$150 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 2/23. 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 from Milwaukee

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

Montego Bay
Montego Bay1 stop$362
Kingston
Kingston1 stop$504

Good to know

Low season

May

High season

March

Cheapest flight

$150
Best time to beat the crowds with an average 9% drop in price.
Most popular time to fly and prices are also 4% lower on average.
Flight from Milwaukee to Montego Bay

FAQs - booking Jamaica flights

  • How long is the flight to Jamaica from Milwaukee?

    Flights to Montego Bay4h 19m
  • What is the cheapest flight to Jamaica from Milwaukee?

    The cheapest ticket to Jamaica from Milwaukee found in the last 72 hours was $150 one-way, and $362 round-trip. The most popular route is from Milwaukee to Montego Bay, and the cheapest round-trip airline ticket found on this route in the last 72 hours was $150.

  • Which airlines fly to Jamaica?

    Sun Country Air flies most frequently to Montego Bay from Milwaukee.

  • 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 from Milwaukee to Jamaica 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 from Milwaukee to Jamaica with an airline and back 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 from Milwaukee to Jamaica 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

  • Book at least 1 week before departure in order to get a below-average price.
  • High season is considered to be January, February and December. The cheapest month to fly from Milwaukee is April.
  • Morning departure is around 20% cheaper 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 4821 reviews
7.7Entertainment
8.2Boarding
8.7Crew
8.1Comfort
7.2Food
Airline reviews

I recently flew Southwest from San Jose to Honolulu. I was very impressed with the flight crew, especially the flight attendant in charge of the front of the plane. She came through the aisle at least five times for drinks and water, and two times for snacks. I have not seen such service since I flew first class. Also, for the first time, they gave us the correct baggage claim number, and the luggage came out quickly. I can't wait for Southwest to have assigned seating! I absolutely hate the Cattle Call boarding procedure and the mad dash to get seats and overhead bins. However, the boarding was efficient.

10.0 ExcellentWilliam Drew, Dec 2024SJC - HNL
Read more Southwest reviews

I recently flew Southwest from San Jose to Honolulu. I was very impressed with the flight crew, especially the flight attendant in charge of the front of the plane. She came through the aisle at least five times for drinks and water, and two times for snacks. I have not seen such service since I flew first class. Also, for the first time, they gave us the correct baggage claim number, and the luggage came out quickly. I can't wait for Southwest to have assigned seating! I absolutely hate the Cattle Call boarding procedure and the mad dash to get seats and overhead bins. However, the boarding was efficient.

Crew was great flight was great baggage claim was a failure. It took over 1 hour for bags to arrive. Poor communication poor effort when I spoke to the supervisor about the delay

Much better than the.last. flight on SW on Thanksgiving day

Fine, but how to board on SW versus othrr airlines, is just lame. Goood staff though and all was solid otherwise.

The movies using Southwest WiFi kept pausing and I had to restart multiple times.

It went well. Plane wasn't full. Will be great when assigned seating is in place

Everything was great except the food. The pretzels are really crappy.

For the first time in a long time we had a flawless experience with Southwest. Both flights were early and no mechanical errors at all. We were shocked and pleasantly surprised 😮.

It was fine. For some reason the flight was much longer than usual. It may have been explained, but I had noise cancelling earbuds on and missed a couple of announcements. The crew was fine, but there was a flight attendant who kept telling dumb jokes, occasionally one I found distasteful. This was my second time with him, but luckily it was a late flight so he didn't do as many. But I heard all of today's jokes twice, which was two times too many. Good takeout and landing.

One of the crew performed a hilarious skit to accompany the standard instructions. Passengers enjoyed it so much they applauded at the end!

I was with one of the last zones to board. It was kind of annoying to finally get called to board and my whole section was already on the plane. Clearly they boarded with previous zones. So by the time I got on board, there were no spaces for my luggage above my head. I had to put my luggage 4+ rows behind me, which meant that I had to wait even longer to get off the plane, since I had to wait for those rows to clear the aisle before I could retrieve my luggage and exit the plane. This also held up the plane cleaners, as they couldn't service my row until I cleared it, so they were all standing there waiting for me, while I'm standing there waiting for the other passengers to clear the aisle. Anyways, I wasn't in a rush this time, so I just waited, but I could see that being a problem in the future. Now, I could have checked my luggage, of course, but coincidentally, a friend of mine on the same flight got their luggage damaged (wheel completely knocked off) and was told by the Baggage Attendant in the airport that Delta doesn't "cover wheel damage" on luggage. This was disappointing to hear. I'm glad I didn't check mine through. If it were my luggage, I'd be highly frustrated to hear that. It makes me not want to check my luggage in the future.

