$119 Find Cheap Flights from Caribbean to Wisconsin - 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 Caribbean to Wisconsin departing on 10/27. 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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Low season

January

Cheapest flight

$119
Best time to beat the crowds but there is an average 11% increase in price.
Most popular time to fly with an average 15% increase in price.
Flight from San Juan to Milwaukee

FAQs for booking flights from Caribbean to Wisconsin

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

    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 Caribbean to Wisconsin.

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

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

    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 Caribbean to Wisconsin 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 Caribbean to Wisconsin?

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

  • How many airports are there in Wisconsin?

    There are 8 airports in Wisconsin. The busiest airport is Milwaukee-Mitchell Airport (MKE), with 44% of all flights arriving there.

  • What is the cheapest month to fly from Caribbean to Wisconsin?

    The cheapest month for flights from Caribbean to Wisconsin is November, when tickets cost $200 (return) on average. On the other hand, the most expensive months are January and July, when the average cost of round-trip tickets is $289 and $286 respectively.

  • How far in advance should I book a flight from Caribbean to Wisconsin?

    To get a below average price on the flight from Caribbean to Wisconsin, you should book around 4 weeks before departure, which saves you about 32% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 25 weeks before departure.

  • How long is the flight to Wisconsin?

    An average nonstop flight from Caribbean to Wisconsin takes 12h 53m, covering a distance of 2079 miles. The shortest route is Nassau (NAS) to Chicago O'Hare Intl Airport (ORD) with an average flight time of 4h 00m.

  • What are the most popular destinations in Wisconsin?

    Based on KAYAK flight searches, the most popular destination is Chicago (84% of total searches to Wisconsin). The next most popular destinations are Minneapolis (10%) and Milwaukee (4%). Searches for flights to Madison (1%), to Appleton (0%) and to La Crosse (0%) are also popular.

Reviews of the top 4 airlines serving from Caribbean to Wisconsin

 
Need help choosing which airline to fly with from Caribbean to Wisconsin? 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 4221 reviews
8.6Crew
8.0Comfort
7.5Entertainment
8.1Boarding
7.0Food
Airline reviews

Fairly good - the seats seemed more comfortable on this flight. The staff out of Detroit were quite friendly. But they directed us to the wrong carousel for luggage. :(

8.0 ExcellentDavid, Aug 2026
Read more Southwest reviews

Fairly good - the seats seemed more comfortable on this flight. The staff out of Detroit were quite friendly. But they directed us to the wrong carousel for luggage. :(

Just crazy with times being pushed and pushed and pushed and gate crew at Philly super rude and unprofessional with many under stress with delays.

I liked the new boarding process. I thought the buyup options (legroom, early boarding) to be easy to request and reasonably priced. All the Southwest team from gate to in-flight were so nice.

Flight time kept changing and so did the gate. It was very frustrating

Exceptional. The gate crew responded quickly and got me onto this earlier flight as the final passenger, saving me more than four hours of wait time for my reserved flight.

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.

Slow boarding, limited food and drink portions. Bad delays and turbulence

The entire travel day was a disaster from beginning to end. Woke up at two in the morning to make it to San Juan airport in time for a 5:30 am flight to Milwaukee which connected in Baltimore. Massive delays lead to me missing original connection out of Baltimore. Sixteen hours of delays/rebooking/layover time later, arrived in Milwaukee to find that only one of two checked bags made it there (despite the fact that Southwest brought another 737 jet to San Juan to fly us out to our original Baltimore connection—-not squeezed into another booked flight). The flight from Baltimore to Milwaukee was barely half full, so there was no logical reason to ship my bags out of Baltimore on a different flight to Chicago to then ship to Milwaukee. Southwest decided that my bags should not have been on the same connecting flight I WAS ON to Milwaukee, and then proceeded to accidentally leave my larger bag with the important items in Chicago. Terrible logic and support all around. Extremely angered and disappointed with SW. What a clownish operation your company has become!

Pushing back flight and ultimately cancelling it after multiple changes and hours of delays. Comm were terrible as to what was going on and what options were available.

Even though we arrived early and checked in, for some unexplained reason, our bags were removed from the plane and put on the next flight. It took over 12 hours after arriving to get our bags.

