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.

Sat, Sep 5 - Sat, Sep 19

BOS

Logan Intl.

MCO

Orlando Intl.

$135 Roundtrip, found 11 hours ago

$135

Roundtrip

found 11 hours ago

Select Frontier Airlines flight, departing Sat, Sep 5 from Logan Intl. to Orlando Intl., returning Sat, Sep 19, priced at $135 found 11 hours ago

Wed, Sep 9 - Sat, Sep 12

BOS

Logan Intl.

MIA

Miami Intl.

$159 Roundtrip, found 19 hours ago

$159

Roundtrip

found 19 hours ago

Select Delta flight, departing Wed, Sep 9 from Logan Intl. to Miami Intl., returning Sat, Sep 12, priced at $159 found 19 hours ago

Tue, Sep 15 - Tue, Sep 29

BOS

Logan Intl.

FLL

Fort Lauderdale - Hollywood Intl.

$159 Roundtrip, found 4 days ago

$159

Roundtrip

found 4 days ago

Select Delta flight, departing Tue, Sep 15 from Logan Intl. to Fort Lauderdale - Hollywood Intl., returning Tue, Sep 29, priced at $159 found 4 days ago

Sun, Aug 30 - Wed, Sep 16

BDL

Bradley Intl.

SJU

Luis Munoz Marin Intl.

$167 Roundtrip, found 2 days ago

$167

Roundtrip

found 2 days ago

Select Frontier Airlines flight, departing Sun, Aug 30 from Bradley Intl. to Luis Munoz Marin Intl., returning Wed, Sep 16, priced at $167 found 2 days ago

Sat, Oct 3 - Tue, Oct 6

BOS

Logan Intl.

RSW

Southwest Florida Intl.

$189 Roundtrip, found 2 days ago

$189

Roundtrip

found 2 days ago

Select Delta flight, departing Sat, Oct 3 from Logan Intl. to Southwest Florida Intl., returning Tue, Oct 6, priced at $189 found 2 days ago

Wed, Aug 19 - Wed, Aug 26

BDL

Bradley Intl.

MCO

Orlando Intl.

$192 Roundtrip, found 6 days ago

$192

Roundtrip

found 6 days ago

Select Frontier Airlines flight, departing Wed, Aug 19 from Bradley Intl. to Orlando Intl., returning Wed, Aug 26, priced at $192 found 6 days ago

Wed, Nov 4 - Sat, Nov 7

BDL

Bradley Intl.

TPA

Tampa Intl.

$193 Roundtrip, found 3 days ago

$193

Roundtrip

found 3 days ago

Select Breeze Airways flight, departing Wed, Nov 4 from Bradley Intl. to Tampa Intl., returning Sat, Nov 7, priced at $193 found 3 days ago

Sat, Oct 3 - Tue, Oct 6

BOS

Logan Intl.

TPA

Tampa Intl.

$199 Roundtrip, found 1 day ago

$199

Roundtrip

found 1 day ago

Select Delta flight, departing Sat, Oct 3 from Logan Intl. to Tampa Intl., returning Tue, Oct 6, priced at $199 found 1 day ago

Fri, Sep 25 - Mon, Oct 5

BOS

Logan Intl.

ATL

Hartsfield-Jackson Atlanta Intl.

$208 Roundtrip, found 3 days ago

$208

Roundtrip

found 3 days ago

Select Frontier Airlines flight, departing Fri, Sep 25 from Logan Intl. to Hartsfield-Jackson Atlanta Intl., returning Mon, Oct 5, priced at $208 found 3 days ago

Sat, Oct 3 - Mon, Oct 19

BDL

Bradley Intl.

ATL

Hartsfield-Jackson Atlanta Intl.

$210 Roundtrip, found 8 hours ago

$210

Roundtrip

found 8 hours ago

Select Frontier Airlines flight, departing Sat, Oct 3 from Bradley Intl. to Hartsfield-Jackson Atlanta Intl., returning Mon, Oct 19, priced at $210 found 8 hours ago

Wed, Sep 23 - Wed, Sep 30

PVD

T.F. Green

FLL

Fort Lauderdale - Hollywood Intl.

