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Chebeague Island

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Chebeague Island Flights as Low as $94

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

Breeze Airways
Fri, Sep 19 - Fri, Sep 26
CHS
Charleston Intl.
PWM
Portland Intl. Jetport
$94 Roundtrip, found 1 hour ago
$94
Roundtrip
found 1 hour ago
Select Breeze Airways flight, departing Fri, Sep 19 from Charleston Intl. to Portland Intl. Jetport, returning Fri, Sep 26, priced at $94 found 1 hour ago
Breeze Airways
Fri, Sep 19 - Fri, Sep 26
CHS
Charleston Intl.
PWM
Portland Intl. Jetport
$99 Roundtrip, found 1 hour ago
$99
Roundtrip
found 1 hour ago
Select Breeze Airways flight, departing Fri, Sep 19 from Charleston Intl. to Portland Intl. Jetport, returning Fri, Sep 26, priced at $99 found 1 hour ago
Breeze Airways
Fri, Sep 19 - Fri, Sep 26
CHS
Charleston Intl.
PWM
Portland Intl. Jetport
$104 Roundtrip, found 1 hour ago
$104
Roundtrip
found 1 hour ago
Select Breeze Airways flight, departing Fri, Sep 19 from Charleston Intl. to Portland Intl. Jetport, returning Fri, Sep 26, priced at $104 found 1 hour ago
Breeze Airways
Wed, Jun 4 - Wed, Jun 11
CHS
Charleston Intl.
PWM
Portland Intl. Jetport
$115 Roundtrip, found 2 hours ago
$115
Roundtrip
found 2 hours ago
Select Breeze Airways flight, departing Wed, Jun 4 from Charleston Intl. to Portland Intl. Jetport, returning Wed, Jun 11, priced at $115 found 2 hours ago
Breeze Airways
Wed, Jun 4 - Wed, Jun 11
CHS
Charleston Intl.
PWM
Portland Intl. Jetport
$119 Roundtrip, found 2 hours ago
$119
Roundtrip
found 2 hours ago
Select Breeze Airways flight, departing Wed, Jun 4 from Charleston Intl. to Portland Intl. Jetport, returning Wed, Jun 11, priced at $119 found 2 hours ago
Delta
Sat, Jul 5 - Wed, Jul 9
FLL
Fort Lauderdale - Hollywood Intl.
PWM
Portland Intl. Jetport
$220 Roundtrip, found 22 hours ago
$220
Roundtrip
found 22 hours ago
Select Delta flight, departing Sat, Jul 5 from Fort Lauderdale - Hollywood Intl. to Portland Intl. Jetport, returning Wed, Jul 9, priced at $220 found 22 hours ago
JetBlue Airways
Sat, Jul 5 - Wed, Jul 9
FLL
Fort Lauderdale - Hollywood Intl.
PWM
Portland Intl. Jetport
$226 Roundtrip, found 22 hours ago
$226
Roundtrip
found 22 hours ago
Select JetBlue Airways flight, departing Sat, Jul 5 from Fort Lauderdale - Hollywood Intl. to Portland Intl. Jetport, returning Wed, Jul 9, priced at $226 found 22 hours ago
Delta
Sat, Jul 5 - Wed, Jul 9
FLL
Fort Lauderdale - Hollywood Intl.
PWM
Portland Intl. Jetport
$245 Roundtrip, found 22 hours ago
$245
Roundtrip
found 22 hours ago
Select Delta flight, departing Sat, Jul 5 from Fort Lauderdale - Hollywood Intl. to Portland Intl. Jetport, returning Wed, Jul 9, priced at $245 found 22 hours ago
Bargain Flight
Fri, Jun 6 - Tue, Jun 10
CHS
Charleston Intl.
PWM
Portland Intl. Jetport
$248 Roundtrip, found 3 days ago
$248
Roundtrip
found 3 days ago
Select Bargain Flight flight, departing Fri, Jun 6 from Charleston Intl. to Portland Intl. Jetport, returning Tue, Jun 10, priced at $248 found 3 days ago
American Airlines
Sat, Jul 5 - Wed, Jul 9
FLL
Fort Lauderdale - Hollywood Intl.
PWM
Portland Intl. Jetport
$298 Roundtrip, found 22 hours ago
$298
Roundtrip
found 22 hours ago
Select American Airlines flight, departing Sat, Jul 5 from Fort Lauderdale - Hollywood Intl. to Portland Intl. Jetport, returning Wed, Jul 9, priced at $298 found 22 hours ago
Delta
Tue, Jun 24 - Thu, Jul 3
LAX
Los Angeles Intl.
PWM
Portland Intl. Jetport
$301 Roundtrip, found 1 day ago
$301
Roundtrip
found 1 day ago
Select Delta flight, departing Tue, Jun 24 from Los Angeles Intl. to Portland Intl. Jetport, returning Thu, Jul 3, priced at $301 found 1 day ago
Delta
Fri, Jul 4 - Thu, Jul 10
BIL
Logan Intl.
PWM
Portland Intl. Jetport
$329 Roundtrip, found 1 day ago
$329
Roundtrip
found 1 day ago
Select Delta flight, departing Fri, Jul 4 from Logan Intl. to Portland Intl. Jetport, returning Thu, Jul 10, priced at $329 found 1 day ago
Delta
Tue, Jul 1 - Wed, Jul 9
DFW
Dallas-Fort Worth Intl.
PWM
Portland Intl. Jetport
$341 Roundtrip, found 3 days ago
$341
Roundtrip
found 3 days ago
Select Delta flight, departing Tue, Jul 1 from Dallas-Fort Worth Intl. to Portland Intl. Jetport, returning Wed, Jul 9, priced at $341 found 3 days ago
Bargain Flight
Sat, May 24 - Thu, May 29
BOS
Logan Intl.
PWM
Portland Intl. Jetport
$342 Roundtrip, found 1 day ago
$342
Roundtrip
found 1 day ago
Select Bargain Flight flight, departing Sat, May 24 from Logan Intl. to Portland Intl. Jetport, returning Thu, May 29, priced at $342 found 1 day ago
Delta
Wed, May 28 - Tue, Jun 10
DAL
Love Field
PWM
Portland Intl. Jetport
$417 Roundtrip, found 3 days ago
$417
Roundtrip
found 3 days ago
Select Delta flight, departing Wed, May 28 from Love Field to Portland Intl. Jetport, returning Tue, Jun 10, priced at $417 found 3 days ago
Alaska Airlines
Sun, Jul 6 - Thu, Jul 10
BIL
Logan Intl.
PWM
Portland Intl. Jetport
$3,210 Roundtrip, found 17 hours ago
$3,210
Roundtrip
found 17 hours ago
Select Alaska Airlines flight, departing Sun, Jul 6 from Logan Intl. to Portland Intl. Jetport, returning Thu, Jul 10, priced at $3,210 found 17 hours 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 $94, 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 $94 right now, why wait?

