$165 Find Cheap Flights from Milwaukee to Caribbean Islands - Compare and Save

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 Caribbean Islands departing on 10/25. 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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Cheap Flights from Milwaukee to Caribbean Islands

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Punta Cana
Punta Cana1 stop$501
Santo Domingo
Santo Domingo1 stop$600
Montego Bay
Montego Bay1 stop$392
Oranjestad
Oranjestad2 stops$476
Nassau
Nassau1 stop$470
Kingston
Kingston2 stops$737
Simpson Bay
Simpson Bay2 stops$457
Providenciales
Providenciales1 stop$423
George Town
George Town1 stop$419
Willemstad
Willemstad2 stops$723
Aguadilla
Aguadilla2 stops$356
St. John's
St. John's2 stops$815
Puerto Plata
Puerto Plata2 stops$749
Punta Cana
Punta Cana1 stop$501
Santo Domingo
Santo Domingo1 stop$600
Montego Bay
Montego Bay1 stop$392
Oranjestad
Oranjestad2 stops$476
Nassau
Nassau1 stop$470
Kingston
Kingston2 stops$737
Simpson Bay
Simpson Bay2 stops$457
Providenciales
Providenciales1 stop$423
George Town
George Town1 stop$419
Willemstad
Willemstad2 stops$723
Aguadilla
Aguadilla2 stops$356
St. John's
St. John's2 stops$815
Puerto Plata
Puerto Plata2 stops$749

Book Cheap Milwaukee to Caribbean Islands 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 Caribbean Islands 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 Caribbean Islands

Thu, Sep 3 - Wed, Sep 9
Frontier Logo
12:10 pm - 2:15 am
MKE
-
SJU
13h 05m
1 stop
Frontier Logo
6:42 pm - 9:08 am
SJU
-
MKE
15h 26m
1 stop
$339Frontier
Thu, Aug 20 - Mon, Aug 24
Frontier Logo
12:10 pm - 2:15 am
MKE
-
SJU
13h 05m
1 stop
Frontier Logo
8:57 pm - 11:13 am
SJU
-
MKE
15h 16m
1 stop
$339Frontier
Fri, Jan 29 - Sat, Feb 6
American Airlines Logo
10:17 am - 11:59 pm
MKE
-
SJU
11h 42m
2 stops
American Airlines Logo
6:00 am - 2:24 pm
SJU
-
MKE
10h 24m
1 stop
$346American Airlines
Sat, Oct 31 - Sat, Nov 7
American Airlines Logo
6:27 pm - 10:44 am
MKE
-
SJU
15h 17m
2 stops
American Airlines Logo
6:28 am - 5:29 pm
SJU
-
MKE
13h 01m
1 stop
$346American Airlines
Mon, Oct 5 - Fri, Oct 30
Delta Logo
2:55 pm - 10:19 pm
MKE
-
SJU
6h 24m
1 stop
Delta Logo
5:59 pm - 11:53 pm
SJU
-
MKE
6h 54m
1 stop
$346Delta
Mon, Oct 5 - Fri, Oct 30
Delta Logo
5:30 am - 1:45 pm
MKE
-
SJU
7h 15m
1 stop
Delta Logo
5:59 pm - 11:53 pm
SJU
-
MKE
6h 54m
1 stop
$346Delta
Sat, Nov 7 - Sat, Nov 14
United Airlines Logo
10:48 am - 9:00 pm
MKE
-
SJU
8h 12m
1 stop
United Airlines Logo
7:40 am - 3:15 pm
SJU
-
MKE
9h 35m
1 stop
$346United Airlines
Wed, Aug 26 - Wed, Sep 2
United Airlines Logo
8:30 am - 8:38 pm
MKE
-
SJU
11h 08m
2 stops
United Airlines Logo
2:20 pm - 10:39 pm
SJU
-
MKE
9h 19m
1 stop
$346United Airlines
Thu, Sep 24 - Tue, Sep 29
Southwest Logo
1:55 pm - 10:15 pm
MKE
-
SJU
7h 20m
1 stop
Southwest Logo
1:20 pm - 9:20 pm
SJU
-
MKE
9h 00m
2 stops
$346Southwest
Sat, Aug 29 - Fri, Sep 4
Southwest Logo
9:05 am - 4:40 pm
MKE
-
SJU
6h 35m
1 stop
Southwest Logo
6:30 am - 3:25 pm
SJU
-
MKE
9h 55m
2 stops
$346Southwest
Booking Insights

KAYAK's insights & trends for Milwaukee to Caribbean Islands flights

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

What is the cheapest Milwaukee to Caribbean Islands flight route?

