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 20 - Tue, Nov 3

BOS

Logan Intl.

FLL

Fort Lauderdale - Hollywood Intl.

$159 Roundtrip, found 2 days ago

$159

Roundtrip

found 2 days ago

Select Delta flight, departing Tue, Oct 20 from Logan Intl. to Fort Lauderdale - Hollywood Intl., returning Tue, Nov 3, priced at $159 found 2 days ago

Tue, Oct 27 - Tue, Nov 17

BOS

Logan Intl.

MCO

Orlando Intl.

$159 Roundtrip, found 11 hours ago

$159

Roundtrip

found 11 hours ago

Select Delta flight, departing Tue, Oct 27 from Logan Intl. to Orlando Intl., returning Tue, Nov 17, priced at $159 found 11 hours ago

Tue, Nov 10 - Sat, Nov 14

BOS

Logan Intl.

MIA

Miami Intl.

$159 Roundtrip, found 12 hours ago

$159

Roundtrip

found 12 hours ago

Select American Airlines flight, departing Tue, Nov 10 from Logan Intl. to Miami Intl., returning Sat, Nov 14, priced at $159 found 12 hours ago

Sat, Nov 14 - Tue, Nov 17

BOS

Logan Intl.

TPA

Tampa Intl.

$179 Roundtrip, found 5 days ago

$179

Roundtrip

found 5 days ago

Select Delta flight, departing Sat, Nov 14 from Logan Intl. to Tampa Intl., returning Tue, Nov 17, priced at $179 found 5 days ago

Sat, Oct 31 - Sat, Nov 7

BOS

Logan Intl.

RSW

Southwest Florida Intl.

$189 Roundtrip, found 1 day ago

$189

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 $189 found 1 day ago

Wed, Jan 6 - Wed, Jan 13

BDL

Bradley Intl.

TPA

Tampa Intl.

$190 Roundtrip, found 4 days ago

$190

Roundtrip

found 4 days ago

Select American Airlines flight, departing Wed, Jan 6 from Bradley Intl. to Tampa Intl., returning Wed, Jan 13, priced at $190 found 4 days ago

Sat, Oct 31 - Sat, Nov 14

PSM

Portsmouth Intl.

MCO

Orlando Intl.

$202 Roundtrip, found 3 days ago

$202

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 $202 found 3 days ago

Mon, Feb 1 - Sat, Feb 6

PVD

T.F. Green

MCO

Orlando Intl.

$203 Roundtrip, found 6 days ago

$203

Roundtrip

found 6 days ago

Select Breeze Airways flight, departing Mon, Feb 1 from T.F. Green to Orlando Intl., returning Sat, Feb 6, priced at $203 found 6 days ago

Mon, Nov 16 - Thu, Nov 19

BDL

Bradley Intl.

FLL

Fort Lauderdale - Hollywood Intl.

$206 Roundtrip, found 2 hours ago

$206

Roundtrip

found 2 hours 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 hours ago

Sun, Dec 6 - Fri, Dec 25

PVD

T.F. Green

RSW

Southwest Florida Intl.

$210 Roundtrip, found 4 days ago

$210

Roundtrip

found 4 days ago

Select Breeze Airways flight, departing Sun, Dec 6 from T.F. Green to Southwest Florida Intl., returning Fri, Dec 25, priced at $210 found 4 days ago

Mon, Oct 26 - Mon, Nov 2

BDL

Bradley Intl.

ATL

Hartsfield-Jackson Atlanta Intl.

$249 Roundtrip, found 3 days ago

$249

Roundtrip

found 3 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 3 days ago

Thu, Dec 10 - Tue, Dec 15

BDL

Bradley Intl.

RSW

Southwest Florida Intl.

$250 Roundtrip, found 6 days ago

$250

Roundtrip

found 6 days ago

Select Breeze Airways flight, departing Thu, Dec 10 from Bradley Intl. to Southwest Florida Intl., returning Tue, Dec 15, priced at $250 found 6 days ago

Wed, Nov 4 - Tue, Nov 17

BOS

Logan Intl.

LAS

Harry Reid Intl.

$254 Roundtrip, found 2 hours ago

$254

Roundtrip

found 2 hours ago

Select Frontier Airlines flight, departing Wed, Nov 4 from Logan Intl. to Harry Reid Intl., returning Tue, Nov 17, priced at $254 found 2 hours ago

Fri, Feb 5 - Mon, Feb 8

MHT

Manchester-Boston Regional

FLL

Fort Lauderdale - Hollywood Intl.

$257 Roundtrip, found 2 days ago

$257

Roundtrip

found 2 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 2 days ago

Fri, Oct 23 - Sun, Nov 1

ALB

Albany Intl.

TPA

Tampa Intl.

$264 Roundtrip, found 6 days ago

$264

Roundtrip

found 6 days ago

Select American Airlines flight, departing Fri, Oct 23 from Albany Intl. to Tampa Intl., returning Sun, Nov 1, priced at $264 found 6 days ago

Fri, Nov 13 - Mon, Nov 16

PVD

T.F. Green

TPA

Tampa Intl.

$265 Roundtrip, found 5 days ago

$265

Roundtrip

found 5 days ago

Select American Airlines flight, departing Fri, Nov 13 from T.F. Green to Tampa Intl., returning Mon, Nov 16, priced at $265 found 5 days ago

Tue, Dec 8 - Wed, Dec 9

ALB

Albany Intl.

FLL

Fort Lauderdale - Hollywood Intl.

$287 Roundtrip, found 6 days ago

$287

Roundtrip

found 6 days ago

Select JetBlue Airways flight, departing Tue, Dec 8 from Albany Intl. to Fort Lauderdale - Hollywood Intl., returning Wed, Dec 9, priced at $287 found 6 days ago

Mon, Oct 19 - Sat, Oct 24

ALB

Albany Intl.

MIA

Miami Intl.

$294 Roundtrip, found 2 days ago

$294

Roundtrip

found 2 days ago

Select Delta flight, departing Mon, Oct 19 from Albany Intl. to Miami Intl., returning Sat, Oct 24, priced at $294 found 2 days ago

Sat, Oct 17 - Tue, Oct 20

BOS

Logan Intl.

ATL

Hartsfield-Jackson Atlanta Intl.

$297 Roundtrip, found 15 hours ago

$297

Roundtrip

found 15 hours 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 15 hours ago

Tue, Feb 16 - Wed, Feb 17

PVD

T.F. Green

FLL

Fort Lauderdale - Hollywood Intl.

$299 Roundtrip, found 6 days ago

$299

Roundtrip

found 6 days ago

Select United flight, departing Tue, Feb 16 from T.F. Green to Fort Lauderdale - Hollywood Intl., returning Wed, Feb 17, priced at $299 found 6 days ago