$97+ Cheap flights from Caribbean Islands to Wisconsin
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 4/15. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — MKE
Mar 2 — Mar 91
1 adult, Economy
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Find cheap flights from Caribbean Islands to Wisconsin with Cheapflights
1. Tell us where you want to go
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Cheapest flights from Caribbean Islands to WisconsinExplore the most affordable flight options available from Caribbean Islands to Wisconsin. Find the lowest fares from popular airlines and budget airlines, with prices last updated on January 31, 2026.
Explore the most affordable flight options available from Caribbean Islands to Wisconsin. Find the lowest fares from popular airlines and budget airlines, with prices last updated on January 31, 2026.
This Travelocity deal was found by Cheapflights users on 1/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/512:32 pm
SJU
- ORD
Nonstop5h 16m
Spirit Airlines
Mon 3/98:16 pm
ORD
- SJU
1 stop17h 15m
Spirit Airlines
Deal found 1/30![Spirit Airlines logo]()
$134
This Expedia deal was found by Cheapflights users on 1/29. Clicking the “Pick Dates” 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 2/2512:32 pm
SJU
- ORD
Nonstop5h 16m
Spirit Airlines
Tue 3/37:00 am
ORD
- SJU
1 stop6h 31m
Spirit Airlines
Deal found 1/29![Spirit Airlines logo]()
$137
This Orbitz deal was found by Cheapflights users on 1/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/2711:52 am
SJU
- ORD
1 stop8h 26m
Spirit Airlines
Mon 3/28:16 pm
ORD
- SJU
1 stop17h 15m
Spirit Airlines
Deal found 1/30![Spirit Airlines logo]()
$144
This Expedia deal was found by Cheapflights users on 1/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/1912:32 pm
SJU
- ORD
Nonstop5h 16m
Spirit Airlines
Mon 2/2312:17 pm
ORD
- SJU
Nonstop4h 32m
Spirit Airlines
Deal found 1/30![Spirit Airlines logo]()
$145
This Orbitz deal was found by Cheapflights users on 1/29. Clicking the “Pick Dates” 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.
Sat 3/712:32 pm
SJU
- ORD
Nonstop5h 16m
Spirit Airlines
Mon 3/912:22 pm
ORD
- SJU
Nonstop4h 32m
Spirit Airlines
Deal found 1/29![Spirit Airlines logo]()
$151
This Expedia deal was found by Cheapflights users on 1/29. Clicking the “Pick Dates” 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 2/2511:07 am
SJU
- ORD
1 stop25h 39m
Multiple Airlines
Tue 3/37:00 am
ORD
- SJU
1 stop6h 31m
Multiple Airlines
Deal found 1/29![Multiple Airlines logo]()
$155
This Kiwi.com deal was found by Cheapflights users on 1/29. Clicking the “Pick Dates” 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.
Wed 3/45:45 pm
SJU
- ORD
1 stop8h 55m
Multiple Airlines
Mon 3/99:05 pm
ORD
- SJU
1 stop27h 14m
Multiple Airlines
Deal found 1/29![Multiple Airlines logo]()
$160
This Expedia deal was found by Cheapflights users on 1/29. Clicking the “Pick Dates” 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 2/244:31 pm
SJU
- ORD
1 stop9h 16m
Spirit Airlines
Sat 2/2812:17 pm
ORD
- SJU
Nonstop4h 32m
Spirit Airlines
Deal found 1/29![Spirit Airlines logo]()
$164
This Travelocity deal was found by Cheapflights users on 1/29. Clicking the “Pick Dates” 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 2/265:40 pm
STT
- ORD
1 stop8h 07m
Spirit Airlines
Thu 3/57:00 am
ORD
- STT
1 stop7h 34m
Spirit Airlines
Deal found 1/29![Spirit Airlines logo]()
$165
This Priceline deal was found by Cheapflights users on 1/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline 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 stop11h 43m
Frontier
Deal found 1/30![Frontier logo]()
$202
This Cheapflightsfares deal was found by Cheapflights users on 1/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/194:35 pm
STT
- ORD
1 stop7h 42m
Spirit Airlines
Wed 3/255:05 am
ORD
- STT
1 stop9h 23m
Spirit Airlines
Deal found 1/30![Spirit Airlines logo]()
$204
This CheapOair deal was found by Cheapflights users on 1/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/254:35 pm
STT
- ORD
1 stop7h 42m
Spirit Airlines
Mon 3/308:58 pm
ORD
- STT
2 stops17h 30m
Spirit Airlines
Deal found 1/30![Spirit Airlines logo]()
$211
Best flights from Caribbean Islands to WisconsinDiscover carefully curated flight deals from Caribbean Islands to Wisconsin that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated January 31, 2026.