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

The cheapest ticket to Caribbean Islands from Milwaukee found in the last 5 days was to Punta Cana, at $584 round-trip. The most popular route is from Milwaukee (MKE) to Punta Cana (PUJ), and the cheapest round-trip airline ticket found on this route in the last 5 days was $584.

Can I save money by flying with a layover from Milwaukee to Caribbean Islands?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

No, with an average price for the route of $429, prices are generally cheapest when you fly direct.

What is the cheapest month to fly from Milwaukee to Caribbean Islands?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Milwaukee to Caribbean Islands, 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 Caribbean Islands is April, when tickets cost $593 (return) on average. On the other hand, the most expensive months are March and November, when the average cost of round-trip tickets is $744 and $741 respectively.

How far in advance should I book a flight from Milwaukee to Caribbean Islands?

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Milwaukee to Caribbean Islands, removes the top 0.1% to account for outliers, and then takes the average of all the values for each week.

To get a below average price on the flight from Milwaukee to Caribbean Islands, you should book around 1 week before departure. For the absolute cheapest price, our data suggests you should book 13 weeks before departure.

Good to know

Low season

September

Cheapest flight

$165
Best time to beat the crowds with an average 7% drop in price.
Most popular time to fly with an average 4% increase in price.
Flight from Milwaukee to San Juan

FAQs - booking Caribbean Islands flights

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

    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 Caribbean Islands.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Milwaukee to Caribbean Islands 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 Caribbean Islands?

    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 Caribbean Islands 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 Caribbean Islands?

    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 Caribbean Islands up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Reviews of the top 5 airlines serving from Milwaukee to Caribbean Islands

 
See real verified KAYAK customer reviews for airlines flying from Milwaukee to Caribbean Islands. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Milwaukee to Caribbean Islands? 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 4230 reviews
8.6Crew
7.0Food
8.1Boarding
7.5Entertainment
8.0Comfort
Airline reviews

The flight was delayed due to earlier issues at other airports. The crew was excellent & made it a good trip.

6.0 GoodJeremy, Aug 2026
STL - PHL
Read more Southwest reviews

The flight was delayed due to earlier issues at other airports. The crew was excellent & made it a good trip.

Boarding process of asking for volunteers to check bags goes against the system you had before with 2 bags checked free. This process is more of a guilt trip than a caring attitude toward the customer. In addition bag-size scrutiny has increased which also slows down the process of boarding. My wife said she will not fly on your airline again unless there is no other option.

Eveeyrime I fly they are begging for bags due to cabin overhead space. What they should so ia take the bags that are clearly too big to fit wheels first on their side. And those of us who give up the bag should really get their bags first. When boarding, nobody wants stupid jokes about how hot it is on board. Give us some cool air. Im usually sick from the heat by the time we take off.

No wifi, seems to be very common with Southwest currently. Everything else was normal.

Poor customer service, no accommodation for passengers when the flight was delayed over 5 hours.

Friendly crew kept coming by to make sure all was ok, provide additional refreshments, etc.

It was good. Last flight was delayed but I always say that is in God's plan

Red eye from San Diego. Temperature of the cabin was way too warm and the air duct flowed very little air.

Overall good, just screaming kids in the area the whole flight.

We were headed for Florida and anxious to get there. Everything was absolutely the best. This is our first time with Southwest and it’s now our go to airline. Best ever.

The ac must have died, it was way to hot on this flight. Boarding g was chaotic. The flight was delayed for boarding. Not a great experience.

Comfortable seats. Nice service online. Short flight, so not a lot of time to enjoy.

Awful. There was an unexpected delay of nearly three hours because there were not enough flight attendants. I understand this is likely due to FAA regulations; but in that case, Delta should coordinate with smaller airports such as RDU to have extra flight attendants on the ground and "on call". In addition, this was the second 2-hour+ delay to Boston on this route in one week.

Probably not the fault of Delta but there was delay after delay after delay and I ended up getting home 4 hours later then I should have at 1:30 in the morning

Staff was exceptional! Everyone was kind, professional and friendly making the trip very pleasant. Thank you!

Very late arrival at PWM. Late jet getting to ATL. Equipment problem with aircraft - could not get enough water onto plane., Another delay getting FAA approval for flight with bottled H2O. Not the crew’s problem.

A little bumpy ride . No food was being provided due the the turbulence. That was ok it was a short flight to my standards.

Pretty standard flight. Delta has a good selection of movies.

The flight was so late that I had to change connecting flights, turning a five-hour trip into a fourteen-hour nightmare.

