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Chebeague Island

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Chebeague Island Flights as Low as $169

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

JetBlue Airways
Tue, Sep 23 - Wed, Sep 24
BNA
Nashville Intl.
PWM
Portland Intl. Jetport
$169 Roundtrip, found 1 day ago
$169
Roundtrip
found 1 day ago
Select JetBlue Airways flight, departing Tue, Sep 23 from Nashville Intl. to Portland Intl. Jetport, returning Wed, Sep 24, priced at $169 found 1 day ago
JetBlue Airways
Sun, Jun 29 - Fri, Jul 4
BNA
Nashville Intl.
PWM
Portland Intl. Jetport
$171 Roundtrip, found 4 hours ago
$171
Roundtrip
found 4 hours ago
Select JetBlue Airways flight, departing Sun, Jun 29 from Nashville Intl. to Portland Intl. Jetport, returning Fri, Jul 4, priced at $171 found 4 hours ago
JetBlue Airways
Sat, Sep 20 - Mon, Sep 22
BNA
Nashville Intl.
PWM
Portland Intl. Jetport
$175 Roundtrip, found 1 day ago
$175
Roundtrip
found 1 day ago
Select JetBlue Airways flight, departing Sat, Sep 20 from Nashville Intl. to Portland Intl. Jetport, returning Mon, Sep 22, priced at $175 found 1 day ago
JetBlue Airways
Mon, Sep 22 - Tue, Sep 23
BNA
Nashville Intl.
PWM
Portland Intl. Jetport
$188 Roundtrip, found 1 day ago
$188
Roundtrip
found 1 day ago
Select JetBlue Airways flight, departing Mon, Sep 22 from Nashville Intl. to Portland Intl. Jetport, returning Tue, Sep 23, priced at $188 found 1 day ago
JetBlue Airways
Mon, Sep 22 - Sat, Sep 27
BNA
Nashville Intl.
PWM
Portland Intl. Jetport
$191 Roundtrip, found 1 day ago
$191
Roundtrip
found 1 day ago
Select JetBlue Airways flight, departing Mon, Sep 22 from Nashville Intl. to Portland Intl. Jetport, returning Sat, Sep 27, priced at $191 found 1 day ago
Breeze Airways
Fri, Sep 19 - Sat, Sep 27
CHS
Charleston Intl.
PWM
Portland Intl. Jetport
$199 Roundtrip, found 1 day ago
$199
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Fri, Sep 19 from Charleston Intl. to Portland Intl. Jetport, returning Sat, Sep 27, priced at $199 found 1 day ago
Bargain Flight
Tue, Jun 3 - Wed, Jun 4
RIC
Richmond Intl.
PWM
Portland Intl. Jetport
$200 Roundtrip, found 20 hours ago
$200
Roundtrip
found 20 hours ago
Select Bargain Flight flight, departing Tue, Jun 3 from Richmond Intl. to Portland Intl. Jetport, returning Wed, Jun 4, priced at $200 found 20 hours ago
Breeze Airways
Fri, Sep 19 - Sat, Sep 27
CHS
Charleston Intl.
PWM
Portland Intl. Jetport
$204 Roundtrip, found 1 day ago
$204
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Fri, Sep 19 from Charleston Intl. to Portland Intl. Jetport, returning Sat, Sep 27, priced at $204 found 1 day ago
Delta
Tue, Jul 1 - Tue, Jul 8
BNA
Nashville Intl.
PWM
Portland Intl. Jetport
$217 Roundtrip, found 4 hours ago
$217
Roundtrip
found 4 hours ago
Select Delta flight, departing Tue, Jul 1 from Nashville Intl. to Portland Intl. Jetport, returning Tue, Jul 8, priced at $217 found 4 hours ago
American Airlines
Tue, Jul 1 - Tue, Jul 8
BNA
Nashville Intl.
PWM
Portland Intl. Jetport
$217 Roundtrip, found 4 hours ago
$217
Roundtrip
found 4 hours ago
Select American Airlines flight, departing Tue, Jul 1 from Nashville Intl. to Portland Intl. Jetport, returning Tue, Jul 8, priced at $217 found 4 hours ago
Frontier Airlines
Sat, May 3 - Fri, May 9
PHX
Sky Harbor Intl.
PWM
Portland Intl. Jetport
$242 Roundtrip, found 1 day ago
$242
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Sat, May 3 from Sky Harbor Intl. to Portland Intl. Jetport, returning Fri, May 9, priced at $242 found 1 day ago
Frontier Airlines
Mon, May 19 - Sat, May 24
CLT
Charlotte-Douglas Intl.
PWM
Portland Intl. Jetport
$245 Roundtrip, found 2 days ago
$245
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Mon, May 19 from Charlotte-Douglas Intl. to Portland Intl. Jetport, returning Sat, May 24, priced at $245 found 2 days ago
Delta
Wed, May 21 - Tue, May 27
MBS
MBS Intl.
PWM
Portland Intl. Jetport
$274 Roundtrip, found 1 day ago
$274
Roundtrip
found 1 day ago
Select Delta flight, departing Wed, May 21 from MBS Intl. to Portland Intl. Jetport, returning Tue, May 27, priced at $274 found 1 day ago
Delta
Tue, Sep 9 - Wed, Sep 10
DSM
Des Moines Intl.
PWM
Portland Intl. Jetport
$285 Roundtrip, found 1 day ago
$285
Roundtrip
found 1 day ago
Select Delta flight, departing Tue, Sep 9 from Des Moines Intl. to Portland Intl. Jetport, returning Wed, Sep 10, priced at $285 found 1 day ago
American Airlines
Sat, Aug 23 - Sun, Aug 24
CLT
Charlotte-Douglas Intl.
PWM
Portland Intl. Jetport
$392 Roundtrip, found 1 day ago
$392
Roundtrip
found 1 day ago
Select American Airlines flight, departing Sat, Aug 23 from Charlotte-Douglas Intl. to Portland Intl. Jetport, returning Sun, Aug 24, priced at $392 found 1 day ago
Breeze Airways
Wed, May 7 - Tue, May 13
CHS
Charleston Intl.
PWM
Portland Intl. Jetport
$419 Roundtrip, found 4 hours ago
$419
Roundtrip
found 4 hours ago
Select Breeze Airways flight, departing Wed, May 7 from Charleston Intl. to Portland Intl. Jetport, returning Tue, May 13, priced at $419 found 4 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 15 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 $169, 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 $169 right now, why wait?

