Flights from Winchester

Cheapest flights from Winchester

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, Oct 27 - Wed, Nov 4

BOS

Logan Intl.

FLL

Fort Lauderdale - Hollywood Intl.

$159 Roundtrip, found 1 day ago

$159

Roundtrip

found 1 day ago

Select Delta flight, departing Tue, Oct 27 from Logan Intl. to Fort Lauderdale - Hollywood Intl., returning Wed, Nov 4, priced at $159 found 1 day ago

Tue, Oct 27 - Wed, Nov 4

BOS

Logan Intl.

MCO

Orlando Intl.

$159 Roundtrip, found 23 hours ago

$159

Roundtrip

found 23 hours ago

Select Delta flight, departing Tue, Oct 27 from Logan Intl. to Orlando Intl., returning Wed, Nov 4, priced at $159 found 23 hours ago

Wed, Oct 21 - Sat, Oct 24

BOS

Logan Intl.

MIA

Miami Intl.

$159 Roundtrip, found 1 day ago

$159

Roundtrip

found 1 day ago

Select Delta flight, departing Wed, Oct 21 from Logan Intl. to Miami Intl., returning Sat, Oct 24, priced at $159 found 1 day ago

Mon, Nov 2 - Fri, Nov 6

BDL

Bradley Intl.

MCO

Orlando Intl.

$165 Roundtrip, found 2 days ago

$165

Roundtrip

found 2 days ago

Select Breeze Airways flight, departing Mon, Nov 2 from Bradley Intl. to Orlando Intl., returning Fri, Nov 6, priced at $165 found 2 days ago

Sat, Oct 31 - Sat, Nov 7

BOS

Logan Intl.

RSW

Southwest Florida Intl.

$179 Roundtrip, found 1 day ago

$179

Roundtrip

found 1 day ago

Select Delta flight, departing Sat, Oct 31 from Logan Intl. to Southwest Florida Intl., returning Sat, Nov 7, priced at $179 found 1 day ago

Tue, Nov 10 - Tue, Nov 17

BOS

Logan Intl.

TPA

Tampa Intl.

$179 Roundtrip, found 11 hours ago

$179

Roundtrip

found 11 hours ago

Select Delta flight, departing Tue, Nov 10 from Logan Intl. to Tampa Intl., returning Tue, Nov 17, priced at $179 found 11 hours ago

Sat, Oct 31 - Sat, Nov 14

PSM

Portsmouth Intl.

MCO

Orlando Intl.

$202 Roundtrip, found 6 days ago

$202

Roundtrip

found 6 days ago

Select Breeze Airways flight, departing Sat, Oct 31 from Portsmouth Intl. to Orlando Intl., returning Sat, Nov 14, priced at $202 found 6 days ago

Sat, Feb 6 - Wed, Feb 10

PVD

T.F. Green

MCO

Orlando Intl.

$204 Roundtrip, found 4 hours ago

$204

Roundtrip

found 4 hours ago

Select Breeze Airways flight, departing Sat, Feb 6 from T.F. Green to Orlando Intl., returning Wed, Feb 10, priced at $204 found 4 hours ago

Mon, Nov 16 - Thu, Nov 19

BDL

Bradley Intl.

FLL

Fort Lauderdale - Hollywood Intl.

$206 Roundtrip, found 2 days ago

$206

Roundtrip

found 2 days ago

Select Breeze Airways flight, departing Mon, Nov 16 from Bradley Intl. to Fort Lauderdale - Hollywood Intl., returning Thu, Nov 19, priced at $206 found 2 days ago

Sat, Dec 5 - Sat, Dec 12

BDL

Bradley Intl.

SJU

Luis Munoz Marin Intl.

$226 Roundtrip, found 1 day ago

$226

Roundtrip

found 1 day ago

Select Frontier Airlines flight, departing Sat, Dec 5 from Bradley Intl. to Luis Munoz Marin Intl., returning Sat, Dec 12, priced at $226 found 1 day ago

Mon, Oct 26 - Mon, Nov 2

BDL

Bradley Intl.

