$88 Find Cheap Flights from Milwaukee to Caribbean Islands

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 5/4. 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

KAYAK searches hundreds of travel sites at once for deals on flights to Caribbean Islands

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Milwaukee to Caribbean Islands.
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Milwaukee to Caribbean Islands.
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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$430
Santo Domingo
Santo Domingo1 stop$516
Montego Bay
Montego Bay1 stop$352
Oranjestad
Oranjestad1 stop$598
Nassau
Nassau1 stop$520
Kingston
Kingston2 stops$692
Simpson Bay
Simpson Bay1 stop$519
Providenciales
Providenciales1 stop$505
George Town
George Town2 stops$501
Willemstad
Willemstad2 stops$502
Puerto Plata
Puerto Plata2 stops$641
St. John's
St. John's2 stops$781
Aguadilla
Aguadilla1 stop$186
Punta Cana
Punta Cana1 stop$430
Santo Domingo
Santo Domingo1 stop$516
Montego Bay
Montego Bay1 stop$352
Oranjestad
Oranjestad1 stop$598
Nassau
Nassau1 stop$520
Kingston
Kingston2 stops$692
Simpson Bay
Simpson Bay1 stop$519
Providenciales
Providenciales1 stop$505
George Town
George Town2 stops$501
Willemstad
Willemstad2 stops$502
Puerto Plata
Puerto Plata2 stops$641
St. John's
St. John's2 stops$781
Aguadilla
Aguadilla1 stop$186

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

Fri, Apr 17 - Mon, Apr 20
Frontier Logo
2:47 pm - 11:29 pm
MKE
-
SJU
7h 42m
1 stop
Frontier Logo
7:15 am - 1:52 pm
SJU
-
MKE
7h 37m
1 stop
$291Frontier
Tue, May 12 - Tue, May 19
Frontier Logo
9:56 am - 1:15 pm
MKE
-
SJU
26h 19m
1 stop
Frontier Logo
3:03 am - 8:01 am
SJU
-
MKE
29h 58m
1 stop
$295Frontier
Tue, May 5 - Tue, May 12
American Airlines Logo
5:29 pm - 9:13 am
MKE
-
MBJ
15h 44m
1 stop
American Airlines Logo
2:19 pm - 9:57 pm
MBJ
-
MKE
7h 38m
1 stop
$352American Airlines
Sat, May 2 - Sat, May 9
United Airlines Logo
5:55 am - 3:10 pm
MKE
-
MBJ
9h 15m
2 stops
United Airlines Logo
1:52 pm - 10:03 pm
MBJ
-
MKE
8h 11m
1 stop
$353United Airlines
Mon, Jun 1 - Fri, Jun 5
American Airlines Logo
6:34 pm - 11:45 am
MKE
-
MBJ
17h 11m
2 stops
American Airlines Logo
2:55 pm - 11:47 pm
MBJ
-
MKE
8h 52m
1 stop
$357American Airlines
Mon, Jun 29 - Thu, Jul 2
Delta Logo
5:40 am - 3:34 pm
MKE
-
MBJ
9h 54m
1 stop
Delta Logo
1:21 pm - 11:59 pm
MBJ
-
MKE
10h 38m
1 stop
$362Delta
Sat, Jun 6 - Thu, Jun 11
Delta Logo
5:00 pm - 11:34 am
MKE
-
MBJ
18h 34m
2 stops
Delta Logo
12:59 pm - 11:50 am
MBJ
-
MKE
22h 51m
2 stops
$367Delta
Mon, Jun 29 - Sat, Jul 4
United Airlines Logo
8:55 pm - 3:10 pm
MKE
-
MBJ
18h 15m
2 stops
United Airlines Logo
2:40 pm - 10:45 pm
MBJ
-
MKE
8h 05m
1 stop
$380United Airlines
Sun, May 17 - Sat, May 23
Southwest Logo
5:00 am - 2:25 pm
MKE
-
SXM
8h 25m
1 stop
Southwest Logo
2:35 pm - 10:55 pm
SXM
-
MKE
9h 20m
1 stop
$519Southwest
Wed, May 20 - Wed, May 27
Southwest Logo
9:15 am - 6:30 pm
MKE
-
NAS
8h 15m
2 stops
Southwest Logo
2:10 pm - 9:45 pm
NAS
-
MKE
8h 35m
2 stops
$557Southwest
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 72 hours was to Montego Bay, at $540 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 72 hours was $628.

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 $427, 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 September, when tickets cost $305 (return) on average. On the other hand, the most expensive months are December and November, when the average cost of round-trip tickets is $675 and $519 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 18 weeks before departure.

