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Chebeague Island

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Chebeague Island Flights as Low as $117

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

Delta
Mon, Jul 28 - Thu, Jul 31
JFK
John F. Kennedy Intl.
PWM
Portland Intl. Jetport
$117 Roundtrip, found 13 hours ago
$117
Roundtrip
found 13 hours ago
Select Delta flight, departing Mon, Jul 28 from John F. Kennedy Intl. to Portland Intl. Jetport, returning Thu, Jul 31, priced at $117 found 13 hours ago
JetBlue Airways
Mon, Jul 28 - Sat, Aug 2
JFK
John F. Kennedy Intl.
PWM
Portland Intl. Jetport
$122 Roundtrip, found 13 hours ago
$122
Roundtrip
found 13 hours ago
Select JetBlue Airways flight, departing Mon, Jul 28 from John F. Kennedy Intl. to Portland Intl. Jetport, returning Sat, Aug 2, priced at $122 found 13 hours ago
JetBlue Airways
Mon, Jul 28 - Tue, Aug 5
JFK
John F. Kennedy Intl.
PWM
Portland Intl. Jetport
$132 Roundtrip, found 13 hours ago
$132
Roundtrip
found 13 hours ago
Select JetBlue Airways flight, departing Mon, Jul 28 from John F. Kennedy Intl. to Portland Intl. Jetport, returning Tue, Aug 5, priced at $132 found 13 hours ago
Delta
Tue, Jul 29 - Thu, Jul 31
JFK
John F. Kennedy Intl.
PWM
Portland Intl. Jetport
$137 Roundtrip, found 13 hours ago
$137
Roundtrip
found 13 hours ago
Select Delta flight, departing Tue, Jul 29 from John F. Kennedy Intl. to Portland Intl. Jetport, returning Thu, Jul 31, priced at $137 found 13 hours ago
JetBlue Airways
Mon, Jun 30 - Sat, Jul 5
JFK
John F. Kennedy Intl.
PWM
Portland Intl. Jetport
$138 Roundtrip, found 5 days ago
$138
Roundtrip
found 5 days ago
Select JetBlue Airways flight, departing Mon, Jun 30 from John F. Kennedy Intl. to Portland Intl. Jetport, returning Sat, Jul 5, priced at $138 found 5 days ago
Delta
Tue, Jul 8 - Fri, Jul 11
JFK
John F. Kennedy Intl.
PWM
Portland Intl. Jetport
$147 Roundtrip, found 4 days ago
$147
Roundtrip
found 4 days ago
Select Delta flight, departing Tue, Jul 8 from John F. Kennedy Intl. to Portland Intl. Jetport, returning Fri, Jul 11, priced at $147 found 4 days ago
Breeze Airways
Mon, Aug 18 - Sat, Aug 23
TPA
Tampa Intl.
PWM
Portland Intl. Jetport
$179 Roundtrip, found 11 hours ago
$179
Roundtrip
found 11 hours ago
Select Breeze Airways flight, departing Mon, Aug 18 from Tampa Intl. to Portland Intl. Jetport, returning Sat, Aug 23, priced at $179 found 11 hours ago
JetBlue Airways
Wed, May 21 - Sat, May 24
ORD
O'Hare Intl.
PWM
Portland Intl. Jetport
$184 Roundtrip, found 1 day ago
$184
Roundtrip
found 1 day ago
Select JetBlue Airways flight, departing Wed, May 21 from O'Hare Intl. to Portland Intl. Jetport, returning Sat, May 24, priced at $184 found 1 day ago
Frontier Airlines
Fri, May 16 - Sat, May 24
ORD
O'Hare Intl.
PWM
Portland Intl. Jetport
$200 Roundtrip, found 1 day ago
$200
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Fri, May 16 from O'Hare Intl. to Portland Intl. Jetport, returning Sat, May 24, priced at $200 found 1 day ago
United
Fri, Sep 5 - Fri, Sep 12
ORD
O'Hare Intl.
PWM
Portland Intl. Jetport
$209 Roundtrip, found 1 day ago
$209
Roundtrip
found 1 day ago
Select United flight, departing Fri, Sep 5 from O'Hare Intl. to Portland Intl. Jetport, returning Fri, Sep 12, priced at $209 found 1 day ago
American Airlines
Fri, Sep 5 - Fri, Sep 12
ORD
O'Hare Intl.
PWM
Portland Intl. Jetport
$229 Roundtrip, found 1 day ago
$229
Roundtrip
found 1 day ago
Select American Airlines flight, departing Fri, Sep 5 from O'Hare Intl. to Portland Intl. Jetport, returning Fri, Sep 12, priced at $229 found 1 day ago
Frontier Airlines
Sat, Apr 12 - Thu, Apr 17
MKE
General Mitchell Intl.
PWM
Portland Intl. Jetport
$262 Roundtrip, found 5 hours ago
$262
Roundtrip
found 5 hours ago
Select Frontier Airlines flight, departing Sat, Apr 12 from General Mitchell Intl. to Portland Intl. Jetport, returning Thu, Apr 17, priced at $262 found 5 hours ago
Delta
Tue, Jun 3 - Sat, Jun 14
AUS
Austin-Bergstrom Intl.
PWM
Portland Intl. Jetport
$297 Roundtrip, found 1 day ago
$297
Roundtrip
found 1 day ago
Select Delta flight, departing Tue, Jun 3 from Austin-Bergstrom Intl. to Portland Intl. Jetport, returning Sat, Jun 14, priced at $297 found 1 day ago
Delta
Fri, Jul 4 - Wed, Jul 9
DFW
Dallas-Fort Worth Intl.
PWM
Portland Intl. Jetport
$324 Roundtrip, found 6 days ago
$324
Roundtrip
found 6 days ago
Select Delta flight, departing Fri, Jul 4 from Dallas-Fort Worth Intl. to Portland Intl. Jetport, returning Wed, Jul 9, priced at $324 found 6 days ago
Delta
Tue, Jul 15 - Tue, Jul 22
DAL
Love Field
PWM
Portland Intl. Jetport
$343 Roundtrip, found 5 days ago
$343
Roundtrip
found 5 days ago
Select Delta flight, departing Tue, Jul 15 from Love Field to Portland Intl. Jetport, returning Tue, Jul 22, priced at $343 found 5 days ago
Delta
Tue, Apr 22 - Sat, May 3
GSP
Greenville-Spartanburg Intl.
PWM
Portland Intl. Jetport
$375 Roundtrip, found 15 hours ago
$375
Roundtrip
found 15 hours ago
Select Delta flight, departing Tue, Apr 22 from Greenville-Spartanburg Intl. to Portland Intl. Jetport, returning Sat, May 3, priced at $375 found 15 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 July, 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 16 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 $117, 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 $117 right now, why wait?

