$87+ Cheap flights from Caribbean 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 2/24. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — MKE
Mar 7 — Mar 141
1 adult, Economy
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Find cheap flights from Caribbean to Wisconsin with Cheapflights
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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 Caribbean to WisconsinExplore the most affordable flight options available from Caribbean to Wisconsin. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 5, 2026.
Explore the most affordable flight options available from Caribbean to Wisconsin. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 5, 2026.
This CheapOair deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/2611:52 am
SJU
- ORD
1 stop8h 26m
Spirit Airlines
Tue 3/35:15 am
ORD
- SJU
1 stop8h 16m
Spirit Airlines
Deal found 2/2![Spirit Airlines logo]()
$136
This Expedia deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/2612:32 pm
SJU
- ORD
Nonstop5h 16m
Spirit Airlines
Mon 3/212:17 pm
ORD
- SJU
Nonstop4h 32m
Spirit Airlines
Deal found 2/2![Spirit Airlines logo]()
$141
This Cheapflightsfares deal was found by Cheapflights users on 2/5. Clicking the “Pick Dates” 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.
Fri 3/611:52 am
SJU
- ORD
1 stop8h 26m
Spirit Airlines
Tue 3/1012:22 pm
ORD
- SJU
Nonstop4h 32m
Spirit Airlines
Deal found 2/5![Spirit Airlines logo]()
$145
This Cheapflightsfares deal was found by Cheapflights users on 2/5. Clicking the “Pick Dates” 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 2/111:22 pm
SJU
- ORD
Nonstop5h 15m
Spirit Airlines
Wed 3/412:17 pm
ORD
- SJU
Nonstop4h 32m
Spirit Airlines
Deal found 2/5![Spirit Airlines logo]()
$147
This Expedia deal was found by Cheapflights users on 2/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure 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
Sat 2/712:17 pm
ORD
- SJU
Nonstop4h 32m
Spirit Airlines
Deal found 2/1![Spirit Airlines logo]()
$149
This Orbitz deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure 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 3/212:17 pm
ORD
- SJU
Nonstop4h 32m
Spirit Airlines
Deal found 2/2![Spirit Airlines logo]()
$150
This Expedia deal was found by Cheapflights users on 2/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/312:32 pm
SJU
- ORD
Nonstop5h 16m
Spirit Airlines
Sat 3/712:17 pm
ORD
- SJU
Nonstop4h 32m
Spirit Airlines
Deal found 2/3![Spirit Airlines logo]()
$151
This Expedia deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/1212:32 pm
SJU
- ORD
Nonstop5h 16m
Spirit Airlines
Tue 2/2412:17 pm
ORD
- SJU
Nonstop4h 32m
Spirit Airlines
Deal found 2/2![Spirit Airlines logo]()
$152
This Cheapflightsfares deal was found by Cheapflights users on 2/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/101:22 pm
SJU
- ORD
Nonstop5h 15m
Spirit Airlines
Sat 2/1412:17 pm
ORD
- SJU
Nonstop4h 32m
Spirit Airlines
Deal found 2/4![Spirit Airlines logo]()
$156
This Orbitz deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Orbitz 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
Sat 2/287:47 pm
MKE
- SJU
1 stop27h 07m
Frontier
Deal found 2/2![Frontier logo]()
$174
This Priceline deal was found by Cheapflights users on 2/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/173:53 am
SJU
- MKE
1 stop29h 47m
Frontier
Mon 2/238:11 pm
MKE
- SJU
1 stop28h 42m
Frontier
Deal found 2/4![Frontier logo]()
$202
This Trip.com deal was found by Cheapflights users on 2/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/196:00 am
SJU
- MKE
1 stop29h 43m
Frontier
Mon 2/238:11 pm
MKE
- SJU
1 stop11h 43m
Frontier
Deal found 2/4![Frontier logo]()
$213
Best flights from Caribbean to WisconsinDiscover carefully curated flight deals from Caribbean to Wisconsin that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated February 5, 2026.
Discover carefully curated flight deals from Caribbean to Wisconsin that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated February 5, 2026.
