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Jamaica

$167+ Cheap flights from Milwaukee (MKE) 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 6/18. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — MBJ
Apr 20 — Apr 271
Sun 4/20
Sun 4/27
1 adult, Economy
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Cheap flight deals from Milwaukee to Jamaica

Keep the following information in mind while searching for Milwaukee to Jamaica flight deals. Data was last updated April 15, 2025.

Most accurate provider

AranGrant
3 stars

Most trusted provider

AranGrant
3 stars

Round-trip from

$399
(Mytrip)

One-way from

$167
(Kiwi.com)

Popular in

June

Cheapest in

May

Average price

$599
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 Milwaukee-Mitchell to Jamaica
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One-way flight from Milwaukee-Mitchell to Jamaica
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Highest demand for flights based on searches. 6% potential increase in price ($43 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 April 2025
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Find flight deals from Milwaukee to Jamaica

Cheapest flights from Milwaukee to Jamaica
Explore the most affordable flight options available from Milwaukee to Jamaica. Find the lowest fares from popular airlines and budget airlines, with prices last updated on April 15, 2025.

This Mytrip deal was found by Cheapflights users on 4/14. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/15:00 pmMKE - MBJ
1 stop17h 55mMultiple Airlines
Tue 5/63:05 pmMBJ - MKE
2 stops20h 22mMultiple Airlines
Deal found 4/14$399
This Booking.com deal was found by Cheapflights users on 4/13. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/2812:22 pmMKE - MBJ
2 stops22h 40mSpirit Airlines
Wed 6/412:07 pmMBJ - MKE
2 stops23h 20mSpirit Airlines
Deal found 4/13$415
This American Airlines deal was found by Cheapflights users on 4/14. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/227:25 amMKE - MBJ
1 stop7h 35mAmerican Airlines
Tue 8/265:05 pmMBJ - MKE
1 stop6h 25mAmerican Airlines
Deal found 4/14$486
This Southwest deal was found by Cheapflights users on 4/13. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/285:10 amMKE - MBJ
1 stop6h 25mSouthwest
Wed 6/412:35 pmMBJ - MKE
1 stop9h 40mSouthwest
Deal found 4/13$538
This Delta deal was found by Cheapflights users on 4/13. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/267:00 amMKE - MBJ
1 stop5h 54mDelta
Fri 10/312:19 pmMBJ - MKE
1 stop9h 06mDelta
Deal found 4/13$541
This Mytrip deal was found by Cheapflights users on 4/15. 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 6/712:22 pmMKE - KIN
2 stops32h 13mMultiple Airlines
Sat 6/141:34 pmKIN - MKE
3 stops42h 32mMultiple Airlines
Deal found 4/15$613
This United deal was found by Cheapflights users on 4/15. 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/75:45 pmMKE - MBJ
2 stops19h 25mUnited Airlines
Fri 7/111:51 pmMBJ - MKE
1 stop8h 54mUnited Airlines
Deal found 4/15$615
This Delta deal was found by Cheapflights users on 4/15. 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 9/110:25 amMKE - KIN
1 stop9h 39mDelta
Thu 9/49:10 amKIN - MKE
1 stop8h 38mDelta
Deal found 4/15$651
This American Airlines deal was found by Cheapflights users on 4/15. 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.
Mon 9/17:25 amMKE - KIN
2 stops11h 00mAmerican Airlines
Thu 9/49:10 amKIN - MKE
2 stops12h 17mAmerican Airlines
Deal found 4/15$656
This Justfly.com deal was found by Cheapflights users on 4/14. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/2510:45 amMKE - MBJ
2 stops25h 25mAir Canada
Sun 11/305:25 pmMBJ - MKE
2 stops29h 44mAir Canada
Deal found 4/14$1,088
This WestJet deal was found by Cheapflights users on 4/14. 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 WestJet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/121:05 pmMKE - MBJ
2 stops23h 48mWestJet
Wed 11/192:55 pmMBJ - MKE
2 stops22h 32mWestJet
Deal found 4/14$3,407

Cheapflights Fare Finder

Customize your flight search to find flights from Milwaukee 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 April 15, 2025.
Use the filters below to find and compare flights from Milwaukee to Jamaica that are best for you.

