$104 Find Cheap Flights from Chicago to Caribbean Islands - Compare and Save

The cheapest ticket to Caribbean Islands from Chicago found in the last 5 days was to San Juan, at $161 round-trip. The most popular route is from Chicago O'Hare Intl Airport (ORD) to San Juan Luis Munoz Marin Intl Airport (SJU), and the cheapest round-trip airline ticket found on this route in the last 5 days was $161.

The cheapest time of day to fly to Caribbean Islands is generally at night, when round-trip flights cost $365 on average. Morning departures are around 19% more expensive than evening flights, on average. The most expensive time of day to fly to Caribbean Islands is generally in the morning, which is peak travel time and where the average cost of a ticket is $525.

No, with an average price for the route of $465, prices are generally cheapest when you fly direct.

The cheapest month for flights from Chicago to Caribbean Islands is January, when tickets cost $535 (return) on average. On the other hand, the most expensive months are June and March, when the average cost of round-trip tickets is $699 and $663 respectively.

If your flying dates are flexible, you should consider flying to Caribbean Islands on a Tuesday, as we generally find the cheapest rates on that day for this route. On the other hand, Friday is the most expensive day to fly from Chicago to Caribbean Islands. For your return ticket, we recommend flying on a Thursday and avoiding Sundays for the best deals.

To get a below average price on the flight from Chicago to Caribbean Islands, you should book around 1 week before departure. For the absolute cheapest price, our data suggests you should book 9 weeks before departure.

There are 8 airlines that fly nonstop from Chicago to Caribbean Islands. They are: American Airlines, Frontier, JetBlue, Southwest, Hahn Air, Arajet, WorldTicket and United Airlines. The cheapest price of all airlines flying this route was found with Frontier at $91 for a round-trip flight to San Juan Luis Munoz Marin Intl Airport (SJU). On average, Arajet offers the best prices for nonstop flights between Chicago and Caribbean Islands.

Chicago and Caribbean Islands are connected by different airlines. The airlines that fly that route the most regularly are United Airlines (39 flights per week), American Airlines (28 flights per week), and Air Canada (14 flights per week).

There are 4 cabin class options for the route. These are First, Business, Economy and Prem Economy. Perform a search on KAYAK to find the latest prices and availability for all cabin fares, which differ across airlines.

Each day, there are between 9 and 12 nonstop flights that take off from Chicago and land in Caribbean Islands, with an average flight time of 4h 40m. The most common departure time is 8:00 am and most flights take off in the morning, while the most flights land at Punta Cana. Each week, there are 70 flights. The most frequent day of departure is Monday, when 17% of all weekly flights depart. The fewest flights depart on a Wednesday.

The earliest flight from Chicago to Caribbean Islands departs at 12:44 am, landing in San Juan at 6:44 am.

If you prefer to fly at night, the latest flight from Chicago to Caribbean Islands jets off at 5:20 pm and lands in San Juan at 11:15 pm.