$98+ Cheap flights from Wisconsin to Jamaica
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.
MKE — MBJ
Mar 3 — Mar 101
1 adult, Economy
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Find cheap flights from Wisconsin to Jamaica with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
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Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from Wisconsin to Jamaica
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Cheapest flights from Wisconsin to JamaicaExplore the most affordable flight options available from Wisconsin to Jamaica. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 1, 2026.
Explore the most affordable flight options available from Wisconsin to Jamaica. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 1, 2026.
This CheapOair 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/118:16 pm
ORD
- KIN
1 stop15h 19m
Spirit Airlines
Wed 3/2512:32 pm
KIN
- ORD
1 stop7h 19m
Spirit Airlines
Deal found 1/31![Spirit Airlines logo]()
$349
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.
Sat 4/255:15 am
ORD
- MBJ
1 stop5h 47m
Spirit Airlines
Wed 4/2912:00 pm
MBJ
- ORD
2 stops19h 59m
Spirit Airlines
Deal found 1/30![Spirit Airlines logo]()
$363
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.
Tue 4/148:58 pm
ORD
- MBJ
2 stops14h 04m
Spirit Airlines
Wed 4/2212:00 pm
MBJ
- ORD
2 stops19h 59m
Spirit Airlines
Deal found 1/30![Spirit Airlines logo]()
$364
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 3/35:15 am
ORD
- MBJ
1 stop5h 47m
Multiple Airlines
Sat 3/74:32 pm
MBJ
- ORD
2 stops16h 50m
Multiple Airlines
Deal found 1/30![Multiple Airlines logo]()
$365
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.
Tue 2/105:15 am
ORD
- MBJ
1 stop5h 47m
Spirit Airlines
Tue 2/171:00 pm
MBJ
- ORD
1 stop9h 13m
Spirit Airlines
Deal found 1/30![Spirit Airlines logo]()
$366
This American 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/38:20 am
ORD
- MBJ
Nonstop4h 06m
American Airlines
Tue 3/1010:07 am
MBJ
- ORD
1 stop13h 10m
American Airlines
Deal found 1/31![American Airlines logo]()
$367
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 3/126:10 pm
ORD
- KIN
1 stop17h 25m
Spirit Airlines
Thu 3/1912:32 pm
KIN
- ORD
1 stop7h 19m
Spirit Airlines
Deal found 1/31![Spirit Airlines logo]()
$367
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.
Sun 4/55:05 am
ORD
- MBJ
1 stop6h 00m
Multiple Airlines
Thu 4/912:00 pm
MBJ
- ORD
1 stop10h 50m
Multiple Airlines
Deal found 1/29![Multiple Airlines logo]()
$368
This Gotogate 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/158:20 pm
ORD
- MBJ
1 stop15h 00m
Air Canada
Mon 6/2212:30 pm
MBJ
- ORD
1 stop20h 30m
Air Canada
Deal found 1/31![Air Canada logo]()
$369
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.
Fri 2/208:42 pm
ORD
- MBJ
2 stops14h 20m
Spirit Airlines
Fri 2/271:00 pm
MBJ
- ORD
1 stop11h 47m
Spirit Airlines
Deal found 1/30![Spirit Airlines logo]()
$370
This CheapOair 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/215:15 am
ORD
- MBJ
1 stop5h 47m
Spirit Airlines
Sat 2/281:00 pm
MBJ
- ORD
1 stop9h 13m
Spirit Airlines
Deal found 1/31![Spirit Airlines logo]()
$371
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 2/910:48 am
ORD
- MBJ
3 stops24h 14m
Spirit Airlines
Thu 2/121:00 pm
MBJ
- ORD
1 stop11h 47m
Spirit Airlines
Deal found 1/30![Spirit Airlines logo]()
$372
Best flights from Wisconsin to JamaicaDiscover carefully curated flight deals from Wisconsin to Jamaica that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated February 1, 2026.
Discover carefully curated flight deals from Wisconsin to Jamaica that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated February 1, 2026.
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/156:10 pm
ORD
- MBJ
1 stop16h 55m
Spirit Airlines
Sun 3/2212:00 pm
MBJ
- ORD
2 stops28h 56m
Spirit Airlines
Deal found 1/31![Spirit Airlines logo]()
$366
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.
