Search Cheap Flights to
Great Diamond Island

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Great Diamond Island Flights as Low as $100

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

Frontier Airlines
Sat, Aug 16 - Sat, Aug 23
MCO
Orlando Intl.
PWM
Portland Intl. Jetport
$100 Roundtrip, found 3 days ago
$100
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Sat, Aug 16 from Orlando Intl. to Portland Intl. Jetport, returning Sat, Aug 23, priced at $100 found 3 days ago
JetBlue Airways
Sun, Oct 12 - Thu, Oct 16
JFK
John F. Kennedy Intl.
PWM
Portland Intl. Jetport
$117 Roundtrip, found 1 day ago
$117
Roundtrip
found 1 day ago
Select JetBlue Airways flight, departing Sun, Oct 12 from John F. Kennedy Intl. to Portland Intl. Jetport, returning Thu, Oct 16, priced at $117 found 1 day ago
JetBlue Airways
Mon, Oct 13 - Thu, Oct 16
JFK
John F. Kennedy Intl.
PWM
Portland Intl. Jetport
$127 Roundtrip, found 1 day ago
$127
Roundtrip
found 1 day ago
Select JetBlue Airways flight, departing Mon, Oct 13 from John F. Kennedy Intl. to Portland Intl. Jetport, returning Thu, Oct 16, priced at $127 found 1 day ago
JetBlue Airways
Sun, Oct 12 - Sun, Oct 19
JFK
John F. Kennedy Intl.
PWM
Portland Intl. Jetport
$137 Roundtrip, found 1 day ago
$137
Roundtrip
found 1 day ago
Select JetBlue Airways flight, departing Sun, Oct 12 from John F. Kennedy Intl. to Portland Intl. Jetport, returning Sun, Oct 19, priced at $137 found 1 day ago
Breeze Airways
Sat, Sep 6 - Sat, Sep 13
MCO
Orlando Intl.
PWM
Portland Intl. Jetport
$143 Roundtrip, found 10 hours ago
$143
Roundtrip
found 10 hours ago
Select Breeze Airways flight, departing Sat, Sep 6 from Orlando Intl. to Portland Intl. Jetport, returning Sat, Sep 13, priced at $143 found 10 hours ago
Breeze Airways
Wed, Aug 27 - Sat, Aug 30
MCO
Orlando Intl.
PWM
Portland Intl. Jetport
$147 Roundtrip, found 3 days ago
$147
Roundtrip
found 3 days ago
Select Breeze Airways flight, departing Wed, Aug 27 from Orlando Intl. to Portland Intl. Jetport, returning Sat, Aug 30, priced at $147 found 3 days ago
Delta
Tue, Oct 14 - Tue, Oct 21
JFK
John F. Kennedy Intl.
PWM
Portland Intl. Jetport
$147 Roundtrip, found 1 day ago
$147
Roundtrip
found 1 day ago
Select Delta flight, departing Tue, Oct 14 from John F. Kennedy Intl. to Portland Intl. Jetport, returning Tue, Oct 21, priced at $147 found 1 day ago
Breeze Airways
Sat, Sep 6 - Sat, Sep 13
MCO
Orlando Intl.
PWM
Portland Intl. Jetport
$148 Roundtrip, found 10 hours ago
$148
Roundtrip
found 10 hours ago
Select Breeze Airways flight, departing Sat, Sep 6 from Orlando Intl. to Portland Intl. Jetport, returning Sat, Sep 13, priced at $148 found 10 hours ago
Breeze Airways
Wed, Aug 27 - Sat, Aug 30
MCO
Orlando Intl.
PWM
Portland Intl. Jetport
$152 Roundtrip, found 3 days ago
$152
Roundtrip
found 3 days ago
Select Breeze Airways flight, departing Wed, Aug 27 from Orlando Intl. to Portland Intl. Jetport, returning Sat, Aug 30, priced at $152 found 3 days ago
Breeze Airways
Sat, Sep 6 - Sat, Sep 13
MCO
Orlando Intl.
PWM
Portland Intl. Jetport
$153 Roundtrip, found 10 hours ago
$153
Roundtrip
found 10 hours ago
Select Breeze Airways flight, departing Sat, Sep 6 from Orlando Intl. to Portland Intl. Jetport, returning Sat, Sep 13, priced at $153 found 10 hours ago
JetBlue Airways
Thu, Sep 25 - Thu, Oct 2
RDU
Raleigh - Durham Intl.
PWM
Portland Intl. Jetport
$201 Roundtrip, found 1 day ago
$201
Roundtrip
found 1 day ago
Select JetBlue Airways flight, departing Thu, Sep 25 from Raleigh - Durham Intl. to Portland Intl. Jetport, returning Thu, Oct 2, priced at $201 found 1 day ago
United
Wed, Sep 3 - Tue, Sep 16
MCO
Orlando Intl.
PWM
Portland Intl. Jetport
$221 Roundtrip, found 8 hours ago
$221
Roundtrip
found 8 hours ago
Select United flight, departing Wed, Sep 3 from Orlando Intl. to Portland Intl. Jetport, returning Tue, Sep 16, priced at $221 found 8 hours ago
American Airlines
Wed, Sep 3 - Tue, Sep 16
MCO
Orlando Intl.
PWM
Portland Intl. Jetport
$221 Roundtrip, found 8 hours ago
$221
Roundtrip
found 8 hours ago
Select American Airlines flight, departing Wed, Sep 3 from Orlando Intl. to Portland Intl. Jetport, returning Tue, Sep 16, priced at $221 found 8 hours ago
JetBlue Airways
Sat, Sep 6 - Tue, Sep 9
ATL
Hartsfield-Jackson Atlanta Intl.
PWM
Portland Intl. Jetport
$240 Roundtrip, found 1 day ago
$240
Roundtrip
found 1 day ago
Select JetBlue Airways flight, departing Sat, Sep 6 from Hartsfield-Jackson Atlanta Intl. to Portland Intl. Jetport, returning Tue, Sep 9, priced at $240 found 1 day ago
Bargain Flight
Wed, Aug 6 - Wed, Aug 13
CLT
Charlotte-Douglas Intl.
PWM
Portland Intl. Jetport
$317 Roundtrip, found 3 days ago
$317
Roundtrip
found 3 days ago
Select Bargain Flight flight, departing Wed, Aug 6 from Charlotte-Douglas Intl. to Portland Intl. Jetport, returning Wed, Aug 13, priced at $317 found 3 days ago
Bargain Flight
Tue, Aug 5 - Tue, Aug 19
PDX
Portland Intl.
PWM
Portland Intl. Jetport
$465 Roundtrip, found 1 day ago
$465
Roundtrip
found 1 day ago
Select Bargain Flight flight, departing Tue, Aug 5 from Portland Intl. to Portland Intl. Jetport, returning Tue, Aug 19, priced at $465 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 August, 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 14 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 $100, 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 $100 right now, why wait?

