$122 Find Cheap Flights from Illinois to Caribbean - 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.

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.

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.

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.

Illinois and Caribbean are connected by different airlines. The airlines that fly that route the most regularly are United Airlines (61 flights per week), American Airlines (34 flights per week), and Air Canada (28 flights per week).

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

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 $251.

Based on KAYAK data, the cheapest day to fly to Caribbean is Tuesday where round-trip tickets can be as cheap as $416. 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 is generally at night, when round-trip flights cost $366 on average. Morning departures are around 22% 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 $520.

The cheapest ticket to Caribbean from Illinois found in the last 5 days was to Punta Cana, at $238 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 $245.

The cheapest month for flights from Illinois to Caribbean is January, when tickets cost $187 (return) on average. On the other hand, the most expensive months are December and March, when the average cost of round-trip tickets is $295 and $293 respectively.

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 9 weeks before departure.

From Illinois, there are direct flights to Caribbean from 1 city. This city is Chicago and there are 165 direct flights each week.

There are around 24 direct flights from within Illinois to Caribbean every day. Most flights (74%) depart in the morning.

Each week there are around 165 direct flights from within Illinois to Caribbean. The most common day for departures is Saturday, with 20% of flights taking off on this day.

An average nonstop flight from Illinois to Caribbean takes 6h 30m, covering a distance of 2035 miles. The shortest route is Chicago O'Hare Intl Airport (ORD) to Nassau (NAS) with an average flight time of 3h 25m.

Each week, there are 164 medium-haul flights (3-6 hour flight duration) and 1 short-haul flights (up to 3 hour flight duration) to Caribbean. There aren't any long-haul flights (6-12 hour flight duration).

Based on KAYAK flight searches, the most popular destination is Punta Cana (48% of total searches to Caribbean). The next most popular destinations are Montego Bay (18%) and Santo Domingo (14%). Searches for flights to Saint Thomas Island (8%), to George Town (6%) and to Christiansted (2%) are also popular.