Good to know

Low seasonJuly
Cheapest flight$88
Best time to beat the crowds with an average 1% drop in price.
Most popular time to fly with an average 12% 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 4340 reviews
7.0Food
8.1Boarding
8.0Comfort
7.5Entertainment
8.6Crew
Airline reviews

Terrible. Even though there’s assigned seating now, they are still the slowest boarding airline of anyone.

2.0 MediocreJames, Apr 2026
LAX - MCO
Read more Southwest reviews

Terrible. Even though there’s assigned seating now, they are still the slowest boarding airline of anyone.

The Air hostess were very rude on my flight from Houston to Austin . Their regular communication itself felt a they are shouting at people.

Communication about the delayed flight was poor. We were told to move gates three times but that was bad information. We went from gate 128 to gate 126 and then to gate 123 and back to gate 126. Communication about the delay was bad. Ended up being 1 1/2 hour late getting home.

Plane was late. Zero service for 2+ hour flight and it was not that bumpy.

It was good from LAX to Phoenix, But the connection in Phoenix to Tulsa was not that great. The staff on both flights were great. The choice of free entertainment was ok nothing to brag about. The 45 min delay because of some electrical issue wasn't great from Phoenix to Tulsa. We sat there with hardly any air, The seat I had was between windows so the side of the plane pushed in on you. My being a bigger man it then made the seating area uncomfortable. The seats on the plane had no power to connect to recharge your phone or anything. I would recommend that they should look into a slot or clamp to hold your phone to enjoy while watching the entertainment choices hands-free. Also make it possible to raise the inner seat by the window be able to raise the arm rest up to make more room for larger people to set more comfortably. I would also say other then that stop price gouging the airfare or nickel and diming everything. Not fair for people having to fly for emergencies and be paying for higher prices due to the season or holidays. Your making your money either way and the cost of flying is still going to be the same regardless if there's 100 people or 200 people.

Had a great flight. Delayed takeoff, but comfortable. Snacks were good.

Love them will get a Southwest card to track my points and keep flying with them. My family and I were pleased with the services.

I have roller bag with food and medication told me I couldn't bring on my 2nd flight today. 15 years flying with SW never an issue with that bag.

Southwest continues to do less for more money. Flight attendants used to be fun and friendly. But now it’s like they don’t even see you. Such a shame.

Great flight. Good snacks and drinks. Grateful it was free. The flight from Nashville to louisville, i think her name was Tracy (not sure that's right) super awesome, nice and cheerful. She really enjoyed being at work today! She was the person who scanned the boarding pass on flight wn941. She should be recommended for a raise !

I am writing to express my dissatisfaction with the poor service and unprofessional staff we encountered when traveling with an infant. Our flight was delayed, and the gate staff failed to manage the boarding process appropriately. Due to incorrect, unavailable, or missing 'pink tag' stroller and car seat check-in procedures at the gate, we were forced to board last. Furthermore, the gate staff was rude and dismissive, causing significant distress to our infant. To make matters worse, one of our checked items—an infant sleeper/lounger—was returned to us broken. Given the unsafe handling of essential equipment and unprofessional treatment, I expect a prompt resolution regarding compensation for the damaged items.

We departed and landed early which was a nice surprise. The boarding process was slow.

N Everything was perfect from boarding to assistance to baggage in Tampa

Subpar. The seating on the plane is almost unbearable. We are literally touching and/or sitting on each other which is totally unacceptable and shameful. Pilots and crew was very accommodating and friendly.

The boarding was organized and informative but the plane was tight meaning that you were sitting on one another and extremely uncomfortable. It’s disappointing that can’t have common seating comfort on the plane.

Loved the crew! Sucks that we went from 1 hour and 8 minute layover to a 3 hour layover. But weather sucks like that.

I was told that they needed to check my bag at the gate and to pick it up at the gate in Richmond. No big deal. I know they can't control the weather, but we flew around RIC for 45 minutes to avoid the storm and were 25 minutes late leaving as well. Once we landed, we were told to go to baggage claim to pick up our luggage. I went to bathroom, paid for parking, and went to the assigned baggage claim location. United flight people came down with us as well. They got their luggage immediately. Next, South West people came down about 10 minutes later. They got their luggage next. We finally got our luggage around 30 minutes in waiting. Was not a wonderful experience. No reflection on Delta, but the ground crew was lousy at best.

Everything could have benn better. Short fly, no food, no entertainment and no wifi.

