Cheap flights from Chicago to Caribbean from $88

In general, September 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 $392. If you don’t want to visit Caribbean in September, then you should wait until April to fly from Chicago, when ticket prices are also cheap, with an average price of $471.

The cheapest day to depart from Chicago to Caribbean is on a Tuesday when prices can be found for as low as $381. If your travel schedule is flexible, try to avoid departing on a Friday because tickets tend to average around $463. 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 $376. Flying to Caribbean in the evening is an ideal time because this is during off-peak travel hours. Flights at noon are often more expensive with an average ticket price of $486.

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 $385 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 $347 on momondo.

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

American Airlines, United Airlines and Spirit Airlines are the top three most popular airlines that fly to Caribbean from Chicago according to our data. American Airlines is the first choice among our users, with 33% 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 13 per day as of May 2026. The most frequent departure time is 8:00AM, with 76% of daily flights leaving at noon.

The number of flights available between Chicago and Caribbean is 95 per week as of May 2026. The most frequent departure day is Sat, with 21% of weekly flights leaving on this day.