed 4/297:01 am
MKE
- SJU
2 stops10h 09m
American Airlines
Deal found 2/9![American Airlines logo]()
$261
This Delta deal was found by Cheapflights users on 2/11. Clicking the “Pick Dates” 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 4/157:30 am
SJU
- MKE
1 stop7h 22m
Delta
Wed 4/2912:32 pm
MKE
- SJU
1 stop6h 52m
Delta
Deal found 2/11![Delta logo]()
$266
This CheapOair deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” 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 2/194:25 pm
SJU
- MKE
1 stop19h 18m
Frontier
Mon 2/238:11 pm
MKE
- SJU
1 stop26h 32m
Frontier
Deal found 2/10![Frontier logo]()
$272
This Frontier deal was found by Cheapflights users on 2/11. Clicking the “Pick Dates” 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 2/233:53 am
SJU
- MKE
1 stop13h 51m
Frontier
Tue 3/176:35 pm
MKE
- SJU
1 stop6h 28m
Frontier
Deal found 2/11![Frontier logo]()
$288
This CheapOair deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” 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.
Tue 3/35:25 pm
SJU
- MKE
1 stop24h 19m
Frontier
Wed 3/116:35 pm
MKE
- SJU
1 stop6h 23m
Frontier
Deal found 2/10![Frontier logo]()
$312
This American Airlines deal was found by Cheapflights users on 2/11. Clicking the “Pick Dates” 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 3/181:27 pm
MBJ
- MKE
1 stop10h 32m
American Airlines
Wed 3/256:20 am
MKE
- MBJ
1 stop7h 44m
American Airlines
Deal found 2/11![American Airlines logo]()
$393
This United Airlines deal was found by Cheapflights users on 2/11. Clicking the “Pick Dates” 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 3/181:48 pm
MBJ
- MKE
1 stop8h 02m
United Airlines
Wed 3/251:25 pm
MKE
- MBJ
2 stops23h 40m
United Airlines
Deal found 2/11![United Airlines logo]()
$394
This United Airlines deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” 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 3/272:20 pm
MBJ
- MKE
2 stops31h 30m
United Airlines
Fri 4/37:22 pm
MKE
- MBJ
2 stops18h 08m
United Airlines
Deal found 2/10![United Airlines logo]()
$425
Best flights from Caribbean to MilwaukeeDiscover carefully curated flight deals from Caribbean to Milwaukee that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated February 12, 2026.
Discover carefully curated flight deals from Caribbean to Milwaukee that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated February 12, 2026.
This CheapOair deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/43:53 am
SJU
- MKE
1 stop16h 49m
Frontier
Sun 3/89:01 pm
MKE
- SJU
1 stop10h 53m
Frontier
Deal found 2/10![Frontier logo]()
$259
This Delta deal was found by Cheapflights users on 2/11. Clicking the “Pick Dates” 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 4/157:30 am
SJU
- MKE
1 stop7h 22m
Delta
Wed 4/2912:32 pm
MKE
- SJU
1 stop6h 52m
Delta
Deal found 2/11![Delta logo]()
$266
This American Airlines deal was found by Cheapflights users on 2/11. Clicking the “Pick Dates” 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 5/84:30 pm
SJU
- MKE
1 stop7h 17m
American Airlines
Sat 5/166:00 am
MKE
- SJU
1 stop15h 05m
American Airlines
Deal found 2/11![American Airlines logo]()
$266
This United Airlines deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” 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 4/307:40 am
SJU
- MKE
1 stop7h 47m
United Airlines
Sat 5/169:23 am
MKE
- SJU
2 stops13h 27m
United Airlines
Deal found 2/9![United Airlines logo]()
$324
This Booking.com deal was found by Cheapflights users on 2/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/23:35 pm
PUJ
- MKE
Nonstop5h 16m
Sun Country Air
Mon 3/98:00 am
MKE
- PUJ
Nonstop4h 35m
Sun Country Air
Deal found 2/8![Sun Country Air logo]()
$512
This Delta deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” 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 5/222:20 pm
SJU
- MKE
1 stop7h 42m
Delta
Mon 5/2510:10 am
MKE
- SJU
1 stop11h 07m
Delta
Deal found 2/9![Delta logo]()
$266
