Cheap flights To Gloucester (BOS) from $119

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Cheap Flights to Gloucester from $119 One Way, $117 Round Trip

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

Wed, Sep 30 - Wed, Oct 7
DCA
Ronald Reagan Washington National
BOS
Logan Intl.
$117 Roundtrip, found 2 hours ago
$117
Roundtrip
found 2 hours ago
Select JetBlue Airways flight, departing Wed, Sep 30 from Ronald Reagan Washington National to Logan Intl., returning Wed, Oct 7, priced at $117 found 2 hours ago
Wed, Aug 26 - Sat, Sep 5
DCA
Ronald Reagan Washington National
BOS
Logan Intl.
$117 Roundtrip, found 5 hours ago
$117
Roundtrip
found 5 hours ago
Select American Airlines flight, departing Wed, Aug 26 from Ronald Reagan Washington National to Logan Intl., returning Sat, Sep 5, priced at $117 found 5 hours ago
Wed, Jul 22 - Wed, Jul 29
DCA
Ronald Reagan Washington National
BOS
Logan Intl.
$120 Roundtrip, found 1 hour ago
$120
Roundtrip
found 1 hour ago
Select JetBlue Airways flight, departing Wed, Jul 22 from Ronald Reagan Washington National to Logan Intl., returning Wed, Jul 29, priced at $120 found 1 hour ago
Wed, Aug 26 - Sat, Sep 5
DCA
Ronald Reagan Washington National
BOS
Logan Intl.
$148 Roundtrip, found 5 hours ago
$148
Roundtrip
found 5 hours ago
Select Delta flight, departing Wed, Aug 26 from Ronald Reagan Washington National to Logan Intl., returning Sat, Sep 5, priced at $148 found 5 hours ago
Thu, Sep 17 - Wed, Sep 23
DCA
Ronald Reagan Washington National
BOS
Logan Intl.
$152 Roundtrip, found 6 days ago
$152
Roundtrip
found 6 days ago
Select JetBlue Airways flight, departing Thu, Sep 17 from Ronald Reagan Washington National to Logan Intl., returning Wed, Sep 23, priced at $152 found 6 days ago
Sat, Sep 19 - Mon, Sep 21
DCA
Ronald Reagan Washington National
BOS
Logan Intl.
$156 Roundtrip, just found
$156
Roundtrip
just found
Select JetBlue Airways flight, departing Sat, Sep 19 from Ronald Reagan Washington National to Logan Intl., returning Mon, Sep 21, priced at $156 just found
Wed, Jul 29 - Thu, Aug 6
DCA
Ronald Reagan Washington National
BOS
Logan Intl.
$160 Roundtrip, found 8 hours ago
$160
Roundtrip
found 8 hours ago
Select JetBlue Airways flight, departing Wed, Jul 29 from Ronald Reagan Washington National to Logan Intl., returning Thu, Aug 6, priced at $160 found 8 hours ago
Tue, Oct 13 - Sun, Oct 18
DCA
Ronald Reagan Washington National
BOS
Logan Intl.
$167 Roundtrip, just found
$167
Roundtrip
just found
Select JetBlue Airways flight, departing Tue, Oct 13 from Ronald Reagan Washington National to Logan Intl., returning Sun, Oct 18, priced at $167 just found
Fri, Aug 21 - Sat, Aug 29
DCA
Ronald Reagan Washington National
BOS
Logan Intl.
$171 Roundtrip, found 1 hour ago
$171
Roundtrip
found 1 hour ago
Select JetBlue Airways flight, departing Fri, Aug 21 from Ronald Reagan Washington National to Logan Intl., returning Sat, Aug 29, priced at $171 found 1 hour ago
Sat, Sep 19 - Mon, Sep 21
DCA
Ronald Reagan Washington National
BOS
Logan Intl.
$176 Roundtrip, just found
$176
Roundtrip
just found
Select Delta flight, departing Sat, Sep 19 from Ronald Reagan Washington National to Logan Intl., returning Mon, Sep 21, priced at $176 just found

