Cheap flights To Gloucester (BOS) from $49

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Cheap Flights to Gloucester from $49 One Way, $89 Round Trip

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

Thu, Jan 14 - Thu, Jan 21
SFB
Orlando Sanford Intl.
PSM
Portsmouth Intl.
$89 Roundtrip, found 2 days ago
$89
Roundtrip
found 2 days ago
Select Allegiant Air flight, departing Thu, Jan 14 from Orlando Sanford Intl. to Portsmouth Intl., returning Thu, Jan 21, priced at $89 found 2 days ago
Thu, Jan 14 - Thu, Jan 21
SFB
Orlando Sanford Intl.
PSM
Portsmouth Intl.
$95 Roundtrip, found 6 hours ago
$95
Roundtrip
found 6 hours ago
Select Allegiant Air flight, departing Thu, Jan 14 from Orlando Sanford Intl. to Portsmouth Intl., returning Thu, Jan 21, priced at $95 found 6 hours ago
Thu, Jan 21 - Sun, Jan 24
SFB
Orlando Sanford Intl.
PSM
Portsmouth Intl.
$97 Roundtrip, found 11 hours ago
$97
Roundtrip
found 11 hours ago
Select Allegiant Air flight, departing Thu, Jan 21 from Orlando Sanford Intl. to Portsmouth Intl., returning Sun, Jan 24, priced at $97 found 11 hours ago
Thu, Jan 14 - Sun, Jan 17
SFB
Orlando Sanford Intl.
PSM
Portsmouth Intl.
$100 Roundtrip, found 16 hours ago
$100
Roundtrip
found 16 hours ago
Select Allegiant Air flight, departing Thu, Jan 14 from Orlando Sanford Intl. to Portsmouth Intl., returning Sun, Jan 17, priced at $100 found 16 hours ago
Sun, Jan 17 - Sun, Jan 24
SFB
Orlando Sanford Intl.
PSM
Portsmouth Intl.
$102 Roundtrip, found 9 hours ago
$102
Roundtrip
found 9 hours ago
Select Allegiant Air flight, departing Sun, Jan 17 from Orlando Sanford Intl. to Portsmouth Intl., returning Sun, Jan 24, priced at $102 found 9 hours ago
Thu, Jan 14 - Thu, Jan 21
SFB
Orlando Sanford Intl.
PSM
Portsmouth Intl.
$107 Roundtrip, found 1 day ago
$107
Roundtrip
found 1 day ago
Select Allegiant Air flight, departing Thu, Jan 14 from Orlando Sanford Intl. to Portsmouth Intl., returning Thu, Jan 21, priced at $107 found 1 day ago
Thu, Feb 4 - Sun, Feb 7
SFB
Orlando Sanford Intl.
PSM
Portsmouth Intl.
$110 Roundtrip, found 9 hours ago
$110
Roundtrip
found 9 hours ago
Select Allegiant Air flight, departing Thu, Feb 4 from Orlando Sanford Intl. to Portsmouth Intl., returning Sun, Feb 7, priced at $110 found 9 hours ago
Thu, Dec 10 - Sun, Dec 13
SFB
Orlando Sanford Intl.
PSM
Portsmouth Intl.
$119 Roundtrip, found 1 day ago
$119
Roundtrip
found 1 day ago
Select Allegiant Air flight, departing Thu, Dec 10 from Orlando Sanford Intl. to Portsmouth Intl., returning Sun, Dec 13, priced at $119 found 1 day ago
Thu, Jan 28 - Sun, Jan 31
SFB
Orlando Sanford Intl.
PSM
Portsmouth Intl.
$120 Roundtrip, found 6 hours ago
$120
Roundtrip
found 6 hours ago
Select Allegiant Air flight, departing Thu, Jan 28 from Orlando Sanford Intl. to Portsmouth Intl., returning Sun, Jan 31, priced at $120 found 6 hours ago
Thu, Jan 28 - Sun, Jan 31
RDU
Raleigh - Durham Intl.
PSM
Portsmouth Intl.
$122 Roundtrip, found 4 hours ago
$122
Roundtrip
found 4 hours ago
Select Breeze Airways flight, departing Thu, Jan 28 from Raleigh - Durham Intl. to Portsmouth Intl., returning Sun, Jan 31, priced at $122 found 4 hours ago

