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Jamaica

$100+ 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 2/7. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — MBJ
Feb 13 — Feb 201
Fri 2/13
Fri 2/20
1 adult, Economy
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Cheap flight deals from Wisconsin to Jamaica

Keep the following information in mind while searching for Wisconsin to Jamaica flight deals. Data was last updated January 14, 2026.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$385
(Priceline)

One-way from

$100
(Cheapflightsfares)

Popular in

June

Cheapest in

October

Average price

$588
Provider with most accurate pricing for Milwaukee-Mitchell-Montego Bay Sangster Intl flight deals.
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Provider most trusted by Cheapflights users for Milwaukee-Mitchell-Montego Bay Sangster Intl flights.
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From Wisconsin to Jamaica
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One-way flight from Wisconsin to Jamaica
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Highest demand for flights based on searches. 9% potential increase in price ($63 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($16 potential savings vs. average RT price).
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Average for round-trip flights in January 2026
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Find flight deals from Wisconsin to Jamaica

Cheapest flights from Wisconsin to Jamaica
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 January 14, 2026.

This Booking.com deal was found by Cheapflights users on 1/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/2010:00 am
MSP
-
MBJ
2 stops46h 17m
Frontier
Sat 2/2812:40 pm
MBJ
-
MSP
2 stops45h 25m
Frontier
Deal found 1/14$378
This Kiwi.com deal was found by Cheapflights users on 1/13. Clicking the “Pick Dates” 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 1/195:15 am
ORD
-
MBJ
1 stop5h 47m
Spirit Airlines
Tue 2/312:57 pm
MBJ
-
ORD
1 stop11h 50m
Spirit Airlines
Deal found 1/13$385
This Expedia deal was found by Cheapflights users on 1/13. Clicking the “Pick Dates” 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 6/189:50 am
ORD
-
MBJ
1 stop25h 30m
Air Canada
Tue 6/2312:30 pm
MBJ
-
ORD
1 stop24h 52m
Air Canada
Deal found 1/13$386
This Cheapflightsfares deal was found by Cheapflights users on 1/13. Clicking the “Pick Dates” 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 1/245:32 pm
ORD
-
MBJ
1 stop17h 30m
Spirit Airlines
Thu 1/2912:57 pm
MBJ
-
ORD
1 stop7h 41m
Spirit Airlines
Deal found 1/13$387
This Kiwi.com deal was found by Cheapflights users on 1/14. Clicking the “Pick Dates” 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 2/125:15 am
ORD
-
MBJ
1 stop5h 47m
Spirit Airlines
Sat 2/141:00 pm
MBJ
-
ORD
1 stop9h 13m
Spirit Airlines
Deal found 1/14$388
This Kiwi.com deal was found by Cheapflights users on 1/13. Clicking the “Pick Dates” 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 1/235:15 am
ORD
-
MBJ
1 stop5h 47m
Spirit Airlines
Sat 2/712:57 pm
MBJ
-
ORD
1 stop11h 50m
Spirit Airlines
Deal found 1/13$390
This Kiwi.com deal was found by Cheapflights users on 1/13. Clicking the “Pick Dates” 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 3/55:15 am
ORD
-
MBJ
1 stop5h 47m
Multiple Airlines
Sun 3/1512:00 pm
MBJ
-
ORD
1 stop29h 24m
Multiple Airlines
Deal found 1/13$391
This Kiwi.com deal was found by Cheapflights users on 1/13. Clicking the “Pick Dates” 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 1/228:43 pm
ORD
-
MBJ
1 stop14h 19m
Spirit Airlines
Mon 2/912:57 pm
MBJ
-
ORD
1 stop23h 25m
Spirit Airlines
Deal found 1/13$392
This Mytrip deal was found by Cheapflights users on 1/13. Clicking the “Pick Dates” 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 2/910:07 am
ORD
-
MBJ
3 stops24h 55m
Spirit Airlines
Sat 2/141:00 pm
MBJ
-
ORD
2 stops12h 40m
Spirit Airlines
Deal found 1/13$393
This Air Canada deal was found by Cheapflights users on 1/13. Clicking the “Pick Dates” 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 5/238:20 pm
ORD
-
MBJ
1 stop15h 00m
Air Canada
Fri 5/2912:15 pm
MBJ
-
ORD
1 stop20h 45m
Air Canada
Deal found 1/13$394
This Kiwi.com deal was found by Cheapflights users on 1/13. Clicking the “Pick Dates” 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 1/292:52 pm
ORD
-
MBJ
1 stop20h 10m
Multiple Airlines
Mon 2/912:57 pm
MBJ
-
ORD
1 stop23h 25m
Multiple Airlines
Deal found 1/13$395
This Mytrip deal was found by Cheapflights users on 1/13. Clicking the “Pick Dates” 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 2/312:44 pm
ORD
-
MBJ
3 stops22h 18m
Spirit Airlines
Wed 2/1112:57 pm
MBJ
-
ORD
3 stops21h 25m
Spirit Airlines
Deal found 1/13$396

