Cheap flights To Great Diamond Island (PWM) from $71

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Cheap Flights to Great Diamond Island from $71 One Way, $140 Round Trip

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

Sat, Nov 14 - Mon, Nov 16
RDU
Raleigh - Durham Intl.
PWM
Portland Intl. Jetport
$140 Roundtrip, found 5 days ago
$140
Roundtrip
found 5 days ago
Select Breeze Airways flight, departing Sat, Nov 14 from Raleigh - Durham Intl. to Portland Intl. Jetport, returning Mon, Nov 16, priced at $140 found 5 days ago
Sat, Jan 23 - Sat, Jan 30
TPA
Tampa Intl.
PWM
Portland Intl. Jetport
$142 Roundtrip, found 3 hours ago
$142
Roundtrip
found 3 hours ago
Select Breeze Airways flight, departing Sat, Jan 23 from Tampa Intl. to Portland Intl. Jetport, returning Sat, Jan 30, priced at $142 found 3 hours ago
Sat, Dec 5 - Sat, Dec 12
RDU
Raleigh - Durham Intl.
PWM
Portland Intl. Jetport
$142 Roundtrip, found 9 hours ago
$142
Roundtrip
found 9 hours ago
Select Breeze Airways flight, departing Sat, Dec 5 from Raleigh - Durham Intl. to Portland Intl. Jetport, returning Sat, Dec 12, priced at $142 found 9 hours ago
Sat, Nov 7 - Sat, Nov 14
RDU
Raleigh - Durham Intl.
PWM
Portland Intl. Jetport
$144 Roundtrip, found 1 day ago
$144
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Sat, Nov 7 from Raleigh - Durham Intl. to Portland Intl. Jetport, returning Sat, Nov 14, priced at $144 found 1 day ago
Wed, Jan 27 - Sat, Jan 30
TPA
Tampa Intl.
PWM
Portland Intl. Jetport
$147 Roundtrip, found 6 days ago
$147
Roundtrip
found 6 days ago
Select Breeze Airways flight, departing Wed, Jan 27 from Tampa Intl. to Portland Intl. Jetport, returning Sat, Jan 30, priced at $147 found 6 days ago
Wed, Oct 28 - Sat, Oct 31
RDU
Raleigh - Durham Intl.
PWM
Portland Intl. Jetport
$149 Roundtrip, found 3 hours ago
$149
Roundtrip
found 3 hours ago
Select Breeze Airways flight, departing Wed, Oct 28 from Raleigh - Durham Intl. to Portland Intl. Jetport, returning Sat, Oct 31, priced at $149 found 3 hours ago
Wed, Jan 27 - Sat, Jan 30
TPA
Tampa Intl.
PWM
Portland Intl. Jetport
$152 Roundtrip, found 6 days ago
$152
Roundtrip
found 6 days ago
Select Breeze Airways flight, departing Wed, Jan 27 from Tampa Intl. to Portland Intl. Jetport, returning Sat, Jan 30, priced at $152 found 6 days ago
Sat, Jan 30 - Sat, Feb 6
RDU
Raleigh - Durham Intl.
PWM
Portland Intl. Jetport
$152 Roundtrip, found 4 days ago
$152
Roundtrip
found 4 days ago
Select Breeze Airways flight, departing Sat, Jan 30 from Raleigh - Durham Intl. to Portland Intl. Jetport, returning Sat, Feb 6, priced at $152 found 4 days ago
Sat, Oct 24 - Sat, Oct 31
RDU
Raleigh - Durham Intl.
PWM
Portland Intl. Jetport
$154 Roundtrip, found 12 hours ago
$154
Roundtrip
found 12 hours ago
Select Breeze Airways flight, departing Sat, Oct 24 from Raleigh - Durham Intl. to Portland Intl. Jetport, returning Sat, Oct 31, priced at $154 found 12 hours ago
Sat, Jan 16 - Sat, Jan 23
TPA
Tampa Intl.
PWM
Portland Intl. Jetport
$157 Roundtrip, found 20 hours ago
$157
Roundtrip
found 20 hours ago
Select Breeze Airways flight, departing Sat, Jan 16 from Tampa Intl. to Portland Intl. Jetport, returning Sat, Jan 23, priced at $157 found 20 hours ago

Great Diamond Island Flight Information

Traveling To
Great Diamond Island
Destination Airport IATA Code
PWM
Number of Airlines Serving
Airlines
Breeze Airways
Flight Price
$140
Earliest Departing Flight
Latest Departing Flight

Book Your Flight & Hotel Together & Save

Great Diamond Island economy flight packages

Price found within the past 48 hours. Click for updated prices.
The Meadowmere Resort
2.5-star property

