$103 Find Cheap Flights from Wisconsin to Caribbean

1 adult
1 adult, Economy

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

Travelers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

Save 22% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Free to useThere are no hidden charges or fees.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Useful Info

Good to know

Low seasonSeptember
Cheapest flight$103
Best time to beat the crowds with an average 15% drop in price.
Most popular time to fly with an average 26% increase in price.
Flight from Chicago O'Hare Airport to Montego Bay

FAQs for booking flights from Wisconsin to Caribbean

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

    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 Wisconsin to Caribbean.

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

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

    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 Wisconsin to Caribbean 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 Wisconsin to Caribbean?

    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 Wisconsin to Caribbean 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 Caribbean?

    There are 81 airports in Caribbean. The busiest airport is San Juan Airport (SJU), with 19% of all flights arriving there.

  • What is the cheapest day to fly to Caribbean?

    Based on KAYAK data, the cheapest day to fly to Caribbean is Tuesday where round-trip tickets can be as cheap as $389. On the other hand, the most expensive day to fly is Friday, where round-trip prices are $477 on average.

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

    The cheapest time of day to fly to Caribbean is generally at night, when round-trip flights cost $360 on average. Morning departures are around 13% more expensive than evening flights, on average. The most expensive time of day to fly to Caribbean is generally in the afternoon, which is peak travel time and where the average cost of a ticket is $458.

  • What is the cheapest flight to Caribbean?

    The cheapest ticket to Caribbean from Wisconsin found in the last 72 hours was to Montego Bay, at $540 round-trip. The most popular route is Milwaukee (MKE) to Punta Cana (PUJ) and the cheapest round-trip airline ticket found on this route in the last 72 hours was $604.

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

    The cheapest month for flights from Wisconsin to Caribbean is February, when tickets cost $634 (return) on average. On the other hand, the most expensive months are March and January, when the average cost of round-trip tickets is $855 and $794 respectively.

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

    To get a below average price on the flight from Wisconsin to Caribbean, you should book around 1 week before departure. For the absolute cheapest price, our data suggests you should book 23 weeks before departure.

  • How long is the flight to Caribbean?

    An average nonstop flight from Wisconsin to Caribbean takes 6h 18m, covering a distance of 2134 miles. The shortest route is Chicago O'Hare Intl Airport (ORD) to Nassau (NAS) with an average flight time of 3h 25m.

  • What are the most popular destinations in Caribbean?

    Based on KAYAK flight searches, the most popular destination is Punta Cana (18% of total searches to Caribbean). The next most popular destinations are Montego Bay (16%) and Saint Thomas Island (12%). Searches for flights to Oranjestad (12%), to Nassau (8%) and to Providenciales (5%) are also popular.

Everything you need to know for your flight to Caribbean

Cabin class types available on flights to Wisconsin

Cabin classes available on flights to Wisconsin. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.
First Class flights to Caribbean
Business Class flights to Caribbean
Prem Econ Class flights to Caribbean
Economy Class flights to Caribbeanfrom $540

Not what you’re looking for? Find thousands of other hotels, flights, car rentals and package deals with KAYAK.