Cheap flights To Gloucester (BOS) from $51

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Cheap Flights to Gloucester from $51 One Way, $92 Round Trip

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

Thu, Jan 7 - Thu, Jan 21
SFB
Orlando Sanford Intl.
PSM
Portsmouth Intl.
$92 Roundtrip, found 1 day ago
$92
Roundtrip
found 1 day ago
Select Allegiant Air flight, departing Thu, Jan 7 from Orlando Sanford Intl. to Portsmouth Intl., returning Thu, Jan 21, priced at $92 found 1 day ago
Thu, Jan 7 - Sun, Jan 10
SFB
Orlando Sanford Intl.
PSM
Portsmouth Intl.
$102 Roundtrip, found 7 hours ago
$102
Roundtrip
found 7 hours ago
Select Allegiant Air flight, departing Thu, Jan 7 from Orlando Sanford Intl. to Portsmouth Intl., returning Sun, Jan 10, priced at $102 found 7 hours ago
Sun, Jan 10 - Sun, Jan 17
SFB
Orlando Sanford Intl.
PSM
Portsmouth Intl.
$110 Roundtrip, found 6 hours ago
$110
Roundtrip
found 6 hours ago
Select Allegiant Air flight, departing Sun, Jan 10 from Orlando Sanford Intl. to Portsmouth Intl., returning Sun, Jan 17, priced at $110 found 6 hours ago
Sun, Nov 1 - Sun, Nov 8
RDU
Raleigh - Durham Intl.
PSM
Portsmouth Intl.
$112 Roundtrip, found 6 hours ago
$112
Roundtrip
found 6 hours ago
Select Breeze Airways flight, departing Sun, Nov 1 from Raleigh - Durham Intl. to Portsmouth Intl., returning Sun, Nov 8, priced at $112 found 6 hours ago
Sun, Nov 1 - Sun, Nov 8
RDU
Raleigh - Durham Intl.
PSM
Portsmouth Intl.
$117 Roundtrip, found 6 hours ago
$117
Roundtrip
found 6 hours ago
Select Breeze Airways flight, departing Sun, Nov 1 from Raleigh - Durham Intl. to Portsmouth Intl., returning Sun, Nov 8, priced at $117 found 6 hours ago
Sat, Jan 16 - Sat, Jan 23
MCO
Orlando Intl.
PSM
Portsmouth Intl.
$117 Roundtrip, found 5 days ago
$117
Roundtrip
found 5 days ago
Select Breeze Airways flight, departing Sat, Jan 16 from Orlando Intl. to Portsmouth Intl., returning Sat, Jan 23, priced at $117 found 5 days ago
Sun, Nov 1 - Sun, Nov 8
RDU
Raleigh - Durham Intl.
PSM
Portsmouth Intl.
$122 Roundtrip, found 6 hours ago
$122
Roundtrip
found 6 hours ago
Select Breeze Airways flight, departing Sun, Nov 1 from Raleigh - Durham Intl. to Portsmouth Intl., returning Sun, Nov 8, priced at $122 found 6 hours ago
Sat, Oct 31 - Sun, Nov 8
MCO
Orlando Intl.
PSM
Portsmouth Intl.
$123 Roundtrip, found 1 day ago
$123
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Sat, Oct 31 from Orlando Intl. to Portsmouth Intl., returning Sun, Nov 8, priced at $123 found 1 day ago
Sun, Jan 10 - Thu, Jan 14
SFB
Orlando Sanford Intl.
PSM
Portsmouth Intl.
$126 Roundtrip, found 5 days ago
$126
Roundtrip
found 5 days ago
Select Allegiant Air flight, departing Sun, Jan 10 from Orlando Sanford Intl. to Portsmouth Intl., returning Thu, Jan 14, priced at $126 found 5 days ago
Sat, Oct 31 - Sun, Nov 8
MCO
Orlando Intl.
PSM
Portsmouth Intl.
$128 Roundtrip, found 1 day ago
$128
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Sat, Oct 31 from Orlando Intl. to Portsmouth Intl., returning Sun, Nov 8, priced at $128 found 1 day ago

Gloucester Flight Information

Traveling To
Gloucester
Destination Airport IATA Code
BOS
Number of Airlines Serving
Airlines
Breeze Airways, Allegiant Air, Frontier Airlines
Flight Price
$92
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 Harbor Hotel
5.0-star property

Boston Harbor Hotel

Oct 2 - Oct 4

2 night stay

Minneapolis (MSP) to Boston (BOS)

Delta • Roundtrip • Coach
Save 100% on your flight
Price was $1,576, price is now $1,136 per person
$1,136
per person
found 1 day ago
The Onset Beach Compound-Cape Cod Beach Resort & Oceanic Habitat
3.0-star property

The Onset Beach Compound-Cape Cod Beach Resort & Oceanic Habitat

Sep 24 - Sep 28

4 night stay

Minneapolis (MSP) to Boston (BOS)

United • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $2,343, price is now $1,730 per person
$1,730
per person
found 1 day ago
Chatham Tides
2.5-star property

Chatham Tides

Oct 1 - Oct 4

3 night stay

Minneapolis (MSP) to Boston (BOS)

Delta • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $1,584, price is now $1,193 per person
$1,193
per person
found 9 hours ago
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Gloucester premium economy flight packages

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

The Charles Hotel

9.4/10 Exceptional! (1,006 reviews)

Sep 25 - Sep 27

2 night stay

Chicago (ORD) to Boston (BOS)

JetBlue Airways • Roundtrip • PremiumEconomy
Price was $1,437, price is now $1,088 per person
$1,088
per person
found 2 days ago
Check in was easy and room was available earlier than expected. Bell service was helpful at check in and out, and the car loop was helpful for even rainy day loading/unloading. The room was spotless, well-maintained, and high quality. The smaller size was well managed and organized well even for a family of four. Small extras of free snacks and Path waters were welcomed by our kids after a long flight on a hot day. Location is great (but it was extremely quiet inside despite being in a very lively area) and restaurants in-house were easy and delicious. Many nooks and books for reading or hanging out between events. All around great hotel in a great location!

Reviewed on Aug 10, 2026

Good Hotels Boston
2.0-star property

Good Hotels Boston

8/10 Very Good! (55 reviews)

Sep 24 - Sep 28

4 night stay

Chicago (ORD) to Boston (BOS)

JetBlue Airways • PremiumEconomy

Boston (BOS) to Chicago (ORD)

Frontier Airlines • PremiumEconomy
Price was $1,982, price is now $1,308 per person
$1,308
per person
found 1 day ago
Very nice people and had excellent help!

Reviewed on Aug 7, 2026

Hotel AKA Back Bay
4.5-star property

Hotel AKA Back Bay

9.4/10 Exceptional! (1,272 reviews)

Sep 24 - Sep 28

4 night stay

Chicago (ORD) to Boston (BOS)

JetBlue Airways • PremiumEconomy

Boston (BOS) to Chicago (ORD)

Frontier Airlines • PremiumEconomy
Price was $2,018, price is now $1,524 per person
$1,524
per person
found 1 day ago

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Gloucester first class flight packages

Price found within the past 48 hours. Click for updated prices.
Eurostars The Boxer
4.0-star property

Eurostars The Boxer

8.8/10 Excellent! (1,549 reviews)

Oct 1 - Oct 4

3 night stay

Minneapolis (MSP) to Boston (BOS)

American Airlines • Non-stop roundtrip • FirstClass
Price was $1,660, price is now $1,408 per person
$1,408
per person
found 1 day ago
Great location a lot of money for what you get safe area shower not the best

Reviewed on Aug 10, 2026

The Langham, Boston
5.0-star property

The Langham, Boston

9.6/10 Exceptional! (1,002 reviews)

Oct 1 - Oct 4

3 night stay

Minneapolis (MSP) to Boston (BOS)

American Airlines • Non-stop roundtrip • FirstClass
Price was $2,096, price is now $1,562 per person
$1,562
per person
found 1 day ago
Beautiful hotel in a perfect location in Boston. Quiet yet walkable to everything you might want from history to water to public transport. The staff are helpful and the bar is excellent

Reviewed on Aug 9, 2026

Boston Harbor Hotel
5.0-star property

Boston Harbor Hotel

9.8/10 Exceptional! (1,006 reviews)

Oct 1 - Oct 4

3 night stay

Minneapolis (MSP) to Boston (BOS)

American Airlines • Non-stop roundtrip • FirstClass
Price was $2,592, price is now $1,969 per person
$1,969
per person
found 1 day ago

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Gloucester

Orbitz uses cutting edge mobile technology to help get you the best deals on Gloucester flights. We offer guaranteed low prices on air tickets that can be combined with hotels and car rentals to save you even more money.

Find Cheap Gloucester Flights And Hotel Rooms Using Our Mobile App

Orbitz not only guarantees low prices for flights to Gloucester, we also offer Mobile Steals on our Orbitz on the Go mobile app where you can find great mobile-only deals on hotel rooms in the area.

Use the Orbitz Flight Matrix To Save Big On Car Rental

Discount flights to Gloucester can be combined with car rental to get you additional savings. Just use our Flight Matrix to see how your budget air ticket can be combined with a car rental to make your trip not only inexpensive but also more convenient.

Use Multiple Airlines To Ensure You Get The Best Deal

Orbitz allows you to use multiple airlines for flights to Gloucester. By using a combination of airlines for discount flights you are guaranteed to get the lowest fares each way and get the schedule that is most convenient for you.

Store Your Frequent Flyer Information on Orbitz For Easy Access

Booking with Orbitz will still allow you to apply miles for flights to Gloucester to your frequent flyer program. Not only that, but your frequent flyer information will be safely stored on our website, so it will be easy to access the next time you book a discount air ticket with Orbitz.

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 $92 and $128. If you were traveling one-way out of Raleigh (RDU), 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.