Flights from Pittsfield

Cheapest flights from Pittsfield

These prices were available within the past 7 days. Prices quoted are per person, round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Wed, Feb 3 - Wed, Feb 10

PSM

Portsmouth Intl.

RSW

Southwest Florida Intl.

$246 Roundtrip, found 18 hours ago

$246

Roundtrip

found 18 hours ago

Select Breeze Airways flight, departing Wed, Feb 3 from Portsmouth Intl. to Southwest Florida Intl., returning Wed, Feb 10, priced at $246 found 18 hours ago

Wed, Feb 3 - Wed, Feb 10

PSM

Portsmouth Intl.

RSW

Southwest Florida Intl.

$251 Roundtrip, found 18 hours ago

$251

Roundtrip

found 18 hours ago

Select Breeze Airways flight, departing Wed, Feb 3 from Portsmouth Intl. to Southwest Florida Intl., returning Wed, Feb 10, priced at $251 found 18 hours ago

Wed, Feb 3 - Wed, Feb 10

PSM

Portsmouth Intl.

RSW

Southwest Florida Intl.

$256 Roundtrip, found 18 hours ago

$256

Roundtrip

found 18 hours ago

Select Breeze Airways flight, departing Wed, Feb 3 from Portsmouth Intl. to Southwest Florida Intl., returning Wed, Feb 10, priced at $256 found 18 hours ago

Thu, Jan 21 - Sun, Jan 24

PSM

Portsmouth Intl.

MCO

Orlando Intl.

$258 Roundtrip, found 4 days ago

$258

Roundtrip

found 4 days ago

Select Breeze Airways flight, departing Thu, Jan 21 from Portsmouth Intl. to Orlando Intl., returning Sun, Jan 24, priced at $258 found 4 days ago

Thu, Jan 21 - Sun, Jan 24

PSM

Portsmouth Intl.

MCO

Orlando Intl.

$263 Roundtrip, found 4 days ago

$263

Roundtrip

found 4 days ago

Select Breeze Airways flight, departing Thu, Jan 21 from Portsmouth Intl. to Orlando Intl., returning Sun, Jan 24, priced at $263 found 4 days ago

Thu, Jan 21 - Sun, Jan 24

MHT

Manchester-Boston Regional

MCO

Orlando Intl.

$266 Roundtrip, found 6 days ago

$266

Roundtrip

found 6 days ago

Select Breeze Airways flight, departing Thu, Jan 21 from Manchester-Boston Regional to Orlando Intl., returning Sun, Jan 24, priced at $266 found 6 days ago

Thu, Jan 21 - Sun, Jan 24

PSM

Portsmouth Intl.

MCO

Orlando Intl.

$268 Roundtrip, found 4 days ago

$268

Roundtrip

found 4 days ago

Select Breeze Airways flight, departing Thu, Jan 21 from Portsmouth Intl. to Orlando Intl., returning Sun, Jan 24, priced at $268 found 4 days ago

Thu, Jan 21 - Sun, Jan 24

MHT

Manchester-Boston Regional

MCO

Orlando Intl.

$271 Roundtrip, found 6 days ago

$271

Roundtrip

found 6 days ago

Select Breeze Airways flight, departing Thu, Jan 21 from Manchester-Boston Regional to Orlando Intl., returning Sun, Jan 24, priced at $271 found 6 days ago

Thu, Dec 3 - Sun, Dec 6

PSM

Portsmouth Intl.

MCO

Orlando Intl.

$275 Roundtrip, found 6 days ago

$275

Roundtrip

found 6 days ago

Select Breeze Airways flight, departing Thu, Dec 3 from Portsmouth Intl. to Orlando Intl., returning Sun, Dec 6, priced at $275 found 6 days ago

Thu, Jan 21 - Sun, Jan 24

MHT

Manchester-Boston Regional

MCO

Orlando Intl.

$276 Roundtrip, found 6 days ago

$276

Roundtrip

found 6 days ago

Select Breeze Airways flight, departing Thu, Jan 21 from Manchester-Boston Regional to Orlando Intl., returning Sun, Jan 24, priced at $276 found 6 days ago

Thu, Dec 3 - Sun, Dec 6

PSM

Portsmouth Intl.