The Meadowmere Resort

Oct 29 - Nov 2

4 night stay

New Orleans (MSY) to Portland (PWM)

American Airlines • Non-stop roundtrip • Coach
Price was $1,141, price is now $873 per person
$873
per person
found 20 hours ago
The Francis
3.5-star property

The Francis

Oct 27 - Nov 1

5 night stay

Newark Liberty Intl. Airport (EWR) to Portland (PWM)

United • Roundtrip • Coach
Save 100% on your flight
Price was $1,590, price is now $1,218 per person
$1,218
per person
found 19 hours ago
Blind Tiger Portland – Carleton Street
3.5-star property

Blind Tiger Portland – Carleton Street

Oct 27 - Nov 1

5 night stay

Newark Liberty Intl. Airport (EWR) to Portland (PWM)

United • Roundtrip • Coach
Save 100% on your flight
Price was $1,589, price is now $1,260 per person
$1,260
per person
found 19 hours ago
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Great Diamond Island first class flight packages

Price found within the past 48 hours. Click for updated prices.
The Docent's Collection at 178 Middle Street
3.5-star property

The Docent's Collection at 178 Middle Street

9.6/10 Exceptional! (61 reviews)

Oct 27 - Oct 29

2 night stay

Detroit (DTW) to Portland (PWM)

Delta • FirstClass

Portland (PWM) to Detroit (DTW)

United • FirstClass
Price was $1,452, price is now $1,347 per person
$1,347
per person
found 19 hours ago
Room was beautiful, new, and clean. Staff upon check in was extremely helpful and courteous, Excellent accommodations. Close to many sights, bars, and restaurants. Would stay again in a heartbeat.

Reviewed on Sep 12, 2026

Blind Tiger Portland - Danforth Street.
3.5-star property

Blind Tiger Portland - Danforth Street.

9.6/10 Exceptional! (192 reviews)

Oct 27 - Oct 29

2 night stay

Detroit (DTW) to Portland (PWM)

Delta • FirstClass

Portland (PWM) to Detroit (DTW)

United • FirstClass
Price was $1,836, price is now $1,700 per person
$1,700
per person
found 19 hours ago
Enjoyable

Reviewed on Aug 28, 2026

Inn By The Sea
4.0-star property

Inn By The Sea

9.6/10 Exceptional! (328 reviews)

Oct 27 - Oct 29

2 night stay

Detroit (DTW) to Portland (PWM)

Delta • FirstClass

Portland (PWM) to Detroit (DTW)

United • FirstClass
Price was $1,622, price is now $1,519 per person
$1,519
per person
found 19 hours ago
Beautiful location, quiet, but close to beach and shorelines. Lots of thoughtful luxuries provided like beach chairs, buckets, snacks, fruit and a nightly fire with smores.

Reviewed on Sep 11, 2026

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Great Diamond Island

Orbitz uses cutting edge mobile technology to help get you the best deals on Great Diamond Island flights. We offer guaranteed low prices on air tickets that can be combined with hotels and car rentals to save you even more money.

Find Cheap Great Diamond Island Flights And Hotel Rooms Using Our Mobile App

Orbitz not only guarantees low prices for flights to Great Diamond Island, we also offer Mobile Steals on our Orbitz on the Go mobile app where you can find great mobile-only deals on hotel rooms in the area.

Use the Orbitz Flight Matrix To Save Big On Car Rental

Discount flights to Great Diamond Island can be combined with car rental to get you additional savings. Just use our Flight Matrix to see how your budget air ticket can be combined with a car rental to make your trip not only inexpensive but also more convenient.

Use Multiple Airlines To Ensure You Get The Best Deal

Orbitz allows you to use multiple airlines for flights to Great Diamond Island. By using a combination of airlines for discount flights you are guaranteed to get the lowest fares each way and get the schedule that is most convenient for you.

Store Your Frequent Flyer Information on Orbitz For Easy Access

Booking with Orbitz will still allow you to apply miles for flights to Great Diamond Island to your frequent flyer program. Not only that, but your frequent flyer information will be safely stored on our website, so it will be easy to access the next time you book a discount air ticket with Orbitz.

