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Bailey Island

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Bailey Island Flights as Low as $197

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

American Airlines
Wed, Aug 19 - Tue, Aug 25
BNA
Nashville Intl.
PWM
Portland Intl. Jetport
$197 Roundtrip, found 7 hours ago
$197
Roundtrip
found 7 hours ago
Select American Airlines flight, departing Wed, Aug 19 from Nashville Intl. to Portland Intl. Jetport, returning Tue, Aug 25, priced at $197 found 7 hours ago
American Airlines
Wed, Aug 19 - Tue, Aug 25
BNA
Nashville Intl.
PWM
Portland Intl. Jetport
$197 Roundtrip, found 7 hours ago
$197
Roundtrip
found 7 hours ago
Select American Airlines flight, departing Wed, Aug 19 from Nashville Intl. to Portland Intl. Jetport, returning Tue, Aug 25, priced at $197 found 7 hours ago
JetBlue Airways
Wed, Aug 19 - Tue, Aug 25
BNA
Nashville Intl.
PWM
Portland Intl. Jetport
$199 Roundtrip, found 7 hours ago
$199
Roundtrip
found 7 hours ago
Select JetBlue Airways flight, departing Wed, Aug 19 from Nashville Intl. to Portland Intl. Jetport, returning Tue, Aug 25, priced at $199 found 7 hours ago
Bargain Flight
Tue, Aug 4 - Wed, Aug 12
DCA
Ronald Reagan Washington National
PWM
Portland Intl. Jetport
$200 Roundtrip, found 1 day ago
$200
Roundtrip
found 1 day ago
Select Bargain Flight flight, departing Tue, Aug 4 from Ronald Reagan Washington National to Portland Intl. Jetport, returning Wed, Aug 12, priced at $200 found 1 day ago
JetBlue Airways
Wed, Aug 19 - Tue, Aug 25
BNA
Nashville Intl.
PWM
Portland Intl. Jetport
$201 Roundtrip, found 7 hours ago
$201
Roundtrip
found 7 hours ago
Select JetBlue Airways flight, departing Wed, Aug 19 from Nashville Intl. to Portland Intl. Jetport, returning Tue, Aug 25, priced at $201 found 7 hours ago
United
Wed, Aug 19 - Tue, Aug 25
BNA
Nashville Intl.
PWM
Portland Intl. Jetport
$203 Roundtrip, found 7 hours ago
$203
Roundtrip
found 7 hours ago
Select United flight, departing Wed, Aug 19 from Nashville Intl. to Portland Intl. Jetport, returning Tue, Aug 25, priced at $203 found 7 hours ago
Delta
Sat, Jul 4 - Wed, Jul 8
FLL
Fort Lauderdale - Hollywood Intl.
PWM
Portland Intl. Jetport
$219 Roundtrip, found 18 hours ago
$219
Roundtrip
found 18 hours ago
Select Delta flight, departing Sat, Jul 4 from Fort Lauderdale - Hollywood Intl. to Portland Intl. Jetport, returning Wed, Jul 8, priced at $219 found 18 hours ago
American Airlines
Tue, Aug 4 - Wed, Aug 12
DCA
Ronald Reagan Washington National
PWM
Portland Intl. Jetport
$220 Roundtrip, found 1 day ago
$220
Roundtrip
found 1 day ago
Select American Airlines flight, departing Tue, Aug 4 from Ronald Reagan Washington National to Portland Intl. Jetport, returning Wed, Aug 12, priced at $220 found 1 day ago
JetBlue Airways
Tue, Jul 7 - Wed, Jul 8
FLL
Fort Lauderdale - Hollywood Intl.
PWM
Portland Intl. Jetport
$224 Roundtrip, found 18 hours ago
$224
Roundtrip
found 18 hours ago
Select JetBlue Airways flight, departing Tue, Jul 7 from Fort Lauderdale - Hollywood Intl. to Portland Intl. Jetport, returning Wed, Jul 8, priced at $224 found 18 hours ago
JetBlue Airways
Tue, Aug 4 - Wed, Aug 12
DCA
Ronald Reagan Washington National
PWM
Portland Intl. Jetport
$224 Roundtrip, found 1 day ago
$224
Roundtrip
found 1 day ago
Select JetBlue Airways flight, departing Tue, Aug 4 from Ronald Reagan Washington National to Portland Intl. Jetport, returning Wed, Aug 12, priced at $224 found 1 day ago
Delta
Tue, Aug 11 - Wed, Aug 19
IAH
George Bush Intercontinental
PWM
Portland Intl. Jetport
$237 Roundtrip, found 1 day ago
$237
Roundtrip
found 1 day ago
Select Delta flight, departing Tue, Aug 11 from George Bush Intercontinental to Portland Intl. Jetport, returning Wed, Aug 19, priced at $237 found 1 day ago
JetBlue Airways
Mon, Aug 17 - Mon, Aug 31
LAX
Los Angeles Intl.
PWM
Portland Intl. Jetport
$296 Roundtrip, found 3 days ago
$296
Roundtrip
found 3 days ago
Select JetBlue Airways flight, departing Mon, Aug 17 from Los Angeles Intl. to Portland Intl. Jetport, returning Mon, Aug 31, priced at $296 found 3 days ago
Delta
Sat, Oct 31 - Sat, Nov 14
DAL
Love Field
PWM
Portland Intl. Jetport
$381 Roundtrip, found 1 day ago
$381
Roundtrip
found 1 day ago
Select Delta flight, departing Sat, Oct 31 from Love Field to Portland Intl. Jetport, returning Sat, Nov 14, priced at $381 found 1 day ago
American Airlines
Wed, Jul 22 - Wed, Jul 29
DFW
Dallas-Fort Worth Intl.
PWM
Portland Intl. Jetport
$390 Roundtrip, found 11 hours ago
$390
Roundtrip
found 11 hours ago
Select American Airlines flight, departing Wed, Jul 22 from Dallas-Fort Worth Intl. to Portland Intl. Jetport, returning Wed, Jul 29, priced at $390 found 11 hours ago
Breeze Airways
Sat, Jul 4 - Mon, Jul 6
FLL
Fort Lauderdale - Hollywood Intl.
PWM
Portland Intl. Jetport
$421 Roundtrip, found 18 hours ago
$421
Roundtrip
found 18 hours ago
Select Breeze Airways flight, departing Sat, Jul 4 from Fort Lauderdale - Hollywood Intl. to Portland Intl. Jetport, returning Mon, Jul 6, priced at $421 found 18 hours ago
Sun Country Airlines
Fri, Jul 3 - Mon, Jul 6
LAX
Los Angeles Intl.
PWM
Portland Intl. Jetport
$842 Roundtrip, found 1 day ago
$842
Roundtrip
found 1 day ago
Select Sun Country Airlines flight, departing Fri, Jul 3 from Los Angeles Intl. to Portland Intl. Jetport, returning Mon, Jul 6, priced at $842 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 August, 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 $197, 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 $197 right now, why wait?