$220 Roundtrip, found 5 days ago

$220

Roundtrip

found 5 days ago

Select Breeze Airways flight, departing Wed, Sep 23 from T.F. Green to Fort Lauderdale - Hollywood Intl., returning Wed, Sep 30, priced at $220 found 5 days ago

Tue, Nov 10 - Fri, Nov 13

ALB

Albany Intl.

MCO

Orlando Intl.

$233 Roundtrip, found 1 day ago

$233

Roundtrip

found 1 day ago

Select Delta flight, departing Tue, Nov 10 from Albany Intl. to Orlando Intl., returning Fri, Nov 13, priced at $233 found 1 day ago

Tue, Jan 5 - Tue, Jan 12

PVD

T.F. Green

MCO

Orlando Intl.

$233 Roundtrip, found 3 days ago

$233

Roundtrip

found 3 days ago

Select Delta flight, departing Tue, Jan 5 from T.F. Green to Orlando Intl., returning Tue, Jan 12, priced at $233 found 3 days ago

Sat, Nov 21 - Tue, Dec 8

PVD

T.F. Green

TPA

Tampa Intl.

$237 Roundtrip, found 3 days ago

$237

Roundtrip

found 3 days ago

Select Breeze Airways flight, departing Sat, Nov 21 from T.F. Green to Tampa Intl., returning Tue, Dec 8, priced at $237 found 3 days ago

Tue, Nov 3 - Tue, Nov 17

ALB

Albany Intl.

MIA

Miami Intl.

$247 Roundtrip, found 6 days ago

$247

Roundtrip

found 6 days ago

Select Delta flight, departing Tue, Nov 3 from Albany Intl. to Miami Intl., returning Tue, Nov 17, priced at $247 found 6 days ago

Thu, Oct 22 - Tue, Oct 27

BOS

Logan Intl.

LAX

Los Angeles Intl.

$250 Roundtrip, found 5 days ago

$250

Roundtrip

found 5 days ago

Select Frontier Airlines flight, departing Thu, Oct 22 from Logan Intl. to Los Angeles Intl., returning Tue, Oct 27, priced at $250 found 5 days ago

Sat, Sep 12 - Mon, Sep 21

BOS

Logan Intl.

LAS

Harry Reid Intl.

$254 Roundtrip, found 4 days ago

$254

Roundtrip

found 4 days ago

Select Frontier Airlines flight, departing Sat, Sep 12 from Logan Intl. to Harry Reid Intl., returning Mon, Sep 21, priced at $254 found 4 days ago

Wed, Aug 19 - Tue, Sep 1

BDL

Bradley Intl.

LAS

Harry Reid Intl.

$257 Roundtrip, found 6 days ago

$257

Roundtrip

found 6 days ago

Select Frontier Airlines flight, departing Wed, Aug 19 from Bradley Intl. to Harry Reid Intl., returning Tue, Sep 1, priced at $257 found 6 days ago

Thu, Sep 3 - Wed, Sep 9

PVD

T.F. Green

ATL

Hartsfield-Jackson Atlanta Intl.

$277 Roundtrip, found 1 day ago

$277

Roundtrip

found 1 day ago

Select JetBlue Airways flight, departing Thu, Sep 3 from T.F. Green to Hartsfield-Jackson Atlanta Intl., returning Wed, Sep 9, priced at $277 found 1 day ago

Wed, Oct 7 - Sat, Oct 17

ORH

Worcester Regional

MCO

Orlando Intl.

$293 Roundtrip, found 5 days ago

$293

Roundtrip

found 5 days ago

Select American Airlines flight, departing Wed, Oct 7 from Worcester Regional to Orlando Intl., returning Sat, Oct 17, priced at $293 found 5 days ago