$163 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 9/16. 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
1 adult, Economy, 0 bags

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Cheap Flights from Milwaukee to Jamaica

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Montego Bay
Montego Bay2 stops$352
Kingston
Kingston3 stops$697
Montego Bay
Montego Bay2 stops$352
Kingston
Kingston3 stops$697

Book Cheap Milwaukee to Jamaica Plane Tickets

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Milwaukee to Jamaica that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Milwaukee to Jamaica

Tue, Apr 21 - Fri, Apr 24
United Airlines Logo
7:41 pm - 3:10 pm
MKE
-
MBJ
19h 29m
2 stops
United Airlines Logo
1:52 pm - 11:43 pm
MBJ
-
MKE
9h 51m
1 stop
$352United Airlines
Mon, Jun 1 - Fri, Jun 5
American Airlines Logo
6:45 pm - 1:08 pm
MKE
-
MBJ
18h 23m
2 stops
American Airlines Logo
5:17 pm - 12:50 pm
MBJ
-
MKE
19h 33m
2 stops
$357American Airlines
Wed, May 6 - Mon, May 11
American Airlines Logo
6:40 pm - 9:13 am
MKE
-
MBJ
14h 33m
2 stops
American Airlines Logo
10:17 am - 5:51 pm
MBJ
-
MKE
7h 34m
1 stop
$362American Airlines
Wed, May 6 - Sun, May 10
United Airlines Logo
6:00 am - 3:10 pm
MKE
-
MBJ
9h 10m
2 stops
United Airlines Logo
2:40 pm - 7:49 am
MBJ
-
MKE
17h 09m
2 stops
$367United Airlines
Mon, Jun 22 - Fri, Jul 3
United Airlines Logo
8:45 pm - 3:10 pm
MKE
-
MBJ
18h 25m
2 stops
United Airlines Logo
4:12 pm - 9:58 am
MBJ
-
MKE
17h 46m
2 stops
$377United Airlines
Tue, Apr 14 - Tue, Apr 28
United Airlines Logo
6:50 am - 3:10 pm
MKE
-
MBJ
8h 20m
2 stops
United Airlines Logo
4:12 pm - 10:00 am
MBJ
-
MKE
17h 48m
2 stops
$409United Airlines
Fri, Apr 17 - Fri, Apr 24
Delta Logo
5:30 am - 8:00 pm
MKE
-
KIN
14h 30m
1 stop
Delta Logo
9:00 am - 11:57 pm
KIN
-
MKE
14h 57m
1 stop
$774Delta
Sat, May 2 - Sat, May 9
American Airlines Logo
6:00 am - 6:54 pm
MKE
-
KIN
12h 54m
2 stops
American Airlines Logo
7:00 am - 10:47 pm
KIN
-
MKE
15h 47m
2 stops
$779American Airlines
Tue, Apr 14 - Tue, Apr 28
Delta Logo
7:00 am - 8:00 pm
MKE
-
KIN
13h 00m
1 stop
Delta Logo
9:00 am - 4:24 pm
KIN
-
MKE
7h 24m
1 stop
$854Delta
Fri, Apr 3 - Thu, Apr 9
Delta Logo
10:09 am - 8:00 pm
MKE
-
KIN
9h 51m
1 stop
Delta Logo
9:00 am - 8:55 pm
KIN
-
MKE
11h 55m
1 stop
$874Delta
Booking Insights

KAYAK's insights & trends for Milwaukee to Jamaica flights

Get data-powered insights and trends into flights from Milwaukee to Jamaica to help you find the cheapest flights, the best time to fly and much more.

What is the cheapest Milwaukee to Jamaica flight route?

Data is based on round-trip flight searches on KAYAK over the past month.

The cheapest ticket to Jamaica from Milwaukee found in the last 72 hours was to Montego Bay, at $540 round-trip. The most popular route is from Milwaukee (MKE) to Montego Bay (MBJ), and the cheapest round-trip airline ticket found on this route in the last 72 hours was $540.

What is the cheapest month to fly from Milwaukee to Jamaica?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Milwaukee to Jamaica, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Milwaukee to Jamaica is May, when tickets cost $558 (return) on average. On the other hand, the most expensive months are June and March, when the average cost of round-trip tickets is $761 and $701 respectively.

Good to know

Low seasonMay
Cheapest flight$163
Best time to beat the crowds with an average 12% drop in price.
Most popular time to fly and prices are also 10% 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 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.

Reviews of the top 3 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
SouthwestOverall score based on 4325 reviews
8.1Boarding
8.6Crew
7.5Entertainment
7.0Food
8.0Comfort
Airline reviews

Southwest was greaat! The most expensive but the least upsetting for those we were flying to see.

10.0 ExcellentMartie, Mar 2026
LGB - BNA
Read more Southwest reviews

Southwest was greaat! The most expensive but the least upsetting for those we were flying to see.

