Cheap flights from Chicago to Caribbean Islands from $106

The month of January is, on average, the cheapest month to fly to Caribbean Islands from Chicago, with most prices found around $540. The month of February is another great option to travel to Caribbean Islands, with average flight prices from Chicago averaging around $549.

The cheapest day to depart from Chicago 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 $415. If your travel schedule is flexible, try to avoid departing on a Thursday because tickets tend to average around $502. 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 Chicago to Caribbean Islands in the evening for as low as $360. 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 $521. 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 Chicago - Caribbean Islands flight prices

You are more likely to see cheaper flights to Caribbean Islands from Chicago when booking weeks ahead of your departure date. In general, you can expect to find flights to Caribbean Islands for around $403 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Caribbean Islands from Chicago for as low as $349 on momondo.

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

United Airlines, Southwest, and Air Canada are the most popular carriers operating from Chicago to Caribbean Islands

United Airlines, American Airlines and Frontier are the top three most popular airlines that fly to Caribbean Islands from Chicago according to our data. United Airlines is the first choice among our users, with 37% 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.

The number of flights available between Chicago and Caribbean Islands is 2 per day as of September 2026. The most frequent departure time is 8:00AM, with 100% of daily flights leaving at noon.

14 flights are operational weekly from Chicago to Caribbean Islands as of September 2026. The most popular departure day for this route is Mon, with 29% of flights per week taking off on this day.