Cheap flights To Gloucester (BOS) from $51

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Cheap Flights to Gloucester from $51 One Way, $112 Round Trip

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

Thu, Sep 3 - Thu, Sep 10
RDU
Raleigh - Durham Intl.
PSM
Portsmouth Intl.
$112 Roundtrip, just found
$112
Roundtrip
just found
Select Breeze Airways flight, departing Thu, Sep 3 from Raleigh - Durham Intl. to Portsmouth Intl., returning Thu, Sep 10, priced at $112 just found
Thu, Sep 24 - Sun, Sep 27
RDU
Raleigh - Durham Intl.
PSM
Portsmouth Intl.
$117 Roundtrip, found 2 days ago
$117
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Thu, Sep 24 from Raleigh - Durham Intl. to Portsmouth Intl., returning Sun, Sep 27, priced at $117 found 2 days ago
Thu, Sep 24 - Sun, Sep 27
RDU
Raleigh - Durham Intl.
PSM
Portsmouth Intl.
$122 Roundtrip, found 5 days ago
$122
Roundtrip
found 5 days ago
Select Breeze Airways flight, departing Thu, Sep 24 from Raleigh - Durham Intl. to Portsmouth Intl., returning Sun, Sep 27, priced at $122 found 5 days ago
Thu, Sep 17 - Sun, Sep 20
RDU
Raleigh - Durham Intl.
PSM
Portsmouth Intl.
$127 Roundtrip, found 1 hour ago
$127
Roundtrip
found 1 hour ago
Select Breeze Airways flight, departing Thu, Sep 17 from Raleigh - Durham Intl. to Portsmouth Intl., returning Sun, Sep 20, priced at $127 found 1 hour ago
Sat, Jun 6 - Wed, Jun 10
RDU
Raleigh - Durham Intl.
BOS
Logan Intl.
$128 Roundtrip, found 2 days ago
$128
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Sat, Jun 6 from Raleigh - Durham Intl. to Logan Intl., returning Wed, Jun 10, priced at $128 found 2 days ago
Mon, Jun 1 - Sat, Jun 6
RDU
Raleigh - Durham Intl.
BOS
Logan Intl.
$132 Roundtrip, found 3 days ago
$132
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Mon, Jun 1 from Raleigh - Durham Intl. to Logan Intl., returning Sat, Jun 6, priced at $132 found 3 days ago
Thu, May 28 - Thu, Jun 4
MCO
Orlando Intl.
PSM
Portsmouth Intl.
$136 Roundtrip, found 4 days ago
$136
Roundtrip
found 4 days ago
Select Breeze Airways flight, departing Thu, May 28 from Orlando Intl. to Portsmouth Intl., returning Thu, Jun 4, priced at $136 found 4 days ago
Sat, Jun 13 - Sat, Jul 4
RDU
Raleigh - Durham Intl.
BOS
Logan Intl.
$137 Roundtrip, found 6 days ago
$137
Roundtrip
found 6 days ago
Select Frontier Airlines flight, departing Sat, Jun 13 from Raleigh - Durham Intl. to Logan Intl., returning Sat, Jul 4, priced at $137 found 6 days ago
Thu, May 28 - Thu, Jun 4
MCO
Orlando Intl.
PSM
Portsmouth Intl.
$139 Roundtrip, found 6 days ago
$139
Roundtrip
found 6 days ago
Select Breeze Airways flight, departing Thu, May 28 from Orlando Intl. to Portsmouth Intl., returning Thu, Jun 4, priced at $139 found 6 days ago
Thu, May 28 - Thu, Jun 4
MCO
Orlando Intl.
PSM
Portsmouth Intl.
$141 Roundtrip, found 6 days ago
$141
Roundtrip
found 6 days ago
Select Breeze Airways flight, departing Thu, May 28 from Orlando Intl. to Portsmouth Intl., returning Thu, Jun 4, priced at $141 found 6 days ago

Gloucester Flight Information

Traveling To
Gloucester
Destination Airport IATA Code
BOS
Number of Airlines Serving
Airlines
Breeze Airways, Frontier Airlines
Flight Price
$112
Earliest Departing Flight
Latest Departing Flight

Book Your Flight & Hotel Together & Save

Gloucester economy flight packages

Price found within the past 48 hours. Click for updated prices.
Hotel Ivy Boston Common
2.5-star property

Hotel Ivy Boston Common

Jul 6 - Jul 8

2 night stay

Cleveland (CLE) to Boston (BOS)

United • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $679, price is now $449 per person
$449
per person
found 1 day ago
Meco Hotel - Hostel
2.0-star property

Meco Hotel - Hostel

Jul 6 - Jul 8

2 night stay

Cleveland (CLE) to Boston (BOS)

United • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $1,041, price is now $687 per person
$687
per person
found 1 day ago
Luxury Apartments by Hyatus at Boston Everett
5.0-star property

Luxury Apartments by Hyatus at Boston Everett

Jul 10 - Jul 15

5 night stay

Cleveland (CLE) to Boston (BOS)

United • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $1,954, price is now $1,295 per person
$1,295
per person
found 4 hours ago
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See all available trips from Cleveland to Gloucester
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Gloucester first class flight packages

Price found within the past 48 hours. Click for updated prices.
Sunbird ANNEX Resort
2.0-star property

Sunbird ANNEX Resort

7.8/10 Good! (826 reviews)

Jun 30 - Jul 6

6 night stay

Chicago (ORD) to Boston (BOS)

American Airlines • Non-stop roundtrip • FirstClass
Price was $1,317, price is now $1,026 per person
$1,026
per person
found 15 hours ago
nice, cozy, not big room, with everything you need. friendly staff, I give 4 stars only for dirty floors

Reviewed on Aug 5, 2025

Bayside Resort Hotel
3.0-star property

Bayside Resort Hotel

8.8/10 Excellent! (1,558 reviews)

Jun 30 - Jul 6

6 night stay

Chicago (ORD) to Boston (BOS)

American Airlines • Non-stop roundtrip • FirstClass
Price was $1,708, price is now $1,352 per person
$1,352
per person
found 15 hours ago
We have stayed before. This time we upgraded to a balcony room. I was glad we did because I was able to sit outside for coffee in the morning and cocktails in the evening. The room was clean and had everything we needed. Seems bigger than the regular 2 queen rooms.

Reviewed on Apr 26, 2026

Sunbird Cape Cod Resort
2.5-star property

Sunbird Cape Cod Resort

7.8/10 Good! (535 reviews)

Jun 30 - Jul 6

6 night stay

Chicago (ORD) to Boston (BOS)

American Airlines • Non-stop roundtrip • FirstClass
Price was $1,386, price is now $1,111 per person
$1,111
per person
found 15 hours ago
The room had a stain on the bed sheet and there was a strange scent to the room

Reviewed on Oct 12, 2025

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Gloucester

Orbitz is your one stop for guaranteed low prices on Gloucester flights, as well as budget deals on hotels and rental cars. Use our state of the art mobile tools to get great deals and constant updates on the status of your trip.

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Orbitz will find you discount air fare for flights to Gloucester and you can rent a car at the same time. With Orbitzyou will get a discount on the rental and have your car waiting for you when you land.

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Our experts will make things even easier by helping you to find the best budget flights to Gloucester Just call our toll free hotline at 1-800-649-9920 and one of our travel advisors will be happy to assist you with everything from your flight to hotel room.

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Our state of the art mobile apps will allow you to book cheap flights to Gloucester from your smartphone too. Discount airfare is not all; you can also find mobile-only hotel deals or check the status of your flight using this free app. So, when you’re on the go, why not take Orbitz with you?

Frequently asked questions

Which airlines fly to Gloucester?
With 20 airlines operating services to Logan Intl. Airport (BOS), the gateway to Gloucester, you have loads of options. Land a fabulous deal among these popular international airlines that'll get you to this city:

  • JetBlue - 175 flights to Gloucester per month
  • Delta - 158 flights to Gloucester per month
  • Air Canada - 151 flights to Gloucester per month

What is the best airport to fly to in Gloucester?
Logan Intl. Airport (BOS). It's the city's main airport and is located around 25 miles southwest of the downtown area. You'll be unpacking your bags and discovering the best of Gloucester not long after touching down.
How much is a flight to Gloucester?
Prices for return flights to Gloucester this week ranged between $112 and $141. If you were traveling one-way out of Orlando (MCO), you could have nabbed ticket prices from just $51.
How to book the cheapest flight to Gloucester?
With some of the most impressive flight deals around, you'll always bag a bargain with Orbitz. The following useful tips will help you pick up cheap flights to Gloucester — and leave you with more money in your pocket:

  • Departing from or landing at nearby airports may save you money. Type in your preferred departure and arrival airports. Next, select the 'Nearby airports' function below the form fields to see what your options are.
  • Also, click on the 'Show flexible dates' option to view the prices on days either side of your chosen departure. You may be able to pick up cheaper flight deals if you're flexible with your dates.
  • You can also use the 'Show options' link to filter results for your preferred airline, seating class, nonstop flights and refundable flights. Under 'Sort & Filter' to the left, you can even choose the time of day you'd prefer to fly.
  • The early bird catches the best deals, so purchase your seats once you've settled on your travel dates. The cheapest airfares sell out first and prices increase as the departure date nears.
  • Think about bundling your hotels, flights and car rental into a package with Orbitz to make your dollar go further.
  • Flying during busier seasons often means expensive airfares. If possible, plan your trip outside of popular periods, such as Thanksgiving, New Year's Eve and Easter.

