Cheap flights To Gloucester (BOS) from $32

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Cheap Flights to Gloucester from $32 One Way, $76 Round Trip

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

Wed, Aug 6 - Sat, Aug 9
BWI
Baltimore Washington Intl. Thurgood Marshall
BOS
Logan Intl.
$76 Roundtrip, just found
$76
Roundtrip
just found
Select Spirit Airlines flight, departing Wed, Aug 6 from Baltimore Washington Intl. Thurgood Marshall to Logan Intl., returning Sat, Aug 9, priced at $76 just found
Mon, Aug 4 - Tue, Aug 5
BWI
Baltimore Washington Intl. Thurgood Marshall
BOS
Logan Intl.
$80 Roundtrip, found 1 day ago
$80
Roundtrip
found 1 day ago
Select Spirit Airlines flight, departing Mon, Aug 4 from Baltimore Washington Intl. Thurgood Marshall to Logan Intl., returning Tue, Aug 5, priced at $80 found 1 day ago
Fri, Oct 24 - Mon, Oct 27
BWI
Baltimore Washington Intl. Thurgood Marshall
BOS
Logan Intl.
$88 Roundtrip, just found
$88
Roundtrip
just found
Select Spirit Airlines flight, departing Fri, Oct 24 from Baltimore Washington Intl. Thurgood Marshall to Logan Intl., returning Mon, Oct 27, priced at $88 just found
Thu, Aug 7 - Mon, Aug 11
BWI
Baltimore Washington Intl. Thurgood Marshall
BOS
Logan Intl.
$89 Roundtrip, just found
$89
Roundtrip
just found
Select Spirit Airlines flight, departing Thu, Aug 7 from Baltimore Washington Intl. Thurgood Marshall to Logan Intl., returning Mon, Aug 11, priced at $89 just found
Thu, Oct 23 - Mon, Oct 27
BWI
Baltimore Washington Intl. Thurgood Marshall
BOS
Logan Intl.
$95 Roundtrip, found 1 day ago
$95
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Thu, Oct 23 from Baltimore Washington Intl. Thurgood Marshall to Logan Intl., returning Mon, Oct 27, priced at $95 found 1 day ago
Sat, Nov 8 - Sun, Nov 9
BWI
Baltimore Washington Intl. Thurgood Marshall
BOS
Logan Intl.
$96 Roundtrip, found 1 day ago
$96
Roundtrip
found 1 day ago
Select Spirit Airlines flight, departing Sat, Nov 8 from Baltimore Washington Intl. Thurgood Marshall to Logan Intl., returning Sun, Nov 9, priced at $96 found 1 day ago
Wed, Jul 30 - Mon, Aug 11
BWI
Baltimore Washington Intl. Thurgood Marshall
BOS
Logan Intl.
$97 Roundtrip, found 1 day ago
$97
Roundtrip
found 1 day ago
Select Spirit Airlines flight, departing Wed, Jul 30 from Baltimore Washington Intl. Thurgood Marshall to Logan Intl., returning Mon, Aug 11, priced at $97 found 1 day ago
Thu, Oct 16 - Sun, Oct 19
BWI
Baltimore Washington Intl. Thurgood Marshall
BOS
Logan Intl.
$99 Roundtrip, just found
$99
Roundtrip
just found
Select Spirit Airlines flight, departing Thu, Oct 16 from Baltimore Washington Intl. Thurgood Marshall to Logan Intl., returning Sun, Oct 19, priced at $99 just found
Thu, Aug 7 - Mon, Aug 11
BWI
Baltimore Washington Intl. Thurgood Marshall
BOS
Logan Intl.
$100 Roundtrip, just found
$100
Roundtrip
just found
Select Spirit Airlines flight, departing Thu, Aug 7 from Baltimore Washington Intl. Thurgood Marshall to Logan Intl., returning Mon, Aug 11, priced at $100 just found
Sat, Aug 2 - Tue, Aug 5
BWI
Baltimore Washington Intl. Thurgood Marshall
BOS
Logan Intl.
$105 Roundtrip, found 19 hours ago
$105
Roundtrip
found 19 hours ago
Select Spirit Airlines flight, departing Sat, Aug 2 from Baltimore Washington Intl. Thurgood Marshall to Logan Intl., returning Tue, Aug 5, priced at $105 found 19 hours ago

Gloucester BOS Flight Information

Traveling To
Gloucester
Destination Airport IATA Code
BOS
Number of Airlines Serving
11
Airlines
Spirit Airlines, Southwest Airlines
Flight Price
$76
Earliest Departing Flight
AA 4642 8:58AM EDT
Latest Departing Flight
IB 4283 Jul 19 5:49PM EDT

