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Bailey Island

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Bailey Island Flights as Low as $78

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

Frontier Airlines
Thu, Jan 16 - Mon, Jan 20
MCO
Orlando Intl.
PWM
Portland Intl. Jetport
$78 Roundtrip, found 17 hours ago
$78
Roundtrip
found 17 hours ago
Select Frontier Airlines flight, departing Thu, Jan 16 from Orlando Intl. to Portland Intl. Jetport, returning Mon, Jan 20, priced at $78 found 17 hours ago
Frontier Airlines
Thu, Jan 16 - Sun, Jan 19
MCO
Orlando Intl.
PWM
Portland Intl. Jetport
$88 Roundtrip, found 17 hours ago
$88
Roundtrip
found 17 hours ago
Select Frontier Airlines flight, departing Thu, Jan 16 from Orlando Intl. to Portland Intl. Jetport, returning Sun, Jan 19, priced at $88 found 17 hours ago
Frontier Airlines
Thu, Jan 16 - Thu, Jan 23
MCO
Orlando Intl.
PWM
Portland Intl. Jetport
$99 Roundtrip, found 17 hours ago
$99
Roundtrip
found 17 hours ago
Select Frontier Airlines flight, departing Thu, Jan 16 from Orlando Intl. to Portland Intl. Jetport, returning Thu, Jan 23, priced at $99 found 17 hours ago
Frontier Airlines
Fri, Dec 6 - Mon, Dec 9
MCO
Orlando Intl.
PWM
Portland Intl. Jetport
$109 Roundtrip, found 17 hours ago
$109
Roundtrip
found 17 hours ago
Select Frontier Airlines flight, departing Fri, Dec 6 from Orlando Intl. to Portland Intl. Jetport, returning Mon, Dec 9, priced at $109 found 17 hours ago
Frontier Airlines
Fri, Jan 17 - Mon, Jan 20
MCO
Orlando Intl.
PWM
Portland Intl. Jetport
$110 Roundtrip, found 17 hours ago
$110
Roundtrip
found 17 hours ago
Select Frontier Airlines flight, departing Fri, Jan 17 from Orlando Intl. to Portland Intl. Jetport, returning Mon, Jan 20, priced at $110 found 17 hours ago
Breeze Airways
Fri, Jan 17 - Mon, Jan 20
MCO
Orlando Intl.
PWM
Portland Intl. Jetport
$116 Roundtrip, found 17 hours ago
$116
Roundtrip
found 17 hours ago
Select Breeze Airways flight, departing Fri, Jan 17 from Orlando Intl. to Portland Intl. Jetport, returning Mon, Jan 20, priced at $116 found 17 hours ago
Frontier Airlines
Sun, Jan 26 - Thu, Jan 30
CLT
Charlotte-Douglas Intl.
PWM
Portland Intl. Jetport
$128 Roundtrip, found 14 hours ago
$128
Roundtrip
found 14 hours ago
Select Frontier Airlines flight, departing Sun, Jan 26 from Charlotte-Douglas Intl. to Portland Intl. Jetport, returning Thu, Jan 30, priced at $128 found 14 hours ago
Frontier Airlines
Mon, Jan 20 - Thu, Jan 23
MCO
Orlando Intl.
PWM
Portland Intl. Jetport
$129 Roundtrip, found 17 hours ago
$129
Roundtrip
found 17 hours ago
Select Frontier Airlines flight, departing Mon, Jan 20 from Orlando Intl. to Portland Intl. Jetport, returning Thu, Jan 23, priced at $129 found 17 hours ago
JetBlue Airways
Wed, Dec 4 - Mon, Dec 9
MCO
Orlando Intl.
PWM
Portland Intl. Jetport
$137 Roundtrip, found 17 hours ago
$137
Roundtrip
found 17 hours ago
Select JetBlue Airways flight, departing Wed, Dec 4 from Orlando Intl. to Portland Intl. Jetport, returning Mon, Dec 9, priced at $137 found 17 hours ago
Breeze Airways
Fri, Jan 17 - Mon, Jan 20
MCO
Orlando Intl.
PWM
Portland Intl. Jetport
$148 Roundtrip, found 17 hours ago
$148
Roundtrip
found 17 hours ago
Select Breeze Airways flight, departing Fri, Jan 17 from Orlando Intl. to Portland Intl. Jetport, returning Mon, Jan 20, priced at $148 found 17 hours ago
Delta
Wed, Dec 4 - Tue, Dec 10
MCO
Orlando Intl.
PWM
Portland Intl. Jetport
$188 Roundtrip, found 17 hours ago
$188
Roundtrip
found 17 hours ago
Select Delta flight, departing Wed, Dec 4 from Orlando Intl. to Portland Intl. Jetport, returning Tue, Dec 10, priced at $188 found 17 hours ago
Delta
Sat, Dec 7 - Tue, Dec 10
DAB
Daytona Beach Intl.
PWM
Portland Intl. Jetport
$216 Roundtrip, found 16 hours ago
$216
Roundtrip
found 16 hours ago
Select Delta flight, departing Sat, Dec 7 from Daytona Beach Intl. to Portland Intl. Jetport, returning Tue, Dec 10, priced at $216 found 16 hours ago
American Airlines
Fri, Jan 17 - Mon, Jan 20
MCO
Orlando Intl.
PWM
Portland Intl. Jetport
$216 Roundtrip, found 17 hours ago
$216
Roundtrip
found 17 hours ago
Select American Airlines flight, departing Fri, Jan 17 from Orlando Intl. to Portland Intl. Jetport, returning Mon, Jan 20, priced at $216 found 17 hours ago
United
Fri, Jan 17 - Mon, Jan 20
MCO
Orlando Intl.
PWM
Portland Intl. Jetport
$267 Roundtrip, found 17 hours ago
$267
Roundtrip
found 17 hours ago
Select United flight, departing Fri, Jan 17 from Orlando Intl. to Portland Intl. Jetport, returning Mon, Jan 20, priced at $267 found 17 hours ago
American Airlines
Tue, Nov 19 - Thu, Nov 28
CID
Eastern Iowa
PWM
Portland Intl. Jetport
$273 Roundtrip, found 5 days ago
$273
Roundtrip
found 5 days ago
Select American Airlines flight, departing Tue, Nov 19 from Eastern Iowa to Portland Intl. Jetport, returning Thu, Nov 28, priced at $273 found 5 days ago
American Airlines
Tue, Dec 24 - Wed, Dec 25
MSP
Minneapolis - St. Paul Intl.
PWM
Portland Intl. Jetport
$308 Roundtrip, found 6 days ago
$308
Roundtrip
found 6 days ago
Select American Airlines flight, departing Tue, Dec 24 from Minneapolis - St. Paul Intl. to Portland Intl. Jetport, returning Wed, Dec 25, priced at $308 found 6 days ago