Discover carefully curated flight deals from Caribbean Islands to Wisconsin that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated January 31, 2026.
This Travelocity deal was found by Cheapflights users on 1/29. Clicking the “Pick Dates” 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 2/265:40 pm
STT
- ORD
1 stop8h 07m
Spirit Airlines
Thu 3/57:00 am
ORD
- STT
1 stop7h 34m
Spirit Airlines
Deal found 1/29![Spirit Airlines logo]()
$165
This Kiwi.com deal was found by Cheapflights users on 1/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/106:39 pm
SJU
- ORD
1 stop16h 00m
Multiple Airlines
Wed 3/1810:55 am
ORD
- SJU
1 stop12h 03m
Multiple Airlines
Deal found 1/30![Multiple Airlines logo]()
$182
This Priceline deal was found by Cheapflights users on 1/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline 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 stop11h 43m
Frontier
Deal found 1/30![Frontier logo]()
$202
This American Airlines deal was found by Cheapflights users on 1/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/248:00 am
SJU
- MKE
2 stops10h 56m
American Airlines
Tue 3/178:49 am
MKE
- SJU
2 stops11h 01m
American Airlines
Deal found 1/30![American Airlines logo]()
$256
This Delta deal was found by Cheapflights users on 1/28. 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 4/152:34 pm
SJU
- MKE
1 stop10h 23m
Delta
Wed 4/292:50 pm
MKE
- SJU
1 stop7h 23m
Delta
Deal found 1/28![Delta logo]()
$256
This United Airlines deal was found by Cheapflights users on 1/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/241:50 pm
PUJ
- ORD
Nonstop5h 09m
United Airlines
Thu 4/308:05 pm
ORD
- PUJ
1 stop18h 25m
United Airlines
Deal found 1/31![United Airlines logo]()
$302
This Mytrip deal was found by Cheapflights users on 1/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/149:10 pm
NAS
- ORD
1 stop25h 53m
Air Canada
Thu 4/169:05 am
ORD
- NAS
1 stop10h 00m
Air Canada
Deal found 1/29![Air Canada logo]()
$351
This Expedia deal was found by Cheapflights users on 1/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/54:40 pm
SJU
- ORD
1 stop9h 07m
Spirit Airlines
Mon 2/910:48 am
ORD
- SJU
1 stop10h 45m
Spirit Airlines
Deal found 1/29![Spirit Airlines logo]()
$192
This Southwest deal was found by Cheapflights users on 1/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/811:25 am
SJU
- MSP
2 stops12h 05m
Southwest
Sun 4/125:10 am
MSP
- SJU
2 stops10h 55m
Southwest
Deal found 1/30![Southwest logo]()
$396
This Kiwi.com deal was found by Cheapflights users on 1/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/1211:03 am
SJU
- ORD
1 stop8h 28m
Spirit Airlines
Tue 3/178:56 pm
ORD
- SJU
Nonstop4h 33m
Spirit Airlines
Deal found 1/30![Spirit Airlines logo]()
$196
This Mytrip deal was found by Cheapflights users on 1/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/233:53 am
SJU
- ORD
1 stop13h 59m
Multiple Airlines
Sun 3/112:17 pm
ORD
- SJU
Nonstop4h 32m
Multiple Airlines
Deal found 1/30![Multiple Airlines logo]()
$226
This FlightHub deal was found by Cheapflights users on 1/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/311:29 am
SJU
- ORD
Nonstop5h 16m
Spirit Airlines
Sun 4/57:26 pm
ORD
- SJU
Nonstop4h 33m
Spirit Airlines
