Cheap flights from Caribbean to Illinois from $99

The cheapest month to fly to Illinois from Caribbean is in February. Flight prices, which tend to average around $218, are often lower during this time because this is during the off-season. If you aren’t able to travel to Illinois during the month of February, then flying in May is also cheap. Prices for this month can be found on momondo for an average of $267.

The cheapest day to depart from Caribbean to Illinois is on a Friday when prices can be found for as low as $380. Flights from Caribbean to Illinois on a Sunday will generally be more expensive and average around $571. Keep in mind that these prices on both days could fluctuate depending on the season and the demand.

Our most recent data shows that the best time of day to fly to Illinois is in the evening. Flights from Caribbean to Illinois during this time can be as low as $267. Flights in the afternoon are often more expensive with an average ticket price of $488.

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

You are more likely to see cheaper flights to Illinois from Caribbean when booking weeks ahead of your departure date. In general, you can expect to find flights to Illinois for around $326 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Illinois from Caribbean for as low as $286 on momondo.

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

Southwest, Delta, and Spirit Airlines are the most popular carriers operating from Caribbean to Illinois

American Airlines, United Airlines and Spirit Airlines are the top three most popular airlines that fly to Illinois from Caribbean according to our data. American Airlines is the first choice among our users, with 34% of people opting to fly with this airline when traveling to Illinois. Keep in mind that there are 7 different airlines that fly to Illinois on a routine basis, so you have a few additional options to choose from.

The number of flights available between Caribbean and Illinois is 15 per day as of March 2026. The most frequent departure time is 4:00PM, with 60% of daily flights leaving in the afternoon.

As of March 2026, 109 flights take off from Caribbean and land in Illinois each week. The most common flight departure day for this route is Mon, with 20% of weekly flights taking off on this day.