Cheap flights from Chicago to Caribbean from $106

In general, August is the cheapest month to fly from Chicago to Caribbean. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around $429. If you don’t want to visit Caribbean in August, then you should wait until September to fly from Chicago, when ticket prices are also cheap, with an average price of $461.

The cheapest day to depart from Chicago to Caribbean is on a Tuesday when prices can be found 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.

In the evening is the cheapest time of day to fly from Chicago to Caribbean when you can find flight prices for as low as $360. 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 $521.

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

You are more likely to see cheaper flights to Caribbean from Chicago when booking weeks ahead of your departure date. In general, you can expect to find flights to Caribbean 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 from Chicago for as low as $349 on momondo.

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

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

United Airlines, American Airlines and Frontier are the top three most popular airlines that fly to Caribbean 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. Keep in mind that there are 12 different airlines that fly to Caribbean on a routine basis, so you have a few additional options to choose from.

The number of flights available between Chicago and Caribbean is 3 per day as of September 2026. The most frequent departure time is 8:00AM, with 100% of daily flights leaving at noon.

The number of flights available between Chicago and Caribbean is 22 per week as of September 2026. The most frequent departure day is Fri, with 18% of weekly flights leaving on this day.