This Priceline deal was found by Cheapflights users on 2/8. Clicking the “Pick Dates” 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 3/23:35 pm
PUJ
- MKE
Nonstop5h 16m
Multiple Airlines
Mon 3/910:48 am
MKE
- PUJ
1 stop26h 29m
Multiple Airlines
Deal found 2/8![Multiple Airlines logo]()
$539
This American Airlines deal was found by Cheapflights users on 2/11. Clicking the “Pick Dates” 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 4/156:00 am
SJU
- MKE
1 stop7h 32m
American Airlines
Wed 4/296:00 am
MKE
- SJU
2 stops11h 10m
American Airlines
Deal found 2/11![American Airlines logo]()
$273
This Frontier deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” 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 2/233:53 am
SJU
- MKE
1 stop13h 51m
Frontier
Tue 3/176:35 pm
MKE
- SJU
1 stop6h 28m
Frontier
Deal found 2/9![Frontier logo]()
$309
This United Airlines deal was found by Cheapflights users on 2/11. Clicking the “Pick Dates” 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 3/181:48 pm
MBJ
- MKE
1 stop8h 02m
United Airlines
Wed 3/251:25 pm
MKE
- MBJ
2 stops23h 40m
United Airlines
Deal found 2/11![United Airlines logo]()
$394
This American Airlines deal was found by Cheapflights users on 2/11. Clicking the “Pick Dates” 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 3/181:27 pm
MBJ
- MKE
1 stop10h 32m
American Airlines
Wed 3/256:20 am
MKE
- MBJ
1 stop7h 44m
American Airlines
Deal found 2/11![American Airlines logo]()
$393
This United Airlines deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” 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 3/272:20 pm
MBJ
- MKE
2 stops31h 30m
United Airlines
Fri 4/37:22 pm
MKE
- MBJ
2 stops18h 08m
United Airlines
Deal found 2/10![United Airlines logo]()
$425
This United Airlines deal was found by Cheapflights users on 2/8. Clicking the “Pick Dates” 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 2/262:55 pm
PUJ
- MKE
1 stop8h 49m
United Airlines
Mon 3/26:00 am
MKE
- PUJ
2 stops9h 25m
United Airlines
Deal found 2/8![United Airlines logo]()
$501
This American Airlines deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” 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 3/2712:28 pm
MBJ
- MKE
1 stop11h 17m
American Airlines
Fri 4/35:04 am
MKE
- MBJ
1 stop7h 07m
American Airlines
Deal found 2/10![American Airlines logo]()
$512
This American Airlines deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” 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 3/111:07 am
MBJ
- MKE
1 stop13h 07m
American Airlines
Wed 3/117:06 am
MKE
- MBJ
1 stop6h 20m
American Airlines
Deal found 2/10![American Airlines logo]()
$549
This American Airlines deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” 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 3/111:07 am
MBJ
- MKE
1 stop13h 07m
American Airlines
Tue 3/176:20 am
MKE
- MBJ
1 stop7h 44m
American Airlines
Deal found 2/10![American Airlines logo]()
$549
This United Airlines deal was found by Cheapflights users on 2/8. Clicking the “Pick Dates” 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 3/1712:30 am
POS
- MKE
2 stops13h 05m
United Airlines
Sun 3/297:22 pm
MKE
- POS
2 stops27h 01m
United Airlines
Deal found 2/8![United Airlines logo]()
$634
This United Airlines deal was found by Cheapflights users on 2/8. Clicking the “Pick Dates” 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 3/1612:30 am
POS
- MKE
2 stops13h 05m
United Airlines
Mon 3/307:22 pm
MKE
- POS
2 stops27h 01m
United Airlines
Deal found 2/8![United Airlines logo]()
$634
This United Airlines deal was found by Cheapflights users on 2/8. Clicking the “Pick Dates” 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 3/1212:30 am
POS
- MKE
2 stops14h 09m
United Airlines
Thu 3/2611:30 am
MKE
- POS
2 stops34h 53m
United Airlines
Deal found 2/8![United Airlines logo]()
$634
This United Airlines deal was found by Cheapflights users on 2/8. Clicking the “Pick Dates” 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 3/1112:30 am
POS
- MKE
1 stop15h 39m
United Airlines
Wed 4/18:00 am