This Priceline deal was found by Cheapflights users on 2/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/1212:32 pm
SJU
- ORD
Nonstop5h 16m
Spirit Airlines
Tue 2/2412:17 pm
ORD
- SJU
Nonstop4h 32m
Spirit Airlines
Deal found 2/4![Spirit Airlines logo]()
$155
This Priceline deal was found by Cheapflights users on 2/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/196:00 am
SJU
- MKE
1 stop29h 43m
Frontier
Mon 2/238:11 pm
MKE
- SJU
1 stop11h 43m
Frontier
Deal found 2/4![Frontier logo]()
$202
This Travelocity deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/910:52 am
SJU
- ORD
1 stop8h 26m
Multiple Airlines
Thu 3/123:21 pm
ORD
- SJU
1 stop8h 08m
Multiple Airlines
Deal found 2/2![Multiple Airlines logo]()
$205
This American Airlines deal was found by Cheapflights users on 2/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/248:00 am
SJU
- MKE
2 stops10h 56m
American Airlines
Tue 3/178:00 am
MKE
- SJU
2 stops11h 50m
American Airlines
Deal found 2/3![American Airlines logo]()
$256
This Delta deal was found by Cheapflights users on 2/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/161:25 pm
SJU
- MKE
1 stop8h 00m
Delta
Sun 4/1912:32 pm
MKE
- SJU
1 stop9h 40m
Delta
Deal found 2/1![Delta logo]()
$256
This United Airlines deal was found by Cheapflights users on 2/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/62:55 pm
PUJ
- ORD
Nonstop5h 13m
United Airlines
Sun 3/89:15 pm
ORD
- PUJ
1 stop18h 10m
United Airlines
Deal found 2/4![United Airlines logo]()
$276
This Spirit deal was found by Cheapflights users on 2/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Spirit is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/511:52 am
SJU
- ORD
1 stop8h 26m
Spirit Airlines
Sun 3/88:16 pm
ORD
- SJU
1 stop17h 15m
Spirit Airlines
Deal found 2/3![Spirit Airlines logo]()
$175
This Air Canada deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/21:50 pm
NAS
- ORD
1 stop20h 20m
Air Canada
Mon 4/63:45 pm
ORD
- NAS
1 stop19h 35m
Air Canada
Deal found 2/2![Air Canada logo]()
$360
This Southwest deal was found by Cheapflights users on 2/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/55:35 am
SJU
- MSP
2 stops10h 00m
Southwest
Sat 5/166:15 am
MSP
- SJU
1 stop11h 50m
Southwest
Deal found 2/3![Southwest logo]()
$372
This Expedia deal was found by Cheapflights users on 2/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia 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
Multiple Airlines
Thu 4/91:02 pm
ORD
- SJU
1 stop10h 51m
Multiple Airlines
Deal found 2/1![Multiple Airlines logo]()
$206
This CheapOair deal was found by Cheapflights users on 2/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/711:03 am
SJU
- ORD
1 stop23h 47m
Spirit Airlines
Tue 4/1410:55 am
ORD
- SJU
1 stop12h 03m
Spirit Airlines
Deal found 2/4![Spirit Airlines logo]()
$196
This CheapOair deal was found by Cheapflights users on 2/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair 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
Multiple Airlines
Sat 4/258:00 am
ORD
- SJU
1 stop6h 37m
Multiple Airlines
Deal found 2/1![Multiple Airlines logo]()
$211
This Cheapflightsfares deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/1411:52 am
SJU
- ORD
1 stop9h 55m
Spirit Airlines
Sun 2/2212:17 pm
ORD
- SJU
Nonstop4h 32m
Spirit Airlines
Deal found 2/2![Spirit Airlines logo]()
$204
This Delta deal was found by Cheapflights users on 2/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/66:15 am
SJU
- MKE
1 stop6h 58m
Delta
Tue 3/1010:09 am
MKE
- SJU
1 stop9h 09m
Delta
Deal found 2/1![Delta logo]()
$256
This Frontier deal was found by Cheapflights users on 2/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/2610:57 am
SJU
- MSP
1 stop10h 35m
Frontier
Mon 3/211:26 am
MSP
- SJU
1 stop11h 17m
Frontier
Deal found 2/3![Frontier logo]()
$258
This American Airlines deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/157:25 am
SJU
- MKE
1 stop16h 32m
American Airlines
Wed 4/296:00 am
MKE
- SJU