Chebeague Island Flight Information
Destination airport
Portland Intl. Jetport
Destination airport IATA code
PWM
Roundtrip price
$168

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 $162 per night from May 26 to May 27
$162
includes taxes & fees
May 26 - May 27
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)
"Hotel in good neighborhood location with a lot of dining options within walking distance. Hotel has access to attached public parking garage with room key, making it very convenient to park, while still being within walking distance of attractions and waterfront. Really good fitness room, and good ..."

Reviewed on Apr 28, 2025

The Westin Portland Harborview
Portland Harbor Hotel
Portland Harbor Hotel
4 out of 5
468 Fore Street, Portland, ME
The price is $225 per night from May 4 to May 5
$225
includes taxes & fees
May 4 - May 5
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! (1,480 reviews)
"Clean, live the vibe"

Reviewed on Apr 28, 2025

Portland Harbor Hotel
Clarion Hotel Portland
Clarion Hotel Portland
2.5 out of 5
1230 Congress St, Portland, ME
The price is $103 per night from May 4 to May 5
$103
includes taxes & fees
May 4 - May 5
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)
"Love the pool"

Reviewed on Apr 25, 2025

Clarion Hotel Portland
Cambria Hotel Portland Downtown-Old Port
Cambria Hotel Portland Downtown-Old Port
3 out of 5
25 HANCOCK STREET, Portland, ME
The price is $177 per night from May 11 to May 12
$177
includes taxes & fees
May 11 - May 12
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! (861 reviews)
Great People
"The team was very helpful in addressing my needs/requests. Would recommend"

Reviewed on Apr 28, 2025

Cambria Hotel Portland Downtown-Old Port
Portland Regency Hotel & Spa
Portland Regency Hotel & Spa
3.5 out of 5
20 Milk Street, Portland, ME
The price is $177 per night from May 4 to May 5
$177
includes taxes & fees
May 4 - May 5
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! (1,246 reviews)
"."

Reviewed on Apr 29, 2025

Portland Regency Hotel & Spa
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 $97 per night from May 6 to May 7
$97
includes taxes & fees
May 6 - May 7
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! (1,000 reviews)
"Charming Inn, rooms were beautiful. Everything you could need for a stay. Very quiet guests. Would definitely return and recommend it to friends."

Reviewed on Apr 27, 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 $104 per night from May 4 to May 5
$104
includes taxes & fees
May 4 - May 5
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! (2,133 reviews)
"Was for a medical surgery"

Reviewed on Apr 29, 2025

La Quinta Inn & Suites by Wyndham Portland
Aloft Portland Downtown Waterfront ME
Aloft Portland Downtown Waterfront ME
3 out of 5
379 Commercial Street, Portland, ME
The price is $128 per night from May 11 to May 12
$128
includes taxes & fees
May 11 - May 12
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! (908 reviews)
Modern Eclectic and Fun property
"Great location on Commercial Street. Modern vibe and feel. Only complaint were the pillows. Way too soft, and $40 per night valet fee."

Reviewed on Apr 26, 2025

Aloft Portland Downtown Waterfront ME
See all 2,238 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.