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Gloucester

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Gloucester Flights as Low as $107

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

JetBlue Airways
Fri, Sep 5 - Mon, Sep 8
ORD
O'Hare Intl.
BOS
Logan Intl.
$107 Roundtrip, found 1 day ago
$107
Roundtrip
found 1 day ago
Select JetBlue Airways flight, departing Fri, Sep 5 from O'Hare Intl. to Logan Intl., returning Mon, Sep 8, priced at $107 found 1 day ago
JetBlue Airways
Sat, Nov 1 - Tue, Nov 4
ORD
O'Hare Intl.
BOS
Logan Intl.
$107 Roundtrip, found 1 day ago
$107
Roundtrip
found 1 day ago
Select JetBlue Airways flight, departing Sat, Nov 1 from O'Hare Intl. to Logan Intl., returning Tue, Nov 4, priced at $107 found 1 day ago
JetBlue Airways
Wed, Sep 3 - Sat, Sep 6
ORD
O'Hare Intl.
BOS
Logan Intl.
$109 Roundtrip, found 1 day ago
$109
Roundtrip
found 1 day ago
Select JetBlue Airways flight, departing Wed, Sep 3 from O'Hare Intl. to Logan Intl., returning Sat, Sep 6, priced at $109 found 1 day ago
Frontier Airlines
Sat, Sep 6 - Sat, Sep 13
ATL
Hartsfield-Jackson Atlanta Intl.
BOS
Logan Intl.
$118 Roundtrip, found 2 days ago
$118
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Sat, Sep 6 from Hartsfield-Jackson Atlanta Intl. to Logan Intl., returning Sat, Sep 13, priced at $118 found 2 days ago
Delta
Sat, Sep 6 - Sat, Sep 6
ORD
O'Hare Intl.
BOS
Logan Intl.
$119 Roundtrip, found 1 day ago
$119
Roundtrip
found 1 day ago
Select Delta flight, departing Sat, Sep 6 from O'Hare Intl. to Logan Intl., returning Sat, Sep 6, priced at $119 found 1 day ago
Frontier Airlines
Mon, Sep 22 - Sat, Sep 27
ATL
Hartsfield-Jackson Atlanta Intl.
BOS
Logan Intl.
$120 Roundtrip, found 2 days ago
$120
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Mon, Sep 22 from Hartsfield-Jackson Atlanta Intl. to Logan Intl., returning Sat, Sep 27, priced at $120 found 2 days ago
Frontier Airlines
Thu, Sep 4 - Sat, Sep 6
ATL
Hartsfield-Jackson Atlanta Intl.
BOS
Logan Intl.
$121 Roundtrip, found 2 days ago
$121
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Thu, Sep 4 from Hartsfield-Jackson Atlanta Intl. to Logan Intl., returning Sat, Sep 6, priced at $121 found 2 days ago
Frontier Airlines
Thu, Sep 4 - Thu, Sep 11
ATL
Hartsfield-Jackson Atlanta Intl.
BOS
Logan Intl.
$123 Roundtrip, found 6 days ago
$123
Roundtrip
found 6 days ago
Select Frontier Airlines flight, departing Thu, Sep 4 from Hartsfield-Jackson Atlanta Intl. to Logan Intl., returning Thu, Sep 11, priced at $123 found 6 days ago
Spirit Airlines
Sat, Sep 13 - Sat, Sep 20
ATL
Hartsfield-Jackson Atlanta Intl.
BOS
Logan Intl.
$123 Roundtrip, found 1 day ago
$123
Roundtrip
found 1 day ago
Select Spirit Airlines flight, departing Sat, Sep 13 from Hartsfield-Jackson Atlanta Intl. to Logan Intl., returning Sat, Sep 20, priced at $123 found 1 day ago
Delta
Thu, Oct 30 - Tue, Nov 4
ORD
O'Hare Intl.
BOS
Logan Intl.
$124 Roundtrip, found 3 days ago
$124
Roundtrip
found 3 days ago
Select Delta flight, departing Thu, Oct 30 from O'Hare Intl. to Logan Intl., returning Tue, Nov 4, priced at $124 found 3 days ago
United
Fri, Sep 5 - Mon, Sep 8
ORD
O'Hare Intl.
BOS
Logan Intl.
$127 Roundtrip, found 8 hours ago
$127
Roundtrip
found 8 hours ago
Select United flight, departing Fri, Sep 5 from O'Hare Intl. to Logan Intl., returning Mon, Sep 8, priced at $127 found 8 hours ago
American Airlines
Fri, Sep 5 - Mon, Sep 8
ORD
O'Hare Intl.
BOS
Logan Intl.
$127 Roundtrip, found 8 hours ago
$127
Roundtrip
found 8 hours ago
Select American Airlines flight, departing Fri, Sep 5 from O'Hare Intl. to Logan Intl., returning Mon, Sep 8, priced at $127 found 8 hours ago
Bargain Flight
Sat, Oct 25 - Wed, Oct 29
SAN
San Diego Intl.
BOS
Logan Intl.
$235 Roundtrip, found 8 hours ago
$235
Roundtrip
found 8 hours ago
Select Bargain Flight flight, departing Sat, Oct 25 from San Diego Intl. to Logan Intl., returning Wed, Oct 29, priced at $235 found 8 hours ago
American Airlines
Sat, Oct 25 - Wed, Oct 29
CLD
McClellan-Palomar
BOS
Logan Intl.
$257 Roundtrip, found 8 hours ago
$257
Roundtrip
found 8 hours ago
Select American Airlines flight, departing Sat, Oct 25 from McClellan-Palomar to Logan Intl., returning Wed, Oct 29, priced at $257 found 8 hours ago
Hawaiian Airlines
Thu, Oct 23 - Wed, Oct 29
SAN
San Diego Intl.
BOS
Logan Intl.
$257 Roundtrip, found 18 hours ago
$257
Roundtrip
found 18 hours ago
Select Hawaiian Airlines flight, departing Thu, Oct 23 from San Diego Intl. to Logan Intl., returning Wed, Oct 29, priced at $257 found 18 hours ago
Sun Country Airlines
Sun, Oct 5 - Wed, Oct 15
SAN
San Diego Intl.
BOS
Logan Intl.
$573 Roundtrip, found 8 hours ago
$573
Roundtrip
found 8 hours ago
Select Sun Country Airlines flight, departing Sun, Oct 5 from San Diego Intl. to Logan Intl., returning Wed, Oct 15, priced at $573 found 8 hours ago

