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Cheap flights from Chicago (CHI) to Caribbean

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Destination information for Caribbean

Things to know before you go. Useful info for your trip from Chicago to Caribbean
Today's exchange rate
$1.00 = $1.00

Airports servicing Chicago

Chicago-O'Hare Intl (ORD)
Rockford (RFD)

Related info for your journey

Useful info, stats and facts about Chicago to Caribbean flights.

Flight FAQs

From Chicago to Caribbean

What days are nonstop flights available from Chicago to Caribbean?

Nonstop flights can be found on the following days: Sunday, Monday, Tuesday, Wednesday, Thursday, Friday, Saturday.

How popular is this flight route?

Flights from Chicago to Caribbean have been viewed 528 times in the past calendar month.

What are the most popular airlines that fly from Chicago to Caribbean?

Consider JetBlue, Delta or Frontier when booking your flight. These represent the most popular airlines when flying from Chicago to Caribbean.

What are the most popular routes from Chicago to Caribbean?

Most travelers choose Chicago O'Hare Intl - San Juan Luis Munoz Marin Intl, Chicago Midway - San Juan Luis Munoz Marin Intl or Chicago O'Hare Intl - Punta Cana when deciding on the best route from Chicago to Caribbean.

What are the cheapest Flights from Chicago to Caribbean?

The cheapest flight price from Chicago to Caribbean is $99. On average you can expect to pay $397. The most popular route, (Chicago O'Hare Intl - San Juan Luis Munoz Marin Intl), can usually be booked for $161.

What are the most reliable airlines from Chicago to Caribbean?

Looking for the most reliable airlines to get you to your destination on time? Our data shows these are most likely to get you from Chicago to Caribbean on time: American Airlines(89%), Alaska Airlines(89%), Iberia(89%.)