Cheap flights from Chicago to Caribbean Islands

The month of February is, on average, the cheapest month to fly to Caribbean Islands from Chicago, with most prices found around $575. The month of January is another great option to travel to Caribbean Islands, with average flight prices from Chicago averaging around $578.

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 $419. If your travel schedule is flexible, try to avoid departing on a Thursday because tickets tend to average around $506. 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 $367. 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 Punta Cana 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 $412 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 $359 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.