Cheap Flights to Great Diamond Island from $64

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How Much Does it Cost To Fly To Great Diamond Island?

The cheapest prices found with in the last 7 days for return flights were $107 and $64 for one-way flights to Great Diamond Island for the period specified. Prices and availability are subject to change. Additional terms apply

Sat, Oct 18 - Wed, Oct 22
JFK
John F. Kennedy Intl.
PWM
Portland Intl. Jetport
$107 Roundtrip, found 15 hours ago
$107
Roundtrip
found 15 hours ago
Select JetBlue Airways flight, departing Sat, Oct 18 from John F. Kennedy Intl. to Portland Intl. Jetport, returning Wed, Oct 22, priced at $107 found 15 hours ago
OriginDestinationTravel DatesFlights From*
JFKPortlandOctober 15 to October 23$107
RDUPortlandDecember 5 to December 12$142
TPAPortlandDecember 6 to December 12$154
MCOPortlandDecember 5 to December 12$162
DCAPortlandOctober 25 to November 1$189
SEAPortlandNovember 18 to November 20$221
ATLPortlandOctober 15 to October 22$234
CLTPortlandDecember 17 to December 18$280
PHLPortlandOctober 18 to October 21$312
FCOPortlandOctober 10 to October 13$842
*Prices include taxes and fees
OriginDestinationTravel DatesFlights From*
JFKPortlandOctober 3 to October 23$214
MCOPortlandOctober 5 to October 22$321
DCAPortlandOctober 3 to October 4$326
CLTPortlandOctober 4 to October 8$332
RDUPortlandOctober 4 to October 10$365
PHLPortlandOctober 4 to October 5$375
SEAPortlandOctober 4 to October 15$383
TPAPortlandOctober 3 to October 15$465
ATLPortlandOctober 4 to October 8$506
*Prices include taxes and fees

Great Diamond Island Flight Information

Traveling to
Great Diamond Island
Lowest Price
$107
Number of Airlines Serving
Airlines Serving
JetBlue Airways
Number of Daily Flights
Airlines with Direct Flights

Find The Perfect Hotel For After Your Flight

Luxury Hotels in Great Diamond Island

Inn at Diamond Cove

Inn at Diamond Cove

3.5 out of 5
22 Mckinley Court, Great Diamond Island, Portland, ME
$284 nightly
The price is $310 total per night from Oct 9 to Oct 10
$310 total
Oct 9 - Oct 10
Total with taxes and fees
Stay at this 3.5-star hotel in Portland. Enjoy free WiFi, 2 restaurants, and a marina. Our guests praise the helpful staff in our reviews. Popular attractions ...
8.8/10 Excellent! (193 reviews)
"it was very unique having to take a ferry over, shuttle by golf cart and bikes. late in season only 1 restaurant available. looking for peace and quiet- this it the place. lots to walk around and look at with the old fort there."

Reviewed on Sep 25, 2025

Opens in a new windowInn at Diamond Cove
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Best Great Diamond Island Flight and Hotel Packages

Great Diamond Island flight + hotel packages - economy flights

Price found within the past 48 hours. Click for updated prices.
The Docent's Collection

The Docent's Collection

3.5 out of 5
Price was $717, price is now $565 per person
$565
per person
Nov 14 - Nov 16
found 8 hours ago
Roundtrip non-stop flight included
Greenville (GSP) to Portland (PWM)
Hilton Garden Inn Freeport Downtown

Hilton Garden Inn Freeport Downtown

3 out of 5
Price was $870, price is now $725 per person
$725
per person
Nov 8 - Nov 13
found 9 hours ago
Roundtrip non-stop flight included
Houston (HOU) to Portland (PWM)
Cliff House Maine

Cliff House Maine

4.5 out of 5
Price was $1,222, price is now $905 per person
$905
per person
Nov 7 - Nov 10
found 2 hours ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Portland (PWM)
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Need a Car For After Your Flight?

Compact

  • 5 people
  • Unlimited mileage
Portland, Maine, USA

$52

$137 total
found 5 hours ago
Compact undefined

Economy

  • 4 people
  • Unlimited mileage
Portland, Maine, USA

$52

$136 total
found 5 hours ago
Economy undefined

Midsize

  • 5 people
  • Unlimited mileage
Portland, Maine, USA

$52

$137 total
found 5 hours ago
Midsize undefined

Premium Pickup Regular Cab

  • 5 people
  • Unlimited mileage
Portland, Maine, USA

$67

$175 total
found 5 hours ago
Premium Pickup Regular Cab undefined
Lowest prices found within the past 5 hours. Prices and availability subject to change. Additional terms may apply.