1 stop15h 05m
American Airlines
Deal found 2/2![American Airlines logo]()
$261
This Spirit deal was found by Cheapflights users on 2/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Spirit is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/67:00 am
SJU
- ORD
1 stop12h 03m
Spirit Airlines
Sun 3/87:00 am
ORD
- SJU
1 stop6h 31m
Spirit Airlines
Deal found 2/4![Spirit Airlines logo]()
$206
This CheapOair deal was found by Cheapflights users on 2/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/196:00 am
SJU
- MSP
1 stop15h 32m
Frontier
Sat 2/217:40 pm
MSP
- SJU
1 stop27h 14m
Frontier
Deal found 2/4![Frontier logo]()
$267
This United Airlines deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/52:48 pm
MBJ
- ORD
Nonstop4h 25m
United Airlines
Wed 3/118:42 am
ORD
- MBJ
Nonstop4h 04m
United Airlines
Deal found 2/2![United Airlines logo]()
$295
This Spirit deal was found by Cheapflights users on 2/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Spirit is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/2612:32 pm
SJU
- ORD
Nonstop5h 16m
Spirit Airlines
Sun 3/112:17 pm
ORD
- SJU
Nonstop4h 32m
Spirit Airlines
Deal found 2/3![Spirit Airlines logo]()
$209
This Kiwi.com deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/243:40 pm
AUA
- ORD
1 stop19h 56m
Multiple Airlines
Tue 3/315:05 am
ORD
- AUA
1 stop8h 30m
Multiple Airlines
Deal found 2/2![Multiple Airlines logo]()
$265
This Delta deal was found by Cheapflights users on 2/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/144:55 pm
MBJ
- ORD
1 stop7h 04m
Delta
Sun 5/176:00 am
ORD
- MBJ
1 stop9h 29m
Delta
Deal found 2/3![Delta logo]()
$307
This United Airlines deal was found by Cheapflights users on 2/5. Clicking the “Pick Dates” 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 3/712:56 pm
PUJ
- ORD
1 stop9h 39m
United Airlines
Sun 3/89:15 pm
ORD
- PUJ
1 stop18h 10m
United Airlines
Deal found 2/5![United Airlines logo]()
$307
This American Airlines deal was found by Cheapflights users on 2/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/182:26 pm
MBJ
- ORD
Nonstop4h 41m
American Airlines
Sun 2/228:54 pm
ORD
- MBJ
1 stop14h 27m
American Airlines
Deal found 2/4![American Airlines logo]()
$310
This Flightnetwork deal was found by Cheapflights users on 2/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Flightnetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/66:39 pm
PUJ
- ORD
Nonstop5h 22m
Frontier
Sun 3/87:20 am
ORD
- PUJ
Nonstop4h 43m
Frontier
Deal found 2/4![Frontier logo]()
$284
This Spirit deal was found by Cheapflights users on 2/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Spirit is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/2011:52 am
SJU
- ORD
1 stop7h 54m
Spirit Airlines
Sun 2/2212:17 pm
ORD
- SJU
Nonstop4h 32m
Spirit Airlines
Deal found 2/3![Spirit Airlines logo]()
$220
This Air Canada deal was found by Cheapflights users on 2/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/11:15 pm
NAS
- ORD
1 stop22h 38m
Air Canada
Tue 4/79:50 am
ORD
- NAS
1 stop9h 15m
Air Canada
Deal found 2/4![Air Canada logo]()
$360
This Expedia deal was found by Cheapflights users on 2/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/45:25 pm
SJU
- MSP
1 stop28h 07m
Frontier
Sun 3/88:04 pm
MSP
- SJU
1 stop28h 54m
Frontier
Deal found 2/3![Frontier logo]()
$287
This Kiwi.com deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/233:40 pm
AUA
- ORD
1 stop19h 56m
Multiple Airlines
Tue 3/315:05 am
ORD
- AUA
1 stop8h 30m
Multiple Airlines
Deal found 2/2![Multiple Airlines logo]()
$292
This Air Canada deal was found by Cheapflights users on 2/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/66:30 pm
NAS
- ORD
1 stop15h 35m
Air Canada
Mon 6/86:23 pm
ORD
- NAS
2 stops22h 07m
Air Canada
Deal found 2/4![Air Canada logo]()
$365
Last-minute flights from Caribbean to WisconsinDiscover last-minute flight deals from Caribbean to Wisconsin. Data last updated February 5, 2026 and is based on user searches.
