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Great Diamond Island

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Great Diamond Island Flights as Low as $159

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

American Airlines
Tue, Sep 9 - Sat, Sep 13
MCO
Orlando Intl.
PWM
Portland Intl. Jetport
$159 Roundtrip, found 8 hours ago
$159
Roundtrip
found 8 hours ago
Select American Airlines flight, departing Tue, Sep 9 from Orlando Intl. to Portland Intl. Jetport, returning Sat, Sep 13, priced at $159 found 8 hours ago
American Airlines
Tue, Sep 9 - Sat, Sep 13
MCO
Orlando Intl.
PWM
Portland Intl. Jetport
$161 Roundtrip, found 8 hours ago
$161
Roundtrip
found 8 hours ago
Select American Airlines flight, departing Tue, Sep 9 from Orlando Intl. to Portland Intl. Jetport, returning Sat, Sep 13, priced at $161 found 8 hours ago
American Airlines
Sat, Sep 6 - Sat, Sep 13
MCO
Orlando Intl.
PWM
Portland Intl. Jetport
$162 Roundtrip, found 7 hours ago
$162
Roundtrip
found 7 hours ago
Select American Airlines flight, departing Sat, Sep 6 from Orlando Intl. to Portland Intl. Jetport, returning Sat, Sep 13, priced at $162 found 7 hours ago
Breeze Airways
Sat, Sep 6 - Sat, Sep 13
MCO
Orlando Intl.
PWM
Portland Intl. Jetport
$164 Roundtrip, found 7 hours ago
$164
Roundtrip
found 7 hours ago
Select Breeze Airways flight, departing Sat, Sep 6 from Orlando Intl. to Portland Intl. Jetport, returning Sat, Sep 13, priced at $164 found 7 hours ago
Breeze Airways
Wed, Sep 3 - Tue, Sep 16
MCO
Orlando Intl.
PWM
Portland Intl. Jetport
$166 Roundtrip, found 22 hours ago
$166
Roundtrip
found 22 hours ago
Select Breeze Airways flight, departing Wed, Sep 3 from Orlando Intl. to Portland Intl. Jetport, returning Tue, Sep 16, priced at $166 found 22 hours ago
Frontier Airlines
Sat, Aug 16 - Sat, Aug 23
MCO
Orlando Intl.
PWM
Portland Intl. Jetport
$166 Roundtrip, found 13 hours ago
$166
Roundtrip
found 13 hours ago
Select Frontier Airlines flight, departing Sat, Aug 16 from Orlando Intl. to Portland Intl. Jetport, returning Sat, Aug 23, priced at $166 found 13 hours ago
Frontier Airlines
Sat, Sep 6 - Fri, Sep 12
MCO
Orlando Intl.
PWM
Portland Intl. Jetport
$168 Roundtrip, found 9 hours ago
$168
Roundtrip
found 9 hours ago
Select Frontier Airlines flight, departing Sat, Sep 6 from Orlando Intl. to Portland Intl. Jetport, returning Fri, Sep 12, priced at $168 found 9 hours ago
Breeze Airways
Sat, Sep 6 - Fri, Sep 12
MCO
Orlando Intl.
PWM
Portland Intl. Jetport
$169 Roundtrip, found 9 hours ago
$169
Roundtrip
found 9 hours ago
Select Breeze Airways flight, departing Sat, Sep 6 from Orlando Intl. to Portland Intl. Jetport, returning Fri, Sep 12, priced at $169 found 9 hours ago
Frontier Airlines
Sat, Sep 6 - Sat, Sep 13
MCO
Orlando Intl.
PWM
Portland Intl. Jetport
$171 Roundtrip, found 7 hours ago
$171
Roundtrip
found 7 hours ago
Select Frontier Airlines flight, departing Sat, Sep 6 from Orlando Intl. to Portland Intl. Jetport, returning Sat, Sep 13, priced at $171 found 7 hours ago
Bargain Flight
Tue, Sep 30 - Wed, Oct 1
DCA
Ronald Reagan Washington National
PWM
Portland Intl. Jetport
$171 Roundtrip, found 6 hours ago
$171
Roundtrip
found 6 hours ago
Select Bargain Flight flight, departing Tue, Sep 30 from Ronald Reagan Washington National to Portland Intl. Jetport, returning Wed, Oct 1, priced at $171 found 6 hours ago
Delta
Tue, Sep 30 - Wed, Oct 1
DCA
Ronald Reagan Washington National
PWM
Portland Intl. Jetport
$177 Roundtrip, found 6 hours ago
$177
Roundtrip
found 6 hours ago
Select Delta flight, departing Tue, Sep 30 from Ronald Reagan Washington National to Portland Intl. Jetport, returning Wed, Oct 1, priced at $177 found 6 hours ago
JetBlue Airways
Thu, Aug 14 - Fri, Aug 15
BOS
Logan Intl.
PWM
Portland Intl. Jetport
$203 Roundtrip, found 2 days ago
$203
Roundtrip
found 2 days ago
Select JetBlue Airways flight, departing Thu, Aug 14 from Logan Intl. to Portland Intl. Jetport, returning Fri, Aug 15, priced at $203 found 2 days ago
JetBlue Airways
Mon, Aug 4 - Tue, Aug 12
DTW
Detroit Metropolitan Wayne County
PWM
Portland Intl. Jetport
$205 Roundtrip, found 1 day ago
$205
Roundtrip
found 1 day ago
Select JetBlue Airways flight, departing Mon, Aug 4 from Detroit Metropolitan Wayne County to Portland Intl. Jetport, returning Tue, Aug 12, priced at $205 found 1 day ago
American Airlines
Mon, Aug 4 - Tue, Aug 12
AUS
Austin-Bergstrom Intl.
PWM
Portland Intl. Jetport
$240 Roundtrip, found 15 hours ago
$240
Roundtrip
found 15 hours ago
Select American Airlines flight, departing Mon, Aug 4 from Austin-Bergstrom Intl. to Portland Intl. Jetport, returning Tue, Aug 12, priced at $240 found 15 hours ago
Delta
Tue, Aug 5 - Wed, Aug 6
LAS
Harry Reid Intl.
PWM
Portland Intl. Jetport
$261 Roundtrip, found 1 day ago
$261
Roundtrip
found 1 day ago
Select Delta flight, departing Tue, Aug 5 from Harry Reid Intl. to Portland Intl. Jetport, returning Wed, Aug 6, priced at $261 found 1 day ago
American Airlines
Wed, Aug 13 - Wed, Aug 20
HSV
Huntsville Intl.
PWM
Portland Intl. Jetport
$263 Roundtrip, found 1 day ago
$263
Roundtrip
found 1 day ago
Select American Airlines flight, departing Wed, Aug 13 from Huntsville Intl. to Portland Intl. Jetport, returning Wed, Aug 20, priced at $263 found 1 day ago