ATL

Hartsfield-Jackson Atlanta Intl.

$249 Roundtrip, found 6 days ago

$249

Roundtrip

found 6 days ago

Select Frontier Airlines flight, departing Mon, Oct 26 from Bradley Intl. to Hartsfield-Jackson Atlanta Intl., returning Mon, Nov 2, priced at $249 found 6 days ago

Thu, Nov 5 - Wed, Nov 11

BDL

Bradley Intl.

TPA

Tampa Intl.

$249 Roundtrip, found 6 days ago

$249

Roundtrip

found 6 days ago

Select Breeze Airways flight, departing Thu, Nov 5 from Bradley Intl. to Tampa Intl., returning Wed, Nov 11, priced at $249 found 6 days ago

Mon, Dec 7 - Thu, Dec 10

BOS

Logan Intl.

LAS

Harry Reid Intl.

$254 Roundtrip, found 1 day ago

$254

Roundtrip

found 1 day ago

Select Frontier Airlines flight, departing Mon, Dec 7 from Logan Intl. to Harry Reid Intl., returning Thu, Dec 10, priced at $254 found 1 day ago

Fri, Feb 5 - Mon, Feb 8

MHT

Manchester-Boston Regional

FLL

Fort Lauderdale - Hollywood Intl.

$257 Roundtrip, found 5 days ago

$257

Roundtrip

found 5 days ago

Select American Airlines flight, departing Fri, Feb 5 from Manchester-Boston Regional to Fort Lauderdale - Hollywood Intl., returning Mon, Feb 8, priced at $257 found 5 days ago

Mon, Oct 26 - Sun, Nov 1

PVD

T.F. Green

RSW

Southwest Florida Intl.

$267 Roundtrip, found 1 day ago

$267

Roundtrip

found 1 day ago

Select American Airlines flight, departing Mon, Oct 26 from T.F. Green to Southwest Florida Intl., returning Sun, Nov 1, priced at $267 found 1 day ago

Sat, Dec 5 - Tue, Dec 15

MHT

Manchester-Boston Regional

MCO

Orlando Intl.

$270 Roundtrip, found 2 hours ago

$270

Roundtrip

found 2 hours ago

Select Breeze Airways flight, departing Sat, Dec 5 from Manchester-Boston Regional to Orlando Intl., returning Tue, Dec 15, priced at $270 found 2 hours ago

Sat, Oct 24 - Sat, Nov 7

ALB

Albany Intl.

FLL

Fort Lauderdale - Hollywood Intl.

$287 Roundtrip, found 2 days ago

$287

Roundtrip

found 2 days ago

Select JetBlue Airways flight, departing Sat, Oct 24 from Albany Intl. to Fort Lauderdale - Hollywood Intl., returning Sat, Nov 7, priced at $287 found 2 days ago

Mon, Oct 19 - Sat, Oct 24

ALB

Albany Intl.

MIA

Miami Intl.

$294 Roundtrip, found 5 days ago

$294

Roundtrip

found 5 days ago

Select Delta flight, departing Mon, Oct 19 from Albany Intl. to Miami Intl., returning Sat, Oct 24, priced at $294 found 5 days ago

Sat, Oct 17 - Tue, Oct 20

BOS

Logan Intl.

ATL

Hartsfield-Jackson Atlanta Intl.

$297 Roundtrip, found 3 days ago

$297

Roundtrip

found 3 days ago

Select Frontier Airlines flight, departing Sat, Oct 17 from Logan Intl. to Hartsfield-Jackson Atlanta Intl., returning Tue, Oct 20, priced at $297 found 3 days ago

Wed, Dec 2 - Tue, Dec 8

MHT

Manchester-Boston Regional

RSW

Southwest Florida Intl.

$306 Roundtrip, found 3 hours ago

$306

Roundtrip

found 3 hours 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 3 hours ago