Cheap flights To Gloucester (BOS) from $27

Earn rewards on top of your airline miles with Orbitz Rewards

Many airlines offer flexible change policies

Sign up to receive text alerts about your trip

Cheap Flights to Gloucester from $27 One Way, $53 Round Trip

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

Thu, May 29 - Mon, Jun 2
BWI
Baltimore Washington Intl. Thurgood Marshall
BOS
Logan Intl.
$53 Roundtrip, just found
$53
Roundtrip
just found
Select Spirit Airlines flight, departing Thu, May 29 from Baltimore Washington Intl. Thurgood Marshall to Logan Intl., returning Mon, Jun 2, priced at $53 just found
Thu, May 29 - Wed, Jun 4
BWI
Baltimore Washington Intl. Thurgood Marshall
BOS
Logan Intl.
$57 Roundtrip, found 1 hour ago
$57
Roundtrip
found 1 hour ago
Select Spirit Airlines flight, departing Thu, May 29 from Baltimore Washington Intl. Thurgood Marshall to Logan Intl., returning Wed, Jun 4, priced at $57 found 1 hour ago
Tue, Jun 3 - Wed, Jun 4
BWI
Baltimore Washington Intl. Thurgood Marshall
BOS
Logan Intl.
$61 Roundtrip, found 1 hour ago
$61
Roundtrip
found 1 hour ago
Select Spirit Airlines flight, departing Tue, Jun 3 from Baltimore Washington Intl. Thurgood Marshall to Logan Intl., returning Wed, Jun 4, priced at $61 found 1 hour ago
Thu, May 29 - Mon, Jun 2
BWI
Baltimore Washington Intl. Thurgood Marshall
BOS
Logan Intl.
$65 Roundtrip, just found
$65
Roundtrip
just found
Select Spirit Airlines flight, departing Thu, May 29 from Baltimore Washington Intl. Thurgood Marshall to Logan Intl., returning Mon, Jun 2, priced at $65 just found
Tue, May 27 - Mon, Jun 2
BWI
Baltimore Washington Intl. Thurgood Marshall
BOS
Logan Intl.
$68 Roundtrip, just found
$68
Roundtrip
just found
Select Spirit Airlines flight, departing Tue, May 27 from Baltimore Washington Intl. Thurgood Marshall to Logan Intl., returning Mon, Jun 2, priced at $68 just found
Wed, May 21 - Wed, May 28
BWI
Baltimore Washington Intl. Thurgood Marshall
BOS
Logan Intl.
$72 Roundtrip, found 2 hours ago
$72
Roundtrip
found 2 hours ago
Select Spirit Airlines flight, departing Wed, May 21 from Baltimore Washington Intl. Thurgood Marshall to Logan Intl., returning Wed, May 28, priced at $72 found 2 hours ago
Thu, May 29 - Mon, Jun 2
BWI
Baltimore Washington Intl. Thurgood Marshall
BOS
Logan Intl.
$74 Roundtrip, just found
$74
Roundtrip
just found
Select Spirit Airlines flight, departing Thu, May 29 from Baltimore Washington Intl. Thurgood Marshall to Logan Intl., returning Mon, Jun 2, priced at $74 just found
Thu, May 29 - Fri, May 30
BWI
Baltimore Washington Intl. Thurgood Marshall
BOS
Logan Intl.
$77 Roundtrip, just found
$77
Roundtrip
just found
Select Spirit Airlines flight, departing Thu, May 29 from Baltimore Washington Intl. Thurgood Marshall to Logan Intl., returning Fri, May 30, priced at $77 just found
Thu, May 29 - Fri, May 30
BWI
Baltimore Washington Intl. Thurgood Marshall
BOS
Logan Intl.
$78 Roundtrip, just found
$78
Roundtrip
just found
Select Spirit Airlines flight, departing Thu, May 29 from Baltimore Washington Intl. Thurgood Marshall to Logan Intl., returning Fri, May 30, priced at $78 just found
Thu, May 29 - Sat, May 31
BWI
Baltimore Washington Intl. Thurgood Marshall
BOS
Logan Intl.
$80 Roundtrip, found 1 hour ago
$80
Roundtrip
found 1 hour ago
Select Spirit Airlines flight, departing Thu, May 29 from Baltimore Washington Intl. Thurgood Marshall to Logan Intl., returning Sat, May 31, priced at $80 found 1 hour ago