Cheap Flights to Great Diamond Island

Fall in love at first flight with your vacation to Great Diamond Island by saving a ton of cash on your last-minute cheap flight. There’s no more scouring the internet for a good deal—book your flight to Great Diamond Island on Hotwire, and you’ll be up, up, and on a getaway in no time.

Because once the wheels are down in Great Diamond Island, the good times start rolling. So buckle up, you’re in for a fun ride.

Frequently Asked Questions About flights to Great Diamond Island

Don’t waste your time on endless searches for cheap airline tickets oneway or roundtrip. We’ll have you on your way to Great Diamond Island with a tiny bag of pretzels in your hand before you can say “tray tables in the upright position”—and for a ticket price that works for your vacay budget.

So all you have to worry about is where you’re headed after the PWM airport.

What is the cheapest month to fly to Great Diamond Island?

Airline ticket prices fluctuate all the time, depending on the day of the week or the month of the year. The cheapest round trip flights to Great Diamond Island are in September, but when you book your flight on Hotwire, savings are always in season.

How many airlines fly to Great Diamond Island?

Variety is the spice of life, even when it comes to booking your next trip. Want options for airlines? You’ll find 15 to choose from for your flight to Great Diamond Island.

What airport is best to fly into Great Diamond Island?

When you’re planning your trip to Great Diamond Island, convenience is the name of the game. Luckily, Great Diamond Island Portland Intl. Jetport Airport is nearby so you can deplane and get going on checking off everything on your Great Diamond Island must-do list.

How much are flights to Great Diamond Island?

Got very cheap flights on your vacation itinerary? When you book your airline tickets to Great Diamond Island on Hotwire, you may just get what’s on your getaway wish list. With tickets as low as $159, you’ll have leftover cash for at least a magazine and a bottle of water at the airport book store.

How to get cheap flights to Great Diamond Island?

