There are 14 non-stop flights from Chicago, Illinois to the Caribbean.

United Airlines
Cayman Airways
Frontier Airlines Inc.
AirTran Airways
American Airlines
US Airways

See the full list of airline routes and airports to book your trip. You may need to drive to a nearby airport to get a direct flight. Use the form below to search for cheap airline tickets.

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Flight path from Chicago, IL to Caribbean

The Caribbean

The Caribbean is a region covering a number of countries including Anguilla, Antigua and Barbuda, Aruba, Bahamas, Barbados, Belize, British Virgin Islands, Cayman Islands, Cuba, Dominica, Dominican Republic, Grenada, Guadeloupe, Haiti, Jamaica, Martinique, Montserrat, Puerto Rico, Saint Barthelemy, Saint Kitts and Nevis, Saint Lucia, Saint Martin, Saint Vincent and the Grenadines, Trinidad and Tobago, Turks and Caicos, and the U.S. Virgin Islands. If you're looking for a direct flight to the Caribbean, try searching for a particular destination or airport to check airlines.

You don’t have to worry about layovers or missing your connecting flights when you take nonstop flights from Chicago to the Caribbean. A mere 4 hours 53 minutes will take you to St. Maarten (St. Martin). Aruba is 5 hours 4 minutes and Bahamas is only 3 hours 16 minutes.

St. Maarten is known for its amazing beaches and more. It is multi-cultural, exotic and the Gastronomic Capital of the Caribbean. The island has over 350 restaurants including pizzerias and the best French cuisine in the Caribbean, The Infinity Restaurant in Oyster Bay Beach Resort which offers great views of the Atlantic Ocean for those who prefer an eclectic menu for lunch or dinner.

Popular beaches in St. Maarten include Oyster Bay, Simpson Bay, Cupecoy, Great Bay, Little Bay, Kim Sha, Mullet Bay and Maho. Maho Beach is the most unusual beach in the world. It is located near Princess Juliana International Airport and serves as the ‘runway’ for airplanes.

Besides St. Maarten, check out direct flights from Chicago to Aruba, Bahamas, Punta Cana (Dominican Republic) and US Virgin Islands.

find a flight to Caribbean

Non-stop flights between Chicago, IL and Caribbean

Here is a list of direct nonstop flights from Chicago, Illinois to Caribbean. This can help you find the best flight on your preferred airline. We found a total of 14 flights to Caribbean nonstop:

Chicago, Illinois

City: Chicago
State: Illinois
Country: United States
Category: cities

Non-stop direct flights

Travelmath provides an online direct flight finder to help you determine whether there is a non-stop flight to your destination. Nonstop flights can be faster, since they don't require you to change planes or stop at a connecting airport. However, sometimes you can't find any non-stop flights between two cities. In that case, you may want to search for a direct connection that goes through an airline's hub. You can use the flight search engine on this site to find the best airline routes for your trip. Enter any city or IATA airport code to check for direct flights.