Find out what a flight from Chicago O'Hare to Santiago de los Caballeros might cost

Prices vary based on date, airline, and availability. Compare several options if you're flying between Chicago and Santiago.

$247 is the best price recorded in the last 15 days.

Try shifting your departure forward or backward by a day to find better options. If you’re looking for a good deal, consider flying outside peak hours as well.

Planning flights between Chicago and Santiago? Don’t forget the airport options

Especially when flying to medium or large cities, it's worth checking all possible airport combinations before booking.

• Airports in Chicago: 3 airports are listed in Chicago - Midway, O'Hare, Rockford.
• Airports in Santiago: Only Santiago - Cibao International is currently available.

Check for differences in transport costs to and from each airport — they affect your total spend. Choosing the right airport can make a real difference in price and timing.

Find the best flight from Chicago O'Hare to Santiago de los Caballeros

With Jetcost, you can filter results by flight time, airline, price range, and layovers. Choose direct or connecting flights, round-trip or one-way, and compare offers from Delta, American, United, and more.

Other popular destinations

Searching for flights to Dominican Republic? Travelers also looked at: La Romana, Puerto Plata, Punta Cana, Santiago, Santo Domingo.

Use filters to exclude options that don’t match your budget or travel preferences and personalize your search for Chicago O'Hare – Santiago de los Caballeros flights.