$91 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 4/9. 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$411
Santo Domingo
Santo Domingo1 stop$539
Montego Bay
Montego Bay1 stop$393
Oranjestad
Oranjestad2 stops$539
Nassau
Nassau1 stop$404
Kingston
Kingston2 stops$823
Simpson Bay
Simpson Bay2 stops$479
Providenciales
Providenciales2 stops$368
George Town
George Town1 stop$409
Willemstad
Willemstad1 stop$545
St. John's
St. John's2 stops$625
Puerto Plata
Puerto Plata2 stops$683
Aguadilla
Aguadilla1 stop$203
Punta Cana
Punta Cana1 stop$411
Santo Domingo
Santo Domingo1 stop$539
Montego Bay
Montego Bay1 stop$393
Oranjestad
Oranjestad2 stops$539
Nassau
Nassau1 stop$404
Kingston
Kingston2 stops$823
Simpson Bay
Simpson Bay2 stops$479
Providenciales
Providenciales2 stops$368
George Town
George Town1 stop$409
Willemstad
Willemstad1 stop$545
St. John's
St. John's2 stops$625
Puerto Plata
Puerto Plata2 stops$683
Aguadilla
Aguadilla1 stop$203

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

Sun, Feb 22 - Wed, Feb 25
Frontier Logo
6:37 pm - 9:54 am
MKE
-
SJU
13h 17m
1 stop
Frontier Logo
5:25 pm - 6:42 pm
SJU
-
MKE
27h 17m
1 stop
$236Frontier
Sat, Feb 21 - Fri, Feb 27
Frontier Logo
7:47 pm - 2:53 am
MKE
-
SJU
29h 06m
1 stop
Frontier Logo
3:53 am - 6:52 pm
SJU
-
MKE
16h 59m
1 stop
$239Frontier
Mon, Apr 20 - Wed, Apr 29
Frontier Logo
12:03 pm - 2:01 am
MKE
-
SJU
12h 58m
1 stop
Frontier Logo
3:08 am - 11:08 am
SJU
-
MKE
9h 00m
1 stop
$240Frontier
Sun, Feb 22 - Wed, Feb 25
American Airlines Logo
6:22 am - 11:31 pm
MKE
-
SJU
15h 09m
1 stop
American Airlines Logo
1:58 pm - 11:24 pm
SJU
-
MKE
11h 26m
2 stops
$256American Airlines
Sat, Feb 28 - Fri, Mar 6
American Airlines Logo
3:11 pm - 10:14 am
MKE
-
PLS
18h 03m
2 stops
American Airlines Logo
3:30 pm - 7:47 am
PLS
-
MKE
17h 17m
2 stops
$368American Airlines
Tue, Mar 10 - Tue, Mar 17
Delta Logo
5:45 am - 2:25 pm
MKE
-
PLS
7h 40m
1 stop
Delta Logo
3:50 pm - 11:58 pm
PLS
-
MKE
9h 08m
1 stop
$374Delta
Tue, Feb 17 - Tue, Feb 24
Delta Logo
7:05 am - 5:02 pm
MKE
-
NAS
8h 57m
1 stop
Delta Logo
2:59 pm - 11:47 pm
NAS
-
MKE
9h 48m
1 stop
$404Delta
Wed, Feb 25 - Mon, Mar 2
United Airlines Logo
8:30 am - 1:45 pm
MKE
-
GCM
28h 15m
1 stop
United Airlines Logo
2:50 pm - 8:55 pm
GCM
-
MKE
7h 05m
1 stop
$425United Airlines
Mon, Mar 2 - Thu, Mar 12
United Airlines Logo
6:00 am - 1:45 pm
MKE
-
GCM
6h 45m
1 stop
United Airlines Logo
1:50 pm - 9:50 pm
GCM
-
MKE
8h 00m
1 stop
$435United Airlines
Wed, May 13 - Thu, May 21
Southwest Logo
5:40 am - 6:30 pm
MKE
-
NAS
11h 50m
1 stop
Southwest Logo
8:45 am - 4:15 pm
NAS
-
MKE
8h 30m
1 stop
$478Southwest
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 $547.

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 $415, 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 $315 (return) on average. On the other hand, the most expensive months are December and November, when the average cost of round-trip tickets is $657 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 seasonSeptember
Cheapest flight$91
Best time to beat the crowds with an average 10% drop in price.
Most popular time to fly with an average 3% 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 4269 reviews
7.0Food
8.0Comfort
7.5Entertainment
8.6Crew
8.1Boarding
Airline reviews

Great vacation. Can't wait till next year for another one.

10.0 ExcellentJohn, Jan 2026
SAT - PHX
Read more Southwest reviews

Great vacation. Can't wait till next year for another one.

Great flight but super high price. Glad it was a business trip and not personal

On time. Friendly staff. Took to long to pre bord all the specialty groups. Cramped small plane

The seats were comfortable, and the boarding process was pretty smooth.

3 hour delay. Had to change plans and was still delayed.

The staff was very friendly, professional, and courteous. The overall flight was a great experience.

The crew canceled the complementary snack and drink in anticipation of turbulence that never materialized. I was counting on the drink (water) to take the the doses of medication - prescribed for my heart condition - that were due during the flight. Since no snack or meal was served on this flight, I cannot rate the food quality. Otherwise, this flight was excellent.

Departure was delayed more than 1/2 hour while we waited for luggage (only) transfer from another flight/plane. Once approved for takeoff, the flight was excellent.

We got exit row seats both flights. Everything was running on time

The flight crew was extremely rude and especially not helpful when our flight was delayed.

was sitting in the jet bridge for 10 minutes in -20 degree weather waiting for my bag

Outdated equipment in disrepair, wifi inoperable. Broken seats, taped air vents, generally poor condition, the 717 showed its age and lack of upkeep.