Frequently asked questions

Can I fly to Great Diamond Island right now?
Before committing to your flights, take a look through Travelocity's Covid-19 Travel Advisor. Enter in your travel dates, destination and vaccination status to check if any additional rules apply, such as quarantine or testing. Be sure to also confirm all guidance with official government websites as well as your travel insurance company.
How much is the cheapest flight to Great Diamond Island?
A roundtrip flight to Great Diamond Island cost as little as $107 in the last seven days. When you've narrowed down your travel dates, we'll help you grab a fantastic deal. This price was available on Travelocity for flights to Great Diamond Island departing within the next year. Prices and availability are subject to change. Additional terms apply.
If I cannot travel due to COVID-19, can I change my booking to a later date?
Explore our Customer Service Portal link for information regarding COVID-19 related refunds, changes and cancellations. The terms of your tickets to Great Diamond Island may differ based on your airline and fare type. Browse the popular topics or use our Virtual Agent to find the answers to your questions.
What is the cheapest month to fly to Great Diamond Island?
For your best chance at securing a superb flight deal, organize your getaway sometime during October. Based on Travelocity's direct flight demand between January and December last year, it's the most affordable month to travel to Great Diamond Island.
How can I check my flight status to Great Diamond Island?
Check out our helpful portal, Trips. You'll find everything related to your flight to Great Diamond Island here, including important information about flight delays, gate changes and more. Look for Trips at the top right of the Travelocity homepage. Just sign up, log in and find what you need. Or, access your itinerary while you're traveling and get real-time notifications with the Travelocity app. You'll find all your itineraries in one place, so you can share details with any members of your family flying with you.
How do I find the best deals on flights to Great Diamond Island?
Be flexible with your travel dates and you might just find an awesome deal. After you've searched for flights on Travelocity, click the "Flexible dates" feature above your results to see all the prices for surrounding days. Also try to book in advance and avoid busy peak periods. In the last seven days, the lowest price for a roundtrip flight to Great Diamond Island was $107. This price was available on Travelocity for flights departing within the next year. Prices and availability are subject to change. Additional terms apply.
Why should I book my flight to Great Diamond Island with Travelocity?
Where to begin! With our cheap flights to Great Diamond Island, accommodations and activities, you'll find all you need for an awesome getaway with Travelocity. Reserve your cheap family flights and make use of our round-the-clock customer assistance and free cancellations on select airlines if necessary. Our aim is to offer stress-free travel when you book with us so that you can spend less time on the nitty-gritty and more time making memories with your travel crew.
What are the most popular flight routes to Great Diamond Island?
With terrific connections, securing flights to Great Diamond Island is hassle-free. Here are several of the most in-demand flight routes to this leading travel destination:

  • New York, NY (JFK-John F. Kennedy Intl.) to Portland Intl. Jetport Airport (PWM) - 949 flights a month.
  • Chicago, IL (ORD-O'Hare Intl.) to Portland Intl. Jetport Airport (PWM) - 676 flights a month.
  • Philadelphia, PA (PHL-Philadelphia Intl.) to Portland Intl. Jetport Airport (PWM) - 645 flights a month.

How much is a flight to Great Diamond Island on average?
Get your next great adventure off to the best start by picking up an amazing deal with Travelocity. In the last seven days, roundtrip flights to Great Diamond Island cost between $107 and $842. Look through our site and secure an airfare that matches your budget. These prices were available on Travelocity for flights departing within the next year. Prices and availability are subject to change. Additional terms apply.
How long is the average flight to Great Diamond Island?
Here are some major direct flights to Great Diamond Island and their average flight times:

  • New York, NY (JFK-John F. Kennedy Intl.) to Portland Intl. Jetport Airport (PWM) - 1 hour and 20 minutes
  • Chicago, IL (ORD-O'Hare Intl.) to Portland Intl. Jetport Airport (PWM) - 2 hours and 21 minutes
  • Philadelphia, PA (PHL-Philadelphia Intl.) to Portland Intl. Jetport Airport (PWM) - 1 hour and 32 minutes

What can I expect on a flight to Great Diamond Island?
Factors like which airline company you're jetting off with and your place of departure will largely determine what you can expect on your trip. You'll likely find all sorts of flights to Great Diamond Island, from cheap flights for family vacations to first class fares. Hot meals, drinks and entertainment are just a small taste what most airlines provide on long-haul trips.

Plane Tickets To Great Diamond Island

Although you may try and resist the urge, you know that when the travel bug comes, there is only one way to get rid of it. Thankfully, Travelocity is here to help nip that travel bug in the bud with great deals on flights to Great Diamond Island. Browse through our inventory to explore a wide range of cheap flights to Great Diamond Island to solidify your next big trip out of town. Whether you are heading out on a business trip, exploring a place you have never been for pleasure or are bringing the family on the annual vacation, we have the perfect getaway waiting for you. In no time, you will be day dreaming of your plane landing in Great Diamond Island as you anxiously await to exit the plane and explore what Great Diamond Island has to offer. Considering all the amazing local food and culture in Great Diamond Island, we won't hold this against you.

When you are ready to embark on your next big adventure, Travelocity will be right here waiting to open the doors to the garden so that you can go and smell the roses. When you decide to book and travel is entirely up to you, but don't wait too long because we have some of the best deals on the web and they won't last long. Take time to go through our huge selection of cheap flights to Great Diamond Island to find the best deals that fit into your budget. If browsing on your phone while your boss isn't looking is more your thing (we promise we won't tell), consider checking out Travelocity's mobile app which allows you to take advantage of all our flights to Great Diamond Island without having to compromise your work computer's search history. If you are looking to save even more, you can easily save up to $537 when you bundle one of our cheap flights to Great Diamond Island with one of our hotels. So why are you waiting around? There is no better time than now to start booking that next trip. Start your search now to book one of our flights to Great Diamond Island today!

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*Price based on the lowest price found within past 24 hours and based upon one night stay for two adults over the next thirty days. Prices and availability subject to change. Additional terms may apply.