Cheap flights To Gloucester (BOS) from $44

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Cheap Flights to Gloucester from $44 One Way, $87 Round Trip

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

Thu, Nov 6 - Wed, Nov 12
FLL
Fort Lauderdale - Hollywood Intl.
BOS
Logan Intl.
$87 Roundtrip, just found
$87
Roundtrip
just found
Select Spirit Airlines flight, departing Thu, Nov 6 from Fort Lauderdale - Hollywood Intl. to Logan Intl., returning Wed, Nov 12, priced at $87 just found
Wed, Nov 5 - Mon, Nov 10
FLL
Fort Lauderdale - Hollywood Intl.
BOS
Logan Intl.
$102 Roundtrip, found 4 hours ago
$102
Roundtrip
found 4 hours ago
Select Spirit Airlines flight, departing Wed, Nov 5 from Fort Lauderdale - Hollywood Intl. to Logan Intl., returning Mon, Nov 10, priced at $102 found 4 hours ago
Mon, Nov 3 - Tue, Nov 11
FLL
Fort Lauderdale - Hollywood Intl.
BOS
Logan Intl.
$102 Roundtrip, just found
$102
Roundtrip
just found
Select Spirit Airlines flight, departing Mon, Nov 3 from Fort Lauderdale - Hollywood Intl. to Logan Intl., returning Tue, Nov 11, priced at $102 just found
Wed, Dec 3 - Mon, Dec 8
FLL
Fort Lauderdale - Hollywood Intl.
BOS
Logan Intl.
$116 Roundtrip, just found
$116
Roundtrip
just found
Select Spirit Airlines flight, departing Wed, Dec 3 from Fort Lauderdale - Hollywood Intl. to Logan Intl., returning Mon, Dec 8, priced at $116 just found
Thu, Nov 13 - Sat, Nov 15
FLL
Fort Lauderdale - Hollywood Intl.
BOS
Logan Intl.
$117 Roundtrip, just found
$117
Roundtrip
just found
Select Spirit Airlines flight, departing Thu, Nov 13 from Fort Lauderdale - Hollywood Intl. to Logan Intl., returning Sat, Nov 15, priced at $117 just found
Fri, Nov 7 - Sat, Nov 15
FLL
Fort Lauderdale - Hollywood Intl.
BOS
Logan Intl.
$118 Roundtrip, just found
$118
Roundtrip
just found
Select Spirit Airlines flight, departing Fri, Nov 7 from Fort Lauderdale - Hollywood Intl. to Logan Intl., returning Sat, Nov 15, priced at $118 just found
Sat, Nov 1 - Tue, Nov 4
FLL
Fort Lauderdale - Hollywood Intl.
BOS
Logan Intl.
$122 Roundtrip, just found
$122
Roundtrip
just found
Select Spirit Airlines flight, departing Sat, Nov 1 from Fort Lauderdale - Hollywood Intl. to Logan Intl., returning Tue, Nov 4, priced at $122 just found
Thu, Nov 6 - Wed, Nov 12
FLL
Fort Lauderdale - Hollywood Intl.
BOS
Logan Intl.
$125 Roundtrip, just found
$125
Roundtrip
just found
Select Spirit Airlines flight, departing Thu, Nov 6 from Fort Lauderdale - Hollywood Intl. to Logan Intl., returning Wed, Nov 12, priced at $125 just found
Wed, Dec 3 - Mon, Dec 8
FLL
Fort Lauderdale - Hollywood Intl.
BOS
Logan Intl.
$127 Roundtrip, just found
$127
Roundtrip
just found
Select Spirit Airlines flight, departing Wed, Dec 3 from Fort Lauderdale - Hollywood Intl. to Logan Intl., returning Mon, Dec 8, priced at $127 just found
Tue, Nov 4 - Sat, Nov 8
FLL
Fort Lauderdale - Hollywood Intl.
BOS
Logan Intl.
$129 Roundtrip, found 1 hour ago
$129
Roundtrip
found 1 hour ago
Select JetBlue Airways flight, departing Tue, Nov 4 from Fort Lauderdale - Hollywood Intl. to Logan Intl., returning Sat, Nov 8, priced at $129 found 1 hour ago

Gloucester Flight Information

Traveling To
Gloucester
Destination Airport IATA Code
BOS
Number of Airlines Serving
Airlines
Spirit Airlines, Southwest Airlines, JetBlue Airways, American Airlines
Flight Price
$87
Earliest Departing Flight
Latest Departing Flight

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Gloucester economy flight packages

Price found within the past 48 hours. Click for updated prices.
DoubleTree Suites by Hilton Hotel Boston - Cambridge
4.0-star property