Great Diamond Island Flight Information
Destination airport
Portland Intl. Jetport
Destination airport IATA code
PWM
Roundtrip price
$99

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! (1,001 reviews)
"Breakfast food served out of a closet was a little odd, but it did taste good."

Reviewed on Aug 1, 2025

Get rates
Clarion Hotel 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! (1,106 reviews)
"It was a nice place. The food was limited and the pool could use a cleaning but not to bad. Overall it was a good experience"

Reviewed on Aug 1, 2025

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Days Inn by Wyndham Airport/Maine Mall
Comfort Inn Airport

Comfort Inn Airport

2.5 out of 5
90 Maine Mall Rd, South Portland, ME
Book a stay at this business-friendly hotel in South Portland. Enjoy free breakfast, free WiFi, and a free airport shuttle. Our guests praise the breakfast and ...
8.4/10 Very Good! (1,444 reviews)
"Very friend staff"

Reviewed on Aug 1, 2025

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Comfort Inn Airport
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! (1,546 reviews)
"We really enjoyed our stay. Great location, staff couldn’t have been more friendly, and a clean comfortable room. Snacks and a Keurig in the hall for all on the floor to share was nice, although there was something wrong with the Keurig. (It worked, but there were multiple times I had to run it ..."

Reviewed on Jul 31, 2025

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Portland Harbor Hotel
Germaine Inn South Portland

Germaine Inn South Portland

2 out of 5
675 Main Street I-95, Rt 1-I95 ex 45-I295 Ex 3, South Portland, ME
Book a stay at this business-friendly hotel in South Portland. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Maine Mall and Thompson's ...
7.4/10 Good! (108 reviews)
"I really liked that they had a pool"

Reviewed on Jul 30, 2025

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Germaine Inn South Portland
Casco Bay Hotel Portland Airport - Maine Mall, Ascend Hotel Collection

Casco Bay Hotel Portland Airport - Maine Mall, Ascend Hotel Collection

3.5 out of 5
80 John Roberts Rd., South Portland, ME
Stay at this 3.5-star business-friendly hotel in South Portland. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
8.4/10 Very Good! (2,767 reviews)
"The overall experience was positive; however, there were no towel racks in the bathroom, and the gentleman receptionist was the unfriendliest person I have met at a hotel. No welcome and no smiles. I rather felt for him to look so miserable."

Reviewed on Jul 31, 2025

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Casco Bay Hotel Portland Airport - Maine Mall, Ascend Hotel Collection
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! (1,041 reviews)
"Most comfortable beds! Room could have used a vacuum but sheets were clean and bathtub was clean. No frills, not modern, but served its purpose. Welcome staff was delightful!"

Reviewed on Jul 27, 2025

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Ramada Plaza by Wyndham Portland
Holiday Inn Portland-By the Bay by IHG

Holiday Inn Portland-By the Bay by IHG

3 out of 5
88 Spring St, Portland, ME
Stay at this 3-star business-friendly hotel in Portland. Enjoy free WiFi, breakfast (surcharge), and a free airport shuttle. Our guests praise the helpful staff ...
8.8/10 Excellent! (1,310 reviews)
Beautiful clean establishment.
"Wonderful stay, very friendly and helpful."

Reviewed on Jul 31, 2025

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Holiday Inn Portland-By the Bay by IHG
See all 2,498 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.