Deal found 1/29![Spirit Airlines logo]()
$199
This American Airlines deal was found by Cheapflights users on 1/29. Clicking the “Pick Dates” 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 3/56:33 am
SJU
- MKE
1 stop18h 24m
American Airlines
Sun 3/86:20 am
MKE
- SJU
1 stop15h 11m
American Airlines
Deal found 1/29![American Airlines logo]()
$256
This Priceline deal was found by Cheapflights users on 1/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/194:25 pm
SJU
- MKE
1 stop19h 18m
Frontier
Sun 2/226:37 pm
MKE
- SJU
1 stop13h 17m
Frontier
Deal found 1/29![Frontier logo]()
$256
This Travelocity deal was found by Cheapflights users on 1/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/113:36 pm
SJU
- ORD
1 stop9h 11m
Spirit Airlines
Sat 3/146:10 pm
ORD
- SJU
1 stop16h 39m
Spirit Airlines
Deal found 1/30![Spirit Airlines logo]()
$201
This American Airlines deal was found by Cheapflights users on 1/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/1511:59 pm
SJU
- MKE
1 stop12h 01m
American Airlines
Wed 4/291:10 pm
MKE
- SJU
1 stop7h 55m
American Airlines
Deal found 1/30![American Airlines logo]()
$265
This Orbitz deal was found by Cheapflights users on 1/28. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/1912:32 pm
SJU
- ORD
Nonstop5h 16m
Spirit Airlines
Sun 2/225:15 am
ORD
- SJU
1 stop8h 16m
Spirit Airlines
Deal found 1/28![Spirit Airlines logo]()
$202
This Delta deal was found by Cheapflights users on 1/29. Clicking the “Pick Dates” 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 4/142:09 pm
MBJ
- ORD
1 stop9h 50m
Delta
Mon 4/207:00 am
ORD
- MBJ
2 stops8h 17m
Delta
Deal found 1/29![Delta logo]()
$307
This Travelocity deal was found by Cheapflights users on 1/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/177:30 pm
PUJ
- ORD
Nonstop5h 10m
Multiple Airlines
Tue 3/105:15 am
ORD
- PUJ
1 stop9h 21m
Multiple Airlines
Deal found 1/30![Multiple Airlines logo]()
$286
This United Airlines deal was found by Cheapflights users on 1/29. Clicking the “Pick Dates” 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 3/241:48 pm
MBJ
- ORD
Nonstop4h 25m
United Airlines
Tue 4/148:45 am
ORD
- MBJ
1 stop6h 25m
United Airlines
Deal found 1/29![United Airlines logo]()
$325
This Cheapflightsfares deal was found by Cheapflights users on 1/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/194:35 pm
STT
- ORD
1 stop7h 42m
Spirit Airlines
Wed 3/255:05 am
ORD
- STT
1 stop9h 23m
Spirit Airlines
Deal found 1/30![Spirit Airlines logo]()
$204
This Travelocity deal was found by Cheapflights users on 1/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/135:02 pm
SJU
- MSP
Nonstop6h 04m
Multiple Airlines
Sun 2/228:12 pm
MSP
- SJU
1 stop11h 42m
Multiple Airlines
Deal found 1/30![Multiple Airlines logo]()
$289
This Air Canada deal was found by Cheapflights users on 1/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/171:15 pm
NAS
- ORD
1 stop23h 03m
Air Canada
Tue 3/2412:50 pm
ORD
- NAS
1 stop22h 35m
Air Canada
Deal found 1/30![Air Canada logo]()
$355
This American Airlines deal was found by Cheapflights users on 1/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/52:26 pm
MBJ
- ORD
Nonstop4h 41m
American Airlines
Wed 3/116:00 am
ORD
- MBJ
1 stop6h 27m
