$138 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 7/5. 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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Flight Deals

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 Cana2 stops$511
Santo Domingo
Santo Domingo1 stop$550
Montego Bay
Montego Bay2 stops$357
Oranjestad
Oranjestad1 stop$597
Nassau
Nassau1 stop$559
Kingston
Kingston2 stops$695
Simpson Bay
Simpson Bay1 stop$483
Providenciales
Providenciales2 stops$518
George Town
George Town2 stops$504
Willemstad
Willemstad1 stop$704
Aguadilla
Aguadilla2 stops$326
Puerto Plata
Puerto Plata2 stops$799
St. John's
St. John's2 stops$760
Punta Cana
Punta Cana2 stops$511
Santo Domingo
Santo Domingo1 stop$550
Montego Bay
Montego Bay2 stops$357
Oranjestad
Oranjestad1 stop$597
Nassau
Nassau1 stop$559
Kingston
Kingston2 stops$695
Simpson Bay
Simpson Bay1 stop$483
Providenciales
Providenciales2 stops$518
George Town
George Town2 stops$504
Willemstad
Willemstad1 stop$704
Aguadilla
Aguadilla2 stops$326
Puerto Plata
Puerto Plata2 stops$799
St. John's
St. John's2 stops$760

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

Wed, Aug 12 - Tue, Aug 18
American Airlines Logo
6:33 am - 11:59 pm
MKE
-
SJU
16h 26m
1 stop
American Airlines Logo
1:38 pm - 11:23 pm
SJU
-
MKE
10h 45m
2 stops
$331American Airlines
Mon, Oct 5 - Fri, Oct 30
American Airlines Logo
2:22 pm - 11:50 pm
MKE
-
SJU
8h 28m
1 stop
American Airlines Logo
8:35 am - 12:11 am
SJU
-
MKE
16h 36m
1 stop
$333American Airlines
Sat, Sep 12 - Fri, Sep 18
United Airlines Logo
10:43 am - 8:38 pm
MKE
-
SJU
8h 55m
1 stop
United Airlines Logo
1:00 am - 10:00 am
SJU
-
MKE
10h 00m
2 stops
$358United Airlines
Sat, Sep 26 - Sun, Sep 27
Southwest Logo
1:15 pm - 8:55 pm
MKE
-
SJU
6h 40m
1 stop
Southwest Logo
5:30 am - 3:25 pm
SJU
-
MKE
10h 55m
1 stop
$360Southwest
Fri, Aug 14 - Mon, Aug 17
Southwest Logo
5:35 am - 4:55 pm
MKE
-
SJU
10h 20m
1 stop
Southwest Logo
6:00 am - 4:10 pm
SJU
-
MKE
11h 10m
1 stop
$365Southwest
Tue, Aug 4 - Wed, Aug 12
Frontier Logo
8:43 am - 5:34 pm
MKE
-
SJU
31h 51m
2 stops
Frontier Logo
6:31 pm - 7:58 am
SJU
-
MKE
14h 27m
1 stop
$375Frontier
Thu, Aug 20 - Mon, Aug 24
Delta Logo
5:34 am - 1:34 pm
MKE
-
STT
7h 00m
1 stop
Delta Logo
2:49 pm - 8:53 pm
STT
-
MKE
7h 04m
1 stop
$420Delta
Sun, Oct 18 - Wed, Oct 28
Delta Logo
5:45 am - 3:34 pm
MKE
-
MBJ
9h 49m
1 stop
Delta Logo
1:32 pm - 11:24 pm
MBJ
-
MKE
9h 52m
1 stop
$422Delta
Mon, Jun 29 - Sat, Jul 4
United Airlines Logo
5:56 pm - 1:30 pm
MKE
-
MBJ
19h 34m
1 stop
United Airlines Logo
2:40 pm - 10:45 pm
MBJ
-
MKE
8h 05m
1 stop
$429United Airlines
Tue, Aug 18 - Sat, Aug 22
Frontier Logo
8:43 am - 8:18 pm
MKE
-
PUJ
34h 35m
2 stops
Frontier Logo
5:30 pm - 7:58 am
PUJ
-
MKE
15h 28m
1 stop
$511Frontier
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 Punta Cana, at $628 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 $438, 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 January, when tickets cost $90 (return) on average. On the other hand, the most expensive months are June and November, when the average cost of round-trip tickets is $394 and $357 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$138
Best time to beat the crowds with an average 5% drop in price.
Most popular time to fly with an average 10% 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.
7.9
SouthwestOverall score based on 4284 reviews
7.5Entertainment
8.1Boarding
8.0Comfort
7.0Food
8.6Crew
Airline reviews

No gluten free snacks. Seats felt worn or bare bones even though it was a new 737 MAX 8.

10.0 ExcellentAnonymous, May 2026
PDX - OAK
Read more Southwest reviews

No gluten free snacks. Seats felt worn or bare bones even though it was a new 737 MAX 8.

One major problem that was very unprofessional and uncalled for. Plane landed and we had to wait 20 minutes to get off the plane since they were waiting for someone to come to the gate to drive the jetway. Southwest couldn't have someone available and waiting for the plane to land? Is there only one person in Hobby airport who knows to drive the jetway? Was he at lunch? In the bar? Uncomfortable and uncalled for!

The checking experience in Orlando was terrible, almost missed the flight. Too many travelers and Southwest completely understaffed.