Discover last-minute flight deals from Caribbean to Wisconsin. Data last updated February 5, 2026 and is based on user searches.
This Cheapflightsfares deal was found by Cheapflights users on 2/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/101:22 pm
SJU
- ORD
Nonstop5h 15m
Spirit Airlines
Sat 2/1412:17 pm
ORD
- SJU
Nonstop4h 32m
Spirit Airlines
Deal found 2/4![Spirit Airlines logo]()
$156
This Cheapflightsfares deal was found by Cheapflights users on 2/5. Clicking the “Pick Dates” 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 2/111:22 pm
SJU
- ORD
Nonstop5h 15m
Spirit Airlines
Wed 3/412:17 pm
ORD
- SJU
Nonstop4h 32m
Spirit Airlines
Deal found 2/5![Spirit Airlines logo]()
$147
This Expedia deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/111:22 pm
SJU
- ORD
Nonstop5h 15m
Spirit Airlines
Tue 2/1712:17 pm
ORD
- SJU
Nonstop4h 32m
Spirit Airlines
Deal found 2/2![Spirit Airlines logo]()
$181
This Expedia deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/1212:32 pm
SJU
- ORD
Nonstop5h 16m
Spirit Airlines
Tue 2/2412:17 pm
ORD
- SJU
Nonstop4h 32m
Spirit Airlines
Deal found 2/2![Spirit Airlines logo]()
$152
This Cheapflightsfares deal was found by Cheapflights users on 2/5. Clicking the “Pick Dates” 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 2/1212:32 pm
SJU
- ORD
Nonstop5h 16m
Spirit Airlines
Tue 2/1712:17 pm
ORD
- SJU
Nonstop4h 32m
Spirit Airlines
Deal found 2/5![Spirit Airlines logo]()
$157
This Cheapflightsfares deal was found by Cheapflights users on 2/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/1211:52 am
SJU
- ORD
1 stop7h 54m
Spirit Airlines
Sat 2/1412:17 pm
ORD
- SJU
Nonstop4h 32m
Spirit Airlines
Deal found 2/4![Spirit Airlines logo]()
$190
This Cheapflightsfares deal was found by Cheapflights users on 2/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/1212:32 pm
SJU
- ORD
Nonstop5h 16m
Spirit Airlines
Mon 2/1612:17 pm
ORD
- SJU
Nonstop4h 32m
Spirit Airlines
Deal found 2/1![Spirit Airlines logo]()
$192
This Cheapflightsfares deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/144:36 pm
SJU
- ORD
1 stop9h 11m
Spirit Airlines
Sun 2/225:15 am
ORD
- SJU
1 stop8h 16m
Spirit Airlines
Deal found 2/2![Spirit Airlines logo]()
$187
This Priceline deal was found by Cheapflights users on 2/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/173:53 am
SJU
- MKE
1 stop29h 47m
Frontier
Mon 2/238:11 pm
MKE
- SJU
1 stop28h 42m
Frontier
Deal found 2/4![Frontier logo]()
$202
This Priceline deal was found by Cheapflights users on 2/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/181:00 pm
MBJ
- ORD
1 stop11h 47m
Spirit Airlines
Sun 2/225:15 am
ORD
- MBJ
1 stop5h 47m
Spirit Airlines
Deal found 2/4![Spirit Airlines logo]()
$228
This Trip.com deal was found by Cheapflights users on 2/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/196:00 am
SJU
- MKE
1 stop29h 43m
Frontier
Mon 2/238:11 pm
MKE
- SJU
1 stop11h 43m
Frontier
Deal found 2/4![Frontier logo]()
$213
This Orbitz deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Orbitz 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
Sat 2/287:47 pm
MKE
- SJU
1 stop27h 07m
Frontier
Deal found 2/2![Frontier logo]()
$174
One-way flights from Caribbean to WisconsinSearch for one-way flight options from Caribbean to Wisconsin. Find affordable one-way fares based on user searches. Data last updated February 5, 2026.
