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Bailey Island

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Bailey Island Flights as Low as $179

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

Breeze Airways
Wed, May 27 - Sat, May 30
MCO
Orlando Intl.
PWM
Portland Intl. Jetport
$179 Roundtrip, found 1 day ago
$179
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Wed, May 27 from Orlando Intl. to Portland Intl. Jetport, returning Sat, May 30, priced at $179 found 1 day ago
Breeze Airways
Wed, May 27 - Sat, May 30
MCO
Orlando Intl.
PWM
Portland Intl. Jetport
$182 Roundtrip, found 1 day ago
$182
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Wed, May 27 from Orlando Intl. to Portland Intl. Jetport, returning Sat, May 30, priced at $182 found 1 day ago
Breeze Airways
Wed, May 27 - Fri, Jun 5
MCO
Orlando Intl.
PWM
Portland Intl. Jetport
$186 Roundtrip, found 2 days ago
$186
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Wed, May 27 from Orlando Intl. to Portland Intl. Jetport, returning Fri, Jun 5, priced at $186 found 2 days ago
Breeze Airways
Fri, May 29 - Sat, May 30
MCO
Orlando Intl.
PWM
Portland Intl. Jetport
$187 Roundtrip, found 22 hours ago
$187
Roundtrip
found 22 hours ago
Select Breeze Airways flight, departing Fri, May 29 from Orlando Intl. to Portland Intl. Jetport, returning Sat, May 30, priced at $187 found 22 hours ago
Breeze Airways
Wed, May 27 - Sat, May 30
MCO
Orlando Intl.
PWM
Portland Intl. Jetport
$189 Roundtrip, found 1 day ago
$189
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Wed, May 27 from Orlando Intl. to Portland Intl. Jetport, returning Sat, May 30, priced at $189 found 1 day ago
Breeze Airways
Wed, Aug 19 - Tue, Aug 25
MCO
Orlando Intl.
PWM
Portland Intl. Jetport
$190 Roundtrip, found 1 day ago
$190
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Wed, Aug 19 from Orlando Intl. to Portland Intl. Jetport, returning Tue, Aug 25, priced at $190 found 1 day ago
Breeze Airways
Fri, May 29 - Wed, Jun 3
MCO
Orlando Intl.
PWM
Portland Intl. Jetport
$192 Roundtrip, found 2 days ago
$192
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Fri, May 29 from Orlando Intl. to Portland Intl. Jetport, returning Wed, Jun 3, priced at $192 found 2 days ago
Breeze Airways
Wed, Aug 19 - Tue, Aug 25
MCO
Orlando Intl.
PWM
Portland Intl. Jetport
$195 Roundtrip, found 1 day ago
$195
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Wed, Aug 19 from Orlando Intl. to Portland Intl. Jetport, returning Tue, Aug 25, priced at $195 found 1 day ago
Delta
Mon, Aug 17 - Tue, Aug 25
BNA
Nashville Intl.
PWM
Portland Intl. Jetport
$208 Roundtrip, found 3 days ago
$208
Roundtrip
found 3 days ago
Select Delta flight, departing Mon, Aug 17 from Nashville Intl. to Portland Intl. Jetport, returning Tue, Aug 25, priced at $208 found 3 days ago
American Airlines
Wed, Aug 19 - Tue, Aug 25
MCO
Orlando Intl.
PWM
Portland Intl. Jetport
$217 Roundtrip, found 1 day ago
$217
Roundtrip
found 1 day ago
Select American Airlines flight, departing Wed, Aug 19 from Orlando Intl. to Portland Intl. Jetport, returning Tue, Aug 25, priced at $217 found 1 day ago
Delta
Tue, Jun 30 - Sat, Jul 4
DFW
Dallas-Fort Worth Intl.
PWM
Portland Intl. Jetport
$217 Roundtrip, found 20 hours ago
$217
Roundtrip
found 20 hours ago
Select Delta flight, departing Tue, Jun 30 from Dallas-Fort Worth Intl. to Portland Intl. Jetport, returning Sat, Jul 4, priced at $217 found 20 hours ago
United
Wed, May 27 - Tue, Jun 2
MCO
Orlando Intl.
PWM
Portland Intl. Jetport
$222 Roundtrip, found 12 hours ago
$222
Roundtrip
found 12 hours ago
Select United flight, departing Wed, May 27 from Orlando Intl. to Portland Intl. Jetport, returning Tue, Jun 2, priced at $222 found 12 hours ago
Delta
Wed, Jul 8 - Tue, Jul 14
DAL
Love Field
PWM
Portland Intl. Jetport
$237 Roundtrip, found 3 days ago
$237
Roundtrip
found 3 days ago
Select Delta flight, departing Wed, Jul 8 from Love Field to Portland Intl. Jetport, returning Tue, Jul 14, priced at $237 found 3 days ago
JetBlue Airways
Wed, Aug 19 - Tue, Aug 25
BNA
Nashville Intl.
PWM
Portland Intl. Jetport
$313 Roundtrip, found 1 day ago
$313
Roundtrip
found 1 day ago
Select JetBlue Airways flight, departing Wed, Aug 19 from Nashville Intl. to Portland Intl. Jetport, returning Tue, Aug 25, priced at $313 found 1 day ago
Delta
Tue, Jun 16 - Tue, Jun 23
LAX
Los Angeles Intl.
PWM
Portland Intl. Jetport
$326 Roundtrip, found 1 hour ago
$326
Roundtrip
found 1 hour ago
Select Delta flight, departing Tue, Jun 16 from Los Angeles Intl. to Portland Intl. Jetport, returning Tue, Jun 23, priced at $326 found 1 hour ago
JetBlue Airways
Tue, Jun 16 - Thu, Jun 25
ONT
Los Angeles - Ontario Intl.
PWM
Portland Intl. Jetport
$412 Roundtrip, found 1 hour ago
$412
Roundtrip
found 1 hour ago
Select JetBlue Airways flight, departing Tue, Jun 16 from Los Angeles - Ontario Intl. to Portland Intl. Jetport, returning Thu, Jun 25, priced at $412 found 1 hour 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 May, 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 $179, 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 $179 right now, why wait?

