$92 Find Cheap Flights from Caribbean Islands to Wisconsin

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Good to know

Low seasonMarch
Cheapest flight$92
Best time to beat the crowds with an average 14% drop in price.
Most popular time to fly with an average 21% increase in price.
Flight from San Juan to Minneapolis

FAQs for booking flights from Caribbean Islands to Wisconsin

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

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

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

  • Which is the cheapest airport to fly into in Wisconsin?

    Prices will differ depending on the departure airport, but generally, the cheapest airport to fly to in Wisconsin is Milwaukee-Mitchell Airport (MKE), with an average flight price of $282.

  • What is the cheapest day to fly to Wisconsin?

    Based on KAYAK data, the cheapest day to fly to Wisconsin is Thursday where round-trip tickets can be as cheap as $331. On the other hand, the most expensive day to fly is Sunday, where round-trip prices are $624 on average.

  • What is the cheapest time of day to fly to Wisconsin?

    The cheapest time of day to fly to Wisconsin is generally at night, when round-trip flights cost $404 on average. Morning departures are around 2% cheaper than evening flights, on average. The most expensive time of day to fly to Wisconsin is generally in the afternoon, which is peak travel time and where the average cost of a ticket is $429.

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

    The cheapest month for flights from Caribbean Islands to Wisconsin is February, when tickets cost $297 (return) on average. On the other hand, the most expensive months are July and August, when the average cost of round-trip tickets is $495 and $488 respectively.

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

    To get a below average price on the flight from Caribbean Islands to Wisconsin, you should book around 3 weeks before departure, which saves you about 11% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 18 weeks before departure.

  • How many cities have direct flights to Wisconsin?

    From Caribbean Islands, there are direct flights to Wisconsin from 1 city. This city is Punta Cana and there are 2 direct flights each week.

  • How many direct flights to Wisconsin are there each day?

    There are around 1 direct flights from within Caribbean Islands to Wisconsin every day. All flights depart in the afternoon.

  • How many direct flights to Wisconsin are there each week?

    Each week there are around 2 direct flights from within Caribbean Islands to Wisconsin. The most common day for departures is Friday, with 50% of flights taking off on this day.

  • How long is the flight to Wisconsin?

    An average nonstop flight from Caribbean Islands to Wisconsin takes 13h 19m, covering a distance of 2065 miles. The shortest route is Nassau (NAS) to Chicago O'Hare Intl Airport (ORD) with an average flight time of 3h 56m.

  • How many long-haul flights are there to Wisconsin each week?

    There are not any long-haul (6-12 hour flight duration) or short-haul (up to 3 hour flight duration) flights to Wisconsin. Instead, there are 2 medium-haul flights (3-6 hour flight duration), with the most arriving from Punta Cana.

  • What are the most popular destinations in Wisconsin?

    Based on KAYAK flight searches, the most popular destination is Chicago (90% of total searches to Wisconsin). The next most popular destinations are Minneapolis (7%) and Milwaukee (2%). Searches for flights to Madison (0%), to Appleton (0%) and to Eau Claire (0%) are also popular.

Reviews of the top 3 airlines serving from Caribbean Islands to Wisconsin

 
Need help choosing which airline to fly with from Caribbean Islands 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.
7.9
DeltaOverall score based on 8010 reviews
7.9Comfort
7.9Entertainment
8.5Crew
8.1Boarding
7.3Food
Airline reviews

I noticed that the planes seem to be outdated. There was no entertainment per se. Also, the waiting area did not have any working electrical outlets

10.0 ExcellentMargaret, Dec 2025
BOS - PIT
Read more Delta reviews

I noticed that the planes seem to be outdated. There was no entertainment per se. Also, the waiting area did not have any working electrical outlets

Original flight was cancelled and when i was rebooked by the airline, they couldn't seat me in the same type of seat as I had originally booked (went from window/aisle to middle/middle and one was a bulkhead seat, and other wasn't in the same class)

Lady Pilot was perfect in every way wheels up to wheels down communication, professionalism, excellent on time departure and on time arrival, excellent communication! Fantastic job with Superb attitude!!

The food is terrible. The staff is wonderful. Comfort is good.

For some reason, I couldn't choose my seat. The airline gave me a seat when I got there. Not happy about that. Otherwise, everything else was great!

Left on time, a bit delayed due to headwinds most of the trip.

I fly Delta all the time, have Platinum Medallion status. But this route seems to have major problems with delays and seems to never leave on time! Have only taken it twice in the last two weeks, and each time it had delays of more than 1 hour... very disappointed!!!!

Good seats in Main cabin, excellent service and excellent landing

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.

Very smooth, on-time, and pleasantly uneventful flight. The team at the gate and on board were professional and genuinely courteous. The pilot kept us well updated throughout, and both takeoff and landing were steady and enjoyable without any drama. Just a good, solid flight. Thank you! 💗

The flight was on time. I generally don’t drink or eat on short flights and the seats were good and the flight attendants were friendly. That’s all I expect

Movie selection is good. Crew did not understand mileage program and were no help. Sick later. Food?

Staff on board was excellent. Positive upbeat helpful- like it used to be.

It was nice to have gotten up upgraded to first class with a meal on a three hour flight

For an expensive flight to another country, United has a lot of nerve serving pretzels and no meals (unless, of course, you want to buy something to eat). Unacceptable.

The food is terrible. The same pasta or chicken with bad taste and presentation

United have really come back. Airport and boarding process is clear and good, app and information also very good

The Sears in the 800s are not too good perfect Airbus why cant the new 737 fix that

Flight was delayed 8 times. We were sitting at the airport for 14 hours. We got 2 hours of sleep (if that) on what was not meant to be a red-eye.

It was probably one of the worst flights I’ve been on. The restrooms were never cleaned or stocked. The food was very subpar, and i usually enjoy airline food, so I was disappointed. It was just all around a bad experience. The only saving grace was the flight attendants.

Gate was overcrowded. Gate agents performed very well. Flight crew was top notch! Efficient & professional & courteous. Both meals not thermalized well. Dinner main dish was actually cold in the center. Almost inedible. Breakfast sandwich was lukewarm.

The boarding was as always, the crew tried their best but not enough. The food was a disaster I had dietary restrictions that were half met because the company did not loaded the food for the flight. The entertainment screen was fine but content was not and also they removed the free messaging option from the flight and they charged 30 dollars for that crappy bandwidth. This flight is not worth the cost and the company is going down on quality.

Awful. They won’t help me with anything. I booked on American but they abdicated to Iberia. The ticket was overpriced. Everything negative

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

I got sick nothing contagious but distressing and the care I received by Kayla? Keighly the flight attendant will be memorable for ever. Thank You

I got sick nothing contagious but distressing enough and the care I received on the flight was astounding.

Waaay too small plane. They also need to up the size of the overhead bins. I would love to keep me 3k with of camera equipment in my hard case baggahe instead of it being thrown into the belly of the plane

Attendants were pleasant and the flight was smooth and relaxed.

A little late at the start but all worked out well.

It was fine. No drinks nor snacks offered though. I thought that was unusual.

Everything you need to know for your flight to Wisconsin

Cabin class types available on flights to Caribbean Islands

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