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Jamaica

$106+ 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 2/18. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — MBJ
ene. 11 — ene. 181
dom. 1/11
dom. 1/18
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 diciembre 12, 2025.

This Booking.com deal was found by Cheapflights users on 12/9. 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.
vie. 12/265:15 amORD - MBJ
1 stop29h 40mFrontier
mar. 12/303:47 pmMBJ - ORD
2 stops29h 19mFrontier
Deal found 12/9$374
This American Airlines deal was found by Cheapflights users on 12/11. 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.
sáb. 12/138:50 pmORD - MBJ
1 stop16h 49mAmerican Airlines
jue. 12/184:27 pmMBJ - ORD
Nonstop4h 37mAmerican Airlines
Deal found 12/11$381
This Frontier deal was found by Cheapflights users on 12/10. 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.
jue. 12/256:00 amORD - MBJ
1 stop7h 29mFrontier
lun. 12/2910:14 amMBJ - ORD
1 stop13h 10mFrontier
Deal found 12/10$392
This Delta deal was found by Cheapflights users on 12/11. 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.
mié. 12/241:35 pmORD - MBJ
2 stops22h 23mDelta
mié. 12/318:00 amMBJ - ORD
2 stops26h 01mDelta
Deal found 12/11$396
This American Airlines deal was found by Cheapflights users on 12/10. 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.
vie. 12/1210:15 amORD - MBJ
Nonstop4h 07mAmerican Airlines
mar. 12/163:12 pmMBJ - ORD
Nonstop4h 47mAmerican Airlines
Deal found 12/10$406
This Expedia deal was found by Cheapflights users on 12/9. 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.
jue. 12/115:00 amORD - MBJ
1 stop6h 10mMultiple Airlines
lun. 12/152:40 pmMBJ - ORD
1 stop8h 25mMultiple Airlines
Deal found 12/9$411
This Expedia deal was found by Cheapflights users on 12/9. 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.
lun. 12/156:11 amORD - MBJ
1 stop7h 01mMultiple Airlines
sáb. 12/201:05 pmMBJ - ORD
1 stop12h 25mMultiple Airlines
Deal found 12/9$412
This Frontier deal was found by Cheapflights users on 12/11. 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.
jue. 12/256:00 amORD - MBJ
1 stop7h 29mFrontier
mié. 12/3110:24 amMBJ - ORD
1 stop9h 09mFrontier
Deal found 12/11$413
This Kiwi.com deal was found by Cheapflights users on 12/9. 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.
mar. 12/306:00 amORD - MBJ
2 stops29h 05mMultiple Airlines
vie. 1/912:57 pmMBJ - ORD
1 stop7h 41mMultiple Airlines
Deal found 12/9$414
This Kiwi.com deal was found by Cheapflights users on 12/9. 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.
mar. 12/306:00 amORD - MBJ
2 stops29h 05mMultiple Airlines
sáb. 1/104:36 pmMBJ - ORD
1 stop7h 00mMultiple Airlines
Deal found 12/9$417
This Delta deal was found by Cheapflights users on 12/9. 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.
sáb. 12/207:55 pmORD - MBJ
1 stop14h 10mDelta
mar. 12/308:00 amMBJ - ORD
1 stop9h 19mDelta
Deal found 12/9$421
This Delta deal was found by Cheapflights users on 12/10. 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.
mié. 12/105:38 amMSN - MBJ
1 stop7h 35mDelta
dom. 12/143:38 pmMBJ - MSN
1 stop7h 48mDelta
Deal found 12/10$503

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 diciembre 12, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$356
(Kiwi.com)

One-way from

$106
(Cheapflightsfares)

Popular in

June

Cheapest in

October

Average price

$697
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. 8% potential increase in price ($59 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($15 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
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 diciembre 12, 2025.
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

mar. 2/3

5:59 pm-11:13 am

1 stop16h 14m

Montego Bay Sangster Intl

jue. 2/5

2:19 pm-9:00 pm

1 stop7h 41m

$391

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

sáb. 1/24

5:50 pm-11:33 am

1 stop16h 43m

Montego Bay Sangster Intl

jue. 1/29

12:33 pm-7:50 pm

1 stop8h 17m

$391

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

mié. 1/7

5:30 am-12:54 pm

1 stop6h 24m

Montego Bay Sangster Intl

mié. 1/14

4:45 pm-11:59 pm

1 stop8h 14m

$391

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

mar. 2/3

5:30 am-12:54 pm

1 stop6h 24m

Montego Bay Sangster Intl

vie. 2/6

12:38 pm-9:00 pm

1 stop9h 22m

$391

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

dom. 1/18

5:30 am-3:20 pm

1 stop8h 50m

Montego Bay Sangster Intl

mié. 1/21

2:19 pm-11:56 pm

1 stop10h 37m

$391

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

lun. 2/2

7:59 pm-11:13 am

1 stop14h 14m

Montego Bay Sangster Intl

mié. 2/4

12:38 pm-7:21 pm

1 stop7h 43m

$391

ChicagoKingston

ORD - KIN

ORDKIN

Chicago O'Hare Intl

dom. 1/25

12:44 pm-12:12 pm

2 stops22h 28m

Kingston Norman Manley

lun. 2/2

1:17 pm-9:03 pm

1 stop8h 46m

$392

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

dom. 1/18

10:09 am-3:22 pm

Nonstop4h 13m

Montego Bay Sangster Intl

lun. 1/26

3:12 pm-6:51 pm

Nonstop4h 39m

$399

ChicagoKingston

ORD - KIN

ORDKIN

Chicago O'Hare Intl

mié. 1/14

5:32 pm-12:12 pm

1 stop17h 40m

Kingston Norman Manley

lun. 1/19

1:17 pm-1:57 pm

2 stops25h 40m

$412

ChicagoMontego Bay

ORD - MBJ

ORDMBJ

Chicago O'Hare Intl

mié. 1/28

5:30 am-3:20 pm

1 stop8h 50m

Montego Bay Sangster Intl

dom. 2/1

12:38 pm-11:56 pm

1 stop12h 18m

$413

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/9

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 $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.

What is the cheapest time of day to fly from WI to JM?

Find hourly flight availability from Wisconsin to Jamaica. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated diciembre 12, 2025.

One of the essential ways to save on airfare from Wisconsin to Jamaica is to remain as flexible as possible. Flights that are in the evening tend to be the most expensive. A flight in the afternoon could potentially save you up to 36% on airfare.

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, American Airlines, and Spirit Airlines can get you from Wisconsin to Jamaica in just under 16h 14m. Your travel time can differ by up to 6h 14m. 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 $238 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 $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.

See more FAQs

Browse thousands of different options on Cheapflights for your next trip

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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 diciembre 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$473Average$636FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$514Average$652FlexibilityNo cancel feeOn-time71%
Sun Country AirCheapest$540Average$541FlexibilityNo cancel feeOn-time83%
United AirlinesCheapest$563Average$780FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$571Average$723FlexibilityNo cancel feeOn-time63%

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