Flights from Gloucester

Cheapest flights from Gloucester

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, Sep 22 - Sat, Sep 26

BOS

Logan Intl.

RSW

Southwest Florida Intl.

$199 Roundtrip, found 1 day ago

$199

Roundtrip

found 1 day ago

Select Delta flight, departing Tue, Sep 22 from Logan Intl. to Southwest Florida Intl., returning Sat, Sep 26, priced at $199 found 1 day ago

Tue, Sep 15 - Sat, Sep 19

BOS

Logan Intl.

MIA

Miami Intl.

$199 Roundtrip, found 6 days ago

$199

Roundtrip

found 6 days ago

Select Delta flight, departing Tue, Sep 15 from Logan Intl. to Miami Intl., returning Sat, Sep 19, priced at $199 found 6 days ago

Tue, Sep 22 - Sat, Sep 26

BOS

Logan Intl.

RSW

Southwest Florida Intl.

$209 Roundtrip, found 1 day ago

$209

Roundtrip

found 1 day ago

Select United flight, departing Tue, Sep 22 from Logan Intl. to Southwest Florida Intl., returning Sat, Sep 26, priced at $209 found 1 day ago

Tue, Sep 22 - Sat, Sep 26

BOS

Logan Intl.

RSW

Southwest Florida Intl.

$209 Roundtrip, found 1 day ago

$209

Roundtrip

found 1 day ago

Select American Airlines flight, departing Tue, Sep 22 from Logan Intl. to Southwest Florida Intl., returning Sat, Sep 26, priced at $209 found 1 day ago

Tue, Sep 22 - Sat, Oct 3

BOS

Logan Intl.

TPA

Tampa Intl.

$209 Roundtrip, found 2 days ago

$209

Roundtrip

found 2 days ago

Select Delta flight, departing Tue, Sep 22 from Logan Intl. to Tampa Intl., returning Sat, Oct 3, priced at $209 found 2 days ago

Tue, Sep 22 - Sat, Sep 26

BOS

Logan Intl.

TPA

Tampa Intl.

$219 Roundtrip, found 2 days ago

$219

Roundtrip

found 2 days ago

Select Delta flight, departing Tue, Sep 22 from Logan Intl. to Tampa Intl., returning Sat, Sep 26, priced at $219 found 2 days ago

Wed, Sep 30 - Sat, Oct 10

BOS

Logan Intl.

TPA

Tampa Intl.

$224 Roundtrip, found 6 days ago

$224

Roundtrip

found 6 days ago

Select United flight, departing Wed, Sep 30 from Logan Intl. to Tampa Intl., returning Sat, Oct 10, priced at $224 found 6 days ago

Tue, Sep 15 - Tue, Sep 22

BOS

Logan Intl.

FLL

Fort Lauderdale - Hollywood Intl.

$228 Roundtrip, found 17 hours ago

$228

Roundtrip

found 17 hours ago

Select Delta flight, departing Tue, Sep 15 from Logan Intl. to Fort Lauderdale - Hollywood Intl., returning Tue, Sep 22, priced at $228 found 17 hours ago

Wed, Sep 16 - Sat, Sep 19

BOS

Logan Intl.

MIA

Miami Intl.

$229 Roundtrip, found 8 hours ago

$229

Roundtrip

found 8 hours ago

Select American Airlines flight, departing Wed, Sep 16 from Logan Intl. to Miami Intl., returning Sat, Sep 19, priced at $229 found 8 hours ago

Wed, Sep 9 - Wed, Sep 16

BOS

Logan Intl.

LAS

Harry Reid Intl.

$238 Roundtrip, found 4 days ago

$238

Roundtrip

found 4 days ago

Select Frontier Airlines flight, departing Wed, Sep 9 from Logan Intl. to Harry Reid Intl., returning Wed, Sep 16, priced at $238 found 4 days ago

Thu, Sep 10 - Sat, Sep 12

BOS

Logan Intl.

