$140 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 2/2. 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$401
Kingston
Kingston1 stop$392

Good to know

Low season

May

High season

March

Cheapest flight

$140
Best time to beat the crowds with an average 5% drop in price.
Most popular time to fly and prices are also 4% lower on average.
Flight from Milwaukee to Kingston

FAQs - booking Jamaica flights

  • How long is the flight to Jamaica from Milwaukee?

    Flights to Montego Bay4h 20m
  • What is the cheapest flight to Jamaica from Milwaukee?

    The cheapest ticket to Jamaica from Milwaukee found in the last 72 hours was $140 one-way, and $392 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 $228.

  • 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 August, September and October. The cheapest month to fly from Milwaukee is April.
  • Morning departure is around 3% 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 4654 reviews
8.1Comfort
8.7Crew
8.2Boarding
7.2Food
7.7Entertainment
Airline reviews

Flight was awfully bumpy and landing was a bit jolting. I was in the restroom when snacks and drinks were served and was not asked if i wanted any. I had to ask for water finally.

10.0 ExcellentRachel, Jan 2025TPA - MDW
Read more Southwest reviews

Flight was awfully bumpy and landing was a bit jolting. I was in the restroom when snacks and drinks were served and was not asked if i wanted any. I had to ask for water finally.

Wi Fi was horrible kept cutting out the whole time and too expensive

I really like open seating. I hate that I've heard this is going away. This is one of the unique things that makes Southwest my goto choice.

Boarding was a little late, but made up for it. It was quick to taxi to the runway, since it's a smallish airport.

Excellent! Only question is how we check in at exactly 24 hours in advance and end up at the end of the B boarding group

Multiple delays and gate changes. Arrived at final destination 6 hours late. All rental cars had been taken.

Employees were kind and funny, as always! Flight was late but no announcements were made for people with tight connections to help them transition quickly. No service due to turbulence.

It was 2 hours 45 minutes late, for no apparently clear reason.

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

Great service. Great staff. Boarding was a little slow, but I think there was a service dog slowing things down.

Flight left early and arrived early. the whole trip was excellent.

Seats were really tight and the seat belts did not give enough slack.

I like in St George and prefer to fly out of CDC than SGU. Hopefully, they will continue the flights out of Cedar

Broken jer bridge. Poor communication about it. Lost 2 of 4 luggage pieces

Overall, it was okay. Seat was a little cramped. Would’ve liked more substantial snacks or opportunity to buy some.

Newer plane, relatively easy boarding, not a full flight and was told that we could not be moved up because of weight and balance issues. Otherwise, a very good experience.

Other then mechanical/ computer problem and 3.5 hours flight delay the flight was great. I guess that what happened when you fly an old airplane now a day.

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?

Maybe add a seat trade app for flyers that didn’t get seats together

It’s been awhile since I have traveled on United. I, along with my family who were on the flight noted how smoothly everything went . Boarding, flight crew and service was excellent.

The seats on this flight were almost roomy enough to be the basic amount needed for human existence. I think my favorite part of this flight was it landed at an A gate, which was the most palatial part of Sea-Tac I've ever seen - a massive improvement from the S gates.

The seats on this flight were almost roomy enough to be the basic amount needed for human existence.

There's just no way to sit fully upright and comfortably in these seats. There needs to be 2 more inches of room, and that's not something that only one person on the flight needs - the whole flight needs 2 more inches of room. If that means you sell 6 less seats, so be it. It's too close for anyone. Forcing people to pay for "premium" economy just to get "barely enough space to breathe" isn't really an answer to that.

The crew were very nice. The Chocolate is good and v there’s no entertainment. Thanks

The crew were very nice. I would have appreciated a pillow for comfort. I had a special meal that was sloppy, but the salad was great. Thanks

I liked all the informational texts. I always knew where to go and when .

Boarding is very confusing. They have Line 1 and Line 2 and many many Boarding groups. Everyone lines up under those two lines long before they call zones. If you have a higher zone 2 like I did due to a Premium Plus ticket, it’s very awkward having to ask each person which zone they have. Extremely chaotic process. On board the flight attendants had no charisma whatsoever, even to us paying extra for an upgraded cabin. I asked for a chamomile tea after dinner (as no coffee or tea was even offered) and the FÃ said they didn’t have even though listed on the drink menu. Also, the mid flight service was entirely skipped which was a soup and sandwich combo. Supposedly had a variety of snacks mid flight too but those never materialized either. A few times I walked Back there, not a single flight attendant acknowledged me as they were all deep into their iPhones. I simply Wanted a glass of water since ZERO water runs were made on this 9hr 30 min flight.

Liked the hospitality . The ight took us 6 hrs to get from fort myers to ewr.

I paid for what I got which was cheap, I brought my own entertainment. I knew what to expect, so I could be prepared. If you’re flying economy, check in early like me. I have no problems with my flight, was on time, staff were friendly, and overall good experience.

Boarded over an hour late, no communication, the sign just changed, no attendant to answer questions - she disappeared forever (hiding). Small plane and couldn’t hear the overhead nor understand.

Service in first class no longer exists on American Airlines .

Customer service in first class does not exist on American Airlines

I never have a good experience with American and this was no different. The airplane was INCREDIBLY hot. Like unbearably so. Everyone was fanning themselves with pamphlets and sweating. When someone asked the flight attendant to turn down the temperature they were told there was nothing the crew could do. Once we pushed back from the gate we then had to wait an hour to take off and the communication from the crew was not good. People were getting up this whole time and a man was even in the bathroom when we took off. Once we landed at our destination we waited another 30 minutes at the gate to deplane with, again, no communication from the crew as to what was going on.

