Cheap flights To Great Diamond Island (PWM) from $48

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Cheap Flights to Great Diamond Island from $48 One Way, $68 Round Trip

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

Sat, Jun 14 - Sat, Jun 14
MCO
Orlando Intl.
PWM
Portland Intl. Jetport
$68 Roundtrip, found 2 days ago
$68
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Sat, Jun 14 from Orlando Intl. to Portland Intl. Jetport, returning Sat, Jun 14, priced at $68 found 2 days ago
Thu, May 15 - Sat, May 17
MCO
Orlando Intl.
PWM
Portland Intl. Jetport
$77 Roundtrip, found 4 days ago
$77
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Thu, May 15 from Orlando Intl. to Portland Intl. Jetport, returning Sat, May 17, priced at $77 found 4 days ago
Sat, May 17 - Mon, May 19
MCO
Orlando Intl.
PWM
Portland Intl. Jetport
$78 Roundtrip, found 4 days ago
$78
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Sat, May 17 from Orlando Intl. to Portland Intl. Jetport, returning Mon, May 19, priced at $78 found 4 days ago
Sat, Jun 7 - Sat, Jun 14
MCO
Orlando Intl.
PWM
Portland Intl. Jetport
$86 Roundtrip, found 1 day ago
$86
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Sat, Jun 7 from Orlando Intl. to Portland Intl. Jetport, returning Sat, Jun 14, priced at $86 found 1 day ago
Sat, May 31 - Sat, May 31
MCO
Orlando Intl.
PWM
Portland Intl. Jetport
$90 Roundtrip, found 5 days ago
$90
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Sat, May 31 from Orlando Intl. to Portland Intl. Jetport, returning Sat, May 31, priced at $90 found 5 days ago
Sun, May 18 - Sat, May 24
MCO
Orlando Intl.
PWM
Portland Intl. Jetport
$94 Roundtrip, found 4 days ago
$94
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Sun, May 18 from Orlando Intl. to Portland Intl. Jetport, returning Sat, May 24, priced at $94 found 4 days ago
Sat, May 24 - Sat, May 31
MCO
Orlando Intl.
PWM
Portland Intl. Jetport
$95 Roundtrip, just found
$95
Roundtrip
just found
Select Frontier Airlines flight, departing Sat, May 24 from Orlando Intl. to Portland Intl. Jetport, returning Sat, May 31, priced at $95 just found
Fri, May 16 - Fri, May 16
MCO
Orlando Intl.
PWM
Portland Intl. Jetport
$98 Roundtrip, found 6 hours ago
$98
Roundtrip
found 6 hours ago
Select Frontier Airlines flight, departing Fri, May 16 from Orlando Intl. to Portland Intl. Jetport, returning Fri, May 16, priced at $98 found 6 hours ago
Fri, May 16 - Sat, May 24
MCO
Orlando Intl.
PWM
Portland Intl. Jetport
$99 Roundtrip, found 5 hours ago
$99
Roundtrip
found 5 hours ago
Select Frontier Airlines flight, departing Fri, May 16 from Orlando Intl. to Portland Intl. Jetport, returning Sat, May 24, priced at $99 found 5 hours ago
Sat, May 17 - Mon, May 19
MCO
Orlando Intl.
PWM
Portland Intl. Jetport
$118 Roundtrip, found 4 days ago
$118
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Sat, May 17 from Orlando Intl. to Portland Intl. Jetport, returning Mon, May 19, priced at $118 found 4 days ago

Great Diamond Island Flight Information

Traveling To
Great Diamond Island
Destination Airport IATA Code
PWM
Number of Airlines Serving
Airlines
Frontier Airlines, Breeze Airways
Flight Price
$68
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.
Nautical Mile
2.5-star property

Nautical Mile

Jun 20 - Jun 23

3 night stay

New York (LGA) to Portland (PWM)

American Airlines • Coach

Portland (PWM) to New York (LGA)

Delta • Coach
per person
found 1 day ago
Chebeague Island Inn
4.0-star property

Chebeague Island Inn

Jun 25 - Jun 29

4 night stay

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

United • Roundtrip • Coach
Save 100% on your flight
per person
found 1 day ago
Portland Harbor Hotel
4.0-star property

Portland Harbor Hotel

Jun 25 - Jun 29

4 night stay

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

United • Roundtrip • Coach
Save 100% on your flight
per person
found 1 day ago
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Great Diamond Island premium economy flight packages

Price found within the past 48 hours. Click for updated prices.
Portland Harbor Hotel
4.0-star property

Portland Harbor Hotel

9.2/10 Wonderful! (1,475 reviews)

Jun 10 - Jun 14

4 night stay

New York (LGA) to Portland (PWM)

Delta • Roundtrip • PremiumEconomy
per person
found 8 hours ago
Service was excellent; pantry on each floor awesome; umbrellas available for our use; easy check in & check out

Reviewed on May 4, 2025

Portland Regency Hotel & Spa
3.5-star property

Portland Regency Hotel & Spa

9.4/10 Exceptional! (1,244 reviews)

Jun 10 - Jun 14

4 night stay

New York (LGA) to Portland (PWM)

Delta • Roundtrip • PremiumEconomy
per person
found 8 hours ago
Great location, convenient

Reviewed on May 5, 2025

Blind Tiger Portland – Carleton Street
3.5-star property

Blind Tiger Portland – Carleton Street

9.8/10 Exceptional! (109 reviews)

Jun 10 - Jun 14

4 night stay

New York (LGA) to Portland (PWM)

Delta • Roundtrip • PremiumEconomy
per person
found 8 hours ago
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Great Diamond Island

End your search for discount fares on flights to Great Diamond Island. Orbitz has all the best prices on Great Diamond Island flights. With Orbitz, you can expect:

Cheap Deals on Flights to Great Diamond Island

We offer big discounts and last-minute savings on Great Diamond Island flights. We make it easy for you to research, plan, and book your flight to Great Diamond Island — all while offering great low fares. With guaranteed low prices and cutting-edge mobile tools, the perfect trip begins on Orbitz.

Travel Convenience on the Go

Get alerts, updates, or book your Great Diamond Island flight or other flights wherever you are. Download our free apps for iPhone, Android, and iPad or visit our mobile site at m.orbitz.com to conveniently review or change your air travel plans. We can also send free alerts about your Great Diamond Island flight to your email or mobile phone, so you get advance warning about potential disruptions and flight delays. Need to book a hotel with your Great Diamond Island flight? Access exclusive, mobile-only deals via our mobile site and free apps – even on the same day.

Great Customer Care

We want to make your travel booking experience smooth and easy, from planning and researching Great Diamond Island flights to the actual booking. If you want to cancel your flight to Great Diamond Island, many tickets can be conveniently cancelled online. Contact our Customer Service to make changes to your air ticket.

Miles or Points Toward Frequent Flyer Programs

Much like booking with an airline directly, you can earn frequent flyer miles or points on qualified flights to Great Diamond Island with Orbitz. When completing your booking, just fill in your frequent flyer number for the airline you are flying with or for one of its available partner airlines.

Frequently asked questions

How much is a flight to Great Diamond Island?
Travelers from far and wide landed return-flight deals ranging between $68 and $118 this week. Kicking off your trip from Orlando (MCO)? The lowest one-way fares started at just $48.
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.

Nearby

Flights To

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.