Cheap flights from Illinois to Caribbean from $98

In general, September is the cheapest month to fly from Illinois to Caribbean. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around $370. If you don’t want to visit Caribbean in September, then you should wait until July to fly from Illinois, when ticket prices are also cheap, with an average price of $429.

The cheapest day to depart from Illinois to Caribbean is on a Monday when prices can be found for as low as $434. If your travel schedule is flexible, try to avoid departing on a Friday because tickets tend to average around $558. These prices are subject to change though, so be sure to set up a Price Alert for flights to Caribbean.

In the evening is the cheapest time of day to fly from Illinois to Caribbean when you can find flight prices for as low as $395. Flying to Caribbean in the evening is an ideal time because this is during off-peak travel hours. Flights in the morning are often more expensive with an average ticket price of $529.

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

You are more likely to see cheaper flights to Caribbean from Illinois when booking weeks ahead of your departure date. In general, you can expect to find flights to Caribbean for around $392 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Caribbean from Illinois for as low as $351 on momondo.

There are 4 cabin classes available to choose from on Illinois to Caribbean 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

American Airlines, United Airlines and Frontier are the top three most popular airlines that fly to Caribbean from Illinois according to our data. American Airlines is the first choice among our users, with 43% of people opting to fly with this airline when traveling to Caribbean. Keep in mind that there are 10 different airlines that fly to Caribbean on a routine basis, so you have a few additional options to choose from.

14 flights are operational daily from Illinois to Caribbean as of June 2026. The most popular departure time for this route is 8:00AM, with 66% of flights per day taking off at noon.

103 flights are operational weekly from Illinois to Caribbean as of June 2026. The most popular departure day for this route is Mon, with 16% of flights per week taking off on this day.