$159 Find Cheap Flights from Milwaukee to Jamaica

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 12/7. 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.
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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$387
Kingston
Kingston1 stop$553

Good to know

Low season

May

High season

March

Cheapest flight

$159
Best time to beat the crowds with an average 7% drop in price.
Most popular time to fly and prices are also 0% 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

  • Morning departure is around 10% more expensive than an evening flight, on average*.
*Average of the lowest prices shown in KAYAK’s search results for departures within the next 30 days

Top 5 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.
8.1
SouthwestOverall score based on 5005 reviews
8.2Boarding
8.7Crew
7.7Entertainment
8.1Comfort
7.2Food
Airline reviews

This was a nicer flight - not fully booked and so we were able to spread out.

10.0 ExcellentJohn, Nov 2024LAS - IND
Read more Southwest reviews

This was a nicer flight - not fully booked and so we were able to spread out.

We had a nice flight. Boarding was easy, our seats were comfortable and the on board service was pleasant.

Planes are aged. The wifi is unreliable and on many fights, no-existent. The flight attendants were very good.

I had a wonderful flight, but the only thing that annoyed me was how crowded TSA was. I still believe airports and all planes work together to bunch everyone together to drive up cost.

Easy to book and to get check in and get on and off.

The last 30 min or so, they put the heat on full. We thought we were being basted.

Excellent experience. WiFi worked on this leg of My trip

Flight was great, but golf bag never made it until later in the day. Even though I had a nonstop flight it was placed on a different one. They made it right with flight credits and I was able to get it the same day.

It seems as though the provisions are even less. Although SWA used to be an economy Airline, that isn't really the case anymore. I paid over $700. for a round trip to Denver and I could have flown just about any airline for the price. The drinks are now in a 6-ounce cup and with ice I'm sure a can would fill more than 2 cups. However, I am very proud of SWA for using paper rather than continuing to contribute to the millions of plastic cups being used each day. I've thought of this fr many years and am so glad to see it come to fruition, if not by only SWA so far.

Exceptional crew! Friendly and professional. Pleasant attitude and treated everyone with respect.

I sat in comfort plus. It was fine. Seats were comfortable. I got drinks and snacks.

Crew was nice. Flight was timely. Seats could be better as well as the food considering it’s first class.

Left on time and arrived early this extending our 31 minute transfer. Bags made it also!

Good and consistent Printer in lounge did not work for me :(

Most of my discomfort was going through TSA. However, the Delta seats had inadequate leg room and I tried my very best to connect to the wi-fi and it was a cumbersome process that finally gave me the info that I needed to sign in AFTER I had completed the flight...Why make it so difficult to use? That said I really really appreciate the pilot taking a little extra time to avoid a bad storm area and both landings in Atlanta and Orlando were flawless to my delight!!!

Delayed in taking off because no flight crew. The in seat entertainment was working properly.

All fine save for the abominable catering. Really gone downhill. We found it all inedible.

I upgraded to first class only to find out that I still had no access to the sky lounge without a sky miles card or AmEx (something that should be emphasized outside of the fine print!) Also, no food or drink service provided during the flight, so I basically paid 4x more just for “free” checked baggage and a bigger seat. Not worth it.

I appreciated friendly service from check-in, to boarding, to in-flight amenities! Attendants were accommodating and helpful. Thank you! Elaine

Delta was really good about being transparent with why we were delayed it’s just that’s the plane was really old and outdated and a lot of the comfort and amenities we know Delta to have did not shine through

There was no USB plug in my section of the plane. So I could not charge my phone. Also, there was no screen to watch movie or anything like that. Wish I had known that in advance, I would’ve brought my iPad.

Had a crying baby and a toddler behind me so it was difficult to get comfortable. Searing was tight even for a relatively small person like myself (5’8” 155). Fast flight but arrived so early the gate assigned was still occupied by another plane so we had to wait for about 20-25 minutes to get reassigned to a new gate and get over there.

Best part: It’s operated by All Nippon Airways. It’s quite literally comfortable, reliable and respected from boarding to landing each and every time. It’s perfection without extremity in lavishness — it’s how flying should always be!

The flight attendants were unhelpful. It was a packed flight, and usually a flight attendant would help find a spot in the bin for your carry on or shift things around. Neither made any effort to do so. Also, I had to then check my bag. I was told it would be on the carousel in YYZ, but it came up on the jetway. So lucky I saw others standing around for their bags. I would have walked straight past this and on to the carousel. They could have at least told me that they had given me wrong information. Very unsatisfactory.

