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Find cheap flights from Milwaukee to Jamaica from $200

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Milwaukee to Jamaica departing on 9/1. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
0 bags
Sun 5/26
Sun 6/2

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Best Jamaica Flight Deals

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours

Montego Bay
Montego Bay1 stop$372
Kingston
Kingston2 stops$735

Good to know

Low season

August

High season

February

Cheapest flight

$200
Best time to beat the crowds with an average 2% drop in price.
Most popular time to fly and prices are also 18% lower on average.
Flight from Milwaukee to Montego Bay

FAQs - booking Jamaica flights

  • How does KAYAK find such low prices on flights from Milwaukee to Jamaica?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Milwaukee to Jamaica.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Milwaukee to Jamaica?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Jamaica from Milwaukee is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Milwaukee to Jamaica?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Jamaica with an airline and back to Milwaukee with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Milwaukee to Jamaica?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Jamaica from Milwaukee up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

See more FAQs

Top tips for finding cheap flights to Jamaica

  • On average*, there is no price difference when choosing to fly in the morning or the evening on this flight route.
*Average of the lowest prices shown in KAYAK’s search results for departures within the next 30 days

Top 4 airlines serving from Milwaukee to Jamaica

 
Need help choosing which airline to fly with from Milwaukee to Jamaica? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
8.0
DeltaOverall score based on 10966 reviews
8.0entertainment
8.6crew
8.2boarding
7.4food
7.9comfort
Airline reviews

Delta is one of the best airlines I have flown

10.0 ExcellentKellie, Apr 2024ANC - SEA
Read more about Delta reviews

Delta is one of the best airlines I have flown

Made the Atlanta to Pittsburgh trip many times, with Delta no issues

I always fly with Delta. My friends tell me their horror stories of flying with other airlines. I just smile and say, “You should fly Delta”

I'm a larger, athletic guy (6'2", 260lbs powerlifter) and I found the seats incredibly uncomfortable with minimal leg room, especially in a window seat. Now, I full understand that being smaller may change my view but even if I was 80lbs less, my legs would be the same size and I was sandwiched between my seat and the seat in front of me.

Horrible. This was not first class. This was a connecting flight whi h was late. My original flight never came. I hated the fact that delta gave me a connecting flight from New York to Orlando Florida. No meals and the television screens were not working. There wasn't even any power to charge your phones. This is NOT FIRST CLASS DELTA!!! Do better next time!

This flight was ridiculous. I had to have a connecting flight from New York to orlando Florida??? The flight left late and because it was a short flight there was no first class amenities. I had one alcohol drink. The flight crew was fine, but it sure did not feel like first class. Delta to me dropped the ball by giving me a connecting flight. By the time we got to Raleigh we would have missed the next flight. Lucky for me the flight never came so now I was stuck waiting for a later flight that came in late also.

Our flight was delayed in Atlanta. The staff could have gave us an explanation for the delay and how long it would be.

I liked the ease of checking in, luggage check in, wheel chair assistance, boarding and flight.

On my way home I had a layover. The flight from ATL to CLT was amended 5x while I was waiting. I could have driven home sooner. Overall from Dallas, Tx to Charlotte, NC I started my trip at 4:30pm, I didn’t get home until past midnight. I know things happen, but 5x to make me run back and forth in an airport from different terminals is excessive. I also upgraded to comfort + , I didn’t feel it was worth it. There was no benefit

On my way home I had a layover. The flight from ATL to CLT was amended 5x while I was waiting. I could have driven home sooner. Overall from Dallas, Tx to Charlotte, NC I started my trip at 4:30pm, I didn’t get home until past midnight. I know things happen, but 5x to make me run back and forth in an airport from different terminals is excessive.

Last minute gate change nearly caused us to miss our flight. Change was not announced or displayed in the main board at the old gate. Terrible communication. When we landed we had to wait 20 minutes because there was another plane at the assigned gate. Not the crew’s fault, but adding 20 minutes to a 45 minute flight sucked.

Nothing beats ANA customer service on my opinion. Maybe because of their Japanese culture (and food). Arigatō

So so. Terrible aircraft choice for that leg of the flight.