Thu 3/58:42 am
ORD
- MBJ
Nonstop4h 04m
United Airlines
Wed 3/111:48 pm
MBJ
- ORD
Nonstop4h 25m
United Airlines
Deal found 1/31![United Airlines logo]()
$387
This Air Canada 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/198:40 pm
ORD
- MBJ
1 stop14h 40m
Air Canada
Thu 6/2512:30 pm
MBJ
- ORD
2 stops19h 05m
Air Canada
Deal found 1/31![Air Canada logo]()
$391
This Trip.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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/288:16 pm
ORD
- KIN
1 stop14h 59m
Multiple Airlines
Sat 3/73:09 pm
KIN
- ORD
1 stop9h 38m
Multiple Airlines
Deal found 1/30![Multiple Airlines logo]()
$426
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/245:25 am
MKE
- MBJ
1 stop6h 28m
Delta
Tue 3/34:44 pm
MBJ
- MKE
1 stop8h 03m
Delta
Deal found 1/31![Delta logo]()
$488
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.
Mon 3/26:20 pm
MSP
- MBJ
2 stops17h 40m
Southwest
Tue 3/101:00 pm
MBJ
- MSP
2 stops10h 30m
Southwest
Deal found 1/30![Southwest logo]()
$533
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.
Fri 3/66:01 am
MKE
- KIN
1 stop7h 28m
American Airlines
Wed 3/116:32 am
KIN
- MKE
2 stops16h 52m
American Airlines
Deal found 1/30![American Airlines logo]()
$731
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 3/186:10 pm
ORD
- MBJ
1 stop16h 55m
Spirit Airlines
Sun 3/2212:00 pm
MBJ
- ORD
1 stop23h 17m
Spirit Airlines
Deal found 1/30![Spirit Airlines logo]()
$367
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.
Wed 3/115:40 am
ORD
- MBJ
1 stop7h 25m
United Airlines
Sun 3/151:48 pm
MBJ
- ORD
Nonstop4h 25m
United Airlines
Deal found 1/30![United Airlines logo]()
$391
This Cheapflightsfares 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/126:10 pm
ORD
- KIN
1 stop17h 25m
Spirit Airlines
Thu 3/1912:32 pm
KIN
- ORD
1 stop7h 19m
Spirit Airlines
Deal found 1/29![Spirit Airlines logo]()
$367
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.
Wed 4/228:45 am
ORD
- MBJ
1 stop6h 25m
United Airlines
Sun 4/261:52 pm
MBJ
- ORD
Nonstop4h 23m
United Airlines
Deal found 1/31![United Airlines logo]()
$391
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 3/187:18 pm
ORD
- KIN
2 stops40h 17m
Multiple Airlines
Wed 4/812:32 pm
KIN
- ORD
1 stop7h 19m
Multiple Airlines
Deal found 1/29![Multiple Airlines logo]()
$437
This CheapOair 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/1110:19 am
ORD
- KIN
2 stops25h 16m
Spirit Airlines
Wed 3/2512:32 pm
KIN
- ORD
1 stop7h 19m
Spirit Airlines
Deal found 1/31![Spirit Airlines logo]()
$367
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/117:00 am
MKE
- MBJ
1 stop6h 16m
Delta
Wed 5/204:55 pm
MBJ
- MKE
1 stop6h 32m
Delta
Deal found 1/30![Delta logo]()
$488
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.
Sun 3/228:58 pm
ORD
- MBJ
2 stops14h 07m
Spirit Airlines
Wed 3/2512:00 pm
MBJ
- ORD
1 stop11h 17m
Spirit Airlines
Deal found 1/30![Spirit Airlines logo]()
$378
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/237:05 am
MKE
- MBJ
1 stop7h 14m
Delta
Tue 3/34:44 pm
MBJ
- MKE
1 stop8h 03m
Delta
Deal found 1/31![Delta logo]()
$488
This CheapOair 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/68:42 pm
ORD
- MBJ
2 stops14h 20m
Spirit Airlines
Mon 3/911:57 am
MBJ
- ORD
2 stops29h 49m
Spirit Airlines
Deal found 1/31![Spirit Airlines logo]()
$379
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/246:15 am
MKE
- MBJ
1 stop7h 25m
Delta
Wed 2/254:44 pm
MBJ
- MKE
1 stop8h 03m
Delta
Deal found 1/31![Delta logo]()
$488
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/156:10 pm
ORD
- MBJ
1 stop16h 55m
Spirit Airlines
Fri 3/2012:00 pm
MBJ
- ORD
2 stops36h 22m
Spirit Airlines
Deal found 1/31![Spirit Airlines logo]()
$382
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/245:06 pm
MSN
- MBJ
1 stop17h 04m
Delta
Wed 3/44:44 pm
MBJ
- MSN
1 stop6h 40m
Delta
Deal found 1/31![Delta logo]()
$488
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.