Made all groups except 2 check despite ample bin space. Inflight WiFi and entertainment didn’t work most of the time.

The check-in process is not the best They should have agents in site to help with any problem especially a rebook. Why does one have to get on the phone when there were at least 8 agents around that could have help?! Flying is stressful as it is and having someone willing to do their customer service will ease some of the stress.

It was a good flight. Nothing comes to mind about how it could have been better. It was a newer plane, seemed like a great upgrade from your older ones. Staff was very good as well.

Seats are smaller and harder than other airlines we have travels with. Food was edible but no good. The sandwich was the only thing I would eat again. They did have a lot of movies to watch.

boarding was uneventful. Snack was pathetic. A tiny fruit bar. Entertainment was limited to just select movies on your own tablet or phone. No live TV. I recently flew Jetblue and they had unlimited snacks and live satellite TV the entire flight. My seat was an exit seat, 20A. It was super uncomfortable. It felt cramped and the middle seat was taken up by a large woman who pushed into my shoulder and arm. Horrible flight.

I liked that the flight to Kosice was on time, the service was excellent and we arrived to Vienna early. The only thing I did not like, is that I had to pay for my suitcase $75. Bummer

It was as expected for such a short flight. No complaints

The departing flight from Newark to Charlotte was fine. It was the returning flight from Charlotte to Newark that was awful. We had scheduled an 8:35pm return flight time. We got delayed TEN times all the way to 5am in the morning! We were told over 4 different excuses as to why the flight kept getting delayed. First it was the flight crew needed to rest, then it was something technical with the plane, then it was something with air traffic control, and finally it was because they couldn’t find a captain and had to wait until the morning so the captain could get some rest. It was terrible sleeping overnight in the airport. They offered a $12 meal voucher. That was it! And the only place open in the middle of the night was Dunkin’ Donuts who didn’t even accept the voucher. They should have cancelled the flight much earlier on in the evening instead of just stringing us along hour by hour with more delays. Not professional and unacceptable. There was no refund for inconvenience. I probably will not be flying American Airlines again.

This leg they tried and did well with what they had to work from.

It was nice being on a flight that had working wifi. The boarding was quick - why don’t all airlines have small boarding groups window to aisle? Makes so much sense!!! I was disappointed to be the first person stopped to have to gate check my carryon. Especially when there was plenty of overhead space at the back! But I get it…keeps it moving. Crew was nice.

The flight was as good as it gets when flying. On time departure and arrival plus no lost luggage.

My boarding pass wouldn't pull up in the app very easily and had to really dig through my email. That caused a delay in TSA..

Packed commercial flight was as comfortable as can be expected

My seat was very worn. Otherwise I had an excellent flight

I'm not a valued flyer so I'm always in the last group to board...that sucks, always

My flight back my reservations were list because they said I didn't pay my pet fee when I had a receipt

I purchased an aisle seat but was put in the middle seat surrounded by families with small sick children (3). That can happen anytime and I was prepared. The ticket agent questioned why I hadn’t paid for my luggage and had to explain that 2 pieces were included with my ticket. I hate that nickel and diming attitude. Please inform your staff better.

I know the airline has been open for 40 years and the flight crew looked just as old. The flight attendants were not friendly and rude. They should think of retiring this crew.

The crew was friendly, but I only got a drink, no food.

Flight was late, boarding was a mess, families separated so they could make extra profit.

Great! A delay in taking off but that’s it

Terrible boarding experience at sea tac. Displayed on time departure despite being about an hour behind in boarding time. Boarded a bus to go to the tarmac to then board onto the plane.

Hidden fees everywhere while we aware of the fees but it quickly added up to a premium airline. From 12+ dollars to pick your set to $55 dollars a checked bag. No counter at the Portland Airport until 2 hrs before the flight made it so we couldn't get anything to eat before the flight. Pre checking your bags wasn't working on-line or at the kiosk, so we had to pay extra 5 dollars per bag for counter checking. So after everything was said and done, we ended up paying an extra $200. Plane was nice and clean plane staff was nice and attentive.

Excellent. Except seat C2 starting to be worned down. Very uncomfortable.

22 hour delayed flight. I will not fly again. I missed training due to this.

Well my connecting flight was initially delayed 2 hours. Then it became a 21 hour delay. When I woke up the next morning the flight was then delayed another hour. I ended up missing a day and a half of training due to this. When asked if there was any way I could be transferred to a different flight I was told no because it was under a 24 hour delay. I will not fly with this airline again.

