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.

Sat, Oct 31 - Sat, Nov 7

PSM

Portsmouth Intl.

MCO

Orlando Intl.

$219 Roundtrip, found 13 hours ago

$219

Roundtrip

found 13 hours ago

Select Breeze Airways flight, departing Sat, Oct 31 from Portsmouth Intl. to Orlando Intl., returning Sat, Nov 7, priced at $219 found 13 hours ago

Sat, Oct 31 - Sat, Nov 7

PSM

Portsmouth Intl.

MCO

Orlando Intl.

$224 Roundtrip, found 13 hours ago

$224

Roundtrip

found 13 hours ago

Select Breeze Airways flight, departing Sat, Oct 31 from Portsmouth Intl. to Orlando Intl., returning Sat, Nov 7, priced at $224 found 13 hours ago

Sat, Oct 31 - Sat, Nov 7

PSM

Portsmouth Intl.

MCO

Orlando Intl.

$229 Roundtrip, found 13 hours ago

$229

Roundtrip

found 13 hours ago

Select Breeze Airways flight, departing Sat, Oct 31 from Portsmouth Intl. to Orlando Intl., returning Sat, Nov 7, priced at $229 found 13 hours ago

Sat, Oct 31 - Sat, Nov 14

PSM

Portsmouth Intl.

MCO

Orlando Intl.

$234 Roundtrip, found 5 days ago

$234

Roundtrip

found 5 days ago

Select Breeze Airways flight, departing Sat, Oct 31 from Portsmouth Intl. to Orlando Intl., returning Sat, Nov 14, priced at $234 found 5 days ago

Sat, Oct 31 - Sat, Nov 14

PSM

Portsmouth Intl.

MCO

Orlando Intl.

$244 Roundtrip, found 5 days ago

$244

Roundtrip

found 5 days ago

Select Breeze Airways flight, departing Sat, Oct 31 from Portsmouth Intl. to Orlando Intl., returning Sat, Nov 14, priced at $244 found 5 days ago

Sat, Oct 31 - Sat, Nov 14

PSM

Portsmouth Intl.

MCO

Orlando Intl.

$260 Roundtrip, found 3 days ago

$260

Roundtrip

found 3 days ago

Select Breeze Airways flight, departing Sat, Oct 31 from Portsmouth Intl. to Orlando Intl., returning Sat, Nov 14, priced at $260 found 3 days ago

Sat, Jan 9 - Sat, Jan 16

PSM

Portsmouth Intl.

MCO

Orlando Intl.

$266 Roundtrip, found 5 days ago

$266

Roundtrip

found 5 days ago

Select Breeze Airways flight, departing Sat, Jan 9 from Portsmouth Intl. to Orlando Intl., returning Sat, Jan 16, priced at $266 found 5 days ago

Thu, Jan 7 - Thu, Jan 14

PSM

Portsmouth Intl.

MCO

Orlando Intl.

$266 Roundtrip, found 5 days ago

$266

Roundtrip

found 5 days ago

Select Breeze Airways flight, departing Thu, Jan 7 from Portsmouth Intl. to Orlando Intl., returning Thu, Jan 14, priced at $266 found 5 days ago

Sat, Dec 5 - Tue, Dec 15

MHT

Manchester-Boston Regional

MCO

Orlando Intl.

$270 Roundtrip, found 1 day ago

$270

Roundtrip

found 1 day ago

Select Breeze Airways flight, departing Sat, Dec 5 from Manchester-Boston Regional to Orlando Intl., returning Tue, Dec 15, priced at $270 found 1 day ago

Sat, Oct 31 - Sat, Nov 14

PSM

Portsmouth Intl.

MCO

Orlando Intl.

$270 Roundtrip, found 3 days ago

$270

Roundtrip

found 3 days ago

Select Breeze Airways flight, departing Sat, Oct 31 from Portsmouth Intl. to Orlando Intl., returning Sat, Nov 14, priced at $270 found 3 days ago

Sat, Dec 5 - Tue, Dec 15

MHT

Manchester-Boston Regional

MCO

Orlando Intl.

