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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 2/8. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — MBJ
Feb 20 — Feb 271
Fri 2/20
Fri 2/27
1 adult, Economy
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Cheap 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 21, 2026.

This Cheapflightsfares deal was found by Cheapflights users on 1/21. Clicking the “Pick Dates” 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.
Mon 1/265:15 am
ORD
-
MBJ
1 stop5h 47m
Spirit Airlines
Fri 2/612:57 pm
MBJ
-
ORD
1 stop7h 41m
Spirit Airlines
Deal found 1/21$368
This Kiwi.com deal was found by Cheapflights users on 1/21. Clicking the “Pick Dates” 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 3/176:36 pm
ORD
-
MBJ
1 stop16h 22m
Multiple Airlines
Tue 3/2412:00 pm
MBJ
-
ORD
1 stop7h 46m
Multiple Airlines
Deal found 1/21$369
This Frontier deal was found by Cheapflights users on 1/20. Clicking the “Pick Dates” 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 4/25:15 am
ORD
-
MBJ
1 stop9h 08m
Frontier
Mon 4/131:57 pm
MBJ
-
ORD
1 stop8h 42m
Frontier
Deal found 1/20$371
This Cheapflightsfares deal was found by Cheapflights users on 1/21. Clicking the “Pick Dates” 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 2/35:15 am
ORD
-
MBJ
1 stop5h 47m
Spirit Airlines
Sun 2/812:57 pm
MBJ
-
ORD
1 stop11h 50m
Spirit Airlines
Deal found 1/21$373
This CheapOair deal was found by Cheapflights users on 1/21. Clicking the “Pick Dates” 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 2/1710:44 am
ORD
-
MBJ
2 stops24h 18m
Spirit Airlines
Wed 2/251:00 pm
MBJ
-
ORD
2 stops29h 46m
Spirit Airlines
Deal found 1/21$374
This Cheapflightsfares deal was found by Cheapflights users on 1/20. Clicking the “Pick Dates” 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 2/145:15 am
ORD
-
MBJ
1 stop5h 47m
Spirit Airlines
Wed 2/181:00 pm
MBJ
-
ORD
1 stop11h 47m
Spirit Airlines
Deal found 1/20$376
This Kiwi.com deal was found by Cheapflights users on 1/20. Clicking the “Pick Dates” 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 1/315:53 pm
ORD
-
MBJ
2 stops17h 09m
Spirit Airlines
Tue 2/1012:57 pm
MBJ
-
ORD
1 stop11h 50m
Spirit Airlines
Deal found 1/20$377
This Kiwi.com deal was found by Cheapflights users on 1/20. Clicking the “Pick Dates” 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 2/58:43 pm
ORD
-
MBJ
1 stop14h 19m
Spirit Airlines
Mon 2/912:57 pm
MBJ
-
ORD
1 stop23h 25m
Spirit Airlines
Deal found 1/20$381
This CheapOair deal was found by Cheapflights users on 1/21. Clicking the “Pick Dates” 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 1/298:43 pm
ORD
-
MBJ
1 stop14h 19m
Spirit Airlines
Thu 2/512:57 pm
MBJ
-
ORD
1 stop7h 41m
Spirit Airlines
Deal found 1/21$382
This CheapOair deal was found by Cheapflights users on 1/21. Clicking the “Pick Dates” 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 3/18:42 pm
ORD
-
MBJ
2 stops14h 20m
Spirit Airlines
Fri 3/61:00 pm
MBJ
-
ORD
1 stop9h 13m
Spirit Airlines
Deal found 1/21$383
This Kiwi.com deal was found by Cheapflights users on 1/21. Clicking the “Pick Dates” 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 3/185:05 am
ORD
-
MBJ
1 stop5h 53m
Spirit Airlines
Wed 3/2512:00 pm
MBJ
-
ORD
1 stop7h 46m
Spirit Airlines
Deal found 1/21$385
This Air Canada deal was found by Cheapflights users on 1/19. Clicking the “Pick Dates” 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.
Sun 6/218:40 pm
ORD
-
MBJ
1 stop14h 40m
Air Canada
Sat 6/2712:30 pm
MBJ
-
ORD
1 stop20h 30m
Air Canada
Deal found 1/19$386

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 January 21, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

Expedia
3 stars

Round-trip from

$368
(Cheapflightsfares)

