How much is a flight from Chicago O'Hare to Santiago de los Caballeros?

Depending on when you travel and how far in advance you book, fares between Chicago and Santiago can differ a lot.

Select your dates to check current offers.

Low-cost airlines offer competitive fares, but often add charges for extra services. Keep that in mind when planning your trip. Also, midweek departures may offer better deals than weekends.

Flying from or to Chicago and Santiago? Here are your airport options

Knowing your full list of nearby airports can make flight planning easier, especially when routes vary.

• Airports in Chicago: You have 3 departure options - Midway, O'Hare, Rockford.
• Airports in Santiago: Santiago - Cibao International is the only arrival option right now.

For families or those traveling with assistance, smaller airports can be easier to navigate. Cities served by multiple airports often allow for more flexible travel planning.

Adjust your flight filters for Chicago O'Hare – Santiago de los Caballeros

Jetcost gives you tools to search smarter. Pick your ideal price range, airline, departure time, and flight type — then compare offers from agencies like Expedia, eDreams, and more.

Other popular destinations

Planning a trip to Dominican Republic? These cities are popular too: La Romana, Puerto Plata, Punta Cana, Santiago, Santo Domingo.

Sorting options let you see the most affordable flights first. Some results may include extra fees shown only at checkout — always read carefully to see what’s included.