$275 Roundtrip, found 1 day ago

$275

Roundtrip

found 1 day ago

Select Breeze Airways flight, departing Sat, Dec 5 from Manchester-Boston Regional to Orlando Intl., returning Tue, Dec 15, priced at $275 found 1 day ago

Sat, Dec 5 - Tue, Dec 15

MHT

Manchester-Boston Regional

MCO

Orlando Intl.

$280 Roundtrip, found 1 day ago

$280

Roundtrip

found 1 day ago

Select Breeze Airways flight, departing Sat, Dec 5 from Manchester-Boston Regional to Orlando Intl., returning Tue, Dec 15, priced at $280 found 1 day ago

Sun, Nov 22 - Sat, Dec 5

PSM

Portsmouth Intl.

MCO

Orlando Intl.

$281 Roundtrip, found 2 days ago

$281

Roundtrip

found 2 days ago

Select Breeze Airways flight, departing Sun, Nov 22 from Portsmouth Intl. to Orlando Intl., returning Sat, Dec 5, priced at $281 found 2 days ago

Sat, Oct 17 - Sat, Oct 31

PSM

Portsmouth Intl.

MCO

Orlando Intl.

$286 Roundtrip, found 5 days ago

$286

Roundtrip

found 5 days ago

Select Breeze Airways flight, departing Sat, Oct 17 from Portsmouth Intl. to Orlando Intl., returning Sat, Oct 31, priced at $286 found 5 days ago

Thu, Nov 19 - Thu, Dec 10

PSM

Portsmouth Intl.

MCO

Orlando Intl.

$296 Roundtrip, found 2 days ago

$296

Roundtrip

found 2 days ago

Select Breeze Airways flight, departing Thu, Nov 19 from Portsmouth Intl. to Orlando Intl., returning Thu, Dec 10, priced at $296 found 2 days ago

Thu, Oct 29 - Thu, Nov 5

PSM

Portsmouth Intl.

MCO

Orlando Intl.

$306 Roundtrip, found 1 day ago

$306

Roundtrip

found 1 day ago

Select Breeze Airways flight, departing Thu, Oct 29 from Portsmouth Intl. to Orlando Intl., returning Thu, Nov 5, priced at $306 found 1 day ago

Wed, Dec 2 - Tue, Dec 8

MHT

Manchester-Boston Regional

RSW

Southwest Florida Intl.

$306 Roundtrip, found 1 day ago

$306

Roundtrip

found 1 day ago

Select Southwest Airlines flight, departing Wed, Dec 2 from Manchester-Boston Regional to Southwest Florida Intl., returning Tue, Dec 8, priced at $306 found 1 day ago

Thu, Nov 5 - Sat, Nov 7

PSM

Portsmouth Intl.

MCO

Orlando Intl.

$311 Roundtrip, found 3 days ago

$311

Roundtrip

found 3 days ago

Select Breeze Airways flight, departing Thu, Nov 5 from Portsmouth Intl. to Orlando Intl., returning Sat, Nov 7, priced at $311 found 3 days ago

Wed, Dec 2 - Tue, Dec 8

MHT

Manchester-Boston Regional

RSW

Southwest Florida Intl.

$313 Roundtrip, found 1 day ago

$313

Roundtrip

found 1 day ago

Select American Airlines flight, departing Wed, Dec 2 from Manchester-Boston Regional to Southwest Florida Intl., returning Tue, Dec 8, priced at $313 found 1 day ago

Wed, Dec 2 - Tue, Dec 8

MHT

Manchester-Boston Regional

RSW

Southwest Florida Intl.

$338 Roundtrip, found 1 day ago

$338

Roundtrip

found 1 day ago

Select United flight, departing Wed, Dec 2 from Manchester-Boston Regional to Southwest Florida Intl., returning Tue, Dec 8, priced at $338 found 1 day ago