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Jamaica

$246+ 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 10/15. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — MBJ
Oct 11 — Oct 181
Sat 10/11
Sat 10/18
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 September 11, 2025.

Round-trip from

$531
(Southwest)

One-way from

$246
(American Airlines)

Popular in

June

Cheapest in

March

Average price

$636
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. 9% potential increase in price ($64 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($14 potential savings vs. average RT price).
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Average for round-trip flights in September 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 September 11, 2025.

This Southwest deal was found by Cheapflights users on 9/9. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/217:35 amMKE - MBJ
1 stop6h 25mSouthwest
Tue 10/281:00 pmMBJ - MKE
1 stop9h 10mSouthwest
Deal found 9/9$527
This Delta deal was found by Cheapflights users on 9/11. 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.
Sun 10/265:47 amMKE - MBJ
1 stop9h 47mDelta
Fri 10/312:45 pmMBJ - MKE
1 stop9h 10mDelta
Deal found 9/11$539
This American Airlines deal was found by Cheapflights users on 9/10. 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.
Sun 10/267:12 amMKE - MBJ
1 stop5h 53mAmerican Airlines
Fri 10/3111:50 amMBJ - MKE
2 stops12h 06mAmerican Airlines
Deal found 9/10$543
This American Airlines deal was found by Cheapflights users on 9/11. 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.
Tue 10/146:00 amMKE - MBJ
1 stop8h 00mAmerican Airlines
Sat 10/254:22 pmMBJ - MKE
1 stop7h 52mAmerican Airlines
Deal found 9/11$564
This American Airlines deal was found by Cheapflights users on 9/11. 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.
Sun 10/267:12 amMKE - MBJ
1 stop8h 10mAmerican Airlines
Sun 11/22:04 pmMBJ - MKE
1 stop10h 01mAmerican Airlines
Deal found 9/11$569
This American Airlines deal was found by Cheapflights users on 9/10. 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.
Sat 10/43:00 pmMKE - MBJ
1 stop23h 05mAmerican Airlines
Sat 10/111:00 pmMBJ - MKE
1 stop9h 30mAmerican Airlines
Deal found 9/10$573
This Mytrip deal was found by Cheapflights users on 9/11. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/267:38 pmMKE - MBJ
2 stops15h 22mSpirit Airlines
Sun 11/21:09 pmMBJ - MKE
3 stops30h 34mSpirit Airlines
Deal found 9/11$580
This Expedia deal was found by Cheapflights users on 9/10. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/14:38 pmMKE - MBJ
2 stops39h 33mJetBlue
Mon 10/69:12 amMBJ - MKE
2 stops30h 31mJetBlue
Deal found 9/10$603
This American Airlines deal was found by Cheapflights users on 9/8. 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 10/68:16 pmMKE - MBJ
1 stop16h 29mAmerican Airlines
Mon 10/133:20 pmMBJ - MKE
2 stops19h 23mAmerican Airlines
Deal found 9/8$604
This Expedia deal was found by Cheapflights users on 9/10. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/114:38 pmMKE - KIN
2 stops26h 28mJetBlue
Fri 10/175:15 pmKIN - MKE
2 stops22h 28mJetBlue
Deal found 9/10$650
This Delta deal was found by Cheapflights users on 9/10. 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.
Sat 10/1112:06 pmMKE - KIN
1 stop7h 54mDelta
Fri 10/179:00 amKIN - MKE
1 stop6h 51mDelta
Deal found 9/10$671
This American Airlines deal was found by Cheapflights users on 9/10. 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.
Thu 12/256:27 pmMKE - KIN
2 stops14h 45mAmerican Airlines
Sat 1/36:25 amKIN - MKE
2 stops18h 34mAmerican Airlines
Deal found 9/10$1,275

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 September 11, 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

