What’s the cost of a flight from Chicago Midway to Santiago de los Caballeros?

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

Choose a date to explore the best fares now.

If possible, avoid holiday periods: ticket prices tend to rise quickly and availability drops, especially on busy routes. Morning and evening flights are often in high demand too — book early to get a good fare.

Best airport options between Chicago and Santiago

If you're open to flying into or out of more than one airport, you’ll have more routes to compare.

• Airports in Chicago: Chicago is served by 3 airports - Midway, O'Hare, Rockford.
• Airports in Santiago: Santiago - Cibao International is the sole airport currently available.

Some airports offer extras like lounges, fast track, or self check-in — good to keep in mind. Comparing airports by services offered helps you balance cost and comfort.

Customize your flight from Chicago Midway to Santiago de los Caballeros

Jetcost allows you to filter by travel dates, duration, layovers, carriers, and booking providers. You’ll find direct and connecting flights, one-way or round-trip, from Delta, American, United, Expedia, eDreams, and more.

Other popular destinations

Thinking about Dominican Republic? You might also consider: La Romana, Puerto Plata, Punta Cana, Santiago, Santo Domingo.

You can sort results by price, duration, or departure time to find the best option for you. When available, results always include both low-cost and traditional airlines.