WiFi was not working. Flight was delayed in Paris as luggage needed to be removed from the plane that didn’t match a passenger on board. Upon arrival in Detroit the plane couldn’t get to the gate as the pilot turned onto a runway with construction in progress . We waited to be towed back onto the runway. We were almost an hour late causing many passengers to miss their connecting flights.

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

Love delta smaller commuter plane so no entertainment and paid wifi on MKE-LGA leg was extremely unreliable and slow

My flight was cancelled with no explanation after I had already cleared security. I was given 4 options to rebook, only one being non-stop like I had paid for. I grabbed it. It was 4 plus hours later and then took off even later. Biggest complaint is that I booked early and had an aisle seat. They gave me a "window" seat in front of the exit row, so the seat did not decline. I weigh all of 103 #s and it was tight for me! For what I paid, I feel I was kind of ripped off. I think they should have given me the empty comfort seat for the inconvenience. There was no apology nor any explanation as to why the flight was cancelled. My guess is it benefitted Delta in some way.

The dear was very limited in space. I could put my water bottle in seat basket. Also, there was no inflight entertainment in the delta app?

Wifi did not work and they only served water, coffee, or tea.

Checking in at the airport the agent only booked the first keg of my trip and had my checked luggage going to the airport with a layover! Never was issued a boarding pass for the second leg or received sticker fir my checked bag. All was well in the end! Delta agents helped to resolve the situation!!!

Had assistance at airport getting from arrivals gate to departure gate; I couldn't have managed without that extra help. Thank you Delta.

Flight was great. Almost miss my connecting flight due to late departure from Haneda. Had to run all through airport in Chicago to make the flight. Experience was great for 1st time flyers using ANA Airlines.

the seat has a problem. the back had a hole.

The back to back mechanical delays from Denver to San Diego and then on my return flight from Denver to Great Falls it added extra time both ways

Really old place. Not as clean as it should be, tray tables needed better cleaning. The items, trays and some other items need to b6 engineered. Anything task you or crew may do is incredibly load, seriously engineer for quiet smooth, easy. Just opening and closing the tray table is actually dangerous and can easily injure a finger. I'm sure it happens as it happened to me! First time I used United and likely will be the last!

The website check in was poor. Baggage fees were in US dollars but registered in Canadian dollars. The site would not accept my credit card. Scanning the passport was the worst. Someone from United needs to try the process. I’m not a novice with tech and I have to say this was a bad experience. Everything else was great.

Like the fact that the boarding was expedited. But the delay and chaos around the onboarding was not appreciated.

Deplaning was delayed because of Jetbridge equipment issues in MKE, causing an issue on an otherwise great flight.

Delays took 2hours and thirty minutes making me miss my connecting flight and make me sit in the Chicago airport for 9 hours

No real agent onsite helping you for missing luggage there. Not like the other airline next to UA desk, they have staff attending in their desk assisting answer/helping luggage issue, even after midnight.

The wi-fi was awful. I paid $8 each way and got little , except frustration. .

The flight from Milwaukee to Dallas was great the staff absolutely amazing. After that EVERYTHING WENT DOWN HILL!!! ABSOLUTELY HORRIBLE!!! WILL NOT FLY THIS AIRLINE AGAIN

not sure why you ask about food, I n3ver get food on flights except maybe cookies or pretzels. wifi was slow and in and out most of the flight not good.

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

Never ontime and always delays. Long waits for customer service and often app doesn’t work

We were upgraded to First Class and it was a great flight

it was fine, decent flight... dont get food besides cookies or pretzels so not sure why you ask about food. same for entertainment..

this plane was really old, had exit row seats and tray was in arm of seat so super uncomfortable to use. another seat they could t even use the tray it was broke. seat i. front of me had duct tape on it cause seat was ripped open... this plane should either be updated or retired.

We loved the steward on the plane. He made the night enjoyable

American airlines suck they delay the flights all the time made me sleep in an airport because my flight was delayed and I miss my connecting flight

Very poor delay in dfw was really bad n long

Everything you need to know for your flight to Wisconsin

Cabin class types available on flights to Caribbean

Cabin classes available on flights to Caribbean. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.