MKE
- POS
1 stop14h 23m
United Airlines
Deal found 2/8![United Airlines logo]()
$634
This United Airlines deal was found by Cheapflights users on 2/8. Clicking the “Pick Dates” 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 3/1712:30 am
POS
- MKE
1 stop15h 39m
United Airlines
Wed 4/18:00 am
MKE
- POS
1 stop14h 23m
United Airlines
Deal found 2/8![United Airlines logo]()
$634
This United Airlines deal was found by Cheapflights users on 2/8. Clicking the “Pick Dates” 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 3/1612:30 am
POS
- MKE
1 stop15h 39m
United Airlines
Wed 4/18:00 am
MKE
- POS
1 stop14h 23m
United Airlines
Deal found 2/8![United Airlines logo]()
$634
This United Airlines deal was found by Cheapflights users on 2/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/1512:30 am
POS
- MKE
2 stops22h 20m
United Airlines
Wed 4/18:00 am
MKE
- POS
1 stop14h 23m
United Airlines
Deal found 2/8![United Airlines logo]()
$634
This United Airlines deal was found by Cheapflights users on 2/8. Clicking the “Pick Dates” 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 3/1212:30 am
POS
- MKE
2 stops21h 15m
United Airlines
Tue 3/316:50 am
MKE
- POS
2 stops15h 33m
United Airlines
Deal found 2/8![United Airlines logo]()
$634
This United Airlines deal was found by Cheapflights users on 2/8. Clicking the “Pick Dates” 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 3/1112:30 am
POS
- MKE
1 stop15h 39m
United Airlines
Tue 3/316:50 am
MKE
- POS
2 stops15h 33m
United Airlines
Deal found 2/8![United Airlines logo]()
$634
This United Airlines deal was found by Cheapflights users on 2/8. Clicking the “Pick Dates” 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 3/1112:30 am
POS
- MKE
2 stops14h 09m
United Airlines
Thu 3/2611:30 am
MKE
- POS
2 stops34h 53m
United Airlines
Deal found 2/8![United Airlines logo]()
$634
This United Airlines deal was found by Cheapflights users on 2/8. Clicking the “Pick Dates” 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 3/1612:30 am
POS
- MKE
2 stops14h 09m
United Airlines
Thu 3/2611:30 am
MKE
- POS
2 stops34h 53m
United Airlines
Deal found 2/8![United Airlines logo]()
$634
This United Airlines deal was found by Cheapflights users on 2/8. Clicking the “Pick Dates” 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 3/610:30 am
CPX
- MKE
2 stops36h 51m
United Airlines
Mon 3/97:00 am
MKE
- CPX
2 stops8h 13m
United Airlines
Deal found 2/8![United Airlines logo]()
$2,854
Last-minute flights from Caribbean to MilwaukeeDiscover last-minute flight deals from Caribbean to Milwaukee. Data last updated February 12, 2026 and is based on user searches.
Discover last-minute flight deals from Caribbean to Milwaukee. Data last updated February 12, 2026 and is based on user searches.
This Travelocity deal was found by Cheapflights users on 2/11. Clicking the “Pick Dates” 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.
Thu 2/193:53 am
SJU
- MKE
1 stop7h 50m
Frontier
Sun 2/226:37 pm
MKE
- SJU
1 stop13h 17m
Frontier
Deal found 2/11![Frontier logo]()
$244
This CheapOair deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” 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 2/194:25 pm
SJU
- MKE
1 stop19h 18m
Frontier
Mon 2/238:11 pm
MKE
- SJU
1 stop26h 32m
Frontier
Deal found 2/10![Frontier logo]()
$272
This Frontier deal was found by Cheapflights users on 2/11. Clicking the “Pick Dates” 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 2/233:53 am
SJU
- MKE
1 stop13h 51m
Frontier
Tue 3/176:35 pm
MKE
- SJU
1 stop6h 28m
Frontier
Deal found 2/11![Frontier logo]()
$288
This United Airlines deal was found by Cheapflights users on 2/8. Clicking the “Pick Dates” 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 2/262:55 pm
PUJ
- MKE
1 stop8h 49m
United Airlines
Mon 3/26:00 am
MKE
- PUJ
1 stop8h 02m
United Airlines
Deal found 2/8![United Airlines logo]()
$496
This CheapOair deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” 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.