Search for one-way flight options from Caribbean to Wisconsin. Find affordable one-way fares based on user searches. Data last updated February 5, 2026.
This Frontier deal was found by Cheapflights users on 2/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/243:53 am
SJU
- MKE
1 stop13h 51m
Frontier
Deal found 2/3![Frontier logo]()
$87
This Mytrip deal was found by Cheapflights users on 2/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/2211:07 am
SJU
- ORD
1 stop8h 08m
Spirit Airlines
Deal found 2/3![Spirit Airlines logo]()
$97
This Kiwi.com deal was found by Cheapflights users on 2/5. Clicking the “Pick Dates” 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 3/511:52 am
SJU
- ORD
1 stop29h 46m
Multiple Airlines
Deal found 2/5![Multiple Airlines logo]()
$98
This WAYA deal was found by Cheapflights users on 2/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure WAYA is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/611:44 am
SJU
- ORD
1 stop8h 34m
Multiple Airlines
Deal found 2/4![Multiple Airlines logo]()
$99
This Kiwi.com deal was found by Cheapflights users on 2/5. Clicking the “Pick Dates” 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 3/411:52 am
SJU
- ORD
1 stop23h 47m
Spirit Airlines
Deal found 2/5![Spirit Airlines logo]()
$100
This Orbitz deal was found by Cheapflights users on 2/5. Clicking the “Pick Dates” 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 3/106:30 am
SJU
- MKE
1 stop12h 20m
Frontier
Deal found 2/5![Frontier logo]()
$101
This Travelocity deal was found by Cheapflights users on 2/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/116:30 am
SJU
- ORD
1 stop10h 08m
Frontier
Deal found 2/3![Frontier logo]()
$101
This CheapOair deal was found by Cheapflights users on 2/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/2511:52 am
SJU
- ORD
1 stop23h 47m
Spirit Airlines
Deal found 2/3![Spirit Airlines logo]()
$102
This Super.com deal was found by Cheapflights users on 2/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/2712:32 pm
SJU
- ORD
Nonstop5h 16m
Spirit Airlines
Deal found 2/5![Spirit Airlines logo]()
$103
This Cheapflightsfares deal was found by Cheapflights users on 2/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/1612:22 pm
SJU
- ORD
Nonstop5h 15m
Spirit Airlines
Deal found 2/3![Spirit Airlines logo]()
$104
This Priceline deal was found by Cheapflights users on 2/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/197:04 pm
SJU
- ORD
1 stop28h 36m
Frontier
Deal found 2/3![Frontier logo]()
$107
This Trip.com deal was found by Cheapflights users on 2/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/71:21 am
SJU
- ORD
1 stop12h 39m
Frontier
Deal found 2/4![Frontier logo]()
$108
Find flight deals from Caribbean to Wisconsin
Keep the following information in mind while searching for Caribbean to Wisconsin flight deals. Data was last updated February 5, 2026.
Round-trip from | $136 (CheapOair) |
|---|---|
One-way from | $87 (Frontier) |
Popular in | July |
Cheapest in | February |
Average price | $279 |
Cheapflights Fare Finder
Customize your flight search to find flights from Caribbean 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 February 5, 2026.
Use the filters below to find and compare flights from Caribbean to Wisconsin that are best for you.
