Cheap flights from Caribbean Islands to Chicago from $118

The month of February is, on average, the cheapest month to fly to Chicago from Caribbean Islands, with most prices found around $189. If you’re not able to fly to Chicago in February, then September is your next best option. Flight prices from Caribbean Islands to Chicago during September average around $272.

The cheapest day to depart on your flight to Chicago is on a Friday when prices can be found for as low as $385. This is often the case because there is less demand to fly during this day of the week. When flying out on a Sunday, the most expensive travel day of the week, you can expect to see flight prices from Caribbean Islands to Chicago for around $570.

Our most recent data shows that the best time of day to fly to Chicago is in the evening. Flights from Caribbean Islands to Chicago during this time can be as low as $287. In contrast, the most expensive time of day to depart to Chicago is in the afternoon when prices are around $488.

Fly from San Juan Luis Munoz Marin Intl to Chicago Midway for the best Caribbean Islands - Chicago flight prices

You are more likely to see cheaper flights to Chicago from Caribbean Islands when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around $329 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from Caribbean Islands for as low as $278 on momondo.

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

Frontier, Spirit Airlines, and Delta are the most popular carriers operating from Caribbean Islands to Chicago

American Airlines, United Airlines and Spirit Airlines are the top three most popular airlines that fly to Chicago from Caribbean Islands 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 Chicago. Keep in mind that there are 8 different airlines that fly to Chicago on a routine basis, so you have a few additional options to choose from.

As of April 2026, there are 16 flights per day flying from Caribbean Islands to Chicago. The most common time of day flights depart is 3:00PM, with 66% of flights taking off in the afternoon.

As of April 2026, 117 flights take off from Caribbean Islands and land in Chicago each week. The most common flight departure day for this route is Mon, with 17% of weekly flights taking off on this day.