American Airlines
Deal found 1/30![American Airlines logo]()
$294
This United Airlines deal was found by Cheapflights users on 1/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/14:12 pm
MBJ
- ORD
1 stop26h 03m
United Airlines
Wed 5/206:00 am
ORD
- MBJ
1 stop9h 10m
United Airlines
Deal found 1/30![United Airlines logo]()
$330
This Cheapflightsfares deal was found by Cheapflights users on 1/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/2212:22 pm
SJU
- ORD
Nonstop5h 15m
Spirit Airlines
Sat 4/2512:22 pm
ORD
- SJU
Nonstop4h 32m
Spirit Airlines
Deal found 1/30![Spirit Airlines logo]()
$208
This Frontier deal was found by Cheapflights users on 1/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/2610:57 am
SJU
- MSP
1 stop10h 35m
Frontier
Mon 3/211:26 am
MSP
- SJU
1 stop13h 27m
Frontier
Deal found 1/30![Frontier logo]()
$344
This Air Canada deal was found by Cheapflights users on 1/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/51:15 pm
NAS
- ORD
1 stop7h 55m
Air Canada
Mon 5/49:55 am
ORD
- NAS
1 stop6h 35m
Air Canada
Deal found 1/29![Air Canada logo]()
$360
This Kiwi.com deal was found by Cheapflights users on 1/29. Clicking the “Pick Dates” 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.
Thu 4/165:02 pm
SDQ
- ORD
1 stop26h 03m
Multiple Airlines
Tue 4/216:34 pm
ORD
- SDQ
1 stop20h 55m
Multiple Airlines
Deal found 1/29![Multiple Airlines logo]()
$307
This Travelocity deal was found by Cheapflights users on 1/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/237:00 am
SJU
- ORD
1 stop12h 03m
Spirit Airlines
Sat 3/78:16 pm
ORD
- SJU
1 stop16h 15m
Spirit Airlines
Deal found 1/30![Spirit Airlines logo]()
$210
Last-minute flights from Caribbean Islands to WisconsinDiscover last-minute flight deals from Caribbean Islands to Wisconsin. Data last updated January 31, 2026 and is based on user searches.
Discover last-minute flight deals from Caribbean Islands to Wisconsin. Data last updated January 31, 2026 and is based on user searches.
This Expedia deal was found by Cheapflights users on 1/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/51:22 pm
SJU
- ORD
Nonstop5h 15m
Spirit Airlines
Mon 2/912:44 pm
ORD
- SJU
1 stop8h 49m
Spirit Airlines
Deal found 1/29![Spirit Airlines logo]()
$165
This Expedia deal was found by Cheapflights users on 1/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/51:22 pm
SJU
- ORD
Nonstop5h 15m
Spirit Airlines
Sun 2/812:17 pm
ORD
- SJU
Nonstop4h 32m
Spirit Airlines
Deal found 1/29![Spirit Airlines logo]()
$197
This Cheapflightsfares deal was found by Cheapflights users on 1/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/51:22 pm
SJU
- ORD
Nonstop5h 15m
Spirit Airlines
Mon 2/1612:17 pm
ORD
- SJU
Nonstop4h 32m
Spirit Airlines
Deal found 1/30![Spirit Airlines logo]()
$217
This Kiwi.com deal was found by Cheapflights users on 1/29. Clicking the “Pick Dates” 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.
Thu 2/51:22 pm
SJU
- ORD
Nonstop5h 15m
Multiple Airlines
Mon 2/912:05 pm
ORD
- SJU
1 stop27h 53m
Multiple Airlines
Deal found 1/29![Multiple Airlines logo]()
$220
This Expedia deal was found by Cheapflights users on 1/29. Clicking the “Pick Dates” 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.
