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Bailey Island

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Bailey Island Flights as Low as $97

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

Frontier Airlines
Sat, Apr 19 - Mon, Apr 28
MCO
Orlando Intl.
PWM
Portland Intl. Jetport
$97 Roundtrip, found 1 day ago
$97
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Sat, Apr 19 from Orlando Intl. to Portland Intl. Jetport, returning Mon, Apr 28, priced at $97 found 1 day ago
Frontier Airlines
Sat, Apr 19 - Sun, May 4
MCO
Orlando Intl.
PWM
Portland Intl. Jetport
$98 Roundtrip, found 1 day ago
$98
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Sat, Apr 19 from Orlando Intl. to Portland Intl. Jetport, returning Sun, May 4, priced at $98 found 1 day ago
Frontier Airlines
Sat, Apr 19 - Thu, May 1
MCO
Orlando Intl.
PWM
Portland Intl. Jetport
$101 Roundtrip, found 1 day ago
$101
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Sat, Apr 19 from Orlando Intl. to Portland Intl. Jetport, returning Thu, May 1, priced at $101 found 1 day ago
Frontier Airlines
Fri, Apr 18 - Sun, May 4
MCO
Orlando Intl.
PWM
Portland Intl. Jetport
$113 Roundtrip, found 1 day ago
$113
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Fri, Apr 18 from Orlando Intl. to Portland Intl. Jetport, returning Sun, May 4, priced at $113 found 1 day ago
Frontier Airlines
Fri, Apr 18 - Thu, May 1
MCO
Orlando Intl.
PWM
Portland Intl. Jetport
$116 Roundtrip, found 1 day ago
$116
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Fri, Apr 18 from Orlando Intl. to Portland Intl. Jetport, returning Thu, May 1, priced at $116 found 1 day ago
Delta
Mon, Jul 28 - Thu, Jul 31
JFK
John F. Kennedy Intl.
PWM
Portland Intl. Jetport
$117 Roundtrip, found 3 days ago
$117
Roundtrip
found 3 days 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 3 days ago
JetBlue Airways
Mon, Jul 28 - Sat, Aug 2
JFK
John F. Kennedy Intl.
PWM
Portland Intl. Jetport
$122 Roundtrip, found 3 days ago
$122
Roundtrip
found 3 days 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 3 days ago
United
Sun, Apr 20 - Sun, May 4
MCO
Orlando Intl.
PWM
Portland Intl. Jetport
$242 Roundtrip, found 1 day ago
$242
Roundtrip
found 1 day ago
Select United flight, departing Sun, Apr 20 from Orlando Intl. to Portland Intl. Jetport, returning Sun, May 4, priced at $242 found 1 day ago
Bargain Flight
Tue, Sep 23 - Tue, Sep 30
SAV
Savannah - Hilton Head Intl.
PWM
Portland Intl. Jetport
$243 Roundtrip, found 1 day ago
$243
Roundtrip
found 1 day ago
Select Bargain Flight flight, departing Tue, Sep 23 from Savannah - Hilton Head Intl. to Portland Intl. Jetport, returning Tue, Sep 30, priced at $243 found 1 day ago
American Airlines
Tue, Jun 17 - Mon, Jun 23
MCO
Orlando Intl.
PWM
Portland Intl. Jetport
$244 Roundtrip, found 1 day ago
$244
Roundtrip
found 1 day ago
Select American Airlines flight, departing Tue, Jun 17 from Orlando Intl. to Portland Intl. Jetport, returning Mon, Jun 23, priced at $244 found 1 day ago
Breeze Airways
Wed, Jun 18 - Sat, Jun 21
MCO
Orlando Intl.
PWM
Portland Intl. Jetport
$291 Roundtrip, found 2 days ago
$291
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Wed, Jun 18 from Orlando Intl. to Portland Intl. Jetport, returning Sat, Jun 21, priced at $291 found 2 days ago
Delta
Tue, May 20 - Sun, May 25
LIT
Clinton National Airport
PWM
Portland Intl. Jetport
$309 Roundtrip, found 16 hours ago
$309
Roundtrip
found 16 hours ago
Select Delta flight, departing Tue, May 20 from Clinton National Airport to Portland Intl. Jetport, returning Sun, May 25, priced at $309 found 16 hours ago
Frontier Airlines
Sat, Apr 19 - Thu, May 1
IAH
George Bush Intercontinental
PWM
Portland Intl. Jetport
$323 Roundtrip, found 14 hours ago
$323
Roundtrip
found 14 hours ago
Select Frontier Airlines flight, departing Sat, Apr 19 from George Bush Intercontinental to Portland Intl. Jetport, returning Thu, May 1, priced at $323 found 14 hours ago
Delta
Sat, Jul 5 - Sat, Jul 12
DFW
Dallas-Fort Worth Intl.
PWM
Portland Intl. Jetport
$326 Roundtrip, found 6 days ago
$326
Roundtrip
found 6 days ago
Select Delta flight, departing Sat, Jul 5 from Dallas-Fort Worth Intl. to Portland Intl. Jetport, returning Sat, Jul 12, priced at $326 found 6 days ago
Delta
Tue, Jul 15 - Wed, Jul 23
OMA
Eppley Field
PWM
Portland Intl. Jetport
$335 Roundtrip, found 1 day ago
$335
Roundtrip
found 1 day ago
Select Delta flight, departing Tue, Jul 15 from Eppley Field to Portland Intl. Jetport, returning Wed, Jul 23, priced at $335 found 1 day ago
Delta
Tue, Jul 1 - Wed, Jul 9
DAL
Love Field
PWM
Portland Intl. Jetport
$363 Roundtrip, found 1 day ago
$363
Roundtrip
found 1 day ago
Select Delta flight, departing Tue, Jul 1 from Love Field to Portland Intl. Jetport, returning Wed, Jul 9, priced at $363 found 1 day 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 April, 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 $97, 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 $97 right now, why wait?