MCO

Orlando Intl.

$285 Roundtrip, found 6 days ago

$285

Roundtrip

found 6 days ago

Select Breeze Airways flight, departing Thu, Dec 3 from Portsmouth Intl. to Orlando Intl., returning Sun, Dec 6, priced at $285 found 6 days ago

Thu, Jan 21 - Sun, Jan 24

MHT

Manchester-Boston Regional

MCO

Orlando Intl.

$301 Roundtrip, found 6 days ago

$301

Roundtrip

found 6 days ago

Select Breeze Airways flight, departing Thu, Jan 21 from Manchester-Boston Regional to Orlando Intl., returning Sun, Jan 24, priced at $301 found 6 days ago

Thu, Jan 21 - Sun, Jan 24

MHT

Manchester-Boston Regional

MCO

Orlando Intl.

$306 Roundtrip, found 6 days ago

$306

Roundtrip

found 6 days ago

Select Breeze Airways flight, departing Thu, Jan 21 from Manchester-Boston Regional to Orlando Intl., returning Sun, Jan 24, priced at $306 found 6 days ago

Thu, Jan 21 - Sun, Jan 24

MHT

Manchester-Boston Regional

MCO

Orlando Intl.

$311 Roundtrip, found 6 days ago

$311

Roundtrip

found 6 days ago

Select Breeze Airways flight, departing Thu, Jan 21 from Manchester-Boston Regional to Orlando Intl., returning Sun, Jan 24, priced at $311 found 6 days ago

Sat, Jan 23 - Sat, Feb 6

PSM

Portsmouth Intl.

RSW

Southwest Florida Intl.

$316 Roundtrip, found 5 hours ago

$316

Roundtrip

found 5 hours ago

Select Breeze Airways flight, departing Sat, Jan 23 from Portsmouth Intl. to Southwest Florida Intl., returning Sat, Feb 6, priced at $316 found 5 hours ago

Sun, Feb 28 - Sat, Mar 6

MHT

Manchester-Boston Regional

MCO

Orlando Intl.

$320 Roundtrip, found 5 days ago

$320

Roundtrip

found 5 days ago

Select Breeze Airways flight, departing Sun, Feb 28 from Manchester-Boston Regional to Orlando Intl., returning Sat, Mar 6, priced at $320 found 5 days ago

Sun, Feb 28 - Sat, Mar 6

MHT

Manchester-Boston Regional

MCO

Orlando Intl.

$325 Roundtrip, found 5 days ago

$325

Roundtrip

found 5 days ago

Select Breeze Airways flight, departing Sun, Feb 28 from Manchester-Boston Regional to Orlando Intl., returning Sat, Mar 6, priced at $325 found 5 days ago

Wed, Feb 24 - Wed, Mar 3

MHT

Manchester-Boston Regional

DJT

President Donald J. Trump Intl. Airport

$339 Roundtrip, found 6 days ago

$339

Roundtrip

found 6 days ago

Select Southwest Airlines flight, departing Wed, Feb 24 from Manchester-Boston Regional to President Donald J. Trump Intl. Airport, returning Wed, Mar 3, priced at $339 found 6 days ago

Wed, Feb 24 - Wed, Mar 3

MHT

Manchester-Boston Regional

DJT

President Donald J. Trump Intl. Airport

$339 Roundtrip, found 6 days ago

$339

Roundtrip

found 6 days ago

Select American Airlines flight, departing Wed, Feb 24 from Manchester-Boston Regional to President Donald J. Trump Intl. Airport, returning Wed, Mar 3, priced at $339 found 6 days ago

Wed, Feb 24 - Wed, Mar 3

MHT

Manchester-Boston Regional

DJT

President Donald J. Trump Intl. Airport

$354 Roundtrip, found 6 days ago

$354

Roundtrip

found 6 days ago

Select United flight, departing Wed, Feb 24 from Manchester-Boston Regional to President Donald J. Trump Intl. Airport, returning Wed, Mar 3, priced at $354 found 6 days ago