Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Indiana to New Windsor as you normally would.
To save up to 70% on this flight, we recommend booking at least 46 days prior to travel. The price may fluctuate and will likely increase closer to your departure date. Users on Cheapflights have found tickets from Indiana to New Windsor from $322 1-2 weeks out and tickets from $452 for flights departing within the next 72 hours.
Due to multiple factors, expect to potentially pay more when booking in November. For low rates, August can be a great choice for travel to New Windsor. Flights to New Windsor from Indiana in August are about $239 on average during August, but can be found for as low as $154.