The four U.S. states (highlighted in green) that are designated Commonwealths: Kentucky, Massachusetts, Pennsylvania, and Virginia

The cheapest way to get from Massachusetts to Kentucky costs only $136, and the quickest way takes just 4¾ hours. Find the travel option that best suits you.

The cheapest way to get from Boston to Kentucky costs only $136, and the quickest way takes just 4¾ hours. Find the travel option that best suits you.

The United States is made up of 50 states, yet four of them — Pennsylvania, Massachusetts, Virginia, and Kentucky — are officially referred to as commonwealths. Their names are technically styled as the Commonwealth of Virginia, the Commonwealth of Massachusetts, etc.

There are 7 ways to get from Kentucky to Massachusetts by plane, bus, train, or car. Select an option below to see step-by-step directions and to compare ticket prices and travel times in Rome2Rio's travel planner.

Find flights to Kentucky from $44. Fly from Massachusetts on Spirit Airlines, Allegiant Air, Frontier and more. Search for Kentucky flights on KAYAK now to find the best deal.

Here's a sample itinerary for a drive from Massachusetts to Kentucky. If you're planning a road trip to Kentucky, you can research locations to stop along the way. Make sure you check road conditions to double check the weather.

Discover carefully curated flight deals from Massachusetts to Kentucky that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated January 23, 2025. This FlightHub deal was found by Cheapflights users on 1/23.

The total driving distance from Massachusetts to Kentucky is 929 miles or 1 495 kilometers. Your trip begins in the state of Massachusetts. It ends in the state of Kentucky.

Search and compare airfare from 1000+ airlines and travel sites to get the cheapest flights from Massachusetts to Kentucky with momondo.