Cheap flights To Gloucester (BOS) from $78

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Cheap Flights to Gloucester from $78 One Way, $156 Round Trip

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

Sat, Oct 24 - Sat, Oct 31
DEN
Denver Intl.
BOS
Logan Intl.
$156 Roundtrip, just found
$156
Roundtrip
just found
Select Frontier Airlines flight, departing Sat, Oct 24 from Denver Intl. to Logan Intl., returning Sat, Oct 31, priced at $156 just found
Wed, Sep 2 - Wed, Sep 16
DEN
Denver Intl.
BOS
Logan Intl.
$159 Roundtrip, found 3 hours ago
$159
Roundtrip
found 3 hours ago
Select Frontier Airlines flight, departing Wed, Sep 2 from Denver Intl. to Logan Intl., returning Wed, Sep 16, priced at $159 found 3 hours ago
Tue, Aug 25 - Fri, Sep 4
DEN
Denver Intl.
BOS
Logan Intl.
$165 Roundtrip, found 1 day ago
$165
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Tue, Aug 25 from Denver Intl. to Logan Intl., returning Fri, Sep 4, priced at $165 found 1 day ago
Mon, Oct 19 - Tue, Oct 20
DEN
Denver Intl.
BOS
Logan Intl.
$166 Roundtrip, found 22 hours ago
$166
Roundtrip
found 22 hours ago
Select Frontier Airlines flight, departing Mon, Oct 19 from Denver Intl. to Logan Intl., returning Tue, Oct 20, priced at $166 found 22 hours ago
Thu, Nov 5 - Sun, Nov 8
DEN
Denver Intl.
BOS
Logan Intl.
$167 Roundtrip, found 17 hours ago
$167
Roundtrip
found 17 hours ago
Select Frontier Airlines flight, departing Thu, Nov 5 from Denver Intl. to Logan Intl., returning Sun, Nov 8, priced at $167 found 17 hours ago
Wed, Sep 16 - Sat, Sep 26
DEN
Denver Intl.
BOS
Logan Intl.
$169 Roundtrip, found 1 day ago
$169
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Wed, Sep 16 from Denver Intl. to Logan Intl., returning Sat, Sep 26, priced at $169 found 1 day ago
Sun, Aug 23 - Wed, Sep 2
DEN
Denver Intl.
BOS
Logan Intl.
$170 Roundtrip, found 3 hours ago
$170
Roundtrip
found 3 hours ago
Select Frontier Airlines flight, departing Sun, Aug 23 from Denver Intl. to Logan Intl., returning Wed, Sep 2, priced at $170 found 3 hours ago
Tue, Aug 25 - Wed, Aug 26
DEN
Denver Intl.
BOS
Logan Intl.
$171 Roundtrip, found 1 day ago
$171
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Tue, Aug 25 from Denver Intl. to Logan Intl., returning Wed, Aug 26, priced at $171 found 1 day ago
Wed, Aug 26 - Sat, Aug 29
DEN
Denver Intl.
BOS
Logan Intl.
$173 Roundtrip, found 6 hours ago
$173
Roundtrip
found 6 hours ago
Select Frontier Airlines flight, departing Wed, Aug 26 from Denver Intl. to Logan Intl., returning Sat, Aug 29, priced at $173 found 6 hours ago
Mon, Sep 14 - Tue, Sep 22
SFO
San Francisco Intl.
BOS
Logan Intl.
$178 Roundtrip, found 7 hours ago
$178
Roundtrip
found 7 hours ago
Select Frontier Airlines flight, departing Mon, Sep 14 from San Francisco Intl. to Logan Intl., returning Tue, Sep 22, priced at $178 found 7 hours ago

Gloucester Flight Information

Traveling To
Gloucester
Destination Airport IATA Code
BOS
Number of Airlines Serving
Airlines
Frontier Airlines, JetBlue Airways
Flight Price
$156
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

Oct 1 - Oct 5

4 night stay

Cleveland (CLE) to Boston (BOS)

JetBlue Airways • Non-stop roundtrip • Coach
Price was $795, price is now $578 per person
$578
per person
just found
The Cove at Yarmouth by Westgate Resorts
3.0-star property

The Cove at Yarmouth by Westgate Resorts

Oct 1 - Oct 5

4 night stay

Cleveland (CLE) to Boston (BOS)

JetBlue Airways • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $1,107, price is now $769 per person
$769
per person
just found
The Bow Hotel
4.0-star property

The Bow Hotel

Sep 15 - Sep 19

4 night stay

Cleveland (CLE) to Boston (BOS)

JetBlue Airways • Roundtrip • Coach
Save 100% on your flight
Price was $1,034, price is now $735 per person
$735
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
Walkable to TD garden, Quincy Market, faneuil hall and many more !

Reviewed on Aug 9, 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
the service was impeccable. the location and cleanliness of hotel unmatched and the pool area and finesse center so wonderful

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
.

Reviewed on Aug 9, 2026

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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

Are you and your family cruise newbies? Orbitz offers Cruising 101 and Cruise FAQ to answer any questions you may have. Book your cruise and air travel with Orbitz On the Go for greater savings on Gloucester flights.

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 $156 and $178. If you were traveling one-way out of Denver (DEN), you could have nabbed ticket prices from just $78.
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.