Fri 2/61:22 pm
SJU
- ORD
Nonstop5h 15m
Spirit Airlines
Mon 2/912:44 pm
ORD
- SJU
1 stop8h 49m
Spirit Airlines
Deal found 1/29![Spirit Airlines logo]()
$187
This Expedia deal was found by Cheapflights users on 1/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/61:22 pm
SJU
- ORD
Nonstop5h 15m
Spirit Airlines
Sun 2/88:43 pm
ORD
- SJU
1 stop16h 52m
Spirit Airlines
Deal found 1/30![Spirit Airlines logo]()
$188
This Kiwi.com deal was found by Cheapflights users on 1/29. Clicking the “Pick Dates” 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.
Fri 2/61:22 pm
SJU
- ORD
Nonstop5h 15m
Multiple Airlines
Sun 2/85:40 am
ORD
- SJU
1 stop7h 32m
Multiple Airlines
Deal found 1/29![Multiple Airlines logo]()
$218
This Travelocity deal was found by Cheapflights users on 1/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/1112:57 pm
MBJ
- ORD
1 stop11h 50m
Spirit Airlines
Sun 2/155:15 am
ORD
- MBJ
1 stop5h 47m
Spirit Airlines
Deal found 1/31![Spirit Airlines logo]()
$242
This Expedia deal was found by Cheapflights users on 1/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/143:36 pm
STT
- ORD
2 stops10h 11m
Spirit Airlines
Wed 2/184:43 pm
ORD
- STT
2 stops19h 48m
Spirit Airlines
Deal found 1/30![Spirit Airlines logo]()
$238
This Priceline deal was found by Cheapflights users on 1/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline 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 stop11h 43m
Frontier
Deal found 1/30![Frontier logo]()
$202
This Travelocity deal was found by Cheapflights users on 1/29. Clicking the “Pick Dates” 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 2/265:40 pm
STT
- ORD
1 stop8h 07m
Spirit Airlines
Thu 3/57:00 am
ORD
- STT
1 stop7h 34m
Spirit Airlines
Deal found 1/29![Spirit Airlines logo]()
$165
This Travelocity deal was found by Cheapflights users on 1/29. Clicking the “Pick Dates” 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 2/263:32 pm
SDQ
- ORD
1 stop7h 41m
Spirit Airlines
Thu 3/58:16 pm
ORD
- SDQ
1 stop16h 04m
Spirit Airlines
Deal found 1/29![Spirit Airlines logo]()
$236
One-way flights from Caribbean Islands to WisconsinSearch for one-way flight options from Caribbean Islands to Wisconsin. Find affordable one-way fares based on user searches. Data last updated January 31, 2026.
Search for one-way flight options from Caribbean Islands to Wisconsin. Find affordable one-way fares based on user searches. Data last updated January 31, 2026.
This Mytrip deal was found by Cheapflights users on 1/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/1511:07 am
SJU
- ORD
1 stop8h 08m
Spirit Airlines
Deal found 1/29![Spirit Airlines logo]()
$97
This Kiwi.com deal was found by Cheapflights users on 1/29. Clicking the “Pick Dates” 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.