Despite being delayed, we would still give a high score for this flight experience. For the first time in quite some time we had excellent customer service throughout our entire round trip. The flight attendants were the most polite we have experienced in our last ten flights at least (non of which were Delta and include business class). The food offered was a better selection than most—we just didn’t have any of it. Overall, almost as good as flying used to be. Thank you to Delta.

Flight staff and all was fine. Food always sucks on planes so nothing new.

The flight crew were very helpful. The seats were very close together. There was barely room to sit without touching the person next to you.

I’m an EP on AA every year for more than a decade but this was a very pleasant and surprising experience. Clean and sizable plane for HOU to CHI. 5 row first class. And excellent food in first class the steak option was really good. Your flight attendants even better. Seat 5A

It was hot and not as comfortable as the flight to Chicago. Must have been a different plane that needs to be worked on or replaced.

The flight was delayed by two de-icings. The seatbelt did not work correctly. It did not stay tight.

The seats on the aircraft are like sitting in a rock. During the boarding process they recognize Active Duty Military, why don’t they recognize Retired Military. I’ve always preferred Delta, this flight confirmed why I still prefer Delta.

It was literally one of the worst travel experiences ever. My flight got delayed by over an hour and there was no communication of this from the gate staff. I realized it by checking the screen periodically. Once on board the flight attendants continued to serve alcohol to a man who was clearly already drunk and that was making a bunch of commotion. Never again will I fly United!

At least the delays were short. Business class, even in the new planes is very crowded now with crappy tray tables

All good except paid for wifi that did not work

Flight cancelled due to fog. No other flights available for 36 hours. Directed by United to book passage on another carrier, and submit receipts for reimbursement. Did that. United now states they will not reimburse. Currently out 2 grand.

The airplane I love and I love I came back safe thank you American airlines

Although there were two delays, they were communicated clearly and the boarding process was expedited. The crew was pleasant and efficient.

Crew was helpful and cheerful especially when they had no refreshments to work with. The plane was never serviced and had nothing but limited water and coffee onboard. For the price point, a concern of services.

I bought wifi and most of the flight could not even use it my apps would just spin. I couldn't even listen to music. super frustrating.

Seating was horrible. Small seats. Access to flight information and extras very iser unfriendly. Kept losing internet after paying for it. Staff in madison was as unprofessional and unhelpful.

There were several different delays but we ended up being delayed a total of 40 mins or so. It was annoying we had a gate change which made it take longer to leave DFW, and we had to check our carry on. Ugh

The counter/baggage counter was busy and so many people missed flights. We got stuck sitting on the plane over 2 hours at the gate while they were doing an inspection is wrong. Many of us missed our connecting flights because of it.

Our flight was changed from Madison to DC to Madison to Charlotte.

We were told we had no flights before our flight was continually delayed then cancelled.

Boarding was relatively fast and easy and the crew was attentive throughout.

My seat was comfortable and I had plenty of leg room.

Boarding and crew were great, but seats are terribly uncomfortable. No food or entertainment options.

Everything went very smoothly! Thanks for a great first experience flying with small children!

Crew members great. Everything else a 0! Got on plane at 530am. Got de boarded for mechanical issue. Supposed to leave by 830 am. Zero communication from gate agents. Then supposed to leave by 230pm. Then delayed till 330pm. Still zero communication with gate agents. All they would say is if you have an issue call the 1800 number. You call and sit on hold minimum 45 minutes for zero answer. Finally board at 345pm didn’t take off till after 4pm! Sat in airport for 11 hours with 4 adults and 3 kids. Finally offered a $100 (we are sorry) voucher for next trip. Missed whole day in Florida had to change reservations in Florida! Absolute joke of an airline! And I usually really like sun country.

Booked through Kayak for $236. They canceled the flight unknown to me; retaining $100 for canceling it. Found out when I went to check in. Rebooked the same flight for $400. Incredibly disappointed. The Sun Country part was as to be expected. Crowded, no food, no arm room but got me where I wanted to go.

3 seperate extremely rude unhelpful staff. Delayed flight. Lost my bag

Sat between 2 big men. I was uncomfortable. Flight was delayed twice. About 2 hours altogether.

It was a good experience. I do wish the seats were roomier. Also, I did not like being charged for my carry on bag

Exceptional take off and landing in snow and wind…thank you to the well skilled pilots!

I liked entertainment system being downloaded on my iPad. The selections were limited but I appreciated being able to use my own screen. The flight was just fine. My only issue was both terminals being far from the main airport. Especially stoning at LAX near midnight and having to wait for a bus to take us to baggage pickup. Very inconvenient.

Everything you need to know for your flight to Caribbean Islands

Information on your arrival and departure airports