| Type | Airport Name | City | IATA Code | Connectivity | Distance |
| Albany International Airport | Albany | ALB | 35 mi | ||
| Bradley International Airport | Hartford | BDL | 45.56 mi | ||
| Rutland - Southern Vermont Regional Airport | Rutland | RUT | 76.05 mi | ||
| Stewart International Airport | Newburgh | SWF | 78.87 mi |
=Medium Airport,
=Large Airport
Connectivity ratings are based on the airport's flight routes to other airports.
The above list contains Regional/Domestic as well as International airports.
| Type | Airport Name | City | IATA Code | Connectivity | Distance |
| Worcester Regional Airport | Worcester | ORH | 71.06 mi |
| City/Town/Village | Distance |
| Pittsfield(Massachusetts) | 0 mi |
| Albany(New York) | 29.53 mi |
| Bennington(Vermont) | 29.68 mi |
| Whitingham(Vermont) | 29.74 mi |
| Troy(New York) | 29.76 mi |
| City/Town/Village | Distance |
| Springfield(Massachusetts) | 41.27 mi |
| Hartford(Connecticut) | 55.44 mi |
| Albany(New York) | 29.53 mi |
| West Albany(New York) | 31.54 mi |
| New Britain(Connecticut) | 59.51 mi |
Airports Near Pittsfield, Massachusetts, US on map