Gloucester Flight Information

Traveling To
Gloucester
Destination Airport IATA Code
BOS
Number of Airlines Serving
Airlines
Allegiant Air, Breeze Airways, Frontier Airlines
Flight Price
$89
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.
Boston Lodge and Suites
4.0-star property

Boston Lodge and Suites

Dec 11 - Dec 14

3 night stay

Austin (AUS) to Boston (BOS)

JetBlue Airways • Roundtrip • Coach
Price was $1,014, price is now $495 per person
$495
per person
found 1 day ago
Boston Harbor Hotel
5.0-star property

Boston Harbor Hotel

Dec 11 - Dec 14

3 night stay

Austin (AUS) to Boston (BOS)

JetBlue Airways • Roundtrip • Coach
Price was $1,513, price is now $940 per person
$940
per person
found 1 day ago
Four Seasons Hotel Boston
5.0-star property

Four Seasons Hotel Boston

Dec 23 - Dec 26

3 night stay

Austin (AUS) to Boston (BOS)

JetBlue Airways • Coach

Boston (BOS) to Austin (AUS)

Southwest Airlines • Coach
Price was $2,166, price is now $1,434 per person
$1,434
per person
found 6 hours ago
Don't see what you're looking for?
See all available trips from Austin to Gloucester
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Gloucester first class flight packages

Price found within the past 48 hours. Click for updated prices.
Boston Harbor Hotel
5.0-star property

Boston Harbor Hotel

9.8/10 Exceptional! (1,004 reviews)

Dec 26 - Jan 1

6 night stay

Charlotte (CLT) to Boston (BOS)

Delta • Roundtrip • FirstClass
Price was $3,159, price is now $2,122 per person
$2,122
per person
found 18 hours ago

Mandarin Oriental, Boston
5.0-star property

Mandarin Oriental, Boston

9.4/10 Exceptional! (465 reviews)

Dec 26 - Jan 1

6 night stay

Charlotte (CLT) to Boston (BOS)

Delta • Roundtrip • FirstClass
Price was $3,264, price is now $2,298 per person
$2,298
per person
found 18 hours ago
Overall Excellent! clean room, very nice staff

Reviewed on Nov 4, 2026

Raffles Boston
5.0-star property

Raffles Boston

9.6/10 Exceptional! (343 reviews)

Dec 26 - Jan 1

6 night stay

Charlotte (CLT) to Boston (BOS)

Delta • Roundtrip • FirstClass
Price was $3,279, price is now $2,347 per person
$2,347
per person
found 18 hours ago

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See all available trips from Charlotte to Gloucester
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Gloucester

Orbitz provides convenient, one-stop shopping for travelers looking for budget flights to Gloucester or any other low fare domestic or international air travel.

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You can find amazing discount fares with Orbitz’s guaranteed low prices or take advantage of last-minute sales and special travel packages. You can also earn points towards your airline frequent flyer programs when you book qualified flights to Gloucester. That means you can rack up money-saving points and miles for future use while saving money now.

We Are Just a Phone Call Away If You Need Us

Booking, changing, or canceling your Gloucester flights is a breeze with Orbitz’s online and mobile tools, but that doesn't mean that we leave you hanging if you want to speak with one of our representatives. If you need help, just contact our Customer Service by email or phone. To enjoy a less stressful trip, be sure to sign up for instant alerts so we can send you any updates or delays relating to your flights to Gloucester to your mobile phone or email.

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 $89 and $122. If you were traveling one-way out of Orlando (SFB), you could have nabbed ticket prices from just $49.
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.