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Jamaica

$277+ 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 9/10. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — MBJ
ago. 4 — ago. 111
lun. 8/4
lun. 8/11
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 julio 30, 2025.

Round-trip from

$434
(Kiwi.com)

One-way from

$277
(American Airlines)

Popular in

June

Cheapest in

March

Average price

$655
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 ($63 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($15 potential savings vs. average RT price).
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Average for round-trip flights in July 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 julio 30, 2025.

This Kiwi.com deal was found by Cheapflights users on 7/29. 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.
sáb. 8/306:00 amMKE - MBJ
1 stop7h 01mSpirit Airlines
mié. 9/312:19 pmMBJ - MKE
2 stops23h 39mSpirit Airlines
Deal found 7/29$434
This FlightHub deal was found by Cheapflights users on 7/30. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 8/256:00 amMKE - KIN
2 stops29h 27mSpirit Airlines
mié. 9/1012:08 pmKIN - MKE
2 stops23h 50mSpirit Airlines
Deal found 7/30$452
This Delta deal was found by Cheapflights users on 7/29. 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.
dom. 9/215:40 amMKE - MBJ
1 stop9h 54mDelta
mié. 9/242:35 pmMBJ - MKE
1 stop9h 13mDelta
Deal found 7/29$473
This American Airlines deal was found by Cheapflights users on 7/30. 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.
dom. 10/265:26 amMKE - MBJ
2 stops9h 56mAmerican Airlines
vie. 10/312:30 pmMBJ - MKE
2 stops19h 48mAmerican Airlines
Deal found 7/30$477
This Southwest deal was found by Cheapflights users on 7/28. 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.
mar. 10/287:35 amMKE - MBJ
1 stop6h 25mSouthwest
mié. 11/53:25 pmMBJ - MKE
1 stop7h 00mSouthwest
Deal found 7/28$494
This Delta deal was found by Cheapflights users on 7/29. 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.
lun. 11/1010:25 amMKE - KIN
1 stop8h 35mDelta
mié. 11/199:00 amKIN - MKE
1 stop11h 03mDelta
Deal found 7/29$657
This American Airlines deal was found by Cheapflights users on 7/29. 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.
dom. 9/216:15 amMKE - KIN
2 stops13h 23mAmerican Airlines
mié. 9/246:00 amKIN - MKE
2 stops14h 00mAmerican Airlines
Deal found 7/29$676
This Expedia deal was found by Cheapflights users on 7/28. 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.
sáb. 8/305:38 pmMKE - KIN
2 stops21h 08mJetBlue
sáb. 9/62:47 amKIN - MKE
2 stops36h 56mJetBlue
Deal found 7/28$698
This United Airlines deal was found by Cheapflights users on 7/29. 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 Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 9/188:00 amMKE - KIN
2 stops29h 53mUnited Airlines
mar. 9/232:59 pmKIN - MKE
2 stops30h 12mUnited Airlines
Deal found 7/29$796
This Air Canada deal was found by Cheapflights users on 7/29. 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.
dom. 9/2112:05 pmMKE - KIN
2 stops24h 30mAir Canada
jue. 9/251:45 pmKIN - MKE
2 stops27h 21mAir Canada
Deal found 7/29$1,464
This WestJet deal was found by Cheapflights users on 7/29. 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.
sáb. 11/155:00 pmMKE - KIN
2 stops45h 33mWestJet
mié. 11/194:30 pmKIN - MKE
2 stops20h 57mWestJet
Deal found 7/29$3,503