Tue 3/35:25 pm
SJU
- MKE
1 stop24h 19m
Frontier
Wed 3/116:35 pm
MKE
- SJU
1 stop6h 23m
Frontier
Deal found 2/10![Frontier logo]()
$312
This CheapOair deal was found by Cheapflights users on 2/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/43:53 am
SJU
- MKE
1 stop16h 49m
Frontier
Sun 3/89:01 pm
MKE
- SJU
1 stop10h 53m
Frontier
Deal found 2/11![Frontier logo]()
$259
This American Airlines deal was found by Cheapflights users on 2/11. Clicking the “Pick Dates” 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 3/52:23 pm
SJU
- MKE
2 stops11h 32m
American Airlines
Sun 3/86:38 am
MKE
- SJU
1 stop15h 20m
American Airlines
Deal found 2/11![American Airlines logo]()
$266
This Priceline deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” 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.
Sun 3/86:30 am
SJU
- MKE
1 stop30h 11m
Frontier
Wed 3/116:35 pm
MKE
- SJU
1 stop6h 23m
Frontier
Deal found 2/10![Frontier logo]()
$316
This American Airlines deal was found by Cheapflights users on 2/11. Clicking the “Pick Dates” 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 3/181:27 pm
MBJ
- MKE
1 stop10h 32m
American Airlines
Wed 3/256:20 am
MKE
- MBJ
1 stop7h 44m
American Airlines
Deal found 2/11![American Airlines logo]()
$393
This United Airlines deal was found by Cheapflights users on 2/11. Clicking the “Pick Dates” 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 3/181:48 pm
MBJ
- MKE
1 stop8h 02m
United Airlines
Wed 3/251:25 pm
MKE
- MBJ
2 stops23h 40m
United Airlines
Deal found 2/11![United Airlines logo]()
$394
This United Airlines deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” 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 3/272:20 pm
MBJ
- MKE
2 stops31h 30m
United Airlines
Fri 4/37:22 pm
MKE
- MBJ
2 stops18h 08m
United Airlines
Deal found 2/10![United Airlines logo]()
$425
This American Airlines deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” 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 3/2712:28 pm
MBJ
- MKE
1 stop11h 17m
American Airlines
Fri 4/35:04 am
MKE
- MBJ
1 stop7h 07m
American Airlines
Deal found 2/10![American Airlines logo]()
$512
One-way flights from Caribbean to MilwaukeeSearch for one-way flight options from Caribbean to Milwaukee. Find affordable one-way fares based on user searches. Data last updated February 12, 2026.
Search for one-way flight options from Caribbean to Milwaukee. Find affordable one-way fares based on user searches. Data last updated February 12, 2026.
This Expedia deal was found by Cheapflights users on 2/11. Clicking the “Pick Dates” 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 2/243:53 am
SJU
- MKE
1 stop13h 51m
Frontier
Deal found 2/11![Frontier logo]()
$101
This Priceline deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” 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 4/1811:07 am
SJU
- MKE
1 stop25h 01m
Frontier
Deal found 2/10![Frontier logo]()
$107
This Frontier deal was found by Cheapflights users on 2/11. Clicking the “Pick Dates” 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.