Fri 3/612:32 pm
SJU
- ORD
Nonstop5h 16m
Spirit Airlines
Deal found 1/29![Spirit Airlines logo]()
$98
This Kiwi.com deal was found by Cheapflights users on 1/29. Clicking the “Pick Dates” 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 3/311:29 am
SJU
- ORD
Nonstop5h 16m
Spirit Airlines
Deal found 1/29![Spirit Airlines logo]()
$99
This Travelocity deal was found by Cheapflights users on 1/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/283:36 pm
STT
- ORD
2 stops18h 18m
Spirit Airlines
Deal found 1/31![Spirit Airlines logo]()
$100
This Cheapflightsfares deal was found by Cheapflights users on 1/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/121:29 am
SJU
- ORD
Nonstop5h 16m
Spirit Airlines
Deal found 1/31![Spirit Airlines logo]()
$100
This Frontier deal was found by Cheapflights users on 1/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/81:11 pm
SJU
- ORD
1 stop10h 28m
Frontier
Deal found 1/30![Frontier logo]()
$101
This Travelocity deal was found by Cheapflights users on 1/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/54:36 pm
SJU
- ORD
1 stop9h 11m
Spirit Airlines
Deal found 1/30![Spirit Airlines logo]()
$102
This Orbitz deal was found by Cheapflights users on 1/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/184:31 pm
SJU
- ORD
1 stop9h 16m
Spirit Airlines
Deal found 1/31![Spirit Airlines logo]()
$103
This Cheapflightsfares deal was found by Cheapflights users on 1/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/81:29 am
SJU
- ORD
Nonstop5h 16m
Spirit Airlines
Deal found 1/30![Spirit Airlines logo]()
$104
This Mytrip deal was found by Cheapflights users on 1/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/411:52 am
SJU
- ORD
2 stops22h 02m
Spirit Airlines
Deal found 1/31![Spirit Airlines logo]()
$105
This Kiwi.com deal was found by Cheapflights users on 1/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/35:40 pm
STT
- ORD
1 stop19h 42m
Spirit Airlines
Deal found 1/30![Spirit Airlines logo]()
$106
This Expedia deal was found by Cheapflights users on 1/29. Clicking the “Pick Dates” 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 3/25:45 pm
SJU
- ORD
1 stop8h 55m
Spirit Airlines
Deal found 1/29![Spirit Airlines logo]()
$106
Find flight deals from Caribbean Islands to Wisconsin
Keep the following information in mind while searching for Caribbean Islands to Wisconsin flight deals. Data was last updated January 31, 2026.
Round-trip from | $134 (Travelocity) |
|---|---|
One-way from | $97 (Mytrip) |
Cheapflights Fare Finder
Customize your flight search to find flights from Caribbean Islands to Wisconsin 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 January 31, 2026.
Use the filters below to find and compare flights from Caribbean Islands to Wisconsin that are best for you.
Fly from
Caribbean Islands
Fly to
Wisconsin
Route
Depart
Return
Price
Saint Thomas IslandChicago
STT - ORD
STTORD
Saint Thomas Island Cyril E King
Thu 2/26
5:40 pm-11:47 pm
1 stop8h 07m
Chicago O'Hare Intl
Thu 3/5
7:00 am-4:34 pm
1 stop7h 34m
$165
San JuanChicago
SJU - ORD
SJUORD
San Juan Luis Munoz Marin Intl
Tue 3/10
6:39 pm-9:39 am
1 stop16h 00m
Chicago O'Hare Intl
Wed 3/18
10:55 am-11:58 pm
1 stop12h 03m
$182
San JuanChicago
SJU - ORD
SJUORD
San Juan Luis Munoz Marin Intl
Thu 2/5
4:40 pm-11:47 pm
1 stop9h 07m
Chicago O'Hare Intl
Mon 2/9
10:48 am-11:33 pm
1 stop10h 45m
$192
San JuanChicago
SJU - ORD
SJUORD
San Juan Luis Munoz Marin Intl
Thu 3/12
11:03 am-6:31 pm
1 stop8h 28m
Chicago O'Hare Intl
Tue 3/17
8:56 pm-2:29 am
Nonstop4h 33m
$196
San JuanChicago
SJU - ORD
SJUORD
San Juan Luis Munoz Marin Intl
Tue 3/31
1:29 am-5:45 am
Nonstop5h 16m
Chicago O'Hare Intl
Sun 4/5
7:26 pm-12:59 am
Nonstop4h 33m
$199
San JuanChicago
SJU - ORD
SJUORD