Flight was delayed due to a steering issue with plane. The delay caused me to miss the connecting flight. The delay caused me to spend an extra 21 hours in airports and flights to get to my destination. The plane issue obviously should have been found and fixed before we even boarded. Ridiculous.

First, to be fair, the flight was on time and the trip through the air was relatively smooth. But the flight was full, and they were checking carryons. As this process went on, the crew got increasingly rude and overbearing. During the drink service, a young girl (maybe 9) who had gotten up to use the lavatory got stuck behind the cart. At some point, she started feeling fearful and overwhelmed. Passengers noticed this and asked the crew to let her return to her seat. They refused. Then she started crying, and they still refused to move the cart forward to let her sit. The poor girl was trying to be brave and compose herself. The crew handled the situation terribly and with zero grace or decency. That episode, to me, encapsulates AA’s attitude toward its passengers. Disgraceful. The plane itself was cramped and miserable, as usual. There was zero inflight media or entertainment, other than the lane and borderline inappropriate jokes the steward made during the safety briefing. Then, of course, it took the better part of an hour for the checked bags to show up at the carousel. AA is no better than the el cheapo airlines these days and a far, far cry from its former self.

This particular flight wasn't very full at the back, so there were three seats available for spreading out and getting relatively comfortable

First class flight attendant was rude and lacked any customer service skills.

Customer service for American Airlines first class is at an all time low.

Flight was delayed in phoenix by 1 hour. When Kenny got to minneapolis st paul, Kenny missed his connecting flight to Duluth on Sun country air. Sun country customer service did nothing to help Kenny get home to Duluth. We will not fly with sun country ever again.

When we landed in Minneapolis from Providence, the ground crew was unable to move the jet bridge to meet our plane because the wheels were frozen. We waited patiently on the plane for about 45 minutes while they tried to solve this problem. It was mind boggling that this would not be more quickly resolved, or anticipated, in a place where sever winter weather is the norm. We stressed about meeting our connecting flight to Portland, which we assumed would be our only option for that day. Fortunately, when we finally raced from our gate to the next one, that Sun Country flight had been delayed so we didn't miss it. We decided not to take anything but direct flights from now on, no matter how much cheaper.

No line to check my bag. Reasonable overweight fee. When the connection was late due to weather, the gate agent opened the door and let me on the second flight. The plane waited for my luggage transfer. My bag arrived on time at my final destination:)

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

Book cheap flights from Milwaukee to Jamaica

Recent round-trip flight deals

5/14Wed
1 stopSpirit Airlines
24h 46mMKE-KIN
5/19Mon
1 stopSpirit Airlines
21h 19mKIN-MKE
$392
2/2Sun
1 stop
17h 42mMKE-MBJ
2/4Tue
2 stops
21h 38mMBJ-MKE
$401
2/4Tue
1 stopDelta
7h 39mMKE-MBJ
2/11Tue
1 stopDelta
9h 16mMBJ-MKE
$521
2/27Thu
1 stopDelta
7h 14mMKE-MBJ
3/4Tue
1 stopDelta
9h 15mMBJ-MKE
$536
4/16Wed
1 stopAmerican Airlines
8h 00mMKE-MBJ
4/23Wed
1 stopAmerican Airlines
7h 47mMBJ-MKE
$541
4/16Wed
2 stopsAmerican Airlines
8h 00mMKE-MBJ
4/23Wed
2 stopsAmerican Airlines
18h 54mMBJ-MKE
$545
2/4Tue
2 stopsUnited Airlines
20h 22mMKE-MBJ
2/11Tue
1 stopUnited Airlines
8h 32mMBJ-MKE
$564
2/4Tue
2 stopsUnited Airlines
20h 22mMKE-MBJ
2/11Tue
2 stopsUnited Airlines
21h 00mMBJ-MKE
$595
2/5Wed
nonstopSun Country Air
4h 16mMKE-MBJ
2/12Wed
nonstopSun Country Air
4h 30mMBJ-MKE
$615
2/19Wed
nonstopSun Country Air
4h 06mMKE-MBJ
2/22Sat
nonstopSun Country Air
4h 31mMBJ-MKE
$932

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Recent one-way flight deals

2/2Sun
1 stopSpirit Airlines
19h 05mMKE-KIN
$140
4/18Fri
1 stopSpirit Airlines
15h 03mMKE-MBJ
$228
4/18Fri
1 stopSpirit Airlines
15h 03mMKE-MBJ
$231
2/2Sun
2 stops
17h 41mMKE-KIN
$243
4/20Sun
1 stopDelta
9h 35mMKE-MBJ
$252
4/20Sun
2 stops
15h 48mMKE-MBJ
$270
3/1Sat
1 stopDelta
9h 24mMKE-MBJ
$277
3/1Sat
2 stopsAmerican Airlines
16h 18mMKE-MBJ
$287
2/13Thu
2 stopsUnited Airlines
49h 46mMKE-MBJ
$365
3/1Sat
nonstopSun Country Air
4h 06mMKE-MBJ
$650

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Last minute flights from Milwaukee to Jamaica

Last minute flight, train and bus deals

1/25Sat
multi-stopAmerican Airlines
11h 50mMKE-KIN
1/27Mon
multi-stopAmerican Airlines
12h 47mKIN-MKE
$774
1/25Sat
multi-stopAmerican Airlines
11h 50mMKE-KIN
1/27Mon
multi-stopAmerican Airlines
9h 37mKIN-MKE
$819
1/25Sat
multi-stop
16h 55mMKE-KIN
1/27Mon
multi-stop
19h 35mKIN-MKE
$1,139

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

Information on your arrival and departure airports

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