Cheap Flights to Great Diamond Island from $59

Wander Wisely with exceptional service, 24/7 supportOpens in a new window

Feel at ease with free flight cancellations within 24 hours of booking

Change your flight without a fee on select flights

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 $97 and $59 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 - Tue, Oct 21
JFK
John F. Kennedy Intl.
PWM
Portland Intl. Jetport
$97 Roundtrip, found 2 hours ago
$97
Roundtrip
found 2 hours ago
Select JetBlue Airways flight, departing Sat, Oct 18 from John F. Kennedy Intl. to Portland Intl. Jetport, returning Tue, Oct 21, priced at $97 found 2 hours ago
OriginDestinationTravel DatesFlights From*
JFKPortlandSeptember 23 to September 27$97
RDUPortlandOctober 25 to November 1$142
TPAPortlandSeptember 6 to September 13$144
MCOPortlandSeptember 15 to September 19$144
DCAPortlandNovember 4 to November 5$177
ATLPortlandSeptember 8 to September 16$219
PHLPortlandSeptember 20 to September 23$222
CLTPortlandOctober 11 to October 15$229
SEAPortlandSeptember 6 to September 12$266
*Prices include taxes and fees
OriginDestinationTravel DatesFlights From*
JFKPortlandAugust 24 to August 29$160
DCAPortlandAugust 23 to August 30$246
RDUPortlandAugust 23 to August 27$274
MCOPortlandAugust 22 to August 25$336
CLTPortlandAugust 24 to August 30$408
TPAPortlandAugust 23 to August 26$441
ATLPortlandAugust 23 to August 27$449
PHLPortlandAugust 23 to August 27$462
SEAPortlandAugust 22 to August 29$620
FCOPortlandAugust 22 to September 1$953
*Prices include taxes and fees

Great Diamond Island Flight Information

Traveling to
Great Diamond Island
Lowest Price
$97
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
$247 nightly
The price is $269 total per night from Sep 15 to Sep 16
$269 total
Sep 15 - Sep 16
Total includes 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 ...
8.6/10 Excellent! (184 reviews)
"We had an amazing stay! What a gem of an experience - all of the staff was wonderful - Antonio at the lobby cafe was so kind and friendly and Kayla at concierge always went above and beyond!!"

Reviewed on Jul 20, 2025

Inn 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.
Cliff House Maine

Cliff House Maine

4.5 out of 5
Save 100% on your flight
per person
Sep 26 - Sep 29
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Portland (PWM)
Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
Save 100% on your flight
per person
Oct 9 - Oct 16
found 11 hours ago
Roundtrip non-stop flight included
Albuquerque (ABQ) to Portland (PWM)
The Docent's Collection

The Docent's Collection

3.5 out of 5
Save 100% on your flight
per person
Oct 9 - Oct 16
found 11 hours ago
Roundtrip non-stop flight included
Albuquerque (ABQ) to Portland (PWM)
Don't see what you're looking for?
See all available trips from Atlanta to Great Diamond Island
View all trips

Great Diamond Island flight + hotel packages - first class flights

Price found within the past 48 hours. Click for updated prices.
The McKernan Inn

The McKernan Inn

3 out of 5
per person
Sep 21 - Sep 23
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) to Portland (PWM)
Inn By The Sea

Inn By The Sea

4 out of 5
per person
Sep 21 - Sep 23
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) to Portland (PWM)
Kennebunkport Captains Collection

Kennebunkport Captains Collection

4.5 out of 5
per person
Sep 21 - Sep 23
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) to Portland (PWM)
Don't see what you're looking for?
See all available trips from Detroit to Great Diamond Island
View all trips

Need a Car For After Your Flight?

Compact

  • 5 people
  • Unlimited mileage
Portland, Maine, USA

$50

$134 total
found 1 day ago
Compact undefined

Special

  • 4 people
  • Unlimited mileage
Portland, Maine, USA

$50

$134 total
found 1 day ago
Special undefined

Midsize

  • 5 people
  • Unlimited mileage
Portland, Maine, USA

$50

$134 total
found 1 day ago
Midsize undefined

Economy

  • 4 people
  • Unlimited mileage
Portland, Maine, USA

$50

$134 total
found 1 day ago
Economy undefined

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 $97 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 $97. 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 $97 and $953. 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!

*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.