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 January 14, 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

Thu 5/14

10:53 am-11:20 am

2 stops24h 27m

Montego Bay Sangster Intl

Mon 5/18

12:15 pm-9:00 am

1 stop20h 45m

$404

ChicagoKingston

ORD - KIN

ORDKIN

Chicago O'Hare Intl

Sun 1/25

8:43 pm-12:12 pm

1 stop14h 29m

Kingston Norman Manley

Thu 2/5

1:17 pm-9:03 pm

1 stop8h 46m

$406

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Thu 3/12

8:41 pm-10:58 am

1 stop14h 17m

Montego Bay Sangster Intl

Sun 3/15

12:00 pm-11:17 pm

1 stop11h 17m

$413

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Mon 2/23

5:25 am-3:19 pm

1 stop8h 54m

Montego Bay Sangster Intl

Tue 3/3

12:20 pm-11:56 pm

1 stop12h 36m

$416

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Wed 2/25

6:40 pm-1:56 pm

1 stop18h 16m

Montego Bay Sangster Intl

Tue 3/3

2:19 pm-11:56 pm

1 stop10h 37m

$416

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Wed 2/25

5:25 am-12:53 pm

1 stop6h 28m

Montego Bay Sangster Intl

Thu 2/26

4:44 pm-11:56 pm

1 stop8h 12m

$416

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Sun 3/1

8:16 pm-12:02 pm

1 stop14h 46m

Montego Bay Sangster Intl

Sun 3/8

11:57 am-5:25 pm

1 stop29h 28m

$419

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Sun 2/15

5:37 pm-3:19 pm

2 stops20h 42m

Montego Bay Sangster Intl

Thu 2/19

2:19 pm-9:41 am

2 stops20h 22m

$421

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Tue 2/17

10:35 am-11:10 am

2 stops23h 35m

Montego Bay Sangster Intl

Tue 2/24

4:44 pm-1:20 pm

2 stops21h 36m

$421

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Sun 2/15

5:37 pm-3:19 pm

2 stops20h 42m

Montego Bay Sangster Intl

Tue 2/17

4:05 pm-8:40 am

1 stop17h 35m

$421

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/14

Showing 1-10 of 60 results
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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.
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

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 $635). 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.

  • How long is the flight from Wisconsin to Jamaica?

    Air Canada, Spirit Airlines, and Delta can get you from Wisconsin to Jamaica in just under 8h 54m. Your travel time can differ by up to 15h 33m. Airlines will cover a distance of 1724 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • What are the cheapest airlines to fly from Wisconsin to Jamaica one-way?

    To fly one-way, consider booking your trip with Alaska Airlines, which is currently one of the cheapest options available, starting at $228. Delta flights start at $236 while deals on United Airlines start at $250 one-way.

  • Can I find deals for flights from Wisconsin to Jamaica that include hotel bookings?

    Yes. In addition to deals on Wisconsin to Jamaica flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Wisconsin to Jamaica?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Wisconsin to Jamaica.

  • Can I find deals for business class flights from Wisconsin to Jamaica?

    Yes. Cheapflights offers flight deals from Wisconsin to Jamaica by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • 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 $635). 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.

See more FAQs

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.
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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 January 14, 2026.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$473Average$637FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$508Average$642FlexibilityNo cancel feeOn-time71%
Sun Country AirCheapest$540Average$541FlexibilityNo cancel feeOn-time83%
United AirlinesCheapest$563Average$759FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$565Average$678FlexibilityNo cancel feeOn-time63%

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