Cheap Flights to Gloucester

Fall in love at first flight with your vacation to Gloucester by saving a ton of cash on your last-minute cheap flight. There’s no more scouring the internet for a good deal—book your flight to Gloucester on Hotwire, and you’ll be up, up, and on a getaway in no time.

Because once the wheels are down in Gloucester, the good times start rolling. So buckle up, you’re in for a fun ride.

Frequently Asked Questions About flights to Gloucester

Don’t waste your time on endless searches for cheap airline tickets oneway or roundtrip. We’ll have you on your way to Gloucester with a tiny bag of pretzels in your hand before you can say “tray tables in the upright position”—and for a ticket price that works for your vacay budget.

So all you have to worry about is where you’re headed after the BOS airport.

What is the cheapest month to fly to Gloucester?

Airline ticket prices fluctuate all the time, depending on the day of the week or the month of the year. The cheapest round trip flights to Gloucester are in September, but when you book your flight on Hotwire, savings are always in season.

How many airlines fly to Gloucester?

Variety is the spice of life, even when it comes to booking your next trip. Want options for airlines? You’ll find 15 to choose from for your flight to Gloucester.

What airport is best to fly into Gloucester?

When you’re planning your trip to Gloucester, convenience is the name of the game. Luckily, Gloucester Beverly Municipal Airport is nearby so you can deplane and get going on checking off everything on your Gloucester must-do list.

How much are flights to Gloucester?

Got very cheap flights on your vacation itinerary? When you book your airline tickets to Gloucester on Hotwire, you may just get what’s on your getaway wish list. With tickets as low as $107, you’ll have leftover cash for at least a magazine and a bottle of water at the airport book store.

How to get cheap flights to Gloucester?

The trick to saving a stack of cash on your flight to Gloucester? Snatch up that Hotwire flight deal when you see a killer rate because it could be gone in a flash. And with flights as low as $107 right now, why wait?

