Although there are no major airports in this part of Massachusetts, the Berkshires are within a two- to three-hour drive of numerous major airports, the closest being Bradley International Airport (in Windsor Locks, CT, about a 30-minute drive south of Springfield) and Albany International Airport (in Albany, NY, an hour northwest of Pittsfield). However, it's also worth checking fares into Logan (in Boston, a 90-minute drive east of Springfield), which is one of the country's major airports, with directs flights from all over the United States, Canada, and Europe.
International fares into Boston are among the least expensive in the country. For domestic flights, compare fares and flying times into the aforementioned three airports that serve the region. If you're not spending time in Boston, it's best to avoid the often chaotically busy facilities at Logan, where car-rental rates also tend to be a bit higher and traffic in and out of Boston congested. Your best strategy is to shop around and be sure to factor in differences in local car-rental rates and the number of connections required to reach different airports from wherever you're flying.
Some sample flying times to Boston are: from Chicago (2 1/2 hours), London (6 1/2 hours), and Los Angeles (6 hours). Times from U.S. destinations are similar, if slightly shorter, to Albany and Hartford, assuming you can find direct flights.
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