Gloucester Flight Information

Traveling To
Gloucester
Destination Airport IATA Code
BOS
Number of Airlines Serving
Airlines
JetBlue Airways, American Airlines, Delta, Frontier Airlines, United
Flight Price
$117
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.
Meco Hotel - Hostel
2.0-star property

Meco Hotel - Hostel

Jul 30 - Aug 2

3 night stay

Atlanta (ATL) to Boston (BOS)

Frontier Airlines • Coach

Boston (BOS) to Atlanta (ATL)

American Airlines • Coach
Save 100% on your flight
Price was $1,277, price is now $835 per person
$835
per person
found 13 hours ago
Comfort Inn & Suites Scarborough - Portland
2.5-star property

Comfort Inn & Suites Scarborough - Portland

Aug 2 - Aug 9

7 night stay

Atlanta (ATL) to Boston (BOS)

JetBlue Airways • Roundtrip • Coach
Price was $1,170, price is now $871 per person
$871
per person
found 1 day ago
Centerboard
2.0-star property

Centerboard

Aug 17 - Aug 21

4 night stay

Chicago (ORD) to Boston (BOS)

JetBlue Airways • Non-stop • Coach

Boston (BOS) to Chicago (ORD)

American Airlines • Non-stop • Coach
Save 100% on your flight
Price was $2,229, price is now $1,663 per person
$1,663
per person
found 19 hours ago
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Gloucester first class flight packages

Price found within the past 48 hours. Click for updated prices.
The Godfrey Hotel Boston
4.0-star property

The Godfrey Hotel Boston

9.4/10 Exceptional! (5,092 reviews)

Aug 1 - Aug 5

4 night stay

Chicago (ORD) to Boston (BOS)

American Airlines • Roundtrip • FirstClass
Price was $1,386, price is now $1,052 per person
$1,052
per person
found 22 hours ago
Great place we always use when visiting Boston. Opens up next to George Howell Coffee which is always a treat. The staff are responsive, the rooms clean, and the location is excellent (next to Emerson, china town, the commons, newbury street, etc.).

Reviewed on May 15, 2026

Raffles Boston
5.0-star property

Raffles Boston

9.6/10 Exceptional! (274 reviews)

Aug 3 - Aug 7

4 night stay

Chicago (ORD) to Boston (BOS)

American Airlines • FirstClass

Boston (BOS) to Chicago (ORD)

Frontier Airlines • FirstClass
Save 100% on your flight
Price was $3,025, price is now $2,255 per person
$2,255
per person
found 23 hours ago
Excellent services.

Reviewed on Dec 29, 2024

Hotel AKA Back Bay
4.5-star property

Hotel AKA Back Bay

9.4/10 Exceptional! (1,288 reviews)

Aug 1 - Aug 5

4 night stay

Chicago (ORD) to Boston (BOS)

American Airlines • Roundtrip • FirstClass
Price was $1,468, price is now $1,137 per person
$1,137
per person
found 22 hours ago
Excellent location. Walkable from Amtrak station and north end and south end. Well maintained property.

Reviewed on Mar 28, 2026

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Gloucester

Start your search for cheap flights to Gloucester on Orbitz. Orbitz is where you will discover guaranteed low prices on Gloucester flights, as well as all of the following conveniences:

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Low Prices Guaranteed on Flights to Gloucester

Orbitz offers large discounts on a wide range of Gloucester flights. Through our easy-to-use site, you can find, plan, and reserve your desired flights to Gloucester while taking advantage of the lowest fares around.

Customer Care When You Need It

Orbitz is dedicated to making your flight booking experience as stress-free as possible. If you need to cancel your reservation, you can do so at your own convenience by going to the Orbitz website. If you need to change your flights to Gloucester to another time or date, you can contact our customer service representatives by phone, and they help you make the flight adjustments you need.

Loyalty Program Participation Opportunities

Orbitz lets you add your loyalty or frequent flyer account numbers when you book qualifying flights to Gloucester. So don’t worry about missing out on earning miles or points simply because you aren’t booking with the airline directly. You can save on your flights, and rack up miles too.

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 $117 and $176. If you were traveling one-way out of Washington (DCA), you could have nabbed ticket prices from just $119.
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.