Cheap Flights from Chicago to Caribbean
Popular Flights from Chicago to Caribbean
- Airfare from Chicago to Nassau from $329 round trip
- Airfare from Chicago to Montego Bay from $363 round trip
- Airfare from Chicago to Port of Spain from $630 round trip
- Airfare from Chicago to Aruba from $403 round trip
Did You Know?
- There are 65 direct flights from Chicago, IL to Caribbean.
- US Airways has the most flights to Caribbean.
- There are 24 carriers with direct flights from United States to Caribbean.
- There are 24 cities in United States with direct flights to Caribbean.
- There are 150 flights from Aruba, AW per week.
Cheap Flights from Chicago to Caribbean Countries
- Chicago to Montserrat
- Chicago to Netherlands Antilles
- Chicago to St Barthelemy
- Chicago to US Virgin Islands
Cheap International Flights from Chicago - CHI
Flights
Airline
Lowest Price
United, Air Canada, Delta, Spirit, American, US Airways, Frontier, AirTran, Copa, JetBlue
$363
American, US Airways, Delta, Spirit, United, Avianca, JetBlue, AirTran, Air Canada, Copa
$403
JetBlue, American, Delta, Spirit, AirTran, US Airways, United, Frontier, Copa
$491
Delta, United, American, JetBlue, Cayman, Air Canada, US Airways
$416