I flew twice this week on Southwest, was delayed over 2 hours both ways. From Pittsburgh to Chicago it was due to weather but the gate agents, pilot etc were great at updating everyone. Today from Midway to Pittsburgh the plane had come from an international location, kept getting delayed, no information was given until we were delayed for the third time. It was ridiculous, whoever scheduled that plane to fly to Pittsburgh after didn’t consider a lot of things.

Boarding was easy. The seats are small and fairly uncomfortable

I was supposed to be on a later flight. When I showed up at the gate, the woman working there was extremely helpful getting moved up to this earlier flight.

We had a 5 hour delay on the tarmac in Baltimore

Long layover between flights to Long Island from BWI - need better coordination between flights

I elected to pay for the upgrades and found very little difference

The new seating arrangement is so over priced for what you get.

The problem with the seat assignments is that there were a lot of rows in the front that were empty but my row at the back was full. Just not so pleasant.

No food or entertainment, just a quick 40 minute flight. A little bumpy due to Santa Ana winds but pilot has no control over that. Good flight and landing!

the crew cancel the morning service due to the weather. Then the flight got deverted to Nashville . we were on the ground for over two hours the only gave us water once... no food or any snacks.... the crew should have handled better and offered something to passengers.

My recent experience was excellent on Delta! I flew with Delta Comfort and I was really comfortable in my seat. I enjoyed the in-flight service. The flight attendants were so friendly and hospitable. I love the snack on the flight as well. This was my first time flying on Delta and I will definitely consider flying with them again.

My flight was cencaled due with the bad weather on Sunday the crew was poorly mistaken my luggage supposed depart with my flight instead I didn’t have my luggage for almost 3 days the website is poorly respond to my complain until I have someone to do it my connection smooth their not even respon or email me even the have my luggage

Delta needs to step its game up get a more reliable internet service. Internet service was non-existent for this flight.

Mechanical Delay of over an hour with multiple gate changes. Entertainment system down for rejuvenation.

This was a Latam operated flight. Seats seemed a bit narrow in business class. Older aircraft.

I had a flight cancel and had it rerouted. When the rerouted they put me at a window seat instead of an isle. It was hard sitting by the window because the couple with masks on were making out. I get motion sickness which is why I need to have the isle seat.

NEVER MADE THE FLIGHT BECAUSE DELTA SAID THEY CAN NOT

THEY FAILED ME AND I NEVER GOT ON THE FLIGHT BECAUSE IT WAS SO DELAYED! I ENDED UP HAVING TO PAY OUT OF POCKET FOR A HOTEL AND STAY IN NASHVILLE TO CATCH A FLIGHT FOR THE FOLLOWING DAY. DELTA IS POOR CUSTOMER SERVICE>

8 hours late and the plane smelled like urine, that smell in the morning when your child wet the bed in the night.

Half of the TSA checkpoints at PHL are closed. Also, there is no standby for first class passengers. You can only standby for coach. Very dated policy and inconsistent with peers.

Flight was scheduled at 11:26am but they keep Delaying until midnight. They waited at airport restless.

Rough flight No beverage service due to turbulence Bottom Seat cushion was non existent

Great experience. Good dinner and service. FA's were very nice and attentive.

It was great. Smooth flight, comfortable, left on time and landed on time.

Perhaps this is an airport issue, but being in a takeoff queue for over an hour in the taxiing lane is unacceptable. We will definitely be seeking alternative avenues for air travel in the future.

We hoarded. Then we deplaned. Then we waited for 10 hours in the MSP airport due to a wheel misfunction. We understand safety but communication between crew and airport staff was horrible. When we did finally board, we were rushed on and because we were waiting for a “fresh” pilot and crew, we sat in a roasting plane with no A/C for an hour. My question is why was this flight not cancelled right away when they knew this would be a huge issue OR, why did AA not get a substitute plane, considering this was already a full flight? To me, this appears to be a complete breakdown in leadership and utter systems failure. The compensation for completely disrupting travel plans for hundreds, which we paid dearly for, was measly. While we appreciated the lodging for the night, $12 in meal vouchers isn’t going to sustain anyone for over 12 hours. “We apologize; our hands are tied” is no longer an acceptable explanation. We are so completely turned off by this experience and will definitely seek alternative avenues when we need to fly.

Mostly good. The WiFi wasn’t working so that was not great.

I rated the experience "mediocre" because of the 2 hour delay in take off. This is the 4th flight from DFW on AA where there was a delay and in one of the instances (after 13 delays), the flight was cancelled. I understand weather but for the March 18th flight, there was no weather issue in Dallas or Detroit. I called Concierge Key and they were wonderful, booking me on a later flight in case my flight was cancelled. I have flown with American for many years and never has there been this consistent pattern of delays. Very disappointing.

They put me on an earlier and I got home sooner

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

Information on your arrival and departure airports