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Gloucester economy flight packages

Price found within the past 48 hours. Click for updated prices.
Sunbird ANNEX Resort
2.0-star property

Sunbird ANNEX Resort

Aug 27 - Aug 31

4 night stay

Chicago (ORD) to Boston (BOS)

American Airlines • Roundtrip • Coach
Save 100% on your flight
per person
found 1 day ago
Ocean Air Suites
2.5-star property

Ocean Air Suites

Aug 27 - Aug 31

4 night stay

Chicago (ORD) to Boston (BOS)

JetBlue Airways • Roundtrip • Coach
Save 100% on your flight
per person
found 1 day ago
Hampton Inn & Suites Portsmouth Downtown
3.0-star property

Hampton Inn & Suites Portsmouth Downtown

Aug 27 - Aug 31

4 night stay

Chicago (ORD) to Boston (BOS)

JetBlue Airways • Roundtrip • Coach
Save 100% on your flight
per person
found 1 day ago
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Gloucester premium economy flight packages

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

The Boxer

8.6/10 Excellent! (1,236 reviews)

Aug 15 - Aug 17

2 night stay

San Juan (SJU) to Boston (BOS)

Delta • Roundtrip • PremiumEconomy
per person
found 21 hours ago
Third time staying here and it’s perfect for sports fans heading to games at TD Garden!

Reviewed on May 6, 2025

Boston Harbor Hotel
5.0-star property

Boston Harbor Hotel

9.8/10 Exceptional! (1,018 reviews)

Aug 15 - Aug 17

2 night stay

San Juan (SJU) to Boston (BOS)

Delta • Roundtrip • PremiumEconomy
per person
found 21 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

Fairmont Copley Plaza, Boston
4.5-star property

Fairmont Copley Plaza, Boston

8.8/10 Excellent! (1,009 reviews)

Aug 15 - Aug 17

2 night stay

San Juan (SJU) to Boston (BOS)

Delta • Roundtrip • PremiumEconomy
per person
found 21 hours ago
Valet parking rate of $72/night was excessive. Other than that, the room was lovely and comfortable for our family of 5, staff was responsive and friendly. Gym is well equipped with nice views. Very convenient to get to Logan airport from this hotel.

Reviewed on Apr 14, 2025

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Gloucester first class flight packages

Price found within the past 48 hours. Click for updated prices.
An English Garden Bed & Breakfast
3.0-star property

An English Garden Bed & Breakfast

9/10 Wonderful! (43 reviews)

Aug 16 - Aug 21

5 night stay

Minneapolis (MSP) to Boston (BOS)

American Airlines • Non-stop roundtrip • FirstClass
per person
found 4 hours ago
Nantucket Inn
3.5-star property

Nantucket Inn

9/10 Wonderful! (482 reviews)

Aug 16 - Aug 21

5 night stay

Minneapolis (MSP) to Boston (BOS)

American Airlines • Non-stop roundtrip • FirstClass
Save 100% on your flight
per person
found 4 hours ago
Excellent all th way around!

Reviewed on Oct 11, 2024

Edgewater Beach Resort, a VRI resort
3.5-star property

Edgewater Beach Resort, a VRI resort

8.8/10 Excellent! (281 reviews)

Aug 16 - Aug 21

5 night stay

Minneapolis (MSP) to Boston (BOS)

American Airlines • Non-stop roundtrip • FirstClass
Save 100% on your flight
per person
found 4 hours ago
The rooms were great, overall good experience. Huge rooms with full size fridge, microwave, and stovetop. The things that I wasn’t happy about was if you need new towels you need to pay 30.00. Also the beds were so thin and you could feel the springs through the mattress. Would stay again but bring a mattress pad.

Reviewed on Nov 7, 2022

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Gloucester

Are you in the mood for a cruise? Shop Orbitz today for cheap cruises and flights to Gloucester. Our award-winning cruise site features exclusive offers, information for first-timers and top destinations and activities. Make discount domestic and international travel plans in an instant with cutting-edge mobile tools from Orbitz.

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First-Timers

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Ports and Play

Be sure to check our cruise page for free shore excursions, onboard spending, balcony upgrades and other perks. Orbitz offers last-minute, luxury, weekend and summer cruises. You can even designate which port you want to sail from and pre-book on-shore activities. Get there on the cheap with discounts on flights to Gloucester and Gloucester flights. Get more bang for your travel buck at 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 $76 and $105. If you were traveling one-way out of Baltimore (BWI), you could have nabbed ticket prices from just $32.
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.

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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.