Sun 3/156:10 pm
ORD
- MBJ
1 stop16h 55m
Spirit Airlines
Sat 3/2112:00 pm
MBJ
- ORD
1 stop11h 17m
Spirit Airlines
Deal found 1/31![Spirit Airlines logo]()
$385
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/245:38 am
MSN
- MBJ
1 stop8h 41m
Delta
Tue 3/32:19 pm
MBJ
- MSN
1 stop9h 05m
Delta
Deal found 1/31![Delta logo]()
$488
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.
Mon 5/46:24 pm
DLH
- MBJ
2 stops19h 06m
United Airlines
Fri 5/84:12 pm
MBJ
- DLH
2 stops25h 08m
United Airlines
Deal found 1/29![United Airlines logo]()
$606
This American 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/286:11 pm
MSP
- KIN
2 stops19h 18m
American Airlines
Sat 4/42:34 pm
KIN
- MSP
2 stops19h 18m
American Airlines
Deal found 1/31![American Airlines logo]()
$749
This Air Canada 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/412:00 pm
MSP
- KIN
1 stop24h 45m
Air Canada
Wed 3/111:55 pm
KIN
- MSP
1 stop25h 54m
Air Canada
Deal found 1/31![Air Canada logo]()
$751
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/236:20 am
MSN
- MBJ
1 stop7h 20m
Delta
Fri 3/612:20 pm
MBJ
- MSN
1 stop11h 04m
Delta
Deal found 1/31![Delta logo]()
$488
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.
Sun 2/226:00 am
MKE
- KIN
2 stops13h 08m
American Airlines
Fri 2/2711:12 am
KIN
- MKE
2 stops13h 12m
American Airlines
Deal found 1/29![American Airlines logo]()
$749
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.
Thu 3/58:16 pm
ORD
- KIN
1 stop14h 59m
Spirit Airlines
Sun 3/812:17 pm
KIN
- ORD
1 stop11h 30m
Spirit Airlines
Deal found 1/31![Spirit Airlines logo]()
$424
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/256:20 am
MSN
- MBJ
1 stop7h 20m
Delta
Thu 3/512:20 pm
MBJ
- MSN
1 stop11h 04m
Delta
Deal found 1/31![Delta logo]()
$488
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 2/195:00 am
MKE
- KIN
2 stops14h 08m
American Airlines
Thu 2/2611:12 am
KIN
- MKE
1 stop13h 02m
American Airlines
Deal found 1/29![American Airlines logo]()
$749
Last-minute flights from Wisconsin to JamaicaDiscover last-minute flight deals from Wisconsin to Jamaica. Data last updated February 1, 2026 and is based on user searches.
Discover last-minute flight deals from Wisconsin to Jamaica. Data last updated February 1, 2026 and is based on user searches.
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 2/68:43 pm
ORD
- MBJ
1 stop14h 19m
Spirit Airlines
Tue 2/1012:57 pm
MBJ
- ORD
1 stop11h 50m
Spirit Airlines
Deal found 1/30![Spirit Airlines logo]()
$364
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.
Sat 2/710:48 am
ORD
- MBJ
3 stops24h 14m
Spirit Airlines
Sat 2/141:00 pm
MBJ
- ORD
1 stop9h 13m
Spirit Airlines
Deal found 1/31![Spirit Airlines logo]()
$374
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 2/910:48 am
ORD
- MBJ
3 stops24h 14m
Spirit Airlines
Thu 2/121:00 pm
MBJ
- ORD
1 stop11h 47m
Spirit Airlines
Deal found 1/30![Spirit Airlines logo]()
$372
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.
Tue 2/105:15 am
ORD
- MBJ
1 stop5h 47m
Spirit Airlines
Tue 2/171:00 pm
MBJ
- ORD
1 stop9h 13m
Spirit Airlines
Deal found 1/30![Spirit Airlines logo]()
$366
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.
Tue 2/1710:19 am
ORD
- MBJ
2 stops24h 43m
Spirit Airlines
Wed 2/251:00 pm
MBJ
- ORD
2 stops29h 46m
Spirit Airlines
Deal found 1/30![Spirit Airlines logo]()
$377
This CheapOair 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/1710:19 am
ORD
- MBJ
2 stops24h 43m
Spirit Airlines
Tue 2/241:00 pm
MBJ
- ORD
2 stops29h 46m
Spirit Airlines
Deal found 1/31![Spirit Airlines logo]()
$379
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/197:23 pm
ORD
- MBJ
2 stops37h 02m
Multiple Airlines
Tue 2/241:00 pm
MBJ
- ORD
1 stop9h 13m
Multiple Airlines
Deal found 1/31![Multiple Airlines logo]()
$373
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.