I'm glad it wasn't only 75% full because I could get a good seat

if I was good. Not happy that I have to pay extra money to get the seat I need for lake room, but I guess that’s a sign of the times.

Seats were very comfortable. They tilted back. Drinks and snacks were free and served 3 times. Attendants were awesome.

Plane was clean and comfortable. Flight attendants and gate staff were professional, friendly and efficient. Boarding and deplaning were orderly and efficient. All in all, the typical excellent Southwest experience.

Truly terrible. Will never willingly fly southwest again. Seats are worse than before they switched to assigned seating. One flight attendant was the opposite of helpful (rude, unhelpful, dismissive, and as my stranger seatmate said unprompted: a total prick). This caused me, 15 minutes into the flight, to book an alternate return flight home on a competing airline (first class 1.2k purchase instead of my existing planned flight) just so I would not have to ever be on that aircraft, with that terrible service person, with those horrific seats ever again.

Not having a five hour delay with little notice! The crew was very kind, though, and just as tired as we passengers were. The flight didn't depart until nearly 1 am...and no reason was ever given.

The entire experience from boarding to landing was amazing! The crew were very friendly. Will definitely be back.

I continue to be satisfied with Delta’s excellent service out of LGA. The digit id works well and gets me through security in no time. Whenever possible, I choose Delta.

Was revoked with Jet Blue due to delay from Kenya Air

The Boarding process was great. Particularly since my wife and I require assistance. The flight attendants were amazing. We travel frequently; they honestly were a cut above. 😀

Enjoyed it very much. Especially liked the free WiFi that Delta offers.

Smooth flight. Left on time, and got in 15 minutes early. Onboard video was great

For some reason, TSA Atlanta didn’t have my bag on the flight on time and they don’t have to provide Delta a reason for that.

WiFi didn’t work on two of four planes. Flight attendants were not overly friendly or welcoming. Planes were extremely slow to board and deplane.

Delta does a great job with entertainment and free wifi. I can still be in touch with my colleagues while in the air.

Aside from a completely packed plane, I really have no complaints.

Bus to plane was delayed for no apparent reason and our luggage was still on the belt when they shut it off. Took about 20 minutes to turn it back on to get our luggage.

Late plane. Only one crew on the ground so we b had to wait for Denver flight to come in, board, and depart. At 78 yrs of age I was not pleased trying to get my connection. What really made me angry was the notification you sent me to hurry up or I would miss my connection. Why tell me to hurry up when you got me in late. It was not a good way of treating customers.

No complaints other than luggage carousel was incorrectly guiding passengers to the wrong carousel on the screen.

Did not like that we couldn't complete check in on-line without providing pictures of our passports. Worry about identity theft. We had no delays and boarding was handled In an efficient manner.

We were a little disappointed to not be able to complete check in online without uploading pics of passports. Also we have KTN's and they weren't on our boarding passes when we got to security. Had to trek back to counter to have them fix.

Excellent service in Polaris class IAD to ZRH. Arrived rested and well fed after the overnight flight.

My flight time was changed without any notification to me which ruined my time sensitive plans so I ended up completely changing my travel plans and no reimbursement.

Excellent! I got to Munich and was transferred to my Lufthansa flight quickly, in 15 to 20 minutes, so I did not miss my flight. However, I had checked my overhead bag at the boarding gate in Tampa. That got to Tunis the next day. That is to be expected.

It's a short hop. My carryon was checked at the gate, I didn't have to drag it all over the airport. Excellent wheelchair assist.

WiFi didn’t exist , seats were super cramped, lights stayed on near my seat for a long time while others were dimmed, the food/trash/drink cart hit my shoulder at least a couple of times while moving, food options were down to just one option by the time it got to my row, the utensils were garbage (knife bent at a couple of places by the time I was done eating) the spoon was very flimsy plastic

Friendliest Flight Attendant I’ve seen since I flew on Southwest Airlines. The whole trip was outstanding…and arrived Early!

Seat bottom cushions are not good. I’m 165# & they hurt my butt. Plenty of legroom.

The wifi experience is awful. I had to try again and again, taking over 30 minutes, to connect to the wifi. I had to watch the same two ads over and over until I was finally successful. Once connected, it was anything but "high speed" and disconnected at least three times during the flight.

Fine. Nothing to write home about. The plane left on time, and arrived on time.

I was downgraded from first class to coach due to an airplane change. They pulled me out of line and I was the very last person to board the plane stuck in the middle seat with no overhead place to put my carry-.on. Very poor customer service.

Seat comfort was poor (no lumbar or lower back support).

The airplane seats were spacious and comfortable, and the flight attendants were friendly and attentive. The food was delicious like never before. The blankets and toiletries were thoughtfully provided. The captain's navigation was steady and reliable. In short, having flown with Starlux, I won't consider any other airline next time.

STOP MAKING THE SEATING SO CRAMPED. WE NEED A PASSENGER BILL OF RIGHTS!

The passenger in front of of me reclined their seat back all the way the entire flight. Their headrest was in my face the entire flight! I barely had room for the little plastic cup of water to fit on my tray table; can you make the seats and space between the rows any smaller??? You can’t even get up to use the restroom! Worst flight I’ve had in a very long time!

We had several flights and they were all on-time and flawless

My Frequent Flyer nber wasn't put on as I was told it was..... This resulted in a last group boarding and no priority tags on My bags.

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.

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

Everything you need to know for your flight to Caribbean Islands

Information on your arrival and departure airports