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Bailey Island

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Bailey Island Flights as Low as $94

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Cheap Flights to Bailey Island

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

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

Frequently Asked Questions About flights to Bailey Island

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

How many airlines fly to Bailey 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 Bailey Island.

What airport is best to fly into Bailey Island?

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

How much are flights to Bailey Island?

Got very cheap flights on your vacation itinerary? When you book your airline tickets to Bailey 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 Bailey Island?

The trick to saving a stack of cash on your flight to Bailey 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?

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

Last Minute Hotel Deals in Bailey 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

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

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

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! (1,002 reviews)
Nice hotel for a quick stay
"Pretty good hotel just outside of downtown. Fairly commutable with buses nearby if you're not driving because you're very drunk from all the craft beers Portland can offer. desk employees were super nice and the breakfast was passable when everyone is realistically going for local donuts and coffee. ..."

Reviewed on May 22, 2025

Inn at St John Portland In-Town
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! (2,169 reviews)
"None"

Reviewed on May 22, 2025

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

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! (1,002 reviews)
"Rooms were clean and comfortable. The bedsheets were very soft!"

Reviewed on May 22, 2025

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

DoubleTree by Hilton Hotel Portland
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.