The dear was very limited in space. I could put my water bottle in seat basket. Also, there was no inflight entertainment in the delta app?

Typically I give delta excellent reviews. Our flight was delayed 2hrs, I was one of the fortunate ones who were able to get to my connecting flight. Also, annoying that on the connecting flight boarding personnel make me put away a small bag into my carryon. It small enough to put in back pocket seat, why hold me and the line up to just push it into my carryon.

Logan airport construction meant that boarding was chaotic crowded and delayed

Everything was great. Great service, excellent communication, and early arrival

We were forced to wait nearly 50 additional minutes before leaving the terminal.

Free Wi-Fi is good. That’s all - food mediocre, unfriendly crew, poor communication after trying to file a claim for my lost bag, which Delta didn’t even know was lost until I told them.

Delta flight attendants poorly managed the boarding process and overhead storage. My bag was checked last minute and no claim ticket was provided. My bag is now lost. Complete incompetence by all flight crew involved.

Inexpensive, got an exit row aisle aeat with no middle passenger, bought a great breakfast sandwich, flight comfortable & arrived ahead of schedule.

Customer service at the gate in the flight was exceptional. On time. Aircraft and seat was decent. Thanks Delta. 💗

We arrived early and finally made it to our gate almost an hour after.

The reason I don’t fly United. No in seat entertainment for a long flight and inconsistent WiFi and entertainment available from my device.

We were delayed 3x and because I didn’t purchase my tickets directly from United Airlines I was told I Have to take care of it myself so I called Underpricer and they helped me but before I changed my flights I took the risk of sticking by what my tickets were and was lucky to have gotten on the original all flight with only 15 mins before take off. not sure if I will do this again

horrible website for checking in- no option just to write the passport number; ludicrous

The planes are so dirty! Food crumbs and finger print smudges, Dust over the vents and carpet stains. It’s disgusting.

Everything good until we waited for jet bridge at SFO. Then pilot gets on speaker & said it won’t reach plane- too short, need to go to different gate. Then 5 min later, adjusted plane/jetbridge & all ok?!?

Nothing, whole flight was a nightmare, was forced to check my carryon bag at the gate, staff was rude and unprofessional

David went above and beyond to make our flight the best that it could be

Was a pain having to leave the plane and reboard but glad the plane was fixed

How badly can you screw up baggage claim? We were told to go to baggage claim too for our bags from this flight. Another flights bags were there. They finished up. More bags from a different flight arrived. Our bags did not Finally the baggage claim belt stopped working and and are flight was still listed on the arrivals for that baggage claim 2. And then nothing It turns out that they had been delivered not only the United baggage claim but far away on a Delta baggage claim No I never told us. It was only the people looking around who had been on the flight But I’m sure there was plenty of time for the employees to raffle through the bags and steal whatever they wanted

Other than being delayed 5.5 hours and having to get a hotel because I missed my connecting flight, it was an okay flight. No in-flight Wi-Fi or entertainment.

Flight areas delayed 3 hours , train in the airport didn’t work

Flight attendant walked away once they landed and we were forced to wait another hour after an already 3hr delay.

No overhead space so all carryons were checked. No internet.

The flight was on time and everything went very smoothly.

A thousand choices for movies and nothing to watch. I avoid 'R' rated shows and others with violence and sexual content, which results in a handful of flicks to view and I have them already.

I think I paid for an extra legroom seat and to be honest, there was not a lot of space available for my not very long legs. The flight was totally full and the staff did everything possible to meet the needs of all passengers. My only concern was for the size and spacing of my seat.

Typically, I am always impressed with American personnel. These you run into the rude old hags that are still around. I can tell over my 40 years of flying with them, they have made strides in improving their attitudes.

Two issues. The plane was old and dirty. The armrest looked like an old car that had the vinyl rubbed off. The Seats in these aircraft are about as hard and uncomfortable. I want to tour Italy for a month and I want to buy a one-way ticket to Thailand but I will not sit in the seats these planes have. It is seriously stupid how hard they are.

The seat could not recline. This was not indicated as such when I paid for the seat. So itvwad not the most comfortable ride. At boarding, the staff could have more pleasant even though it may be an intense time.

I had paid for a seat assignment at the time of reservation but when I checked in the night before it wasn’t there. Had to purchase another seat.