DoubleTree Suites by Hilton Hotel Boston - Cambridge

Nov 24 - Dec 1

7 night stay

Mesa (AZA) to Boston (BOS)

Delta • Coach

Boston (BOS) to Mesa (AZA)

Frontier Airlines • Coach
Save 100% on your flight
Price was $980, price is now $644 per person
$644
per person
found 11 hours ago
Boston Harbor Hotel
5.0-star property

Boston Harbor Hotel

Dec 3 - Dec 7

4 night stay

Miami (MIA) to Boston (BOS)

Delta • Roundtrip • Coach
Save 100% on your flight
Price was $1,867, price is now $1,088 per person
$1,088
per person
found 1 day ago
Battery Wharf Hotel, Boston Waterfront
4.5-star property

Battery Wharf Hotel, Boston Waterfront

Nov 24 - Dec 1

7 night stay

Mesa (AZA) to Boston (BOS)

Delta • Coach

Boston (BOS) to Mesa (AZA)

Frontier Airlines • Coach
Save 100% on your flight
Price was $1,243, price is now $827 per person
$827
per person
found 11 hours ago
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Gloucester premium economy flight packages

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

The Whitney Hotel

9.6/10 Exceptional! (475 reviews)

Dec 12 - Dec 18

6 night stay

San Diego (SAN) to Boston (BOS)

Delta • Roundtrip • PremiumEconomy
Price was $2,196, price is now $1,685 per person
$1,685
per person
found 3 hours ago
What a gem in Boston! I've been to Boston many times and usually stay closer to the Downtown Crossing area. This time we stayed at the Whitney, choosing to try out that part of town. We loved it! Bigger than a boutique hotel, but small enough to feel intimate. Charles St is a great walking street, and we loved the location. The room was on the ground level (actually partly below ground) but was excellent! Well-appointed room, a good amount of space for Boston, and super professional staff. I'll be back when I come back to Boston

Reviewed on Jul 30, 2024

Boston Harbor Hotel
5.0-star property

Boston Harbor Hotel

9.8/10 Exceptional! (1,019 reviews)

Dec 12 - Dec 18

6 night stay

San Diego (SAN) to Boston (BOS)

Delta • Roundtrip • PremiumEconomy
Save 100% on your flight
Price was $3,108, price is now $2,241 per person
$2,241
per person
found 3 hours ago
The staff is VERY attentive to all your needs. It just makes everything easy and more comfortable: room service to concierge to valet parking etc. etc.

Reviewed on Mar 24, 2024

Encore Boston Harbor
5.0-star property

Encore Boston Harbor

9.6/10 Exceptional! (3,325 reviews)

Dec 12 - Dec 18

6 night stay

San Diego (SAN) to Boston (BOS)

Delta • Roundtrip • PremiumEconomy
Price was $2,169, price is now $1,804 per person
$1,804
per person
found 3 hours ago
Everything was beautiful and the front desk and cleaning team were so nice, friendly and amazing at their jobs. Thank you for a fabulous visit!

Reviewed on Aug 13, 2025

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See all available trips from San Diego to Gloucester
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Gloucester first class flight packages

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

The Bostonian Boston

8.4/10 Very Good! (1,952 reviews)

Nov 20 - Nov 23

3 night stay

Miami (MIA) to Boston (BOS)

Delta • Roundtrip • FirstClass
Price was $1,144, price is now $949 per person
$949
per person
found 6 hours ago
Nice hotel, great location, friendly staff. The only thing - I expected a complimentary shuttle to airport (was mentioned on Orbitz) - no. Noon checkout time is good.

Reviewed on Oct 19, 2025

Raffles Boston
5.0-star property

Raffles Boston

9.6/10 Exceptional! (169 reviews)

Nov 20 - Nov 23

3 night stay

Miami (MIA) to Boston (BOS)

Delta • Roundtrip • FirstClass
Price was $1,860, price is now $1,435 per person
$1,435
per person
found 6 hours ago
Excellent services.

Reviewed on Dec 29, 2024

The Inn at Hastings Park, Relais & Chateaux - Boston
4.0-star property

The Inn at Hastings Park, Relais & Chateaux - Boston

9.6/10 Exceptional! (245 reviews)

Nov 20 - Nov 23

3 night stay

Miami (MIA) to Boston (BOS)

Delta • Roundtrip • FirstClass
Price was $1,612, price is now $1,290 per person
$1,290
per person
found 5 hours ago
The heater in Room 37 did not maintain a steady, dependable temperature (it varied \- by 5 degrees F). Otherwise, superb restaurant onsite and superb continental breakfast.

Reviewed on Feb 13, 2025

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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 $87 and $129. If you were traveling one-way out of Fort Lauderdale (FLL), you could have nabbed ticket prices from just $44.
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.