San Juan Luis Munoz Marin Intl
Wed 3/11
3:36 pm-11:47 pm
1 stop9h 11m
Chicago O'Hare Intl
Sat 3/14
6:10 pm-11:49 am
1 stop16h 39m
$201
San JuanMilwaukee
SJU - MKE
SJUMKE
San Juan Luis Munoz Marin Intl
Thu 2/19
4:25 pm-9:43 am
1 stop19h 18m
Milwaukee-Mitchell
Mon 2/23
8:11 pm-9:54 am
1 stop11h 43m
$202
San JuanChicago
SJU - ORD
SJUORD
San Juan Luis Munoz Marin Intl
Thu 2/19
12:32 pm-3:48 pm
Nonstop5h 16m
Chicago O'Hare Intl
Sun 2/22
5:15 am-3:31 pm
1 stop8h 16m
$202
Saint Thomas IslandChicago
STT - ORD
STTORD
Saint Thomas Island Cyril E King
Thu 3/19
4:35 pm-11:17 pm
1 stop7h 42m
Chicago O'Hare Intl
Wed 3/25
5:05 am-3:28 pm
1 stop9h 23m
$204
San JuanChicago
SJU - ORD
SJUORD
San Juan Luis Munoz Marin Intl
Wed 4/22
12:22 pm-4:37 pm
Nonstop5h 15m
Chicago O'Hare Intl
Sat 4/25
12:22 pm-5:54 pm
Nonstop4h 32m
$208
Showing 1-10 of 60 results
Best time to book a flight from Caribbean Islands to Wisconsin
Have a flexible travel schedule? Discover the best time to fly to Wisconsin from Caribbean Islands with our price prediction graph.
STT-ORD
SJU-ORD
SJU-MKE
SDQ-ORD
MBJ-ORD
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 Islands to Wisconsin
zzEPX-USWI
STT-ORD
SJU-ORD
SJU-MKE
SDQ-ORD
What is the cheapest month to book a flight from Caribbean Islands to Wisconsin?
Currently, September is the cheapest month in which you can book a flight from Caribbean Islands to Wisconsin (average of $113). Flying from Caribbean Islands to Wisconsin in June is currently the most expensive (average of $355). 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 EPX to WI?
Find hourly flight availability from Caribbean Islands to Wisconsin. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated January 31, 2026.
Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Caribbean Islands to Wisconsin as you normally would.
Reviews of airlines servicing Wisconsin
Get insights into the airlines that provide service to Wisconsin. 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 Wisconsin. Reviews last updated January 31, 2026.
Read through reviews of airlines operating flights from Caribbean Islands to Wisconsin, such as Delta, United Airlines, and American Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Boarding
8.1
Food
7.2
Overall
7.9
Crew
8.5
Comfort
7.9
Entertainment
7.8
Reviews
1 / 20
6.0
GoodJim,Nov 2025
AVL - ATL
Boarding
8.1
Food
7.2
Overall
7.9
Crew
8.5
Comfort
7.9
Entertainment
7.8
Reviews
1 / 20
6.0
GoodJim,Nov 2025
AVL - ATL
Boarding
8.1
Food
7.2
Overall
7.9
Crew
8.5
Comfort
7.9
Entertainment
7.8
Reviews
1 / 20
6.0
GoodJim,Nov 2025
AVL - ATL
Boarding
8.1
Food
7.2
Overall
7.9
Crew
8.5
Comfort
7.9
Entertainment
7.8
Reviews
1 / 20
6.0
GoodJim,Nov 2025
AVL - ATL
Related info for your journey
Find useful and relevant information for your journey from Caribbean Islands to Wisconsin. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Browse thousands of different options on Cheapflights for your next trip
Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
Alternative routes for Caribbean Islands to Wisconsin
See prices for flight routes from nearby airports that may be better suited for you.
Top 5 airlines flying from Caribbean Islands to Wisconsin
Discover the top 5 airlines that operate flights from Caribbean Islands to Wisconsin. 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 January 31, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$112 | Average$460 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$140 | Average$299 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$215 | Average$371 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$235 | Average$468 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$305 | Average$490 | FlexibilityNo cancel fee | On-time63% |