Book cheap flights from Milwaukee to Jamaica

Recent round-trip flight deals

1/10Fri
1 stopSpirit Airlines
18h 46mMKE-MBJ
1/12Sun
1 stopSpirit Airlines
27h 14mMBJ-MKE
$387
1/17Fri
1 stop
17h 56mMKE-MBJ
1/22Wed
1 stop
27h 14mMBJ-MKE
$437
1/11Sat
1 stopDelta
9h 26mMKE-MBJ
1/14Tue
1 stopDelta
9h 16mMBJ-MKE
$509
1/19Sun
1 stopAmerican Airlines
7h 11mMKE-MBJ
1/23Thu
2 stopsAmerican Airlines
9h 10mMBJ-MKE
$520
1/10Fri
2 stopsAmerican Airlines
17h 10mMKE-MBJ
1/12Sun
1 stopAmerican Airlines
6h 57mMBJ-MKE
$534
2/4Tue
1 stopDelta
8h 40mMKE-MBJ
2/11Tue
1 stopDelta
8h 05mMBJ-MKE
$539
1/5Sun
2 stopsUnited Airlines
19h 14mMKE-MBJ
1/12Sun
1 stopUnited Airlines
25h 22mMBJ-MKE
$604
1/5Sun
1 stopUnited Airlines
28h 11mMKE-MBJ
1/12Sun
1 stopUnited Airlines
24h 22mMBJ-MKE
$606
3/15Sat
nonstopSun Country Air
4h 06mMKE-MBJ
3/22Sat
nonstopSun Country Air
4h 31mMBJ-MKE
$1,074
2/1Sat
nonstopSun Country Air
4h 16mMKE-MBJ
2/8Sat
nonstopSun Country Air
4h 30mMBJ-MKE
$1,179

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Recent one-way flight deals

12/7Sat
1 stopSpirit Airlines
7h 33mMKE-MBJ
$159
12/7Sat
1 stopSpirit Airlines
7h 33mMKE-MBJ
$164
12/15Sun
1 stopSpirit Airlines
6h 07mMKE-KIN
$167
12/24Tue
1 stop
16h 23mMKE-MBJ
$245
2/12Wed
1 stopUnited Airlines
6h 01mMKE-MBJ
$253
12/7Sat
2 stopsUnited Airlines
9h 14mMKE-MBJ
$271
2/12Wed
nonstopSun Country Air
4h 16mMKE-MBJ
$274
2/12Wed
2 stopsAmerican Airlines
19h 31mMKE-MBJ
$304
12/15Sun
2 stopsAmerican Airlines
12h 07mMKE-KIN
$321
2/12Wed
3 stops
24h 40mMKE-MBJ
$422

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Last minute flights from Milwaukee to Jamaica

Last minute flight, train and bus deals

11/25Mon
multi-stopSpirit Airlines
28h 28mMKE-MBJ
12/2Mon
multi-stopSpirit Airlines
17h 32mMBJ-MKE
$552
11/25Mon
multi-stopSpirit Airlines
28h 28mMKE-MBJ
12/2Mon
multi-stopSpirit Airlines
17h 32mMBJ-MKE
$556
11/24Sun
multi-stopSpirit Airlines
29h 41mMKE-MBJ
11/26Tue
multi-stopSpirit Airlines
17h 32mMBJ-MKE
$664
11/25Mon
multi-stop
28h 28mMKE-MBJ
12/2Mon
multi-stop
28h 20mMBJ-MKE
$666
11/24Sun
multi-stopUnited Airlines
6h 46mMKE-MBJ
11/26Tue
multi-stopUnited Airlines
8h 33mMBJ-MKE
$698
11/24Sun
multi-stopUnited Airlines
19h 55mMKE-MBJ
11/26Tue
multi-stopUnited Airlines
8h 33mMBJ-MKE
$702
11/25Mon
multi-stopDelta
8h 33mMKE-MBJ
12/2Mon
multi-stopDelta
6h 57mMBJ-MKE
$718
11/24Sun
multi-stopSouthwest
18h 50mMKE-MBJ
11/26Tue
multi-stopSouthwest
11h 30mMBJ-MKE
$780
11/25Mon
multi-stopSouthwest
18h 50mMKE-MBJ
12/2Mon
multi-stopSouthwest
9h 25mMBJ-MKE
$805
11/24Sun
multi-stop
29h 41mMKE-MBJ
11/26Tue
multi-stop
27h 50mMBJ-MKE
$848

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