Cheap flights to Dominican Republic from Chicago

Round trips from Chicago from $372. Cheapest dates, deal ratings and where to book.

• Punta Cana: $372, 2026-10-31 to 2026-11-01

Nearby

• Haiti
• Jamaica
• Saint Kitts and Nevis
• Antigua and Barbuda
• Bahamas
• Dominica
• Cuba
• Saint Lucia