The trick to saving a stack of cash on your flight to Great Diamond Island? Snatch up that Hotwire flight deal when you see a killer rate because it could be gone in a flash. And with flights as low as $159 right now, why wait?

Great Diamond Island Flight Information
Destination airport
Portland Intl. Jetport
Destination airport IATA code
PWM
Roundtrip price
$158

Last Minute Hotel Deals in Great Diamond Island

Clarion Hotel Portland
Clarion Hotel Portland
2.5 out of 5
1230 Congress St, Portland, ME
Book a stay at this business-friendly hotel in Portland. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the ...
7.8/10 Good! (1,013 reviews)
"Nice hotel close to the airport with shuttle service"

Reviewed on Jul 7, 2025

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Clarion Hotel Portland
Ramada Plaza by Wyndham Portland
Ramada Plaza by Wyndham Portland
3 out of 5
155 Riverside St, Portland, ME
Stay at this 3-star business-friendly hotel in Portland. Enjoy free WiFi, free parking, and 2 hot tubs. Our guests praise the restaurant and the helpful staff ...
7.6/10 Good! (1,033 reviews)
"The pool was nice, it was deeper than expected and was clean. The room was decent. Walls are a little thin but it didn’t seem to bother my 7 month old, 5 year old, and 8 year old. I would visit this location again"

Reviewed on Jul 7, 2025

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Ramada Plaza by Wyndham Portland
Days Inn by Wyndham Airport/Maine Mall
Days Inn by Wyndham Airport/Maine Mall
2 out of 5
461 Maine Mall Rd, South Portland, ME
Book a stay at this business-friendly hotel in South Portland. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the ...
7.8/10 Good! (1,004 reviews)
"Very convenient stay super close to the airport and downtown. Would definitely stay again."

Reviewed on Jul 9, 2025

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Days Inn by Wyndham Airport/Maine Mall
Hyatt Place Portland Downtown - Old Port Square
Hyatt Place Portland Downtown - Old Port Square
3 out of 5
433 Fore St, Portland, ME
Stay at this 3-star business-friendly hotel in Portland. Enjoy free WiFi, 2 bars/lounges, and breakfast (surcharge). Our guests praise the breakfast and the ...
8.8/10 Excellent! (1,153 reviews)
"Great stay!"

Reviewed on Jul 4, 2025

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Hyatt Place Portland Downtown - Old Port Square
Portland Harbor Hotel
Portland Harbor Hotel
4 out of 5
468 Fore Street, Portland, ME
Stay at this 4-star business-friendly hotel in Portland. Enjoy free WiFi, 3 coffee shops/cafes, and breakfast (surcharge). Our guests praise the bar and the ...
9.2/10 Wonderful! (1,523 reviews)
"The beds were super comfortable! The entire staff was helpful and kind."

Reviewed on Jul 6, 2025

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Portland Harbor Hotel
The Westin Portland Harborview
The Westin Portland Harborview
4 out of 5
157 High St, Portland, ME
Book a stay at this spa hotel in Portland. Enjoy free WiFi, a full-service spa, and breakfast (surcharge). Our guests praise the bar and the helpful staff in ...
8.8/10 Excellent! (1,004 reviews)
"Nice hotel"

Reviewed on Jul 6, 2025

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The Westin Portland Harborview
Portland Regency Hotel & Spa
Portland Regency Hotel & Spa
3.5 out of 5
20 Milk Street, Portland, ME
Stay at this 3.5-star spa hotel in Portland. Enjoy free WiFi, a full-service spa, and 2 bars/lounges. Our guests praise the helpful staff and the clean rooms ...
9.2/10 Wonderful! (1,336 reviews)
"Loved everything about this place"

Reviewed on Jul 7, 2025

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Portland Regency Hotel & Spa
Canopy by Hilton Portland Waterfront
Canopy by Hilton Portland Waterfront
4 out of 5
9 Center Street, Portland, ME
Stay at this 4-star hotel in Portland. Enjoy free WiFi, 2 restaurants, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in ...
9.4/10 Exceptional! (1,003 reviews)
"This is probably one of most favorite hotels I’ve ever stayed at. I love the rooftop bar in the location is great along the waterfront which has a lot of old historic buildings. The hotel lobby is amazing. It is so beautiful and so are the rooms. Very modern and comfortable. The breakfast Café and ..."

Reviewed on Jul 4, 2025

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Canopy by Hilton Portland Waterfront
See all 2,513 properties in Great Diamond Island
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.