So unprofessional. They changed my connecting flight to a time that made it literally impossible to make the flight with no way to contact them or reject the changes. When I missed the flight as expected, there was no one to be found at their ticketing counter and the phone support put me on hold for an indefinite time. Since they didn't have another flight that day, all sun country air personell had left the airport (this was at 7pm) and my only options were to get a hotel for the night and come back the next afternoon to hopefully get rescheduled or buy a flight with another airline.

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.

Book cheap flights from Milwaukee to Jamaica

Recent round-trip flight deals

2/24Mon
1 stopSpirit Airlines
17h 49mMKE-MBJ
2/27Thu
1 stopSpirit Airlines
28h 11mMBJ-MKE
$362
2/23Sun
1 stopSpirit Airlines
17h 49mMKE-MBJ
2/27Thu
1 stopSpirit Airlines
28h 11mMBJ-MKE
$366
1/22Wed
1 stopDelta
7h 39mMKE-MBJ
1/27Mon
1 stopDelta
9h 15mMBJ-MKE
$519
2/11Tue
1 stopDelta
6h 03mMKE-MBJ
2/18Tue
1 stopDelta
9h 15mMBJ-MKE
$534
2/22Sat
nonstopSun Country Air
4h 06mMKE-MBJ
3/1Sat
nonstopSun Country Air
4h 31mMBJ-MKE
$541
2/12Wed
nonstopSun Country Air
4h 16mMKE-MBJ
2/19Wed
nonstopSun Country Air
4h 31mMBJ-MKE
$542
2/4Tue
2 stopsAmerican Airlines
20h 18mMKE-MBJ
2/11Tue
2 stopsAmerican Airlines
20h 00mMBJ-MKE
$544
2/23Sun
2 stopsUnited Airlines
20h 16mMKE-MBJ
2/27Thu
1 stopUnited Airlines
7h 20mMBJ-MKE
$554
2/4Tue
2 stopsUnited Airlines
20h 22mMKE-MBJ
2/11Tue
2 stopsUnited Airlines
21h 00mMBJ-MKE
$594
2/22Sat
2 stopsAmerican Airlines
17h 16mMKE-MBJ
3/1Sat
1 stopAmerican Airlines
8h 12mMBJ-MKE
$629

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Recent one-way flight deals

2/23Sun
1 stopSpirit Airlines
17h 49mMKE-MBJ
$150
2/23Sun
3 stops
26h 04mMKE-MBJ
$219
2/22Sat
2 stops
22h 22mMKE-MBJ
$248
2/23Sun
2 stopsUnited Airlines
20h 16mMKE-MBJ
$257
2/22Sat
1 stopDelta
9h 24mMKE-MBJ
$276
2/22Sat
nonstopSun Country Air
4h 06mMKE-MBJ
$909

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Last minute flights from Milwaukee to Jamaica

Last minute flight, train and bus deals

12/22Sun
multi-stopUnited Airlines
29h 00mMKE-MBJ
12/28Sat
multi-stopUnited Airlines
26h 51mMBJ-MKE
$819
12/22Sun
multi-stop
26h 08mMKE-MBJ
12/28Sat
multi-stop
19h 52mMBJ-MKE
$839
12/22Sun
multi-stopUnited Airlines
29h 00mMKE-MBJ
12/28Sat
multi-stopUnited Airlines
6h 59mMBJ-MKE
$894
12/23Mon
multi-stopSouthwest
8h 20mMKE-MBJ
12/24Tue
multi-stopSouthwest
8h 10mMBJ-MKE
$951
12/23Mon
multi-stopSouthwest
9h 05mMKE-MBJ
12/24Tue
multi-stopSouthwest
8h 35mMBJ-MKE
$955
12/22Sun
multi-stopDelta
7h 40mMKE-MBJ
12/29Sun
multi-stopDelta
7h 06mMBJ-MKE
$986
12/23Mon
multi-stopDelta
6h 18mMKE-MBJ
12/24Tue
multi-stopDelta
7h 06mMBJ-MKE
$1,006
12/23Mon
multi-stopUnited Airlines
21h 10mMKE-MBJ
12/24Tue
multi-stopUnited Airlines
24h 53mMBJ-MKE
$1,052
12/23Mon
multi-stopUnited Airlines
24h 50mMKE-MBJ
12/24Tue
multi-stopUnited Airlines
24h 53mMBJ-MKE
$1,080
12/22Sun
multi-stopAmerican Airlines
15h 11mMKE-MBJ
12/29Sun
multi-stopAmerican Airlines
10h 52mMBJ-MKE
$1,182

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Everything you need to know for your flight from Milwaukee to Jamaica

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