How long is a flight to Gloucester?
The duration of your flight will depend on where you're setting off from, whether that's the Northern states, the South or anywhere else. Listed below are some of the busiest routes to Gloucester and how long they take:

  • Washington, DC (DCA-Ronald Reagan Washington National) to Logan Intl. Airport (BOS) - 1 hour and 44 minutes
  • New York, NY (LGA-LaGuardia) to Logan Intl. Airport (BOS) - 1 hour and 34 minutes
  • New York, NY (JFK-John F. Kennedy Intl.) to Logan Intl. Airport (BOS) - 1 hour and 17 minutes

What is the best time to book a flight to Gloucester?
Generally speaking, the cheapest time to book your airfare is in January. This is closely followed by February and August. When seeking a cheap flight to Gloucester, it's always good to be ready to book. Cheap deals appear in an instant and don't hang around!
What day of the week is the cheapest to book a flight to Gloucester?
You can get a great flight deal by booking on a Tuesday, Wednesday or Saturday. These are typically the best days of the week to pick up cheap airfares to Gloucester.
What is the cheapest day of the week to fly to Gloucester?
Everyone enjoys a bargain, so we suggest setting off earlier in the week for cheap flights to Gloucester. Orbitz data from 2020 shows you can score the best deals on flights that take off on Mondays. Tuesdays are the next cheapest day, while Saturdays are likely to cost an arm and a leg. Many passengers prefer to travel on weekends, so leave those Saturdays for catching up with pals.
What is the cheapest month to fly to Gloucester?
Consider jetting off in August if you're on a tight budget. Orbitz data shows that this is generally the best month for cheap flights to Gloucester. June is when ticket prices are at their most expensive.
Which airlines allow free cancellation?
We know that plans can change and flexibility matters. That's why you can search for flights that include free cancellation and no change fees on Orbitz. Just click on "Filter by flexible change policies" and we'll show you fares more flexible than a lip balm left in the sun!
What do I need for the flight to Gloucester?
The trick to a comfortable flight is being well prepared. Here are some of our top tips that'll help get you ready for your adventure:

  • Before you board the plane, you'll need to present a valid form of government ID, such as your passport. You'll also need your boarding pass. If you're traveling with kids, check with your airline about which documents they may need.
  • Take some activities to keep you entertained on your journey to Gloucester. Magazines, books and devices like e-readers and tablets are good ideas. Remember to take a refillable water bottle too. Even on short flights, it's important to stay well-hydrated.
  • Even if you're flying when it's 90 degrees outside, carry a hoodie or sweater on board with you. Cabins are notorious for getting chilly!

How many direct flights are there to Gloucester?
Your exciting adventure is one easy plane trip away, with 1,287 direct flights to Gloucester every month. Search for a suitable flight with Orbitz and lock in a fantastic deal with JetBlue Airways, Delta Air Lines or American Airlines. Other popular airlines that provide nonstop services include Cape Air, United Airlines and Southwest Airlines.
How do I get cheap first-class/business deals to Gloucester?
Savvy travelers have a knack for finding business or first-class flights to Gloucester that don't cost an arm and a leg. Be like them with these useful tips:

  • Be more flexible with your travel dates and wait for sales on first or business-class airfares.
  • Many low-cost carriers have comfortable business or premium-class seating that doesn't cost an arm and a leg.
  • Bid for an upgrade. Some airlines hold online auctions that let you offer a price for a seat at the front of the plane. You can also try upgrading with points earned through a flight rewards program.

How to get into Gloucester from the airport?
If you prefer the convenience of having your own wheels, reserve a Logan Intl. Airport (BOS) car rental with one of the reputable providers at Logan Intl. Airport (BOS). Enterprise and Advantage Rent-A-Car have some terrific vehicles to pick from. Once you've collected your wheels, the center of Gloucester is around 25 miles to the northeast. Or, you might prefer to take a taxi into town and rent a car from the downtown area after you've explored the area on foot? Gloucester car rentals always has plenty of great offers available.
What is the best time to go to Gloucester?
You'll have all the fun you can handle no matter what time of year you decide to go to Gloucester, but June, July and August are the liveliest months. Like to fill up your schedule with warm-weather experiences? Book your trip close to June 20. This is when the summer season kicks off in the Northern Hemisphere. Expect the mercury to hover between 65 ºF and 70 ºF during this time.
Travel tips for Gloucester

  • Slip into your most comfy sneakers and tour this city on foot. There are tons of top attractions to make your way to, such as Good Harbor Beach and Wingaersheek Beach.
  • You'll also want to check out the sights a short drive from Gloucester's center. Find your way to Fenway Park and TD Garden and experience a different side of this awesome destination.
  • Slip into the driver's seat and discover what else makes Massachusetts a magnet for travelers. Arrange a car rental with Orbitz and check out the wonders of two other fabulous cities — Springfield and Worcester.

More to Explore

Fare, taxes & fees: Fares include all taxes and fees, except baggage fees. Rates shown reflect fares found by other Orbitz users over the past 7 days. Due to rapidly changing airline prices & seat availability, these fares may no longer be available.

Refunds/changes/cancellations: Itinerary changes, if permitted for the fare, will have a $30 service fee charged by Orbitz. Additional airline charges may apply.

Other conditions: Schedules, fares and rules are subject to change without notice. Seats are limited and may not be available on all flights/dates or in all markets. Lower fares may be available. Fares will not be honored retroactively or in exchange for any wholly/partially unused ticket. Tickets are non-transferable and non-refundable. Fare rules are provided for the selected itinerary before booking.