Tue 10/21

7:35 am-2:00 pm

1 stop6h 25m

Montego Bay Sangster Intl

Tue 10/28

1:00 pm-10:10 pm

1 stop9h 10m

$527

MilwaukeeMontego Bay

MKE - MBJ

MKEMBJ

Milwaukee-Mitchell

Sun 10/26

5:47 am-1:20 pm

1 stop7h 33m

Montego Bay Sangster Intl

Fri 10/31

1:32 pm-11:55 pm

1 stop10h 23m

$539

MilwaukeeMontego Bay

MKE - MBJ

MKEMBJ

Milwaukee-Mitchell

Wed 10/8

5:25 am-12:45 pm

1 stop7h 20m

Montego Bay Sangster Intl

Wed 10/15

11:50 am-11:16 pm

1 stop11h 26m

$539

MilwaukeeMontego Bay

MKE - MBJ

MKEMBJ

Milwaukee-Mitchell

Sat 11/29

6:46 pm-10:08 am

1 stop14h 22m

Montego Bay Sangster Intl

Thu 12/4

2:30 pm-11:05 pm

1 stop9h 35m

$539

MilwaukeeMontego Bay

MKE - MBJ

MKEMBJ

Milwaukee-Mitchell

Sun 10/26

7:12 am-1:05 pm

1 stop5h 53m

Montego Bay Sangster Intl

Fri 10/31

12:22 pm-11:30 pm

2 stops11h 08m

$543

MilwaukeeKingston

MKE - KIN

MKEKIN

Milwaukee-Mitchell

Sat 10/11

4:38 pm-7:06 pm

2 stops26h 28m

Kingston Norman Manley

Fri 10/17

5:15 pm-3:43 pm

2 stops22h 28m

$650

MilwaukeeKingston

MKE - KIN

MKEKIN

Milwaukee-Mitchell

Sat 10/11

12:06 pm-8:00 pm

1 stop7h 54m

Kingston Norman Manley

Fri 10/17

9:00 am-3:51 pm

1 stop6h 51m

$671

MilwaukeeKingston

MKE - KIN

MKEKIN

Milwaukee-Mitchell

Fri 3/6

7:00 am-8:00 pm

1 stop12h 00m

Kingston Norman Manley

Thu 3/12

9:00 am-4:17 pm

1 stop7h 17m

$683

MilwaukeeKingston

MKE - KIN

MKEKIN

Milwaukee-Mitchell

Tue 3/3

10:25 am-8:00 pm

1 stop8h 35m

Kingston Norman Manley

Fri 3/6

9:00 am-11:27 pm

1 stop15h 27m

$683

MilwaukeeKingston

MKE - KIN

MKEKIN

Milwaukee-Mitchell

Fri 3/6

6:21 am-7:10 pm

2 stops11h 49m

Kingston Norman Manley

Thu 3/12

5:20 am-10:25 pm

1 stop17h 05m

$687

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/8

Showing 1-10 of 18 results
1
2

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 $560). 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 September 11, 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.

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 September 11, 2025.
Get a feel of what it's like to fly with Southwest, Delta, and American Airlines from Milwaukee to Jamaica by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,248 reviews

Boarding

8.1

Crew

8.6

Entertainment

7.5

Overall

8.0

Comfort

8.0

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Southwest
8.0
Very good
4,248 reviews
Southwest
8.0
Very good
4,248 reviews

Boarding

8.1

Crew

8.6

Entertainment

7.5

Overall

8.0

Comfort

8.0

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Delta
8.0
Very good
7,960 reviews
Southwest
8.0
Very good
4,248 reviews

Boarding

8.1

Crew

8.6

Entertainment

7.5

Overall

8.0

Comfort

8.0

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,248 reviews

Boarding

8.1

Crew

8.6

Entertainment

7.5

Overall

8.0

Comfort

8.0

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Sun Country Air
6.9
Okay
330 reviews
Southwest
8.0
Very good
4,248 reviews

Boarding

8.1

Crew

8.6

Entertainment

7.5

Overall

8.0

Comfort

8.0

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Spirit Airlines
6.3
Okay
8,023 reviews
Southwest
8.0
Very good
4,248 reviews

Boarding

8.1

Crew

8.6

Entertainment

7.5

Overall

8.0

Comfort

8.0

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

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.

  • How long is the flight from Milwaukee to Jamaica?

    Departing from Milwaukee to Jamaica will take you 6h 25m. The distance from Milwaukee to Jamaica is about 1786 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 Milwaukee to Jamaica one-way?

    One-way options have recently been found by users for as low as $246 on American Airlines. Other airlines that offer cheap prices include Spirit Airlines from $248 and WestJet from $1,691 one-way.

  • 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 $560). 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 Milwaukee to Jamaica

See prices for flight routes from nearby airports that may be better suited for you.
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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 September 11, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$328Average$385FlexibilityNo cancel feeOn-time65%
United AirlinesCheapest$443Average$680FlexibilityNo cancel feeOn-time69%
DeltaCheapest$477Average$642FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$538Average$623FlexibilityNo cancel feeOn-time71%
Sun Country AirCheapest$540Average$540FlexibilityNo cancel feeOn-time83%
SouthwestCheapest$565Average$718FlexibilityNo cancel feeOn-time63%

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