Cheap flights to Jamaica from Chicago

Round trips from Chicago from $463. Cheapest dates, deal ratings and where to book.

• Montego Bay: $463, 2026-11-03 to 2026-11-07
• Kingston: $679, 2026-11-08 to 2026-11-11

Nearby

• Cuba
• Haiti
• Bahamas
• Dominican Republic
• Nicaragua
• Panama
• Honduras
• Costa Rica