Flights from Orlando to The Berkshires

Cheapest flights from Orlando

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.

Tue, Aug 12 - Wed, Aug 13

MCO

Orlando Intl.

ALB

Albany Intl.

$137 Roundtrip, found 4 days ago

$137

Roundtrip

found 4 days ago

Select JetBlue Airways flight, departing Tue, Aug 12 from Orlando Intl. to Albany Intl., returning Wed, Aug 13, priced at $137 found 4 days ago

Sat, Jun 21 - Sat, Jun 28

MCO

Orlando Intl.

BDL

Bradley Intl.

$159 Roundtrip, found 4 days ago

$159

Roundtrip

found 4 days ago

Select Frontier Airlines flight, departing Sat, Jun 21 from Orlando Intl. to Bradley Intl., returning Sat, Jun 28, priced at $159 found 4 days ago

Wed, Jun 25 - Mon, Jun 30

MCO

Orlando Intl.

BDL

Bradley Intl.

$163 Roundtrip, found 1 day ago

$163

Roundtrip

found 1 day ago

Select Breeze Airways flight, departing Wed, Jun 25 from Orlando Intl. to Bradley Intl., returning Mon, Jun 30, priced at $163 found 1 day ago

Wed, Jun 25 - Mon, Jun 30

MCO

Orlando Intl.

BDL

Bradley Intl.

$166 Roundtrip, found 1 day ago

$166

Roundtrip

found 1 day ago

Select Breeze Airways flight, departing Wed, Jun 25 from Orlando Intl. to Bradley Intl., returning Mon, Jun 30, priced at $166 found 1 day ago

Wed, Jun 25 - Mon, Jun 30

MCO

Orlando Intl.

BDL

Bradley Intl.

$168 Roundtrip, found 1 day ago

$168

Roundtrip

found 1 day ago

Select Breeze Airways flight, departing Wed, Jun 25 from Orlando Intl. to Bradley Intl., returning Mon, Jun 30, priced at $168 found 1 day ago

Wed, Jun 25 - Mon, Jun 30

MCO

Orlando Intl.

BDL

Bradley Intl.

$170 Roundtrip, found 1 day ago

$170

Roundtrip

found 1 day ago

Select Spirit Airlines flight, departing Wed, Jun 25 from Orlando Intl. to Bradley Intl., returning Mon, Jun 30, priced at $170 found 1 day ago

Tue, Aug 12 - Thu, Aug 14

MCO

Orlando Intl.

ALB

Albany Intl.

$172 Roundtrip, found 4 days ago

$172

Roundtrip

found 4 days ago

Select JetBlue Airways flight, departing Tue, Aug 12 from Orlando Intl. to Albany Intl., returning Thu, Aug 14, priced at $172 found 4 days ago

Wed, Jun 25 - Mon, Jun 30

MCO

Orlando Intl.

BDL

Bradley Intl.

$173 Roundtrip, found 1 day ago

$173

Roundtrip

found 1 day ago

Select Breeze Airways flight, departing Wed, Jun 25 from Orlando Intl. to Bradley Intl., returning Mon, Jun 30, priced at $173 found 1 day ago

Wed, Jun 25 - Mon, Jun 30

MCO

Orlando Intl.

BDL

Bradley Intl.

$176 Roundtrip, found 1 day ago

$176

Roundtrip

found 1 day ago

Select Breeze Airways flight, departing Wed, Jun 25 from Orlando Intl. to Bradley Intl., returning Mon, Jun 30, priced at $176 found 1 day ago

Tue, Aug 12 - Mon, Aug 18

MCO

Orlando Intl.

ALB

Albany Intl.

$178 Roundtrip, found 4 days ago

$178

Roundtrip

found 4 days ago

Select JetBlue Airways flight, departing Tue, Aug 12 from Orlando Intl. to Albany Intl., returning Mon, Aug 18, priced at $178 found 4 days ago

Sat, Jun 21 - Thu, Jun 26

MCO

Orlando Intl.

BDL

Bradley Intl.

$183 Roundtrip, found 4 days ago

$183

Roundtrip

found 4 days ago

Select Frontier Airlines flight, departing Sat, Jun 21 from Orlando Intl. to Bradley Intl., returning Thu, Jun 26, priced at $183 found 4 days ago

Wed, Jun 25 - Mon, Jun 30

MCO

Orlando Intl.

BDL

Bradley Intl.

$186 Roundtrip, found 1 day ago

$186

Roundtrip

found 1 day ago

Select Spirit Airlines flight, departing Wed, Jun 25 from Orlando Intl. to Bradley Intl., returning Mon, Jun 30, priced at $186 found 1 day ago

Sat, Jun 21 - Sat, Jun 28

MCO

Orlando Intl.

BDL

Bradley Intl.

$187 Roundtrip, found 4 days ago

$187

Roundtrip

found 4 days ago

Select Breeze Airways flight, departing Sat, Jun 21 from Orlando Intl. to Bradley Intl., returning Sat, Jun 28, priced at $187 found 4 days ago

Wed, Jun 25 - Mon, Jun 30

MCO

Orlando Intl.

BDL

Bradley Intl.

$187 Roundtrip, found 1 day ago

$187

Roundtrip

found 1 day ago

Select United flight, departing Wed, Jun 25 from Orlando Intl. to Bradley Intl., returning Mon, Jun 30, priced at $187 found 1 day ago

Sat, Jun 21 - Sat, Jun 28

MCO

Orlando Intl.

BDL

Bradley Intl.

$188 Roundtrip, found 4 days ago

$188

Roundtrip

found 4 days ago

Select Frontier Airlines flight, departing Sat, Jun 21 from Orlando Intl. to Bradley Intl., returning Sat, Jun 28, priced at $188 found 4 days ago

Wed, Aug 13 - Mon, Aug 18

MCO

Orlando Intl.

ALB

Albany Intl.

$189 Roundtrip, found 4 days ago

$189

Roundtrip

found 4 days ago

Select American Airlines flight, departing Wed, Aug 13 from Orlando Intl. to Albany Intl., returning Mon, Aug 18, priced at $189 found 4 days ago

Sat, Aug 9 - Tue, Aug 12

MCO

Orlando Intl.

ALB

Albany Intl.

$197 Roundtrip, found 4 days ago

$197

Roundtrip

found 4 days ago

Select Delta flight, departing Sat, Aug 9 from Orlando Intl. to Albany Intl., returning Tue, Aug 12, priced at $197 found 4 days ago

Tue, Jun 24 - Mon, Jun 30

MCO

Orlando Intl.

BDL

Bradley Intl.

$200 Roundtrip, found 4 days ago

$200

Roundtrip

found 4 days ago

Select Spirit Airlines flight, departing Tue, Jun 24 from Orlando Intl. to Bradley Intl., returning Mon, Jun 30, priced at $200 found 4 days ago

Wed, Aug 13 - Mon, Aug 18

MCO

Orlando Intl.

ALB

Albany Intl.

$233 Roundtrip, found 4 days ago

$233

Roundtrip

found 4 days ago

Select American Airlines flight, departing Wed, Aug 13 from Orlando Intl. to Albany Intl., returning Mon, Aug 18, priced at $233 found 4 days ago

Wed, Jun 25 - Mon, Jun 30

MCO

Orlando Intl.

BDL

Bradley Intl.

$251 Roundtrip, found 1 day ago

$251

Roundtrip

found 1 day ago

Select United flight, departing Wed, Jun 25 from Orlando Intl. to Bradley Intl., returning Mon, Jun 30, priced at $251 found 1 day ago