1.5 hours from Boston and 5 from NYC.
If you have access to a car, this is probably the easiest way to get to Chatham. We recommend budgeting some extra time for traffic even in the shoulder season, or breaking it up with a night on the road.
If you are landing in Boston
and would like to pre-arrange a ride to Chatham, there are many chauffeur services that will take you directly to the Cape from Logan Most cost around ~$300. Some options include: Elite Car Service: https://elitecarserviceandairport.com/ ($295) Boston Coach: https://bostoncorporatecoach.com/
Peter Pan
Take the bus from either Logan Airport or South Station. The bus costs $34 and they have frequent, daily rides starting at 9am. https://peterpanbus.com/destinations/cape-cod/