Sat 4/183:08 am
SJU
- MKE
1 stop9h 00m
Frontier
Deal found 2/11![Frontier logo]()
$122
This American Airlines deal was found by Cheapflights users on 2/11. Clicking the “Pick Dates” 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 4/161:31 pm
SJU
- MKE
2 stops10h 26m
American Airlines
Deal found 2/11![American Airlines logo]()
$133
This OneTravel deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure OneTravel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/194:25 pm
SJU
- MKE
1 stop19h 18m
Frontier
Deal found 2/10![Frontier logo]()
$147
This United Airlines deal was found by Cheapflights users on 2/11. Clicking the “Pick Dates” 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 4/171:00 am
SJU
- MKE
2 stops11h 32m
United Airlines
Deal found 2/11![United Airlines logo]()
$149
This Frontier deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” 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 3/186:30 am
SJU
- MKE
1 stop12h 20m
Frontier
Deal found 2/9![Frontier logo]()
$158
This American Airlines deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” 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 3/186:00 am
SJU
- MKE
2 stops18h 24m
American Airlines
Deal found 2/9![American Airlines logo]()
$162
This Kiwi.com deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” 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 3/102:36 pm
STT
- MKE
1 stop28h 14m
Multiple Airlines
Deal found 2/10![Multiple Airlines logo]()
$172
This Kiwi.com deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” 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 3/172:36 pm
STT
- MKE
1 stop28h 14m
Multiple Airlines
Deal found 2/10![Multiple Airlines logo]()
$182
This Kiwi.com deal was found by Cheapflights users on 2/11. Clicking the “Pick Dates” 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.
Sat 3/282:36 pm
STT
- MKE
1 stop17h 49m
Multiple Airlines
Deal found 2/11![Multiple Airlines logo]()
$221
This American Airlines deal was found by Cheapflights users on 2/11. Clicking the “Pick Dates” 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 4/64:42 pm
STT
- MKE
1 stop18h 27m
American Airlines
Deal found 2/11![American Airlines logo]()
$241
Find flight deals from Caribbean to Milwaukee
Keep the following information in mind while searching for Caribbean to Milwaukee flight deals. Data was last updated February 12, 2026.
Round-trip from | $223 (Expedia) |
|---|---|
One-way from | $101 (Expedia) |
Popular in | August |
Cheapest in | January |
Average price | $259 |
Cheapflights Fare Finder
Customize your flight search to find flights from Caribbean to Milwaukee 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 12, 2026.
Use the filters below to find and compare flights from Caribbean to Milwaukee that are best for you.
Fly from
Caribbean
Fly to
Milwaukee
Route
Depart
Return
Price
San JuanMilwaukee
SJU - MKE
SJUMKE
San Juan Luis Munoz Marin Intl
Wed 3/4
3:53 am-6:42 pm
1 stop16h 49m
Milwaukee-Mitchell
Sun 3/8
9:01 pm-8:54 am
1 stop10h 53m
$259
San JuanMilwaukee
SJU - MKE
SJUMKE
San Juan Luis Munoz Marin Intl
Wed 4/15
7:30 am-1:52 pm
1 stop7h 22m
Milwaukee-Mitchell
Wed 4/29
12:32 pm-8:24 pm
1 stop6h 52m
$266
San JuanMilwaukee
SJU - MKE
SJUMKE
San Juan Luis Munoz Marin Intl
Fri 5/8
4:30 pm-10:47 pm
1 stop7h 17m
Milwaukee-Mitchell
Sat 5/16
6:00 am-10:05 pm
1 stop15h 05m
$266
San JuanMilwaukee
SJU - MKE
SJUMKE
San Juan Luis Munoz Marin Intl
Fri 5/22
2:20 pm-9:02 pm
1 stop7h 42m
Milwaukee-Mitchell
Mon 5/25
10:10 am-10:17 pm
1 stop11h 07m
$266
San JuanMilwaukee
SJU - MKE
SJUMKE
San Juan Luis Munoz Marin Intl
Wed 4/15
6:00 am-12:32 pm
1 stop7h 32m
Milwaukee-Mitchell
Wed 4/29
6:00 am-6:10 pm
2 stops11h 10m
$273
San JuanMilwaukee
SJU - MKE
SJUMKE
San Juan Luis Munoz Marin Intl
Mon 2/23
3:53 am-3:44 pm
1 stop13h 51m
Milwaukee-Mitchell
Tue 3/17
6:35 pm-2:03 am
1 stop6h 28m
$309
San JuanMilwaukee
SJU - MKE
SJUMKE
San Juan Luis Munoz Marin Intl
Thu 4/30
7:40 am-2:27 pm
1 stop7h 47m
Milwaukee-Mitchell
Sat 5/16
9:23 am-11:50 pm
2 stops13h 27m
$324
Montego BayMilwaukee
MBJ - MKE
MBJMKE
Montego Bay Sangster Intl
Wed 3/18
1:27 pm-11:59 pm
1 stop10h 32m
