Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Chicago O'Hare Intl Airport to La Romana as you normally would.
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Yes, Cheapflights offers price alerts on O'Hare Intl to La Romana flights so you can book your travel at the perfect time. Price Alerts can be enabled by clicking the bell icon next to the flight deals above and providing your email address where you want to receive the alerts.