Cheap Flight Deals to Gloucester MA from CA $155

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How to find cheap flights to Gloucester?

The cheapest prices found with in the last 7 days for return flights were CA $265 and CA $155 for one-way flights to Gloucester for the period specified. Prices and availability are subject to change. Additional terms apply

OriginDestinationTravel datesFlights from*
LAXBostonOctober 23 to October 29CA $265
PDXBostonSeptember 11 to September 15CA $511
PEKBostonOctober 8 to October 24CA $1,265
HKGBostonSeptember 8 to September 21CA $1,311
*Prices include taxes and fees
OriginDestinationTravel datesFlights from*
LAXBostonAugust 1 to August 6CA $449
*Prices include taxes and fees

Your guide to flights to Gloucester, MA

Porter Airlines, Air Canada fly to Gloucester, so use Travelocity to search, find, and compare some truly tempting deals from the 2 airlines—that way you can be sure you’ve found the best deal for you. A flight to Gloucester MA currently costs between CA $265 and CA $1,311. Prices vary, but for the best fares, travel in October when prices are at their lowest.  

Top tips for finding cheap flights to Gloucester  

The cheapest flight for a round trip to Gloucester is currently CA $265. When you search for flights to Gloucester, enter your preferred travel dates then click on ‘flexible dates’ to compare cheap flight tickets to Gloucester for nearby days.  The cheapest month to travel to Gloucester is September from our list of deals available.  

But if you’re flexible about when you travel, you can find great deals on flights across the year. If you’re planning a vacation, you can save more on Travelocity when you bundle flights with car rental and hotel bookings, too. Many airlines currently offer flexible booking options, so look for flights offering no change fees.   

How to cancel flights to Gloucester 

We know plans change, that’s why at Travelocity, we make it as easy as possible for you to cancel or amend your plane tickets. Go to My Trips, enter your itinerary number, then follow the instructions. Many airlines let you cancel flights online free of charge if you booked it in the last 24 hours. Visit Customer Service for more advice.  

Why you should book your flight to Gloucester with Travelocity 

We have top deals on plane tickets even for last minute flights to Gloucester, so you can simply type in your travel dates and compare our best prices. Booking with Travelocity means you get flexible cancellation options, 24/7 support, and, thanks to our Price Match Promise, if the airfare drops after you book, you can get a refund! Whether you’re planning a business trip, weekend getaway, or a family vacation—let Travelocity get you to Gloucester for less. 

Find The Perfect Hotel For After Your Flight

Luxury Hotels in Gloucester

Castle Manor Inn

Castle Manor Inn

2.5 out of 5
141 Essex Avenue, Gloucester, MA
The price is CA $222 per night from Aug 7 to Aug 8
CA $222
CA $248 total
Aug 7 - Aug 8
includes taxes & fees
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! (1,006 reviews)
"Check in was easy, and friendly. The room was clean and looked like it went through some updating. The tv was small and the cable service was old school. It could definitely use some updating. It would be nice if the tiny refrigerator wasn’t on the floor. Our balcony had a nice view and the window ..."

Reviewed on Jul. 27, 2025

Castle Manor Inn
The Vista

The Vista

2.5 out of 5
22 Thatcher Rd., Gloucester, MA
The price is CA $406 per night from Aug 10 to Aug 11
CA $406
CA $454 total
Aug 10 - Aug 11
includes taxes & fees
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! (381 reviews)
Great place
"Friendly, very clean and easy access! The breakfast was awesome"

Reviewed on Jul. 15, 2025

The Vista
Sea Lion Motel and Cottages

Sea Lion Motel and Cottages

2.5 out of 5
138 Eastern Avenue, Gloucester, MA
The price is CA $241 per night from Jul 31 to Aug 1
CA $241
CA $269 total
Jul 31 - Aug 1
includes taxes & fees
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! (401 reviews)
A few minor changes needed.
"The included breakfast is takeaway muffins, yogurt, and snack bars; there isn’t a dining area. The bathroom fan is very noisy and connected to the light via a single switch. The switch can’t be turned on at night as the fan noise will awaken anyone sleeping."

Reviewed on Jul. 28, 2025

Sea Lion Motel and Cottages
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.

Family Friendly Hotels in Gloucester

The Vista

The Vista

2.5 out of 5
22 Thatcher Rd., Gloucester, MA
The price is CA $406 per night from Aug 10 to Aug 11
CA $406
CA $454 total
Aug 10 - Aug 11
includes taxes & fees
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! (381 reviews)
Great place
"Friendly, very clean and easy access! The breakfast was awesome"

Reviewed on Jul. 15, 2025

The Vista
Ocean House Hotel at Bass Rocks

Ocean House Hotel at Bass Rocks

4 out of 5
107 Atlantic Rd, Gloucester, MA
The price is CA $456 per night from Aug 25 to Aug 26
CA $456
CA $542 total
Aug 25 - Aug 26
includes taxes & fees
Stay at this 4-star golf hotel in Gloucester. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff in our reviews. Popular ...
9/10 Wonderful! (721 reviews)
"Gorgeous views."