Gloucester Flight Information

Traveling To
Gloucester
Destination Airport IATA Code
BOS
Number of Airlines Serving
Airlines
Spirit Airlines
Flight Price
$53
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.
By the Sea Guests Bed & Breakfast & Suites
3.5-star property

By the Sea Guests Bed & Breakfast & Suites

Jun 27 - Jun 30

3 night stay

Dallas (DFW) to Boston (BOS)

Frontier Airlines • Roundtrip • Coach
per person
found 20 hours ago
Newly Renovated 2 floor Getaway
3.5-star property

Newly Renovated 2 floor Getaway

Jun 13 - Jun 15

2 night stay

Los Angeles (LAX) to Boston (BOS)

Breeze Airways • Coach

Boston (BOS) to Los Angeles (LAX)

Spirit Airlines • Coach
per person
found 4 hours ago
An English Garden Bed & Breakfast
3.0-star property

An English Garden Bed & Breakfast

Jun 27 - Jun 30

3 night stay

Dallas (DFW) to Boston (BOS)

Frontier Airlines • Roundtrip • Coach
per person
found 20 hours ago
Don't see what you're looking for?
See all available trips from Dallas to Gloucester
View all trips

Gloucester premium economy flight packages

Price found within the past 48 hours. Click for updated prices.
Omni Boston Hotel at the Seaport
4.0-star property

Omni Boston Hotel at the Seaport

9.2/10 Wonderful! (3,329 reviews)

Jun 3 - Jun 6

3 night stay

Orlando (MCO) to Boston (BOS)

Delta • Non-stop roundtrip • PremiumEconomy
per person
found 6 hours ago
Loved it! Exceeded expectations.

Reviewed on Apr 23, 2025

The Whitney Hotel
4.0-star property

The Whitney Hotel

9.6/10 Exceptional! (384 reviews)

Jun 3 - Jun 6

3 night stay

Orlando (MCO) to Boston (BOS)

Delta • Non-stop roundtrip • PremiumEconomy
per person
found 6 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

The Dagny Boston
4.0-star property

The Dagny Boston

9.4/10 Exceptional! (5,574 reviews)

Jun 3 - Jun 6

3 night stay

Orlando (MCO) to Boston (BOS)

Delta • Non-stop roundtrip • PremiumEconomy
per person
found 6 hours ago
Really nice restaurant on-site. All staff were helpful and friendly.

Reviewed on Apr 28, 2025

Don't see what you're looking for?
See all available trips from Orlando to Gloucester
View all trips

Gloucester

When you plan to buy tickets for flights to Gloucester, you don’t have to look any further than Orbitz! We offer bargain rates and low fares on thousands of flights.

Reliable Customer Service

Along with our low prices, Orbitz is well known for exceptional customer care. We make it simple to find the best Gloucester flights for you. If you need to cancel your booking or change your flight plans, simply contact our Customer Service department to make any adjustments.

Bargain Tickets for Gloucester Flights

Orbitz offers deeply discounted flights to Gloucester, and we provide the resources to research your travel destination and plan your complete itinerary.

Use Orbitz to Earn Points with Your Frequent Flyer Program

Saving your frequent flyer miles for your flights to Gloucester? You can use Orbitz to make your budget ticket reservation for all your flights and still earn points or miles on your frequent flyer program! Just enter your program account number while you’re booking your ticket to have your points added automatically, every time you book with Orbitz.

Convenient Travel Planning Services

If you like the ease of making your travel plans on the move, you’ll love the free Orbitz apps for iPhones, iPads, and Android devices. You can use these apps to review your travel reservations or make a change to your itinerary. Orbitz also offers additional travel assistance such as free mobile alerts that keep you up-to-date about sudden changes to your upcoming flights. You can also browse Orbitz easily on your smartphone by using the mobile version of the website to find budget Gloucester flights.

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 $53 and $80. If you were traveling one-way out of Baltimore (BWI), you could have nabbed ticket prices from just $27.
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.

Nearby

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.