Chebeague Island Flight Information
Destination airport
Portland Intl. Jetport
Destination airport IATA code
PWM
Roundtrip price
$117

Last Minute Hotel Deals in Chebeague Island

The Westin Portland Harborview
The Westin Portland Harborview
4 out of 5
157 High St, Portland, ME
The price is $128 per night from Apr 27 to Apr 28
$128
includes taxes & fees
Apr 27 - Apr 28
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)
"Parking cpensive"

Reviewed on Apr 6, 2025

The Westin Portland Harborview
Portland Harbor Hotel
Portland Harbor Hotel
4 out of 5
468 Fore Street, Portland, ME
The price is $216 per night from Apr 13 to Apr 14
$216
includes taxes & fees
Apr 13 - Apr 14
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! (1,479 reviews)
"Had a very pleasant stay recently at the Portland Harbor Hotel. The rooms are spacious with a great view of downtown Portland. The front desk service was good and the room rate was reasonable. When I checked in I would have appreciated being told that I needed to use my room key to make the elevator ..."

Reviewed on Apr 7, 2025

Portland Harbor Hotel
Cambria Hotel Portland Downtown-Old Port
Cambria Hotel Portland Downtown-Old Port
3 out of 5
25 HANCOCK STREET, Portland, ME
The price is $158 per night from Apr 20 to Apr 21
$158
includes taxes & fees
Apr 20 - Apr 21
Stay at this 3-star business-friendly hotel in Portland. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the restaurant ...
9.2/10 Wonderful! (840 reviews)
"We loved staying at Cambria. The rooms are beautiful with amazing views. Very quiet & the staff are very friendly and helpful"

Reviewed on Apr 2, 2025

Cambria Hotel Portland Downtown-Old Port
Clarion Hotel Portland
Clarion Hotel Portland
2.5 out of 5
1230 Congress St, Portland, ME
The price is $93 per night from Apr 13 to Apr 14
$93
includes taxes & fees
Apr 13 - Apr 14
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 ...
7.6/10 Good! (1,001 reviews)
"Very comfortable bed and pillows."

Reviewed on Apr 8, 2025

Clarion Hotel Portland
Inn at St John Portland In-Town
Inn at St John Portland In-Town
2.5 out of 5
939 Congress St, Portland, ME
The price is $87 per night from Apr 15 to Apr 16
$87
includes taxes & fees
Apr 15 - Apr 16
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! (1,015 reviews)
"The rooms are small. I opted for a private bathroom. The staff was friendly. I was hoping for a hot breakfast but the bagels, oatmeal, cereal, and yogurt was adequate. Limited parking."

Reviewed on Apr 7, 2025

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
The price is $97 per night from Apr 20 to Apr 21
$97
includes taxes & fees
Apr 20 - Apr 21
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! (2,119 reviews)
"Very close to the hospital, surgery the next day, so convenient."

Reviewed on Apr 7, 2025

La Quinta Inn & Suites by Wyndham Portland
Canopy by Hilton Portland Waterfront
Canopy by Hilton Portland Waterfront
4 out of 5
9 Center Street, Portland, ME
The price is $168 per night from Apr 21 to Apr 22
$168
includes taxes & fees
Apr 21 - Apr 22
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 ...
9.2/10 Wonderful! (979 reviews)
"Great hotel and location"

Reviewed on Apr 6, 2025

Canopy by Hilton Portland Waterfront
Aloft Portland Downtown Waterfront ME
Aloft Portland Downtown Waterfront ME
3 out of 5
379 Commercial Street, Portland, ME
The price is $112 per night from Apr 20 to Apr 21
$112
includes taxes & fees
Apr 20 - Apr 21
Stay at this 3-star hotel in Portland. Enjoy free WiFi, breakfast (surcharge), and valet parking (surcharge). Our guests praise the bar and the helpful staff ...
8.8/10 Excellent! (892 reviews)
"We loved the property. It was clean, nice bar and within walking distance to all the restaurants. We would stay again for sure..."

Reviewed on Apr 4, 2025

Aloft Portland Downtown Waterfront ME
See all 2,211 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.