Frequently asked questions

How much is a flight to Great Diamond Island?
Travelers from far and wide landed return-flight deals ranging between $140 and $157 this week. Kicking off your trip from Raleigh (RDU)? The lowest one-way fares started at just $71.
How to book the cheapest flight to Great Diamond Island?
With Orbitz, you'll find some of the most incredible flight deals around from a wide range of airlines. But if you want to boost your prospects of landing cheap flights to Great Diamond Island, here are some suggestions to keep in mind:

  • Taking off from or landing at other airports may save you money. Enter your preferred departure and arrival points. Next, click on the 'Nearby airports' function below to see your options.
  • If you're flexible with your plans, click on the 'Show flexible dates' option. It'll bring up flight deals for the days around your chosen departure. Ticket prices often vary depending on the day of the week.
  • Select 'Show options' to narrow down your search results. You can pick your preferred seating class and airline here. Under 'Sort & Filter' to the left, you can even select whether you'd like to fly in the morning, afternoon or evening.
  • Lock in your fare as soon as you've sorted your travel dates. While you can get lucky now and then, tickets rarely get cheaper as your date of departure nears.
  • Make big savings on your getaway by bundling your hotel, flights and car rental into a package deal. Your budget will thank you.
  • Flying during busier seasons means costly airfares. Try to plan your trip outside of popular periods, such as Thanksgiving, New Year's Eve and Easter.

How long is a flight to Great Diamond Island?
The time you spend in the air will depend on where you're jetting in from, whether that's the Northern states, the South or someplace else. Listed below are some of the major routes to Great Diamond Island and how long they take:

  • New York, NY (LGA-LaGuardia) to Portland Intl. Jetport Airport (PWM) - 1 hour and 29 minutes
  • New York, NY (JFK-John F. Kennedy Intl.) to Portland Intl. Jetport Airport (PWM) - 1 hour and 22 minutes
  • Newark, NJ (EWR-Liberty Intl.) to Portland Intl. Jetport Airport (PWM) - 1 hour and 20 minutes

What is the best time to book a flight to Great Diamond Island?
Generally speaking, the cheapest month to book your airfare is in January. This is closely followed by February then August. When seeking a cheap flight to Great Diamond Island, it always pays to be ready to book. Cheap deals pop up suddenly and don't hang around!
What day of the week is the cheapest to book a flight to Great Diamond Island?
Typically, Tuesdays, Wednesdays and Saturdays are the cheapest days to book a flight to Great Diamond Island. If you want unbeatable airfares, search across those days and you're likely to find a fantastic flight deal.
What is the cheapest day of the week to fly to Great Diamond Island?
If you're on the hunt for cheap flights to Great Diamond Island, leave early in the week. Orbitz data from 2020 shows Monday is the most affordable day to travel, followed by Tuesday. Saturday has the most expensive fares, so avoid flying on this day and do your wallet a favor.
What is the cheapest month to fly to Great Diamond Island?
To secure cheap flights to Great Diamond Island, you should depart in August. If saving money on your plane ticket is your main concern, Orbitz data shows that this is generally an excellent month to take a trip. June is when fares are the most expensive.
Which airlines allow free cancellation?
When you search for flights on Orbitz, click on "Filter by flexible change policies." This filter will show you all the airlines offering free cancellation within 24 hours of booking and no change fees. Breathe easy knowing that if things change, your flight can too.
What do I need for the flight to Great Diamond Island?
There's so much to sort out for any big trip, so it's useful to get a little bit of help before you set out. Here are a few pointers to ensure you're organized for your flight:

  • Ensure that you have your travel documents and identification. For overseas journeys, you'll need to take your passport. When you book your flights, always use the same name, gender and birth date as written on your current ID.
  • Pack your carry-on bag with activities and snacks and watch time whiz by on this medium-haul flight. If possible, jump on the airport's Wi-Fi and save your favorite podcast or playlist to your device ahead of your journey.
  • Plane cabins can often get chilly. Even if you're traveling during the height of the Great Diamond Island summer, make sure you bring a sweater on board with you.

How many direct flights are there to Great Diamond Island?
Every month, there are 92 direct flights to Great Diamond Island. Choose from an excellent range of airline companies, including American Airlines, Delta Air Lines and United Airlines. Other reputable airlines that jet to Great Diamond Island nonstop are Southwest Airlines, JetBlue Airways and Sun Country Airlines.
How do I get cheap first-class/business deals to Great Diamond Island?
There are ways of booking business or first-class fares to Great Diamond Island that won't burn through your wallet. Bag a seat in the pointy end of the plane for less with these useful tips:

  • Flexibility is everything. By being open to a few travel dates, you'll have more chances of picking up a great deal on business or first-class airfares.
  • A lot of low-cost airlines have top-notch business-class seating for a reasonable price.
  • Make a bid for an upgrade. Some carriers hold online auctions that let you put down a price for a seat up the front. You may also be able to upgrade with points earned through a flight loyalty program.

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.