Milwaukee-Mitchell
Wed 3/25
6:20 am-2:04 pm
1 stop7h 44m
$393
Montego BayMilwaukee
MBJ - MKE
MBJMKE
Montego Bay Sangster Intl
Wed 3/18
1:48 pm-9:50 pm
1 stop8h 02m
Milwaukee-Mitchell
Wed 3/25
1:25 pm-1:05 pm
2 stops23h 40m
$394
Montego BayMilwaukee
MBJ - MKE
MBJMKE
Montego Bay Sangster Intl
Fri 3/27
2:20 pm-9:50 pm
2 stops31h 30m
Milwaukee-Mitchell
Fri 4/3
7:22 pm-1:30 pm
2 stops18h 08m
$425
Showing 1-10 of 53 results
Best time to book a flight from Caribbean to Milwaukee
Have a flexible travel schedule? Discover the best time to fly to Milwaukee from Caribbean with our price prediction graph.
SJU-MKE
PUJ-MKE
MBJ-MKE
POS-MKE
CPX-MKE
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 Caribbean to Milwaukee
0CB-MKE
SJU-MKE
PUJ-MKE
MBJ-MKE
POS-MKE
What is the cheapest month to book a flight from Caribbean to Milwaukee?
Currently, February is the cheapest month in which you can book a flight from Caribbean to Milwaukee (average of $101). Flying from Caribbean to Milwaukee in June is currently the most expensive (average of $152). 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 CB to MKE?
Find hourly flight availability from Caribbean to Milwaukee. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated February 12, 2026.
Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Caribbean to Milwaukee as you normally would.
Reviews of airlines servicing Milwaukee
Get insights into the airlines that provide service to Milwaukee. 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 Milwaukee. Reviews last updated February 12, 2026.
Read through reviews of airlines operating flights from Caribbean to Milwaukee, 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
Comfort
8.0
Overall
8.0
Boarding
8.1
Entertainment
7.5
Food
7.0
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Crew
8.6
Comfort
8.0
Overall
8.0
Boarding
8.1
Entertainment
7.5
Food
7.0
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Crew
8.6
Comfort
8.0
Overall
8.0
Boarding
8.1
Entertainment
7.5
Food
7.0
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Crew
8.6
Comfort
8.0
Overall
8.0
Boarding
8.1
Entertainment
7.5
Food
7.0
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Crew
8.6
Comfort
8.0
Overall
8.0
Boarding
8.1
Entertainment
7.5
Food
7.0
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Crew
8.6
Comfort
8.0
Overall
8.0
Boarding
8.1
Entertainment
7.5
Food
7.0
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Related info for your journey
Find useful and relevant information for your journey from Caribbean to Milwaukee. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Traveling to a place near Milwaukee?
Book flights to Milwaukee if you plan to visit one of these locationsSheboygan
New Berlin
Oak Creek
Wauwatosa
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 Caribbean to Milwaukee
See prices for flight routes from nearby airports that may be better suited for you.
Complete your trip
Complete your trip to Milwaukee by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Caribbean to Milwaukee by cabin class
Find flights from Caribbean to Milwaukee, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Other flights to Milwaukee
Explore flights to Milwaukee departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on February 12, 2026.
Caribbean and Milwaukee flights
Browse other Caribbean and Milwaukee flight options. Last updated on February 12, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Caribbean to Milwaukee flights
Consider these flights traveling from Caribbean to Milwaukee.
Top 5 airlines flying from Caribbean to Milwaukee
Discover the top 5 airlines that operate flights from Caribbean to Milwaukee. 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 12, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$112 | Average$436 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$140 | Average$299 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$215 | Average$356 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$235 | Average$427 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$256 | Average$439 | FlexibilityNo cancel fee | On-time63% |