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

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 21, 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

Sat 2/28

6:45 am-3:19 pm

1 stop7h 34m

Montego Bay Sangster Intl

Thu 3/5

12:20 pm-6:49 pm

1 stop7h 29m

$409

ChicagoKingston

ORD - KIN

ORDKIN

Chicago O'Hare Intl

Thu 2/19

3:40 pm-12:15 pm

1 stop19h 35m

Kingston Norman Manley

Mon 2/23

1:17 pm-11:22 am

1 stop23h 05m

$419

ChicagoKingston

ORD - KIN

ORDKIN

Chicago O'Hare Intl

Mon 3/16

8:41 pm-11:00 am

1 stop14h 19m

Kingston Norman Manley

Wed 3/25

12:17 pm-7:46 pm

1 stop7h 29m

$437

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Tue 4/14

7:00 am-3:29 pm

2 stops8h 29m

Montego Bay Sangster Intl

Wed 4/22

4:55 pm-7:35 am

2 stops14h 40m

$437

ChicagoKingston

ORD - KIN

ORDKIN

Chicago O'Hare Intl

Sat 3/7

8:16 pm-11:15 am

1 stop13h 59m

Kingston Norman Manley

Thu 3/12

12:17 pm-11:17 pm

1 stop11h 00m

$444

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Wed 3/4

6:15 am-2:40 pm

1 stop7h 25m

Montego Bay Sangster Intl

Mon 3/9

12:45 pm-9:49 pm

1 stop9h 04m

$448

ChicagoKingston

ORD - KIN

ORDKIN

Chicago O'Hare Intl

Mon 4/13

6:21 pm-12:35 pm

2 stops18h 14m

Kingston Norman Manley

Wed 4/22

12:00 pm-11:41 pm

1 stop11h 41m

$450

ChicagoKingston

ORD - KIN

ORDKIN

Chicago O'Hare Intl

Thu 4/16

9:50 am-12:35 pm

1 stop26h 45m

Kingston Norman Manley

Tue 4/21

12:00 pm-11:41 pm

1 stop11h 41m

$454

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Tue 4/7

6:15 am-1:27 pm

1 stop7h 12m

Montego Bay Sangster Intl

Thu 4/16

4:55 pm-10:01 am

2 stops17h 06m

$455

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

Sun 4/5

6:15 am-1:27 pm

1 stop7h 12m

Montego Bay Sangster Intl

Wed 4/15

4:55 pm-10:01 am

2 stops17h 06m

$455

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/20

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?

    Delta, Spirit Airlines, and Southwest can get you from Wisconsin to Jamaica in just under 7h 34m. Your travel time can differ by up to 6h 45m. 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.
John F Kennedy Intl to Luis Munoz Marin Intl flights
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LaGuardia to Luis Munoz Marin Intl flights
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John F Kennedy Intl to Montego Bay flights
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John F Kennedy Intl to Nassau flights
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Newark to Nassau flights
John F Kennedy Intl to Port of Spain flights
Boston to Oranjestad flights
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LaGuardia to Punta Cana flights
Minneapolis to Luis Munoz Marin Intl flights
Detroit to Luis Munoz Marin Intl flights
Fort Lauderdale to Luis Munoz Marin Intl flights
Dulles Intl to Punta Cana flights
Newark to Simpson Bay flights
Hobby to Luis Munoz Marin Intl flights
LaGuardia to Nassau flights
Boston to Punta Cana flights
John F Kennedy Intl to Simpson Bay flights
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Newark to Montego Bay flights
Midway to Luis Munoz Marin Intl flights
Atlanta to Punta Cana flights
O'Hare Intl to Punta Cana flights
Tampa to Luis Munoz Marin Intl flights
LaGuardia to Santo Domingo flights
Newark to Providenciales flights
George Bush Intcntl to Luis Munoz Marin Intl flights
LaGuardia to Santiago de los Caballeros flights
LaGuardia to Oranjestad flights
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John F Kennedy Intl to Saint Thomas Island flights

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 21, 2026.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$470Average$634FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$508Average$640FlexibilityNo cancel feeOn-time71%
Sun Country AirCheapest$540Average$540FlexibilityNo cancel feeOn-time83%
United AirlinesCheapest$563Average$739FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$565Average$678FlexibilityNo cancel feeOn-time63%

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