Chebeague Island Flight Information
Destination airport
Portland Intl. Jetport
Destination airport IATA code
PWM
Roundtrip price
$93

Last Minute Hotel Deals in Chebeague Island

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! (1,001 reviews)
"Hotel was very nice, clean and well kept. Only issue is the unfortunate, significant homeless population around the hotel. Very sad."

Reviewed on May 22, 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! (1,277 reviews)
"Hotel is very clean and well maintained. Staff is very welcoming, location is perfect and restaurants and bars all very nice with excellent foods."

Reviewed on May 20, 2025

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Portland Regency Hotel & Spa
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 ...
9/10 Wonderful! (1,509 reviews)
"What a great place to stay. Would highly recommend this place."

Reviewed on May 22, 2025

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Portland Harbor Hotel
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! (1,016 reviews)
"Nice breakfast, lovely staff, cool building"

Reviewed on May 20, 2025

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Inn at St John Portland In-Town
La Quinta Inn & Suites by Wyndham Portland
La Quinta Inn & Suites by Wyndham Portland
2.5 out of 5
340 Park Ave, Portland, ME
Book a stay at this 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! (2,164 reviews)
"It was good value. Price was right. Staff was helpful. Room tidy."

Reviewed on May 20, 2025

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La Quinta Inn & Suites 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! (1,216 reviews)
"no restaurant on site, only a coffee bar."

Reviewed on May 17, 2025

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Holiday Inn Portland-By the Bay by IHG
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! (1,021 reviews)
Good
"Worked fine for short overnight stay."

Reviewed on May 21, 2025

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Clarion Hotel Portland
DoubleTree by Hilton Hotel Portland
DoubleTree by Hilton Hotel Portland
4 out of 5
363 Maine Mall Rd, South Portland, ME
Stay at this hotel in South Portland. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the pool and the helpful staff in our reviews. ...
7.8/10 Good! (1,194 reviews)
"Good stay"

Reviewed on May 20, 2025

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DoubleTree by Hilton Hotel Portland
See all 2,291 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.