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Chebeague Island

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Chebeague Island Flights as Low as $162

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

Breeze Airways
Sat, Sep 6 - Sat, Sep 13
MCO
Orlando Intl.
PWM
Portland Intl. Jetport
$162 Roundtrip, found 1 day ago
$162
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Sat, Sep 6 from Orlando Intl. to Portland Intl. Jetport, returning Sat, Sep 13, priced at $162 found 1 day ago
Breeze Airways
Sat, Sep 6 - Sat, Sep 13
MCO
Orlando Intl.
PWM
Portland Intl. Jetport
$167 Roundtrip, found 1 day ago
$167
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Sat, Sep 6 from Orlando Intl. to Portland Intl. Jetport, returning Sat, Sep 13, priced at $167 found 1 day ago
Frontier Airlines
Sat, Sep 6 - Sat, Sep 13
MCO
Orlando Intl.
PWM
Portland Intl. Jetport
$169 Roundtrip, found 1 day ago
$169
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Sat, Sep 6 from Orlando Intl. to Portland Intl. Jetport, returning Sat, Sep 13, priced at $169 found 1 day ago
Breeze Airways
Sat, Sep 6 - Sat, Sep 13
MCO
Orlando Intl.
PWM
Portland Intl. Jetport
$172 Roundtrip, found 1 day ago
$172
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Sat, Sep 6 from Orlando Intl. to Portland Intl. Jetport, returning Sat, Sep 13, priced at $172 found 1 day ago
Frontier Airlines
Sat, Sep 6 - Sat, Sep 13
MCO
Orlando Intl.
PWM
Portland Intl. Jetport
$176 Roundtrip, found 1 day ago
$176
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Sat, Sep 6 from Orlando Intl. to Portland Intl. Jetport, returning Sat, Sep 13, priced at $176 found 1 day ago
Breeze Airways
Wed, Aug 13 - Wed, Aug 20
MCO
Orlando Intl.
PWM
Portland Intl. Jetport
$183 Roundtrip, found 1 day ago
$183
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Wed, Aug 13 from Orlando Intl. to Portland Intl. Jetport, returning Wed, Aug 20, priced at $183 found 1 day ago
JetBlue Airways
Sat, Jul 5 - Wed, Jul 9
PBI
Palm Beach Intl.
PWM
Portland Intl. Jetport
$202 Roundtrip, found 11 hours ago
$202
Roundtrip
found 11 hours ago
Select JetBlue Airways flight, departing Sat, Jul 5 from Palm Beach Intl. to Portland Intl. Jetport, returning Wed, Jul 9, priced at $202 found 11 hours ago
United
Sat, Jul 5 - Wed, Jul 9
FLL
Fort Lauderdale - Hollywood Intl.
PWM
Portland Intl. Jetport
$212 Roundtrip, found 1 day ago
$212
Roundtrip
found 1 day ago
Select United flight, departing Sat, Jul 5 from Fort Lauderdale - Hollywood Intl. to Portland Intl. Jetport, returning Wed, Jul 9, priced at $212 found 1 day ago
Delta
Sat, Jul 5 - Wed, Jul 9
FLL
Fort Lauderdale - Hollywood Intl.
PWM
Portland Intl. Jetport
$217 Roundtrip, found 11 hours ago
$217
Roundtrip
found 11 hours ago
Select Delta flight, departing Sat, Jul 5 from Fort Lauderdale - Hollywood Intl. to Portland Intl. Jetport, returning Wed, Jul 9, priced at $217 found 11 hours ago
American Airlines
Tue, Sep 9 - Sat, Sep 13
MCO
Orlando Intl.
PWM
Portland Intl. Jetport
$219 Roundtrip, found 16 hours ago
$219
Roundtrip
found 16 hours ago
Select American Airlines flight, departing Tue, Sep 9 from Orlando Intl. to Portland Intl. Jetport, returning Sat, Sep 13, priced at $219 found 16 hours ago
Delta
Sat, Jul 12 - Tue, Jul 22
JAX
Jacksonville Intl.
PWM
Portland Intl. Jetport
$240 Roundtrip, found 5 days ago
$240
Roundtrip
found 5 days ago
Select Delta flight, departing Sat, Jul 12 from Jacksonville Intl. to Portland Intl. Jetport, returning Tue, Jul 22, priced at $240 found 5 days ago
Bargain Flight
Mon, Aug 11 - Thu, Aug 14
DFW
Dallas-Fort Worth Intl.
PWM
Portland Intl. Jetport
$267 Roundtrip, found 2 days ago
$267
Roundtrip
found 2 days ago
Select Bargain Flight flight, departing Mon, Aug 11 from Dallas-Fort Worth Intl. to Portland Intl. Jetport, returning Thu, Aug 14, priced at $267 found 2 days ago
Delta
Tue, Oct 14 - Tue, Oct 21
LAS
Harry Reid Intl.
PWM
Portland Intl. Jetport
$273 Roundtrip, found 8 hours ago
$273
Roundtrip
found 8 hours ago
Select Delta flight, departing Tue, Oct 14 from Harry Reid Intl. to Portland Intl. Jetport, returning Tue, Oct 21, priced at $273 found 8 hours ago
Bargain Flight
Wed, Oct 22 - Tue, Oct 28
PDX
Portland Intl.
PWM
Portland Intl. Jetport
$284 Roundtrip, found 2 days ago
$284
Roundtrip
found 2 days ago
Select Bargain Flight flight, departing Wed, Oct 22 from Portland Intl. to Portland Intl. Jetport, returning Tue, Oct 28, priced at $284 found 2 days ago
Delta
Mon, Aug 11 - Thu, Aug 14
DAL
Love Field
PWM
Portland Intl. Jetport
$343 Roundtrip, found 2 days ago
$343
Roundtrip
found 2 days ago
Select Delta flight, departing Mon, Aug 11 from Love Field to Portland Intl. Jetport, returning Thu, Aug 14, priced at $343 found 2 days ago
Alaska Airlines
Wed, Oct 22 - Tue, Oct 28
PDX
Portland Intl.
PWM
Portland Intl. Jetport
$576 Roundtrip, found 2 days ago
$576
Roundtrip
found 2 days ago
Select Alaska Airlines flight, departing Wed, Oct 22 from Portland Intl. to Portland Intl. Jetport, returning Tue, Oct 28, priced at $576 found 2 days ago