Due to one crew member not showing up to work, our flight was significantly delayed causing us to miss our connecting flight in Houston to Mississippi causing us to be delayed by more than 6 hours and missing our event all together. Very disappointing. All because ONE crew member called in sick. United did grant us a $15 meal voucher, which was a small but appreciated concession that I wasn’t able to use because I ordered my lunch and paid for it before applying the concession, and the staff said it was too late to use it. Ugh! We also had a TWO delay coming back from Mississippi, but that was on American Airlines and it was due to weather, so not their fault. Anyway, not at all impressed with United’s handling of our flight and the HUGE disappointment of missing our important family event for our 90 year old mother. All that money and all that stress and emotions for nothing. Having to wait the hour to bring an employee from LAX seemed like something that should not have happened. Why don’t you have a local back-up? Santa Ana is not a little airport in a rural area.

Flight delayed from Cape Town to Washington then got diverted to miami and in miami we had to fend for ourselves , im still trying to get to Shreveport now

delay several times and wait extra long to board. no entertainment service because there are problem for some rows. always encounter some delays for the last flight of the day.

I just wrote a text which was supposed to be for the flight from Denver to spokane not Frankfurt to Denver.

On time every leg of the journey and exceptional staff at counter, gate, and on board. I haven’t travelled in US for a long time and was genuinely surprised how pleasant this was.

Hated every minute of it. This flight should have only taken 1.5hrs but was delayed over 10hours. Now I am being told I cannot be compensated or refunded my ticket price or extra leg room, which I purchased but did not receive, because the airline is throwing the blame on the 3rd party I purchased tickets through and 3rd party putting the blame on airline. No one wants to help. They received their money and that's all they care about. Im going on 3 days of still trying to get to my final destination, had to cancel car rental, car insurance and hotel. Currently staying in airport until hotels open up. Thank you Lufthansa, Kayak, Underpricer and United for making this trip the worst ever.

The delays (5 hrs) were a comedy of errors, and the multiple safety issues encountered were very concerning.

I think the seats on some of their planes are uncomfortable. You can be ok on a short flight of two hours but no more than that. The delays, and also the refreshments on the plane were not enough.

Flight delayed over an over all day until it cancelled at 1:30am. Would not repeatedly delay that late. Offer hotel rooms and rebook early. Very difficult for families with small children

Not sure why JAL partnered with American Airlines because their service is no where near similar. Flight attendants were not friendly and didn’t smile. Food was horrible…

this is starting to seem like an american airlines standard. delayed flights and fake apologies… getting tired of it

Terrible boarding , Business class seats are sub standard. As usual crew will miss your food too

Just get Economy Plus for international flights, so worth it the extra room, bigger seats…

This flight is frequently delayed. The connections seemingly are more frequently delayed. I’ve missed connections as a result twice on the same route to charlotte then Charleston. Final destination arrival has been the next day, twice in a row. No pilots, no crew. Too many excuses. Unfortunately, my days with American are over.

Entertainment was okay not because anything was wrong but it is a short flight so having no wifi is annoying but understandable. Crew was outstanding as usual

It was spectacular. I had basic Economy and was given so much space and their seats lean back so far. Staff was superb, food was superb, everything was superb, Finnair is Fantastic.

Those seats were way too narrow. I had the middle seat, one person was a very skinny person and we still couldn’t avoid touching each other anytime one of us moved. The other person was larger and we were basically sitting in each others lap the entire flight. There was zero entertainment. The flight was long enough to justify tvs, but no. Gotta sit there in your infant seat and twiddle your thumbs.

Not much seat room, but that was unexpected. But the seat headrest was very uncomfortable.

First the good, everyone was friendly and efficient. Flight was smooth and plane was very clean and new. Now the bad, seats have almost no padding on your behind. I was in exit row so I had tons of leg room for a 6' 2" bean pole with long legs. Everything was extra - water, soda, snacks everything besides oxygen. Ya get what you pay for, and my flight was cheap as you could ever want it, so no worries.

First the good, everyone was friendly and efficient. Flight was smooth and plane was very clean and new. Now the bad, seats have almost no padding on your behind. I was in exit row so I had tons of leg room for a 6' 2" bean pole with long legs. Everything was extra - water, soda, snacks everything besides oxygen. Ya get what you pay for, and my flight was cheap as you could ever want it, so no worries. They dont really bother you about carry-on size, I brought a descent sized backpack and they didnt even check.