Gloucester Flight Information
Destination airport
Logan Intl.
Destination airport IATA code
BOS
Roundtrip price
$68

Last Minute Hotel Deals in Gloucester

Castle Manor Inn

Castle Manor Inn

2.5 out of 5
141 Essex Avenue, Gloucester, MA
Stay at this hotel in Gloucester. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. ...
8.2/10 Very Good! (1,003 reviews)
"We checked in with John, he is excellent. He knows people and suggested the perfect place for us to eat."

Reviewed on Aug 20, 2025

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Castle Manor Inn
The Hotel at Cape Ann Marina

The Hotel at Cape Ann Marina

3.5 out of 5
75 Essex Avenue, Gloucester, MA
Stay at this 3.5-star hotel in Gloucester. Enjoy free parking, a marina, and a 24-hour front desk. Our guests praise the breakfast and the restaurant in our ...
8.2/10 Very Good! (725 reviews)
Lovely Getaway
"The staff was great, our room was lovely. Had dinner at Mile Marker 1, and it was delicious with a great view."

Reviewed on Aug 15, 2025

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The Hotel at Cape Ann Marina
Beauport Hotel Gloucester

Beauport Hotel Gloucester

3.5 out of 5
55 Commercial Street, Gloucester, MA
Stay at this 3.5-star beach hotel in Gloucester. Enjoy free WiFi, a beach locale, and a rooftop terrace. Our guests praise the helpful staff and the property ...
9.6/10 Exceptional! (874 reviews)
"Above and beyond my expectations"

Reviewed on Aug 16, 2025

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Beauport Hotel Gloucester
The Vista

The Vista

2.5 out of 5
22 Thatcher Rd., Gloucester, MA
Book a stay at this business-friendly hotel in Gloucester. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. ...
9.2/10 Wonderful! (386 reviews)
"Loved the view, the heated pool and the included breakfast! The staff was also very friendly!"

Reviewed on Aug 21, 2025

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The Vista
Atlantis Oceanfront Inn

Atlantis Oceanfront Inn

3 out of 5
125 Atlantic Road, Gloucester, MA
Stay at this 3-star beach motel in Gloucester. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff in our reviews. Popular ...
9.4/10 Exceptional! (431 reviews)
"The scenery"

Reviewed on Aug 19, 2025

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Atlantis Oceanfront Inn
Sea Lion Motel and Cottages

Sea Lion Motel and Cottages

2.5 out of 5
138 Eastern Avenue, Gloucester, MA
Book a stay at this business-friendly motel in Gloucester. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
9/10 Wonderful! (411 reviews)
Perfect spot!
"Great location, easy to find. The hotel/cottages were clean and welcoming. The pool area was perfect! The rooms were comfortable and the staff was very nice. Only stayed for 2 nights but wished we could have stayed longer! We Will definitely return!!!"

Reviewed on Aug 19, 2025

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Sea Lion Motel and Cottages
Sonesta Select Boston Danvers

Sonesta Select Boston Danvers

3 out of 5
275 Independence Way, Danvers, MA
Stay at this 3-star business-friendly hotel in Danvers. Enjoy free WiFi, an outdoor pool, and breakfast (surcharge). Our guests praise the helpful staff and ...
8.4/10 Very Good! (1,003 reviews)
"Travelled with my parents to take a quick trip to Salem. Loved that there was shopping right next door, also choice of restaurants nearby. They weren’t thrilled with the breakfast options, as they are used to more of a continental buffet style, but it met our needs for our first day and we found ..."

Reviewed on Aug 22, 2025

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Sonesta Select Boston Danvers
DoubleTree by Hilton Boston North Shore

DoubleTree by Hilton Boston North Shore

4 out of 5
50 Ferncroft Rd, Danvers, MA
Stay at this 4-star golf hotel in Danvers. Enjoy free parking, 2 restaurants, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms ...
8/10 Very Good! (2,075 reviews)
"Very inviting and convenient, staff members were friendly and welcoming. I enjoyed my stay there."

Reviewed on Aug 19, 2025

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DoubleTree by Hilton Boston North Shore
See all 1,764 properties in Gloucester
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.