Fri 2/208:42 pm
ORD
- MBJ
2 stops14h 20m
Spirit Airlines
Fri 2/271:00 pm
MBJ
- ORD
1 stop11h 47m
Spirit Airlines
Deal found 1/30![Spirit Airlines logo]()
$370
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/214:42 pm
ORD
- MBJ
1 stop15h 35m
Multiple Airlines
Tue 2/241:00 pm
MBJ
- ORD
1 stop9h 13m
Multiple Airlines
Deal found 1/31![Multiple Airlines logo]()
$368
This CheapOair 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/215:15 am
ORD
- MBJ
1 stop5h 47m
Spirit Airlines
Sat 2/281:00 pm
MBJ
- ORD
1 stop9h 13m
Spirit Airlines
Deal found 1/31![Spirit Airlines logo]()
$371
This CheapOair 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 2/225:15 am
ORD
- MBJ
1 stop5h 47m
Spirit Airlines
Sun 3/11:00 pm
MBJ
- ORD
1 stop23h 22m
Spirit Airlines
Deal found 1/31![Spirit Airlines logo]()
$378
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.
Sat 2/288:16 pm
ORD
- MBJ
1 stop14h 46m
Multiple Airlines
Sat 3/74:32 pm
MBJ
- ORD
2 stops16h 50m
Multiple Airlines
Deal found 1/30![Multiple Airlines logo]()
$381
One-way flights from Wisconsin to JamaicaSearch for one-way flight options from Wisconsin to Jamaica. Find affordable one-way fares based on user searches. Data last updated February 1, 2026.
Search for one-way flight options from Wisconsin to Jamaica. Find affordable one-way fares based on user searches. Data last updated February 1, 2026.
This Super.com 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/248:16 pm
ORD
- MBJ
1 stop14h 46m
Spirit Airlines
Deal found 1/31![Spirit Airlines logo]()
$98
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.
Tue 3/35:15 am
ORD
- MBJ
1 stop5h 47m
Spirit Airlines
Deal found 1/30![Spirit Airlines logo]()
$100
This Expedia 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/235:15 am
ORD
- MBJ
1 stop5h 47m
Spirit Airlines
Deal found 1/31![Spirit Airlines logo]()
$103
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.
Wed 2/255:15 am
ORD
- MBJ
1 stop5h 47m
Spirit Airlines
Deal found 1/30![Spirit Airlines logo]()
$104
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 2/185:15 am
ORD
- MBJ
1 stop5h 47m
Spirit Airlines
Deal found 1/30![Spirit Airlines logo]()
$105
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.
Thu 2/195:15 am
ORD
- MBJ
1 stop5h 47m
Spirit Airlines
Deal found 1/31![Spirit Airlines logo]()
$107
This Super.com 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 2/225:15 am
ORD
- MBJ
1 stop5h 47m
Spirit Airlines
Deal found 1/31![Spirit Airlines logo]()
$110
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.
Fri 2/278:16 pm
ORD
- MBJ
1 stop14h 46m
Spirit Airlines
Deal found 1/30![Spirit Airlines logo]()
$111
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.
Tue 3/245:05 am
ORD
- MBJ
1 stop6h 00m
Spirit Airlines
Deal found 1/30![Spirit Airlines logo]()
$112
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.
Sat 2/288:16 pm
ORD
- MBJ
1 stop14h 46m
Spirit Airlines
Deal found 1/30![Spirit Airlines logo]()
$114
This FlightHub 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/185:15 am
ORD
- MBJ
1 stop5h 47m
Spirit Airlines
Deal found 1/31![Spirit Airlines logo]()
$116
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 3/58:16 pm
ORD
- MBJ
1 stop14h 46m
Spirit Airlines
Deal found 1/30![Spirit Airlines logo]()
$117
Find flight deals from Wisconsin to Jamaica
Keep the following information in mind while searching for Wisconsin to Jamaica flight deals. Data was last updated February 1, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $349 (CheapOair) |
One-way from | $98 (Super.com) |
Popular in | June |
Cheapest in | October |
Average price | $572 |
Cheapflights Fare Finder
Customize your flight search to find flights from Wisconsin to Jamaica 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 1, 2026.
