Flights from Portland to Great Barrington

Cheapest flights from Portland

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, Jul 2 - Tue, Jul 8

PDX

Portland Intl.

BDL

Bradley Intl.

$363 Roundtrip, found 2 days ago

$363

Roundtrip

found 2 days ago

Select Delta flight, departing Wed, Jul 2 from Portland Intl. to Bradley Intl., returning Tue, Jul 8, priced at $363 found 2 days ago

Fri, Jul 4 - Tue, Jul 8

PDX

Portland Intl.

BDL

Bradley Intl.

$376 Roundtrip, found 2 days ago

$376

Roundtrip

found 2 days ago

Select Delta flight, departing Fri, Jul 4 from Portland Intl. to Bradley Intl., returning Tue, Jul 8, priced at $376 found 2 days ago

Wed, Jul 2 - Tue, Jul 8

PDX

Portland Intl.

BDL

Bradley Intl.

$376 Roundtrip, found 2 days ago

$376

Roundtrip

found 2 days ago

Select Sun Country Airlines flight, departing Wed, Jul 2 from Portland Intl. to Bradley Intl., returning Tue, Jul 8, priced at $376 found 2 days ago

Fri, Jul 4 - Wed, Jul 16

PDX

Portland Intl.

ALB

Albany Intl.

$389 Roundtrip, found 1 day ago

$389

Roundtrip

found 1 day ago

Select Delta flight, departing Fri, Jul 4 from Portland Intl. to Albany Intl., returning Wed, Jul 16, priced at $389 found 1 day ago

Wed, Jul 2 - Tue, Jul 8

PDX

Portland Intl.

BDL

Bradley Intl.

$403 Roundtrip, found 2 days ago

$403

Roundtrip

found 2 days ago

Select Delta flight, departing Wed, Jul 2 from Portland Intl. to Bradley Intl., returning Tue, Jul 8, priced at $403 found 2 days ago

Tue, Jul 8 - Tue, Jul 8

PDX

Portland Intl.

BDL

Bradley Intl.

$405 Roundtrip, found 2 days ago

$405

Roundtrip

found 2 days ago

Select Delta flight, departing Tue, Jul 8 from Portland Intl. to Bradley Intl., returning Tue, Jul 8, priced at $405 found 2 days ago

Wed, Jul 2 - Tue, Jul 8

PDX

Portland Intl.

BDL

Bradley Intl.

$409 Roundtrip, found 2 days ago

$409

Roundtrip

found 2 days ago

Select American Airlines flight, departing Wed, Jul 2 from Portland Intl. to Bradley Intl., returning Tue, Jul 8, priced at $409 found 2 days ago

Wed, Jul 2 - Tue, Jul 8

PDX

Portland Intl.

BDL

Bradley Intl.

$411 Roundtrip, found 2 days ago

$411

Roundtrip

found 2 days ago

Select Sun Country Airlines flight, departing Wed, Jul 2 from Portland Intl. to Bradley Intl., returning Tue, Jul 8, priced at $411 found 2 days ago

Wed, Jul 2 - Tue, Jul 8

PDX

Portland Intl.

BDL

Bradley Intl.

$413 Roundtrip, found 2 days ago

$413

Roundtrip

found 2 days ago

Select Delta flight, departing Wed, Jul 2 from Portland Intl. to Bradley Intl., returning Tue, Jul 8, priced at $413 found 2 days ago

Wed, Jul 2 - Tue, Jul 8

PDX

Portland Intl.

BDL

Bradley Intl.

$419 Roundtrip, found 2 days ago

$419

Roundtrip

found 2 days ago

Select Delta flight, departing Wed, Jul 2 from Portland Intl. to Bradley Intl., returning Tue, Jul 8, priced at $419 found 2 days ago

Wed, Jul 30 - Wed, Aug 13

PDX

Portland Intl.

ALB

Albany Intl.

$419 Roundtrip, found 1 day ago

$419

Roundtrip

found 1 day ago

Select Delta flight, departing Wed, Jul 30 from Portland Intl. to Albany Intl., returning Wed, Aug 13, priced at $419 found 1 day ago

Wed, Jul 2 - Tue, Jul 8

PDX

Portland Intl.

BDL

Bradley Intl.

$422 Roundtrip, found 2 days ago

$422

Roundtrip

found 2 days ago

Select American Airlines flight, departing Wed, Jul 2 from Portland Intl. to Bradley Intl., returning Tue, Jul 8, priced at $422 found 2 days ago

Mon, Jul 28 - Wed, Aug 13

PDX

Portland Intl.

ALB

Albany Intl.

$427 Roundtrip, found 1 day ago

$427

Roundtrip

found 1 day ago

Select Delta flight, departing Mon, Jul 28 from Portland Intl. to Albany Intl., returning Wed, Aug 13, priced at $427 found 1 day ago

Wed, Jul 9 - Wed, Jul 9

PDX

Portland Intl.

BDL

Bradley Intl.

$432 Roundtrip, found 2 days ago

$432

Roundtrip

found 2 days ago

Select Delta flight, departing Wed, Jul 9 from Portland Intl. to Bradley Intl., returning Wed, Jul 9, priced at $432 found 2 days ago

Wed, Jul 2 - Tue, Jul 8

PDX

Portland Intl.

BDL

Bradley Intl.

$435 Roundtrip, found 2 days ago

$435

Roundtrip

found 2 days ago

Select Spirit Airlines flight, departing Wed, Jul 2 from Portland Intl. to Bradley Intl., returning Tue, Jul 8, priced at $435 found 2 days ago

Wed, Jul 30 - Thu, Aug 14

PDX

Portland Intl.

ALB

Albany Intl.

$445 Roundtrip, found 1 day ago

$445

Roundtrip

found 1 day ago

Select Delta flight, departing Wed, Jul 30 from Portland Intl. to Albany Intl., returning Thu, Aug 14, priced at $445 found 1 day ago

Wed, Jul 2 - Tue, Jul 8

PDX

Portland Intl.

BDL

Bradley Intl.

$448 Roundtrip, found 2 days ago

$448

Roundtrip

found 2 days ago

Select United flight, departing Wed, Jul 2 from Portland Intl. to Bradley Intl., returning Tue, Jul 8, priced at $448 found 2 days ago

Fri, Jul 4 - Sat, Jul 12

PDX

Portland Intl.

BDL

Bradley Intl.

$463 Roundtrip, found 2 days ago

$463

Roundtrip

found 2 days ago

Select United flight, departing Fri, Jul 4 from Portland Intl. to Bradley Intl., returning Sat, Jul 12, priced at $463 found 2 days ago

Mon, Jul 7 - Mon, Jul 14

PDX

Portland Intl.

BDL

Bradley Intl.

$547 Roundtrip, found 2 days ago

$547

Roundtrip

found 2 days ago

Select Alaska Airlines flight, departing Mon, Jul 7 from Portland Intl. to Bradley Intl., returning Mon, Jul 14, priced at $547 found 2 days ago

Mon, Jul 7 - Fri, Jul 11

PDX

Portland Intl.

BDL

Bradley Intl.

$783 Roundtrip, found 2 days ago

$783

Roundtrip

found 2 days ago

Select JetBlue Airways flight, departing Mon, Jul 7 from Portland Intl. to Bradley Intl., returning Fri, Jul 11, priced at $783 found 2 days ago