Reviewed on Jul. 22, 2025

Ocean House Hotel at Bass Rocks
Atlantis Oceanfront Inn

Atlantis Oceanfront Inn

3 out of 5
125 Atlantic Road, Gloucester, MA
The price is CA $446 per night from Aug 25 to Aug 26
CA $446
CA $498 total
Aug 25 - Aug 26
includes taxes & fees
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! (427 reviews)
"Oceanview"

Reviewed on Jul. 26, 2025

Atlantis Oceanfront Inn
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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! (863 reviews)
"Loved everything, oceanside boujiness, friendly staff, great meals !"

Reviewed on Jul. 25, 2025

Beauport Hotel 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.

Best Gloucester Flight and Hotel Packages

Gloucester flight + hotel packages - economy flights

Price found within the past 48 hours. Click for updated prices.
Encore Boston Harbor
Raffles Boston
Mandarin Oriental, Boston
Don't see what you're looking for?
See all available trips from Toronto to Gloucester
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Gloucester flight + hotel packages - business class flights

Price found within the past 48 hours. Click for updated prices.
DoubleTree Suites by Hilton Hotel Boston - Cambridge
Hilton Garden Inn Boston Brookline, MA
Hilton Boston Logan Airport
Don't see what you're looking for?
See all available trips from Toronto to Gloucester
View all trips

Gloucester flight + hotel packages - first class flights

Price found within the past 48 hours. Click for updated prices.
The Langham, Boston
Raffles Boston
Boston Harbor Hotel
Don't see what you're looking for?
See all available trips from Toronto to Gloucester
View all trips

Need a car after flight to Gloucester?

Frequently asked questions

Which airlines fly to Gloucester?
All ready to wander the world? Hoping to kick off your adventure in Gloucester? Some of the 20 airlines that fly here include:

  • Delta Air Lines
  • JetBlue Airways
  • American Airlines

What airport is best to fly into Gloucester?
Logan Intl. Airport is approximately 40 kilometers from downtown Gloucester. It's the only airport in the city, so you don't have to worry about your cab driver delivering you to the wrong one!
Where to stay in Gloucester
Few things are as enjoyable as sliding into bed after a huge day of seeing the sights. With an impressive 541 properties in Gloucester, you can take your pick of the cushiest of them.Looking for someplace to get some rest in Gloucester? The Beauport Hotel Gloucester and the Julietta House are some of our favorite properties in the area.
Places to visit in Gloucester
0 Seeking some more options? 0 But that's not all there is. 0
How to get through airport security fast when traveling to Gloucester
Make your flight to Gloucester a little easier by following these clever security tips:

  • Keep your passport and boarding pass in an easily accessible place. They'll be the first things you'll be asked for by airport security personnel.
  • Be aware that belts with metal buckles can set off the body scanner's alarms. If you have one on, you may be told to step back and remove it before continuing.
  • Laptops and other electronic devices must be placed in separate bins to be X-rayed.
  • Toothpaste, lip balm and other toiletry items in cream, liquid or gel form need to be stored in containers no larger than 3.4 ounces (100 milliliters). They also need to fit in a 1-quart (1-liter) clear zip-lock plastic bag.
  • Untie your shoelaces as you approach the body scanner. Depending on what sort of shoes you're wearing, security may tell you to remove them.
  • Pocketknives and corkscrews are prohibited from entering the plane. Stash them away in your checked luggage to avoid leaving them at the airport security checkpoint.

Plane Tickets To Gloucester

Although you may try and resist the urge, you know that when the travel bug comes, there is only one way to get rid of it. Thankfully, Travelocity is here to help nip that travel bug in the bud with great deals on flights to Gloucester. Browse through our inventory to explore a wide range of cheap flights to Gloucester to solidify your next big trip out of town. Whether you are heading out on a business trip, exploring a place you have never been for pleasure or are bringing the family on the annual vacation, we have the perfect getaway waiting for you. In no time, you will be day dreaming of your plane landing in Gloucester as you anxiously await to exit the plane and explore what Gloucester has to offer. Considering all the amazing local food and culture in Gloucester, we won't hold this against you.

When you are ready to embark on your next big adventure, Travelocity will be right here waiting to open the doors to the garden so that you can go and smell the roses. When you decide to book and travel is entirely up to you, but don't wait too long because we have some of the best deals on the web and they won't last long. Take time to go through our huge selection of cheap flights to Gloucester to find the best deals that fit into your budget. If browsing on your phone while your boss isn't looking is more your thing (we promise we won't tell), consider checking out Travelocity's mobile app which allows you to take advantage of all our flights to Gloucester without having to compromise your work computer's search history. If you are looking to save even more, you can easily save up to $537 when you bundle one of our cheap flights to Gloucester with one of our hotels. So why are you waiting around? There is no better time than now to start booking that next trip. Start your search now to book one of our flights to Gloucester today!

*Price based on the lowest price found within past 24 hours and based upon one night stay for two adults over the next thirty days. Prices and availability subject to change. Additional terms may apply.