MCO

Orlando Intl.

$242 Roundtrip, found 2 days ago

$242

Roundtrip

found 2 days ago

Select Frontier Airlines flight, departing Thu, Sep 10 from Logan Intl. to Orlando Intl., returning Sat, Sep 12, priced at $242 found 2 days ago

Wed, Sep 16 - Wed, Oct 7

BOS

Logan Intl.

RSW

Southwest Florida Intl.

$248 Roundtrip, found 7 hours ago

$248

Roundtrip

found 7 hours ago

Select Southwest Airlines flight, departing Wed, Sep 16 from Logan Intl. to Southwest Florida Intl., returning Wed, Oct 7, priced at $248 found 7 hours ago

Thu, Oct 1 - Sat, Oct 10

BOS

Logan Intl.

ATL

Hartsfield-Jackson Atlanta Intl.

$248 Roundtrip, found 2 days ago

$248

Roundtrip

found 2 days ago

Select Frontier Airlines flight, departing Thu, Oct 1 from Logan Intl. to Hartsfield-Jackson Atlanta Intl., returning Sat, Oct 10, priced at $248 found 2 days ago

Tue, Sep 15 - Tue, Sep 22

BOS

Logan Intl.

RSW

Southwest Florida Intl.

$267 Roundtrip, found 6 days ago

$267

Roundtrip

found 6 days ago

Select JetBlue Airways flight, departing Tue, Sep 15 from Logan Intl. to Southwest Florida Intl., returning Tue, Sep 22, priced at $267 found 6 days ago

Wed, Nov 11 - Tue, Nov 17

BOS

Logan Intl.

LAX

Los Angeles Intl.

$278 Roundtrip, found 5 days ago

$278

Roundtrip

found 5 days ago

Select Frontier Airlines flight, departing Wed, Nov 11 from Logan Intl. to Los Angeles Intl., returning Tue, Nov 17, priced at $278 found 5 days ago

Thu, Nov 19 - Tue, Nov 24

PSM

Portsmouth Intl.

MCO

Orlando Intl.

$291 Roundtrip, found 2 days ago

$291

Roundtrip

found 2 days ago

Select Breeze Airways flight, departing Thu, Nov 19 from Portsmouth Intl. to Orlando Intl., returning Tue, Nov 24, priced at $291 found 2 days ago

Sat, Jan 23 - Sat, Feb 6

PSM

Portsmouth Intl.

RSW

Southwest Florida Intl.

$296 Roundtrip, found 3 days ago

$296

Roundtrip

found 3 days ago

Select Breeze Airways flight, departing Sat, Jan 23 from Portsmouth Intl. to Southwest Florida Intl., returning Sat, Feb 6, priced at $296 found 3 days ago

Sat, Oct 10 - Mon, Oct 19

BOS

Logan Intl.

SJU

Luis Munoz Marin Intl.

$307 Roundtrip, found 16 hours ago

$307

Roundtrip

found 16 hours ago

Select JetBlue Airways flight, departing Sat, Oct 10 from Logan Intl. to Luis Munoz Marin Intl., returning Mon, Oct 19, priced at $307 found 16 hours ago

Wed, Sep 9 - Fri, Sep 18

BOS

Logan Intl.

LAS

Harry Reid Intl.

$330 Roundtrip, found 4 days ago

$330

Roundtrip

found 4 days ago

Select Alaska Airlines flight, departing Wed, Sep 9 from Logan Intl. to Harry Reid Intl., returning Fri, Sep 18, priced at $330 found 4 days ago

Thu, Dec 17 - Wed, Dec 23

BOS

Logan Intl.

LAS

Harry Reid Intl.

$498 Roundtrip, found 2 days ago

$498

Roundtrip

found 2 days ago

Select Sun Country Airlines flight, departing Thu, Dec 17 from Logan Intl. to Harry Reid Intl., returning Wed, Dec 23, priced at $498 found 2 days ago