Find cheap flights from Illinois to Caribbean Islands - Compare and Save

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 Islands.

KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Illinois to Caribbean Islands is likely to change within 7 days, so travelers know whether to wait or book now.

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 Islands with an airline and back with another airline.

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

Illinois and Caribbean Islands are connected by different airlines. The airlines that fly that route the most regularly are American Airlines (14 flights per week), United Airlines (9 flights per week), and Air Canada (7 flights per week).

There are 21 airports in Caribbean Islands. The busiest airport is San Juan Airport (SJU), with 24% of all flights arriving there.

Prices will differ depending on the departure airport, but generally, the cheapest airport to fly to in Caribbean Islands is San Juan Luis Munoz Marin Intl Airport (SJU), with an average flight price of $251.

Based on KAYAK data, the cheapest day to fly to Caribbean Islands is Tuesday where round-trip tickets can be as cheap as $417. On the other hand, the most expensive day to fly is Thursday, where round-trip prices are $504 on average.

The cheapest time of day to fly to Caribbean Islands is generally at night, when round-trip flights cost $362 on average. Morning departures are around 22% more expensive than evening flights, on average. The most expensive time of day to fly to Caribbean Islands is generally in the morning, which is peak travel time and where the average cost of a ticket is $524.

The cheapest ticket to Caribbean Islands from Illinois found in the last 5 days was to San Juan Luis Munoz Marin Intl Airport, at $218 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 5 days was $218.

The cheapest month for flights from Illinois to Caribbean Islands is January, when tickets cost $237 (return) on average. On the other hand, the most expensive months are December and March, when the average cost of round-trip tickets is $345 and $324 respectively.

To get a below average price on the flight from Illinois to Caribbean Islands, you should book around 1 week before departure. For the absolute cheapest price, our data suggests you should book 9 weeks before departure.

From Illinois, there are direct flights to Caribbean Islands from 1 city. This city is Chicago and there are 47 direct flights each week.

There are around 7 direct flights from within Illinois to Caribbean Islands every day. Most flights (98%) depart in the morning.

Each week there are around 47 direct flights from within Illinois to Caribbean Islands. The most common day for departures is Saturday, with 17% of flights taking off on this day.

An average nonstop flight from Illinois to Caribbean Islands takes 6h 05m, covering a distance of 2016 miles. The shortest route is Chicago O'Hare Intl Airport (ORD) to Nassau (NAS) with an average flight time of 3h 25m.

There are not any long-haul (6-12 hour flight duration) or short-haul (up to 3 hour flight duration) flights to Caribbean Islands. Instead, there are 47 medium-haul flights (3-6 hour flight duration), with the most arriving from Chicago.

Based on KAYAK flight searches, the most popular destination is Punta Cana (52% of total searches to Caribbean Islands). The next most popular destinations are Santo Domingo (17%) and Montego Bay (15%). Searches for flights to Saint Thomas Island (7%), to George Town (4%) and to Christiansted (1%) are also popular.