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 julio 30, 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

sáb. 8/30

6:00 am-1:01 pm

1 stop7h 01m

Montego Bay Sangster Intl

mié. 9/3

12:19 pm-11:58 am

2 stops23h 39m

$434

MilwaukeeKingston

MKE - KIN

MKEKIN

Milwaukee-Mitchell

lun. 8/25

6:00 am-11:27 am

2 stops29h 27m

Kingston Norman Manley

mié. 9/10

12:08 pm-11:58 am

2 stops23h 50m

$452

MilwaukeeMontego Bay

MKE - MBJ

MKEMBJ

Milwaukee-Mitchell

dom. 9/21

5:40 am-3:34 pm

1 stop9h 54m

Montego Bay Sangster Intl

mié. 9/24

2:35 pm-11:48 pm

1 stop9h 13m

$473

MilwaukeeMontego Bay

MKE - MBJ

MKEMBJ

Milwaukee-Mitchell

dom. 10/26

5:26 am-3:22 pm

2 stops9h 56m

Montego Bay Sangster Intl

vie. 10/31

2:30 pm-10:18 am

2 stops19h 48m

$477

MilwaukeeMontego Bay

MKE - MBJ

MKEMBJ

Milwaukee-Mitchell

mar. 10/28

7:35 am-2:00 pm

1 stop6h 25m

Montego Bay Sangster Intl

mié. 11/5

3:25 pm-9:25 pm

1 stop7h 00m

$494

MilwaukeeMontego Bay

MKE - MBJ

MKEMBJ

Milwaukee-Mitchell

vie. 9/19

7:15 pm-1:30 pm

2 stops18h 15m

Montego Bay Sangster Intl

vie. 9/26

12:52 pm-11:24 pm

1 stop10h 32m

$592

MilwaukeeKingston

MKE - KIN

MKEKIN

Milwaukee-Mitchell

lun. 11/10

10:25 am-8:00 pm

1 stop8h 35m

Kingston Norman Manley

mié. 11/19

9:00 am-7:03 pm

1 stop11h 03m

$657

MilwaukeeKingston

MKE - KIN

MKEKIN

Milwaukee-Mitchell

dom. 9/21

6:15 am-7:38 pm

2 stops13h 23m

Kingston Norman Manley

mié. 9/24

6:00 am-8:00 pm

2 stops14h 00m

$676

MilwaukeeKingston

MKE - KIN

MKEKIN

Milwaukee-Mitchell

sáb. 8/30

5:38 pm-2:46 pm

2 stops21h 08m

Kingston Norman Manley

sáb. 9/6

2:47 am-3:43 pm

2 stops36h 56m

$698

MilwaukeeKingston

MKE - KIN

MKEKIN

Milwaukee-Mitchell

jue. 9/18

8:00 am-1:53 pm

2 stops29h 53m

Kingston Norman Manley

mar. 9/23

2:59 pm-9:11 pm

2 stops30h 12m

$796

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/30

Showing 1-10 of 15 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 $562). 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 julio 30, 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 julio 30, 2025.
Get a feel of what it's like to fly with Southwest, Delta, and United 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
4,241 reviews

Crew

8.6

Entertainment

7.5

Boarding

8.1

Food

7.0

Comfort

8.0

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Southwest
8.0
Very good
4,241 reviews
Southwest
8.0
Very good
4,241 reviews

Crew

8.6

Entertainment

7.5

Boarding

8.1

Food

7.0

Comfort

8.0

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Delta
8.0
Very good
7,980 reviews
Southwest
8.0
Very good
4,241 reviews

Crew

8.6

Entertainment

7.5

Boarding

8.1

Food

7.0

Comfort

8.0

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
United Airlines
7.4
Good
8,896 reviews
Southwest
8.0
Very good
4,241 reviews

Crew

8.6

Entertainment

7.5

Boarding

8.1

Food

7.0

Comfort

8.0

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
JetBlue
7.3
Good
2,913 reviews
Southwest
8.0
Very good
4,241 reviews

Crew

8.6

Entertainment

7.5

Boarding

8.1

Food

7.0

Comfort

8.0

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,241 reviews

Crew

8.6

Entertainment

7.5

Boarding

8.1

Food

7.0

Comfort

8.0

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.

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 $562). 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.
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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 julio 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$328Average$385FlexibilityNo cancel feeOn-time65%
United AirlinesCheapest$443Average$603FlexibilityNo cancel feeOn-time69%
DeltaCheapest$469Average$643FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$502Average$703FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$512Average$623FlexibilityNo cancel feeOn-time71%
Sun Country AirCheapest$519Average$540FlexibilityNo cancel feeOn-time83%

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