Cheap Flights to Chebeague Island

Fall in love at first flight with your vacation to Chebeague 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 Chebeague Island on Hotwire, and you’ll be up, up, and on a getaway in no time.

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

Frequently Asked Questions About flights to Chebeague Island

Don’t waste your time on endless searches for cheap airline tickets oneway or roundtrip. We’ll have you on your way to Chebeague 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 Chebeague 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 Chebeague Island are in September, but when you book your flight on Hotwire, savings are always in season.

How many airlines fly to Chebeague 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 Chebeague Island.

What airport is best to fly into Chebeague Island?

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

How much are flights to Chebeague Island?

Got very cheap flights on your vacation itinerary? When you book your airline tickets to Chebeague Island on Hotwire, you may just get what’s on your getaway wish list. With tickets as low as $162, 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 Chebeague Island?

The trick to saving a stack of cash on your flight to Chebeague 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 $162 right now, why wait?

Chebeague Island Flight Information
Destination airport
Portland Intl. Jetport
Destination airport IATA code
PWM
Roundtrip price
$162

Last Minute Hotel Deals in Chebeague Island

La Quinta Inn & Suites by Wyndham Portland
La Quinta Inn & Suites by Wyndham Portland
3 out of 5
340 Park Ave, Portland, ME
Stay at this 3-star business-friendly hotel in Portland. Enjoy free breakfast, free WiFi, and an outdoor pool. Our guests praise the breakfast and the helpful ...
8.8/10 Excellent! (2,167 reviews)
"Hotel is clean and staff was nice. The pool is a decent size. Hot breakfast food could use some improvement and our bed was quite uncomfortable. The hotel is quite a bit away from Portland city center. We walked one morning and found ourselves in a questionable area while walking to city center past ..."

Reviewed on Jun 10, 2025

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La Quinta Inn & Suites by Wyndham Portland
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! (1,000 reviews)
"The weather was not great, so we spent more time than we thought in our room - comfortable, great layout for hanging out"

Reviewed on May 25, 2025

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The Westin Portland Harborview
Inn at St John Portland In-Town
Inn at St John Portland In-Town
2.5 out of 5
939 Congress St, Portland, ME
Stay at this B&B in Portland. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular ...
8.8/10 Excellent! (1,010 reviews)
"Unique style of a hotel. We did book the room with a separate bathroom which was right next door to our room. Not a big deal to us. We were out most of the day so just needed a place for rest and sleep. Good location. Short drive to downtown Portland. Nice breakfast set up. Coffee and tea always ..."

Reviewed on Jun 10, 2025

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Inn at St John Portland In-Town
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! (1,000 reviews)
"Everyone was very nice. I would have liked to have coffee in the afternoon and evenings. Also having to use the keycards on the elevator was not user friendly"

Reviewed on Jun 10, 2025

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Canopy by Hilton Portland Waterfront
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! (1,511 reviews)
"Loved the complimentary items in the pantry on each floor."

Reviewed on Jun 12, 2025

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Portland Harbor Hotel
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! (1,288 reviews)
"The Portland Regency was great. Centrally located,we could walk anywhere we wanted.Hotel room was beautiful clean and up to date. I would highly recommend this hotel to friends and family."

Reviewed on Jun 12, 2025

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Portland Regency Hotel & Spa
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! (1,037 reviews)
"Good value."

Reviewed on Jun 8, 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! (1,007 reviews)
"Great price, convenient location for airport access. No community gathering areas, pool very small, no tables."

Reviewed on Jun 11, 2025

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Days Inn by Wyndham Airport/Maine Mall
See all 2,310 properties in Chebeague 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.