Spirit canceled the flight in March and never notified me!

Seats suck, not enough room, overcrowded planes, hectic situation all together.

Pretty good. Would’ve been excellent if we would have left on time and the crew wasn’t late.

I do not like the customer service, I had an emergency and needed to cancel a pet reservation right after I had booked it and they would not do anything but issue a credit. I haven't flown in years as I have 7 kids and don't have spare time. I want my $125 back on my card please

Spirit airline tries to screw you at every opportunity. Spirit wanted 65$ for an extra pound in the suitcase Made me open the suitcase at the counter to remove 1 pound. Staff very cold and rude Will never fly spirit again and will recommend same to family and friends

Delayed..4 times...completely disorganized boarding. After 5 hours they scrambled to move ppl off plane bc they overbooked. Then they didn't have a cabin crew. WiFi on plane didn't work. Zero amenities. Once we boarded we sat on tarmac for an hour. Explore all alternate options including purchasing a pair of hiking boots and walking to your destination instead of flying spirit.

what I like about Spirit is that the pilot and crew are good communicators. The plane itself - well, its a budget airline and you get what is expected, But I generally just feel safer, somehow, when I know more about what is going on - and Spirit has always done a good job of telling me what is going on: why the delay, why the turbulence, why this and that... and that means a lot to me.

Book cheap flights from Milwaukee to Jamaica

Recent round-trip flight deals

5/22Wed
1 stopSpirit Airlines
6h 45mMKE-MBJ
5/25Sat
1 stopSpirit Airlines
7h 56mMBJ-MKE
$372
8/17Sat
1 stopAmerican Airlines
16h 25mMKE-MBJ
8/20Tue
1 stopAmerican Airlines
6h 28mMBJ-MKE
$445
8/25Sun
1 stopDelta
5h 36mMKE-MBJ
8/30Fri
1 stopDelta
7h 30mMBJ-MKE
$448
8/25Sun
1 stopDelta
9h 05mMKE-MBJ
9/4Wed
1 stopDelta
11h 05mMBJ-MKE
$460
8/17Sat
2 stopsFrontier
21h 21mMKE-MBJ
8/20Tue
2 stopsFrontier
49h 42mMBJ-MKE
$481
6/22Sat
1 stop
9h 10mMKE-MBJ
6/29Sat
1 stop
23h 18mMBJ-MKE
$517
6/22Sat
2 stopsFrontier
50h 43mMKE-MBJ
6/29Sat
1 stopFrontier
23h 18mMBJ-MKE
$550
6/22Sat
2 stopsUnited Airlines
20h 04mMKE-MBJ
6/29Sat
2 stopsUnited Airlines
26h 28mMBJ-MKE
$592
6/22Sat
2 stopsUnited Airlines
20h 04mMKE-MBJ
6/29Sat
1 stopUnited Airlines
7h 24mMBJ-MKE
$642
5/23Thu
3 stops
41h 11mMKE-MBJ
5/26Sun
3 stops
35h 06mMBJ-MKE
$702

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Recent one-way flight deals

9/1Sun
1 stopAmerican Airlines
14h 22mMKE-MBJ
$200
10/19Sat
2 stopsAmerican Airlines
16h 25mMKE-MBJ
$201
9/1Sun
2 stopsAmerican Airlines
16h 21mMKE-MBJ
$205
10/19Sat
1 stopAmerican Airlines
16h 25mMKE-MBJ
$465
10/19Sat
2 stopsAmerican Airlines
18h 06mMKE-MBJ
$466
10/20Sun
2 stopsAmerican Airlines
29h 46mMKE-MBJ
$472

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Last minute flights from Milwaukee to Jamaica

Last minute flight, train and bus deals

4/29Mon
multi-stopDelta
5h 40mMKE-MBJ
5/2Thu
multi-stopDelta
6h 56mMBJ-MKE
$493
4/29Mon
multi-stopUnited Airlines
7h 30mMKE-MBJ
5/2Thu
multi-stopUnited Airlines
20h 52mMBJ-MKE
$567

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Milwaukee - Jamaica Flights

Departure:

Milwaukee (MKE)United States

Return flight deals:

Jamaica - Milwaukee

Cabin classes: