$98 Find Cheap Flights from Illinois to Caribbean

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Good to know

Low seasonSeptember
Cheapest flight$98
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 Illinois to Caribbean

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

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Illinois 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 Illinois 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 Illinois 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 Illinois 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 Illinois to Caribbean up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

  • Which airlines fly most frequently to Caribbean?

    Illinois and Caribbean are connected by different airlines. The airlines that fly that route the most regularly are American Airlines (28 flights per week), United Airlines (27 flights per week), and Air Canada (15 flights per week).

  • 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.

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

    Prices will differ depending on the departure airport, but generally, the cheapest airport to fly to in Caribbean is San Juan Luis Munoz Marin Intl Airport (SJU), with an average flight price of $192.

  • What is the cheapest day to fly to Caribbean?

    Based on KAYAK data, the cheapest day to fly to Caribbean is Monday where round-trip tickets can be as cheap as $392. On the other hand, the most expensive day to fly is Sunday, where round-trip prices are $446 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 $306 on average. Morning departures are around 12% more expensive than evening flights, on average. The most expensive time of day to fly to Caribbean is generally in the morning, which is peak travel time and where the average cost of a ticket is $444.

  • What is the cheapest flight to Caribbean?

    The cheapest ticket to Caribbean from Illinois found in the last 72 hours was to Punta Cana, at $192 round-trip. The most popular route is Chicago Midway Airport (MDW) to San Juan Luis Munoz Marin Intl Airport (SJU) and the cheapest round-trip airline ticket found on this route in the last 72 hours was $208.

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

    The cheapest month for flights from Illinois to Caribbean is July, when tickets cost $555 (return) on average. On the other hand, the most expensive months are October and June, when the average cost of round-trip tickets is $938 and $925 respectively.

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

    To get a below average price on the flight from Illinois to Caribbean, you should book around 1 week before departure. For the absolute cheapest price, our data suggests you should book 7 weeks before departure.

  • How many cities have direct flights to Caribbean?

    From Illinois, there are direct flights to Caribbean from 1 city. This city is Chicago and there are 103 direct flights each week.

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

    There are around 15 direct flights from within Illinois to Caribbean every day. Most flights (88%) depart in the morning.

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

    Each week there are around 103 direct flights from within Illinois to Caribbean. The most common day for departures is Saturday, with 20% of flights taking off on this day.

  • How long is the flight to Caribbean?

    An average nonstop flight from Illinois to Caribbean takes 6h 13m, covering a distance of 2027 miles. The shortest route is Chicago O'Hare Intl Airport (ORD) to Nassau (NAS) with an average flight time of 3h 25m.

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

    Each week, there are 101 medium-haul flights (3-6 hour flight duration) and 2 short-haul flights (up to 3 hour flight duration) to Caribbean. There aren't any long-haul flights (6-12 hour flight duration).

  • What are the most popular destinations in Caribbean?

    Based on KAYAK flight searches, the most popular destination is Punta Cana (19% of total searches to Caribbean). The next most popular destinations are Montego Bay (16%) and Oranjestad (14%). Searches for flights to Saint Thomas Island (10%), to Nassau (7%) and to Providenciales (5%) are also popular.

Everything you need to know for your flight to Caribbean

Cabin class types available on flights to Illinois

Cabin classes available on flights to Illinois. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.
First Class flights to Caribbeanfrom $486
Business Class flights to Caribbeanfrom $608
Prem Econ Class flights to Caribbeanfrom $378
Economy Class flights to Caribbeanfrom $192

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