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 January, 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 16 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 $78, 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 $78 right now, why wait?

Bailey Island Flight Information
Destination airport
Portland Intl. Jetport
Destination airport IATA code
PWM
Roundtrip price
$78

Last Minute Hotel Deals in Bailey Island

Casco Bay Hotel, Ascend Hotel Collection
Casco Bay Hotel, Ascend Hotel Collection
3.5 out of 5
80 John Roberts Rd., South Portland, ME
The price is $86 per night from Nov 18 to Nov 19
$86
includes taxes & fees
Nov 18 - Nov 19
Stay at this 3.5-star business-friendly hotel in South Portland. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
8.4/10 Very Good! (2,336 reviews)
Comfortable
"Very comfortable stay"

Reviewed on Nov 4, 2024

Casco Bay Hotel, Ascend Hotel Collection
The Westin Portland Harborview
The Westin Portland Harborview
4 out of 5
157 High St, Portland, ME
The price is $100 per night from Dec 1 to Dec 2
$100
includes taxes & fees
Dec 1 - Dec 2
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 ...
8.6/10 Excellent! (1,008 reviews)
"There was nothing about the property i did not like. The bar on the 15th floor was beautiful!"

Reviewed on Nov 3, 2024

The Westin Portland Harborview
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
The price is $97 per night from Nov 6 to Nov 7
$97
includes taxes & fees
Nov 6 - Nov 7
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 ...
7.6/10 Good! (1,000 reviews)
"Good for one night stay for work"

Reviewed on Nov 4, 2024

Days Inn by Wyndham Airport/Maine Mall
Portland Harbor Hotel
Portland Harbor Hotel
4 out of 5
468 Fore Street, Portland, ME
The price is $201 per night from Dec 1 to Dec 2
$201
includes taxes & fees
Dec 1 - Dec 2
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! (1,382 reviews)
"Terrific location and very friendly staff."

Reviewed on Nov 2, 2024

Portland Harbor Hotel
Clarion Hotel Portland
Clarion Hotel Portland
2.5 out of 5
1230 Congress St, Portland, ME
The price is $88 per night from Nov 24 to Nov 25
$88
includes taxes & fees
Nov 24 - Nov 25
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! (1,000 reviews)
"Staff are friendly and efficient"

Reviewed on Oct 30, 2024

Clarion Hotel Portland
Comfort Inn Airport
Comfort Inn Airport
2.5 out of 5
90 Maine Mall Rd, South Portland, ME
The price is $69 per night from Dec 2 to Dec 3
$69
includes taxes & fees
Dec 2 - Dec 3
Book a stay at this business-friendly hotel in South Portland. Enjoy free breakfast, free WiFi, and a free airport shuttle. Our guests praise the breakfast and ...
8.2/10 Very Good! (1,003 reviews)
Nice stay
"Was a quick overnight stay at the start of our vacation. Quick check in and clean hotel"

Reviewed on Nov 3, 2024

Comfort Inn Airport
Canopy by Hilton Portland Waterfront
Canopy by Hilton Portland Waterfront
4 out of 5
9 Center Street, Portland, ME
The price is $141 per night from Nov 25 to Nov 26
$141
includes taxes & fees
Nov 25 - Nov 26
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! (824 reviews)
"."

Reviewed on Nov 3, 2024

Canopy by Hilton Portland Waterfront
Holiday Inn Portland-By the Bay, an IHG Hotel
Holiday Inn Portland-By the Bay, an IHG Hotel
3 out of 5
88 Spring St, Portland, ME
The price is $104 per night from Nov 25 to Nov 26
$104
includes taxes & fees
Nov 25 - Nov 26
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! (1,065 reviews)
"Z"

Reviewed on Nov 4, 2024

Holiday Inn Portland-By the Bay, an IHG Hotel
See all 1,609 properties in Bailey 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.