Fly from
Caribbean
Fly to
Wisconsin
Route
Depart
Return
Price
San JuanChicago
SJU - ORD
SJUORD
San Juan Luis Munoz Marin Intl
Thu 2/12
12:32 pm-3:48 pm
Nonstop5h 16m
Chicago O'Hare Intl
Tue 2/24
12:17 pm-6:49 pm
Nonstop4h 32m
$155
San JuanChicago
SJU - ORD
SJUORD
San Juan Luis Munoz Marin Intl
Thu 3/5
11:52 am-6:18 pm
1 stop8h 26m
Chicago O'Hare Intl
Sun 3/8
8:16 pm-2:31 pm
1 stop17h 15m
$175
San JuanChicago
SJU - ORD
SJUORD
San Juan Luis Munoz Marin Intl
Tue 4/7
11:03 am-9:50 am
1 stop23h 47m
Chicago O'Hare Intl
Tue 4/14
10:55 am-11:58 pm
1 stop12h 03m
$196
San JuanMilwaukee
SJU - MKE
SJUMKE
San Juan Luis Munoz Marin Intl
Thu 2/19
6:00 am-9:43 am
1 stop29h 43m
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
Sat 2/14
11:52 am-7:47 pm
1 stop9h 55m
Chicago O'Hare Intl
Sun 2/22
12:17 pm-6:49 pm
Nonstop4h 32m
$204
San JuanChicago
SJU - ORD
SJUORD
San Juan Luis Munoz Marin Intl
Mon 3/9
10:52 am-6:18 pm
1 stop8h 26m
Chicago O'Hare Intl
Thu 3/12
3:21 pm-12:29 am
1 stop8h 08m
$205
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
Thu 4/9
1:02 pm-12:53 am
1 stop10h 51m
$206
San JuanChicago
SJU - ORD
SJUORD
San Juan Luis Munoz Marin Intl
Fri 3/6
7:00 am-5:03 pm
1 stop12h 03m
Chicago O'Hare Intl
Sun 3/8
7:00 am-2:31 pm
1 stop6h 31m
$206
San JuanChicago
SJU - ORD
SJUORD
San Juan Luis Munoz Marin Intl
Thu 2/26
12:32 pm-3:48 pm
Nonstop5h 16m
Chicago O'Hare Intl
Sun 3/1
12:17 pm-6:49 pm
Nonstop4h 32m
$209
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
8:00 am-3:37 pm
1 stop6h 37m
$211
Showing 1-10 of 60 results
Best time to book a flight from Caribbean to Wisconsin
Have a flexible travel schedule? Discover the best time to fly to Wisconsin from Caribbean with our price prediction graph.
SJU-ORD
SJU-MKE
MBJ-ORD
PUJ-ORD
AUA-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 to Wisconsin
0CB-USWI
SJU-ORD
SJU-MKE
MBJ-ORD
PUJ-ORD
What is the cheapest month to book a flight from Caribbean to Wisconsin?
Currently, September is the cheapest month in which you can book a flight from Caribbean to Wisconsin (average of $113). Flying from Caribbean 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 CB to WI?
Find hourly flight availability from Caribbean 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 February 5, 2026.
When flying from Caribbean to Wisconsin, 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 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 February 5, 2026.
Get a feel of what it's like to fly with Southwest, Delta, and United Airlines from Caribbean to Wisconsin by reading reviews from past customers. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Boarding
8.1
Overall
8.0
Food
7.0
Crew
8.6
Comfort
8.0
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Boarding
8.1
Overall
8.0
Food
7.0
Crew
8.6
Comfort
8.0
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Boarding
8.1
Overall
8.0
Food
7.0
Crew
8.6
Comfort
8.0
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Boarding
8.1
Overall
8.0
Food
7.0
Crew
8.6
Comfort
8.0
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Boarding
8.1
Overall
8.0
Food
7.0
Crew
8.6
Comfort
8.0
Entertainment
7.5
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Boarding
8.1
Overall
8.0
Food
7.0
Crew
8.6
Comfort
8.0
Entertainment
7.5
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 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.
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Alternative routes for Caribbean to Wisconsin
See prices for flight routes from nearby airports that may be better suited for you.
Complete your trip
Complete your trip to Wisconsin by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Caribbean to Wisconsin by cabin class
Find flights from Caribbean to Wisconsin, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Caribbean and Wisconsin flights
Browse other Caribbean and Wisconsin flight options. Last updated on February 5, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Find a return flight route from Wisconsin
Find the right flight back to Caribbean after your stay in Wisconsin
Caribbean to Wisconsin flights
Consider these flights traveling from Caribbean to Wisconsin.
Top 5 airlines flying from Caribbean to Wisconsin
Discover the top 5 airlines that operate flights from Caribbean 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 February 5, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$112 | Average$456 | 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$468 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$256 | Average$439 | FlexibilityNo cancel fee | On-time63% |