Bailey Island Flight Information
Destination airport
Portland Intl. Jetport
Destination airport IATA code
PWM
Roundtrip price
$196

Last Minute Hotel Deals in Bailey Island

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! (1,490 reviews)
"Clean Property, rooms were spacious and comfortable. Easy 10 minute walk to Bissell Brewery and Thompson’s Point if you’re catching a show!"

Reviewed on Jun 10, 2026

Get rates
Clarion Hotel Portland Airport ME
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 ...
9.4/10 Exceptional! (1,782 reviews)
"Wonderful stay, very clean. Staff at front desk very helpful."

Reviewed on Jun 10, 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! (1,244 reviews)
"Hotel was in great condition very new feeling. Great location and rooms were spacious."

Reviewed on Jun 11, 2026

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Cambria Hotel Portland Downtown-Old Port
Quality Inn & Suites South Portland

Quality Inn & Suites South Portland

2.5 out of 5
738 Main Street South Portland ME
Book a stay at this business-friendly hotel in South Portland. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
6.6/10 (1,005 reviews)
"Run down hotel, they are trying to upgrade but doing so cheap and it shows"

Reviewed on Jun 10, 2026

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Quality Inn & Suites South Portland
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! (1,686 reviews)
"We had a great stay at the Regency. Our room was very comfortable and the location is ideal, right in the Old Port with many excellent restaurants, fun stores, and the waterfront steps away. Very friendly and helpful staff. We appreciated the airport shuttle. Our only disappointment was that the ..."

Reviewed on Jun 9, 2026

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Portland Regency Hotel & Spa
La Quinta Inn & Suites by Wyndham Portland DT/Maine Med

La Quinta Inn & Suites by Wyndham Portland DT/Maine Med

3 out of 5
340 Park Ave Portland ME
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 ...
8.6/10 Excellent! (2,219 reviews)
"Excellent staff. Easy location. Well kept and clean’n"

Reviewed on Jun 9, 2026

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La Quinta Inn & Suites by Wyndham Portland DT/Maine Med
Clarion Pointe South Portland

Clarion Pointe South Portland

2 out of 5
675 Main Street I-95 South Portland ME
Book a stay at this business-friendly hotel in South Portland. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Maine Mall and Thompson's ...
7.6/10 Good! (471 reviews)
"The room smelled bad. The carpets were dirty. The area the hotel was in was a bad neighborhood. Drug dealers and street women in hotel parking lot. Left after 20 minutes."

Reviewed on Jun 11, 2026

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Clarion Pointe South Portland
Casco Bay Hotel Portland Airport - Maine Mall, an Ascend Collection Hotel

Casco Bay Hotel Portland Airport - Maine Mall, an Ascend Collection Hotel

3.5 out of 5
80 John Roberts Rd. South Portland ME
Book a stay at this 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! (2,925 reviews)
"Nice free breakfast, very comfortable room and bed, always a great stay."

Reviewed on Jun 10, 2026

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Casco Bay Hotel Portland Airport - Maine Mall, an Ascend Collection Hotel
See all 1,857 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.