Cheap flights from Illinois to Caribbean Islands from $107

The month of October is, on average, the cheapest month to fly to Caribbean Islands from Illinois, with most prices found around $494. The month of August is another great option to travel to Caribbean Islands, with average flight prices from Illinois averaging around $526.

The cheapest day to depart from Illinois to Caribbean Islands is on a Monday. Travelers who choose to depart for Caribbean Islands on a Monday will often find tickets for as low as $435. If your travel schedule is flexible, try to avoid departing on a Friday because tickets tend to average around $536. 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 $382. 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 in the morning because they tend to be around $526. 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 $394 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 $356 on momondo.

There are 4 cabin classes available to choose from on Illinois to Caribbean Islands flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

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

American Airlines, United Airlines and Frontier 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 42% 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 July 2026, there are 15 flights per day flying from Illinois to Caribbean Islands. The most common time of day flights depart is 8:00AM, with 63% of flights taking off at noon.

As of July 2026, there are 105 flights per week flying from Illinois to Caribbean Islands. The most common day of the week flights depart is Fri, with 18% of flights taking off on this day.