Use the filters below to find and compare flights from Wisconsin to Jamaica that are best for you.
Fly from
Wisconsin
Fly to
Jamaica
Route
Depart
Return
Price
ChicagoMontego Bay
ORD - MBJ
ORDMBJ
Chicago O'Hare Intl
Sun 3/15
6:10 pm-11:05 am
1 stop16h 55m
Montego Bay Sangster Intl
Sun 3/22
12:00 pm-4:56 pm
2 stops28h 56m
$366
ChicagoMontego Bay
ORD - MBJ
ORDMBJ
Chicago O'Hare Intl
Wed 3/18
6:10 pm-11:05 am
1 stop16h 55m
Montego Bay Sangster Intl
Sun 3/22
12:00 pm-11:17 am
1 stop23h 17m
$367
ChicagoKingston
ORD - KIN
ORDKIN
Chicago O'Hare Intl
Thu 3/12
6:10 pm-11:35 am
1 stop17h 25m
Kingston Norman Manley
Thu 3/19
12:32 pm-7:51 pm
1 stop7h 19m
$367
ChicagoKingston
ORD - KIN
ORDKIN
Chicago O'Hare Intl
Wed 3/11
10:19 am-11:35 am
2 stops25h 16m
Kingston Norman Manley
Wed 3/25
12:32 pm-7:51 pm
1 stop7h 19m
$367
ChicagoMontego Bay
ORD - MBJ
ORDMBJ
Chicago O'Hare Intl
Sun 3/22
8:58 pm-11:05 am
2 stops14h 07m
Montego Bay Sangster Intl
Wed 3/25
12:00 pm-11:17 pm
1 stop11h 17m
$378
ChicagoMontego Bay
ORD - MBJ
ORDMBJ
Chicago O'Hare Intl
Fri 3/6
8:42 pm-12:02 pm
2 stops14h 20m
Montego Bay Sangster Intl
Mon 3/9
11:57 am-5:46 pm
2 stops29h 49m
$379
ChicagoMontego Bay
ORD - MBJ
ORDMBJ
Chicago O'Hare Intl
Sun 3/15
6:10 pm-11:05 am
1 stop16h 55m
Montego Bay Sangster Intl
Fri 3/20
12:00 pm-12:22 am
2 stops36h 22m
$382
ChicagoMontego Bay
ORD - MBJ
ORDMBJ
Chicago O'Hare Intl
Sun 3/15
6:10 pm-11:05 am
1 stop16h 55m
Montego Bay Sangster Intl
Sat 3/21
12:00 pm-11:17 pm
1 stop11h 17m
$385
ChicagoMontego Bay
ORD - MBJ
ORDMBJ
Chicago O'Hare Intl
Thu 3/5
8:42 am-1:46 pm
Nonstop4h 04m
Montego Bay Sangster Intl
Wed 3/11
1:48 pm-6:13 pm
Nonstop4h 25m
$387
ChicagoMontego Bay
ORD - MBJ
ORDMBJ
Chicago O'Hare Intl
Fri 6/19
8:40 pm-11:20 am
1 stop14h 40m
Montego Bay Sangster Intl
Thu 6/25
12:30 pm-7:35 am
2 stops19h 05m
$391
Showing 1-10 of 60 results
Best time to book a flight from Wisconsin to Jamaica
Have a flexible travel schedule? Discover the best time to fly to Jamaica from Wisconsin with our price prediction graph.
ORD-MBJ
ORD-KIN
MKE-MBJ
MSP-MBJ
MKE-KIN
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 Wisconsin to Jamaica
USWI-JM0
ORD-MBJ
ORD-KIN
MKE-MBJ
MSP-MBJ
What is the cheapest month to book a flight from Wisconsin to Jamaica?
Currently, October is the cheapest month in which you can book a flight from Wisconsin to Jamaica (average of $312). Flying from Wisconsin to Jamaica in July is currently the most expensive (average of $637). 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.
Related info for your journey
Find useful and relevant information for your journey from Wisconsin to Jamaica. 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 Wisconsin to Jamaica
See prices for flight routes from nearby airports that may be better suited for you.
Top 5 airlines flying from Wisconsin to Jamaica
Discover the top 5 airlines that operate flights from Wisconsin to Jamaica. 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 1, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$277 | Average$634 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$490 | Average$649 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$540 | Average$540 | FlexibilityNo cancel fee | On-time83% | |
| Cheapest$563 | Average$729 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$571 | Average$763 | FlexibilityNo cancel fee | On-time63% |