Fly from

Milwaukee

Fly to

Jamaica

Route

Depart

Return

Price

MilwaukeeMontego Bay

MKE - MBJ

MKEMBJ

Milwaukee-Mitchell

Thu 5/1

5:00 pm-10:55 am

1 stop17h 55m

Montego Bay Sangster Intl

Tue 5/6

3:05 pm-11:27 am

2 stops20h 22m

$399

MilwaukeeMontego Bay

MKE - MBJ

MKEMBJ

Milwaukee-Mitchell

Wed 5/28

12:22 pm-11:02 am

2 stops22h 40m

Montego Bay Sangster Intl

Wed 6/4

12:07 pm-11:27 am

2 stops23h 20m

$415

MilwaukeeMontego Bay

MKE - MBJ

MKEMBJ

Milwaukee-Mitchell

Fri 8/22

7:25 am-3:00 pm

1 stop7h 35m

Montego Bay Sangster Intl

Tue 8/26

5:05 pm-11:30 pm

1 stop6h 25m

$486

MilwaukeeMontego Bay

MKE - MBJ

MKEMBJ

Milwaukee-Mitchell

Wed 5/28

5:10 am-11:35 am

1 stop6h 25m

Montego Bay Sangster Intl

Wed 6/4

12:35 pm-10:15 pm

1 stop9h 40m

$538

MilwaukeeKingston

MKE - KIN

MKEKIN

Milwaukee-Mitchell

Sat 6/7

12:22 pm-8:35 pm

2 stops32h 13m

Kingston Norman Manley

Sat 6/14

1:34 pm-8:06 am

3 stops42h 32m

$613

MilwaukeeMontego Bay

MKE - MBJ

MKEMBJ

Milwaukee-Mitchell

Mon 7/7

5:45 pm-1:10 pm

2 stops19h 25m

Montego Bay Sangster Intl

Fri 7/11

1:51 pm-10:45 pm

1 stop8h 54m

$615

MilwaukeeKingston

MKE - KIN

MKEKIN

Milwaukee-Mitchell

Mon 9/1

10:25 am-8:04 pm

1 stop9h 39m

Kingston Norman Manley

Thu 9/4

9:10 am-5:48 pm

1 stop8h 38m

$651

MilwaukeeKingston

MKE - KIN

MKEKIN

Milwaukee-Mitchell

Mon 9/1

7:25 am-6:25 pm

2 stops11h 00m

Kingston Norman Manley

Thu 9/4

9:10 am-9:27 pm

2 stops12h 17m

$656

MilwaukeeMontego Bay

MKE - MBJ

MKEMBJ

Milwaukee-Mitchell

Tue 7/22

6:00 am-11:49 am

1 stop5h 49m

Montego Bay Sangster Intl

Sun 8/3

1:15 pm-11:25 pm

1 stop10h 10m

$666

MilwaukeeMontego Bay

MKE - MBJ

MKEMBJ

Milwaukee-Mitchell

Wed 6/18

7:14 pm-9:10 am

2 stops37h 56m

$167

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/14

Showing 1-10 of 11 results
1
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Best time to book a flight from Milwaukee to Jamaica

Have a flexible travel schedule? Discover the best time to fly to Jamaica from Milwaukee 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 Milwaukee to Jamaica

What is the cheapest month to book a flight from Milwaukee to Jamaica?

Currently, January is the cheapest month in which you can book a flight from Milwaukee to Jamaica (average of $403). Flying from Milwaukee to Jamaica in July is currently the most expensive (average of $569). 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 MKE to JM?

Find hourly flight availability from Milwaukee 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 April 15, 2025.

When flying from Milwaukee to Jamaica, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

Rainfall in Jamaica by month

Plan your trip to Jamaica by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Jamaica ranges from 1.6 - 7.1 inches per month. October is typically the wettest month, when rainfall can reach 7.1 in. February is typically the driest time to visit Jamaica when rainfall is around 1.6 in.

Temperature in Jamaica by month

Plan your trip to Jamaica by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Jamaica, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 82.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 77.0 F).

Reviews of airlines servicing Jamaica

Get insights into the airlines that provide service to Jamaica. 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 Jamaica. Reviews last updated April 15, 2025.
Read through reviews of airlines operating flights from Milwaukee to Jamaica, such as Southwest, Delta and United Airlines. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,279 reviews

Boarding

8.2

Crew

8.6

Overall

8.0

Comfort

8.0

Entertainment

7.6

Food

7.1

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Southwest
8.0
Very good
4,279 reviews
Southwest
8.0
Very good
4,279 reviews

Boarding

8.2

Crew

8.6

Overall

8.0

Comfort

8.0

Entertainment

7.6

Food

7.1

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Delta
8.0
Very good
7,918 reviews
Southwest
8.0
Very good
4,279 reviews

Boarding

8.2

Crew

8.6

Overall

8.0

Comfort

8.0

Entertainment

7.6

Food

7.1

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
United Airlines
7.4
Good
8,658 reviews
Southwest
8.0
Very good
4,279 reviews

Boarding

8.2

Crew

8.6

Overall

8.0

Comfort

8.0

Entertainment

7.6

Food

7.1

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,279 reviews

Boarding

8.2

Crew

8.6

Overall

8.0

Comfort

8.0

Entertainment

7.6

Food

7.1

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Spirit Airlines
6.3
Okay
7,921 reviews
Southwest
8.0
Very good
4,279 reviews

Boarding

8.2

Crew

8.6

Overall

8.0

Comfort

8.0

Entertainment

7.6

Food

7.1

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.

Related info for your journey

Find useful and relevant information for your journey from Milwaukee to Jamaica. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly from for flights from Milwaukee to Jamaica?

    Most people fly from Milwaukee-Mitchell (MKE) if they book a flight from Milwaukee to Jamaica. Milwaukee-Mitchell is conveniently located just 6.4 mi from Milwaukee’s city center.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Milwaukee 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 Milwaukee to Jamaica?

    Currently, January is the cheapest month in which you can book a flight from Milwaukee to Jamaica (average of $403). Flying from Milwaukee to Jamaica in July is currently the most expensive (average of $569). 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 Milwaukee to Jamaica

See prices for flight routes from nearby airports that may be better suited for you.
O'Hare Intl to Luis Munoz Marin Intl flights
O'Hare Intl to Punta Cana flights
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O'Hare Intl to Oranjestad flights
O'Hare Intl to Nassau flights
Milwaukee to Luis Munoz Marin Intl flights
Minneapolis to Luis Munoz Marin Intl flights
O'Hare Intl to Saint Thomas Island flights
Minneapolis to Punta Cana flights
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O'Hare Intl to Bridgetown flights
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O'Hare Intl to St. John's flights
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Milwaukee to Nassau flights
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Top 6 airlines flying from Milwaukee to Jamaica

Discover the top 6 airlines that operate flights from Milwaukee 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 April 15, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$311Average$399FlexibilityNo cancel feeOn-time65%
DeltaCheapest$459Average$628FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$479Average$613FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$486Average$611FlexibilityNo cancel feeOn-time71%
Sun Country AirCheapest$502Average$540FlexibilityNo cancel feeOn-time83%
SouthwestCheapest$502Average$705FlexibilityNo cancel feeOn-time63%

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