Nonstop Flights from Chicago to the Caribbean

Flee from chilling winds, and plan your next escape to one of the wondrous islands of the Caribbean.

Want a nonstop flight to your next island destination? Here are all of the nonstops from Chicago to the Caribbean.

Escape the chilling breeze of the Windy City (actually dubbed so metaphorically for the city’s history of braggadocious and greedy figureheads) for warm, exotic climes with the perfect amount of wind that helps make a welcoming warmth more comfortable. It’s in the Caribbean islands that you’ll find luxury, relaxation and peace mixed into one vacation or even a quick getaway.

Nonstop flights from Chicago can sometimes be too difficult to find, but read on for our list of the best direct flights from Chicago to the Caribbean.

Chicago to Aruba

Nonstop Flights from Chicago to Caribbean | Direct Flights to Caribbean | Aruba Travel
Aruba

Airlines: United Airlines

Flight time: 5 hours, 10 minutes

Chicago to Bahamas

Nonstop Flights from Chicago to Caribbean | Direct Flights to Caribbean | Bahamas Travel
Bahamas

Airlines: United

Flight time: 3 hours, 16 minutes

Chicago to Belize

Nonstop Flights from Chicago to Caribbean | Direct Flights to Caribbean | Belize Travel
Belize

Airlines: United

Flight time: 3 hours, 54 minutes

Chicago to Cancún

Nonstop Flights from Chicago to Caribbean | Direct Flights to Caribbean | Cancun Travel
Cancun

Airlines: American Airlines, United

Flight time: 4 hours, 10 minutes

Chicago to the Cayman Islands

Nonstop Flights from Chicago to Caribbean | Direct Flights to Caribbean | Grand Cayman Travel
Grand Cayman

Airlines: JetBlue

Flight time: 3 hours, 42 minutes

Chicago to Jamaica

Nonstop Flights from Chicago to Caribbean | Direct Flights to Caribbean | Jamaica Travel
Jamaica

Airlines: American Airlines, United

Flight time: 3 hours, 58 minutes

Chicago to Puerto Rico

Nonstop Flights from Chicago to Caribbean | Direct Flights to Caribbean | Puerto Rico Travel
Puerto Rico

Airlines: American Airlines, JetBlue, United

Flight time: 4 hours, 36 minutes

Chicago to St. Lucia

Nonstop Flights from Chicago to Caribbean | Direct Flights to Caribbean | St. Lucia Travel
St. Lucia

Airlines: United

Flight time: 6 hours, 6 minutes

Chicago to St. Thomas

Nonstop Flights from Chicago to Caribbean | Direct Flights to Caribbean | St. Thomas Travel
St. Thomas

Airlines: United

Flight time: 4 hours 40 minutes