Bailey Island Flight Information
Destination airport
Portland Intl. Jetport
Destination airport IATA code
PWM
Roundtrip price
$178

Last Minute Hotel Deals in Bailey Island

Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
468 Fore Street Portland ME
Book a stay at this business-friendly hotel in Portland. Enjoy free WiFi, 3 coffee shops/cafes, and breakfast (surcharge). Our guests praise the helpful staff ...
9.2/10 Wonderful! (1,748 reviews)
Rooms are decent at best. The lighting in the bathroom is very dark and dim which made it difficult to get ready in. The beds are comfortable but the sheets and comforter are pretty thin. The pantry which was advertised on the website (located on each floor) is a joke and was never stocked.

Reviewed on Apr 26, 2026

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Portland Harbor Hotel
Cambria Hotel Portland Downtown-Old Port

Cambria Hotel Portland Downtown-Old Port

3 out of 5
25 HANCOCK STREET Portland ME
Book a stay at this business-friendly hotel in Portland. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the restaurant ...
9.4/10 Exceptional! (1,194 reviews)
Clean room and helpful staff!

Reviewed on Apr 26, 2026

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Cambria Hotel Portland Downtown-Old Port
HomeAwhile

HomeAwhile

4 out of 5
205 Southborough Drive Scarborough ME
Stay at this aparthotel in Scarborough. Enjoy free WiFi, free parking, and laundry facilities. Popular attractions Maine Mall and Thompson's Point are located ...
9.6/10 Exceptional! (27 reviews)
Air conditioning system was making loud clap every 10 minutes, not restful sleep. We arrived late at night, so unfortunately, did not notice right away. We reserved two rooms via Expedia. Upon arrival we were told we have only one room reserved. At the end, hotel was able to find another room for ...

Reviewed on Apr 26, 2026

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HomeAwhile
Portland Regency Hotel & Spa

Portland Regency Hotel & Spa

3.5 out of 5
20 Milk Street Portland ME
Book a stay at this 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 in ...
9.4/10 Exceptional! (1,631 reviews)
The hotel was excellent. I just wish they had told us about the $35 overnight parking charge up front. Every time we needed the car we had to tip the valet and then the overnight charge was a bit much.

Reviewed on Apr 26, 2026

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Portland Regency Hotel & Spa
Clarion Hotel Portland Airport ME

Clarion Hotel Portland Airport ME

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 ...
8/10 Very Good! (1,420 reviews)
When I booked my stay I was under the impression that there was breakfast and there wasn't which wasn't ideal for traveling with kids and when I asked for a wash cloth the person didn't know what a wash cloth was and just gave me a towel and he was upset that I took his time from his phone. Then ...

Reviewed on Apr 24, 2026

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Clarion Hotel Portland Airport ME
Holiday Inn Portland-By the Bay by IHG

Holiday Inn Portland-By the Bay by IHG

4 out of 5
88 Spring St Portland ME
Book a stay at this business-friendly hotel in Portland. Enjoy free WiFi, breakfast (surcharge), and a free airport shuttle. Our guests praise the helpful staff ...
9/10 Wonderful! (1,520 reviews)
Staff was friendly. Would be nice if there was better signage for the gym/pool though.

Reviewed on Apr 26, 2026

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Holiday Inn Portland-By the Bay by IHG
Hyatt Place Portland Downtown - Old Port Square

Hyatt Place Portland Downtown - Old Port Square

3 out of 5
433 Fore St Portland ME
Book a stay at this business-friendly hotel in Portland. Enjoy free WiFi, breakfast (surcharge), and a free airport shuttle. Our guests praise the breakfast ...
9/10 Wonderful! (1,323 reviews)
The hotel was clean and in a great spot. The staff was helpful. I was disappointed in some of the tech. You are asked to text to retrieve your car. Our car was “not recognized by the system”. We also were unable to cast to the TV in our room with a streaming app. The service kept on recognizing an ...

Reviewed on Apr 24, 2026

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Hyatt Place Portland Downtown - Old Port Square
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! (1,134 reviews)
All good

Reviewed on Apr 26, 2026

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Inn at St John Portland In-Town
See all 1,721 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.