Flight delayed. Air broken. Cabin was hot enough to pass out. Delta shuttle’s becoming worse and worse.

my mom urmila patel needed a wheelchair which was not available on the curbside. she needed to walk almost 50 meters inside (at the risk of falling) and then had to wait in line to get a wheelchair (this is not ok). Once obtained she had to seat in it for 30-45 minutes for someone to take her in thru the checkin process (which was fairly smooth and easy). the lady who helped her with her checkin process was very courteous and helpful

Boarding was again a "free for all". We were boarding group 4, and almost the entire plane was able to board before us. It's a shame that someone who follows the rules, gets the short end of the stick. Not fair.

Flight left on time, arrived early, pleasant staff provided water, coffee, etc. access to bathrooms was reasonable and were well maintained. blankets were available, lots of entertainment options. LUGGAGE SERVICE WAS GREAT. I got my one checked bag quickly and was able to make a bus connection for a 2 hour bus ride saving me from waiting another 1.5 hours.

The boarding process was straightforward. One pertinent observation regarding all boarding procedures is that if an individual requires assistance or possesses a special status and is part of preboarding, it is advisable to limit the number of passengers who can preboard with them, rather than the entire, sometimes large, companion groups. The seats are uncomfortable, and the entertainment options are significantly inferior compared to other airlines. During the snack service, I requested an additional bag of snacks, but my request was denied. Initially, the flight attendant agreed to my request.becoming a strange accurate moment. The flight duration was four hours.

The flight was officially delayed 3 times, and was actually later than that. Combined, it was a 3 hour delay, but there was no recognition (miles, voucher, etc). The crew seemed stressed. The captain sounded nervous in his announcements. The flight itself was smooth and uneventful.

United didn’t even try to hold the flight for me. They knew I had a tight connection and when I arrived at the gate less than 10 mins after final boarding the flight had already gone. The gate agent wasn’t even notified that I was on my way. She was told I wasn’t at the airport

Great until we got to FRA. The next trip leg we were put in Business Class where seats had minimal padding!!!! They were awful and United Airlines needs to have their Lufthansa partner up their game or I won’t fly with them again!!

I had a good time. However, I paid for the wifi and it was in and out the whole flight.

one staffer was frustrated (it happen); the flight was late and the pilot mentioned they'll make amend but the snacks were the same, other than that the aircraft was clean and everything went smooth, no complaints

The wheelchair service is useless. They live you in different spots, not tell you anything just wait. I waited 30 minutes in Frankfurt when decided to walk the 25 minutes distance. In Budapest nobody came.

It was perfect! I've never flown with United before, but I definitely will in the future

Delays experienced in boarding/take off due to incoming plane delayed. However, the boarding time/depart time in the app was significantly delayed in providing these updates. Usually not updated until an hour after we should have already boarded. Poorly managed.

Bag drop was very disorganized in Miami. All main cabin passengers were shunted to just a few lanes and they had an equal number of lanes for first class passengers but there was nobody on those lines. They did nothing to bring the main cab and passengers over to the open lines and they just had employees standing there and doing nothing

there are no options s for snack besides cookies would ve nice to have a salty option n

We did not have enough time to make our connecting flight. As a result, we were put onto a different airline for our second leg. The different airline was NOT comparable to British Airlines, and our arrival was significantly delayed. The actual flight on BA was amazing.

We left at 1030 am pacific from LA and supposed to land at 7 pm Eastern in NY. They made a detour, stopped in Philadelphia and didn’t land till 1130 PM Eastern!!! Worst flight experience with no pilot communication with no explanation as to what was going on. Everyone was very frustrated to say the least.

Going non stop to lax like I paid for. Not stopping in MCI for gas. Too long of delays

Human interaction. Thought there would be more service-even a smile would have been nice.

It was canceled at the last minute. While I was literally at the airport. Messed my entire trip up.

Seat was VERY uncomfortable. Flight was delayed and then boarded slowly. The crew was super helpful with boarding and supporting maximizing the luggage in the overhead.

Crew at the gate was very crabby and not at all polite. The plane was very hot the entire flight. And the seat cushion was very worn out.

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.

Just fine but comfort is always an issue since the seats are so close

The Flight was fine, the staff treated me well, the flight got delayed over 5 1/2 hours for maintenance issues....but it worked out OK,, they were very apologetic about it, and it is better to not fly if there is any issue than endanger peoples lives, so in reality that was a good thing, It did cost me extra for parking because I went beyond the time I had purchased for parking at MSP. But all in all, Good flight

Everything you need to know for your flight to Caribbean Islands

Information on your arrival and departure airports