Cheap flights from Illinois to Caribbean Islands from $88

The month of October is, on average, the cheapest month to fly to Caribbean Islands from Illinois, with most prices found around $503. The month of August is another great option to travel to Caribbean Islands, with average flight prices from Illinois averaging around $552.

The cheapest day to depart from Illinois to Caribbean Islands is on a Tuesday. Travelers who choose to depart for Caribbean Islands on a Tuesday will often find tickets for as low as $382. If your travel schedule is flexible, try to avoid departing on a Friday because tickets tend to average around $465. These prices are subject to change though, so be sure to set up a Price Alert for flights to Caribbean Islands.

According to our data, the cheapest time of day to fly to Caribbean Islands is in the evening. momondo users have found flights departing from Illinois to Caribbean Islands in the evening for as low as $374. Keep in mind that these prices may fluctuate based on what airline you choose and the time of year you plan to travel. Try not to purchase tickets at noon because they tend to be around $484. Of course, these prices can vary depending on the time of year and what airport you fly to.

Fly from Chicago O'Hare Intl to San Juan Luis Munoz Marin Intl for the best Illinois - Caribbean Islands flight prices

You are more likely to see cheaper flights to Caribbean Islands from Illinois when booking weeks ahead of your departure date. In general, you can expect to find flights to Caribbean Islands for around $388 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Caribbean Islands from Illinois for as low as $349 on momondo.

JetBlue, Delta, and Southwest are the most popular carriers operating from Illinois to Caribbean Islands

American Airlines, United Airlines and Spirit Airlines are the top three most popular airlines that fly to Caribbean Islands from Illinois according to our data. American Airlines is the first choice among our users, with 34% of people opting to fly with this airline when traveling to Caribbean Islands. Keep in mind that there are 12 different airlines that fly to Caribbean Islands on a routine basis, so you have a few additional options to choose from.

As of May 2026, there are 12 flights per day flying from Illinois to Caribbean Islands. The most common time of day flights depart is 8:00AM, with 76% of flights taking off at noon.

As of May 2026, there are 89 flights per week flying from Illinois to Caribbean Islands. The most common day of the week flights depart is Sat, with 19% of flights taking off on this day.