Direct Flights from Chicago to the Caribbean
12 nonstop destinations in the Caribbean you can reach direct from Chicago ORD, ranked by flight frequency.
- Punta CanaPUJDominican Republic→
- San JuanSJUPuerto Rico→
- ArubaAUAAruba→
- George TownGCMCayman Islands→
- Montego BayMBJJamaica→
- NassauNASBahamas→
- St. ThomasSTTU.S. Virgin Islands→
- CuraçaoCURCuraçao→
- ProvidencialesPLSTurks and Caicos Islands→
- Saint LuciaUVFSaint Lucia→
- Sint MaartenSXMSint Maarten→
- St. CroixSTXU.S. Virgin Islands→
Frequently asked questions
- Which Caribbean destinations can I fly to nonstop from Chicago?
- You can fly nonstop from Chicago (ORD) to 12 destinations in the Caribbean, including Punta Cana, San Juan, Aruba, George Town, Montego Bay, Nassau, and more.
- What's the closest Caribbean destination to Chicago by nonstop flight?
- Nassau (NAS) is the closest, about 1,313 miles from Chicago.
- Which airlines fly nonstop from Chicago to the Caribbean?
- American, Arajet, Frontier, Southwest, United operate nonstop service from Chicago to the Caribbean.
Airports near Chicago
The closest other departure airports to Chicago — each opens up more nonstop destinations.