Bailey Island Flight Information
Destination airport
Portland Intl. Jetport
Destination airport IATA code
PWM
Roundtrip price
$97

Last Minute Hotel Deals in Bailey Island

The Westin Portland Harborview
The Westin Portland Harborview
4 out of 5
157 High St, Portland, ME
The price is $137 per night from Apr 29 to Apr 30
$137
includes taxes & fees
Apr 29 - Apr 30
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! (1,002 reviews)
"Great staff and facility."

Reviewed on Apr 9, 2025

The Westin Portland Harborview
Portland Harbor Hotel
Portland Harbor Hotel
4 out of 5
468 Fore Street, Portland, ME
The price is $206 per night from Apr 20 to Apr 21
$206
includes taxes & fees
Apr 20 - Apr 21
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! (1,482 reviews)
Wonderful anniversary weekend
"We visited for a long weekend to celebrate our anniversary. Everything was amazing. Staff was courteous and friendly. We ate at many of the areas fine dining establishments but had breakfast each day at the hotel and ended each night with drinks and dessert at the bar. We will definitely be back ..."

Reviewed on Apr 13, 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 $167 per night from Apr 21 to Apr 22
$167
includes taxes & fees
Apr 21 - Apr 22
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! (843 reviews)
"So far we love everything! The 4th floor lounge is a great amenity when your family is taking up too much space in the room. Welcoming fire place and kind staff. I’ll see what the beds are like shortly."

Reviewed on Apr 14, 2025

Cambria Hotel Portland Downtown-Old Port
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 27 to Apr 28
$87
includes taxes & fees
Apr 27 - Apr 28
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)
"I’ve stayed at the Inn on St John many times. I have a long commute from home to Portland. I stay when the weather is bad and the travel is dangerous. I like to stay at the inn because the it very affordable, comfortable and very easy to check in, find food nearby and relax in my room. I’ve stayed ..."

Reviewed on Apr 9, 2025

Inn at St John Portland In-Town
Clarion Hotel Portland
Clarion Hotel Portland
2.5 out of 5
1230 Congress St, Portland, ME
The price is $93 per night from Apr 17 to Apr 18
$93
includes taxes & fees
Apr 17 - Apr 18
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! (1,004 reviews)
"This was our third stay there and already have a fourth booked. Great location!"

Reviewed on Apr 10, 2025

Clarion Hotel Portland
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! (2,123 reviews)
"Thank you so much for your hard work I truly appreciate it"

Reviewed on Apr 11, 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 $171 per night from Apr 21 to Apr 22
$171
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! (984 reviews)
"Great time in Portland and the hotel was great!"

Reviewed on Apr 10, 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 $126 per night from Apr 20 to Apr 21
$126
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! (896 reviews)
"Easy check in. Let us check in 6 hours early. Great bar inside. Great bartender. Clean facilities. Very much worth the cost!"

Reviewed on Apr 11, 2025

Aloft Portland Downtown Waterfront ME
See all 1,699 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.