My flight out of Baton Rouge to Atlanta was delayed by a half hour. This got us into Atlanta airport 30 minutes late. I ran through the airport to get to my connecting flight. As I approached the boarding gate, I saw the boarding door was still open and a passenger was being checked in. But when I got to the gate, the boarding agent told me they had already given away my seat and there were no empty seats on that flight. So I had to take a later flight. That has never happened to me before. Very frustrating.

Connection through Atlanta was difficult. Mechanical issue on plane caused a two hour delay. New gate was a mile away.

No WiFi. Comfort plus should have alcohol provided, crew only offered water or tea. Who the heck wants tea?

The flight was delayed and oversold. I volunteered to give up my seat for compensation. Thinking I could get a good night's sleep instead of arriving home at 2 am. It took over an hour to get the new reservation confirmed, three different gate attendants, and two red coats. It took even longer to confirm the overnight hotel, and when I arrived, the line was 45 minutes long, with two people checking in, and at least 15 people slowly, very slowly—no food except frozen convenience food, no coupon for food from airlines. Slept, headed back to the airport, and that flight had an equipment change and a gate change just as they were about to board. It took an additional hour to board as they cleaned the plane from storage.

There was no wifi available on this flight. And there were no screens, no onboard entertainment, no entertainment options at all. It was like travelling in the 1990s again, except without even a main screen for options. Seats, as usual, were tight and uncomfortable.

Good seat comfort ORF to ATL. Bad seat ATL to SEA (terrible lumbar support, hard, ouch)..

Because I was moved to an exit row, the snacks in economy comfort, the selection of snacks was better.

I upgraded to first. Quick and easy boarding. Comfortable seat with power and a nice IPA.

Flight arrived 30 min early and bag was waiting at the baggage pickup. United Club HNL was one of the nicest in the system

Unfortunately weather delayed our flight waiting for our plane to arrive and due to a little snow time was needed to deice the plane so departure was very delayed and I missed the connecting flight

Very good. Because of the delays with my previous flight, I missed my connection, but I was able to book another flight through the United app easily.

I wish there were outlets to charge my iPhone. The crew was great; we had a female pilot who was great with explaining what was happening and delays,

The flight crew where really good. Better then the crew from BNE to SFO

Food should be changed in menu Many muslims travels in this airlime they need to add one Halal meal

Delayed, toilets did not flush, pilot parked to far away from Gate

Was happy we finally got upgraded in 1st class. The seat getting old. The cushiness need some improvement.

Yet another flight in which beverage and snack service was skipped. Other that that, firmly mediocre. Landed early, to gate late due to congestion at the gates. Airline's fault or airports fault: unknown.

Ineffective communication with United resulted in lost baggage. Their Baggage Tracing counter at MUC was shut down from 11:00-14:15 on my arrival. Undertrained, underinformed staff had me Running all over MUC to find someone to help me to no avail. Staff was rude, unhelpful, and unable to effectively use the systems they did have operational. They refused to contact United in any way or provide any accommodation or other resources while I waited for my luggage. This has destroyed my downstream itinerary. If they had even the slightest visibility I may have been able to reschedule/plan, but again, their staff provided nothing, and did nothing more than their website, which doesn’t even work on a standard phone browser. Miserable failure at all levels that weren’t associated with the operation of the aircraft.

one crew said "he" didn't serve double alcohol drinks for travelers in exit rows. crew on prior flight did. Is this a AA rule, and the prior crew was being nice? Also, I think we deserve more than a 25% refund for losing first class seats when rescheduling a flight due to weather

It was a little concerning to hear the ground crew arguing with the flight crew over baggage space. Instead of taking them and checking them, they started checking for space in the first class cabin moving items around like the flight crew didn't know what they were doing. I was embarrassed for them.

2 hour delay due to equipment failure. No updates via the app and airport screens (which continued to show a departure time in the past). AA eventually switched planes and the new plane was not catered or cleaned correctly.

I booked an aisle seat and was given a middle. At 6'4" 230lbs, it is not ideal to fly in the middle row for myself and passengers.

Trip delayed for 2 hours because of rain. We boarded and have to get down the flight and reboard again.

The aircraft had several problems - from excess fuel to non operational ac. Two hours of delay in Chicago could have been avoided with proper planning and aircraft maintenance.

This flight captain and crew were amazing, started ahead of time of departure and reached 30 mins before arrival time. Amazing!

Long delays, lack of information about the status of the flight. The flight was delayed 4 times.

Could we please end the loud announcements about credit card offers on your flights? We are trying to sleep, work, watch videos, etc. and if we need a credit card, we will ask for one. Flying is already not what it used to be.

I would like the crew to talk LESS over the PA and specifically about credit card offers. I am trying to work, sleep, watch a movie and the PA was booming about a credit card offer. Could we go back to the days when the customer was more important than selling a credit card?

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

I did not take this flight because the reservation made by Kayak was wrong! Kayak owes me a trip from Minneapolis to Duluth.

When I got to the airport in Seattle, they told me the flight "did not exist". Kayak reserved me a seat on a flight that did not exist. This is inexcusable. I was able to change my reservation to a flight that actually did exist, but the flight was later and then I didn't make it in time for the next leg of my trip from Minneapolis to Duluth. Kayak owes me a trip from Minneapolis to Duluth, and a big apology for messing up my reservation.

The plane was freezing cold. Asked for a blanket and there were none. Was told twice that the pilots would warm the plane and it never happened Worst experience flying ever

Everything you need to know for your flight to Caribbean Islands

Information on your arrival and departure airports