Cheap flights to Dominican Republic from Chicago

Round trips from Chicago from $347. Cheapest dates, deal ratings and where to book.

• Punta Cana: $347, 2026-10-23 to 2026-10-27
• Santo Domingo: $518, 2026-11-07 to 2026-11-11
• La Romana: $854, 2027-02-01 to 2027-02-15

Nearby

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