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Bailey Island

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Bailey Island Flights as Low as $157

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

American Airlines
Tue, Sep 30 - Wed, Oct 1
DCA
Ronald Reagan Washington National
PWM
Portland Intl. Jetport
$157 Roundtrip, found 10 hours ago
$157
Roundtrip
found 10 hours ago
Select American Airlines flight, departing Tue, Sep 30 from Ronald Reagan Washington National to Portland Intl. Jetport, returning Wed, Oct 1, priced at $157 found 10 hours ago
Frontier Airlines
Sat, Aug 16 - Sat, Aug 23
MCO
Orlando Intl.
PWM
Portland Intl. Jetport
$164 Roundtrip, found 3 days ago
$164
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Sat, Aug 16 from Orlando Intl. to Portland Intl. Jetport, returning Sat, Aug 23, priced at $164 found 3 days ago
Frontier Airlines
Sat, Sep 6 - Sat, Sep 13
MCO
Orlando Intl.
PWM
Portland Intl. Jetport
$168 Roundtrip, found 1 day ago
$168
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Sat, Sep 6 from Orlando Intl. to Portland Intl. Jetport, returning Sat, Sep 13, priced at $168 found 1 day ago
JetBlue Airways
Tue, Oct 7 - Wed, Oct 15
BNA
Nashville Intl.
PWM
Portland Intl. Jetport
$169 Roundtrip, found 23 hours ago
$169
Roundtrip
found 23 hours ago
Select JetBlue Airways flight, departing Tue, Oct 7 from Nashville Intl. to Portland Intl. Jetport, returning Wed, Oct 15, priced at $169 found 23 hours ago
Breeze Airways
Sat, Aug 16 - Sat, Aug 23
MCO
Orlando Intl.
PWM
Portland Intl. Jetport
$169 Roundtrip, found 3 days ago
$169
Roundtrip
found 3 days ago
Select Breeze Airways flight, departing Sat, Aug 16 from Orlando Intl. to Portland Intl. Jetport, returning Sat, Aug 23, priced at $169 found 3 days ago
Bargain Flight
Tue, Sep 30 - Sat, Oct 4
DCA
Ronald Reagan Washington National
PWM
Portland Intl. Jetport
$170 Roundtrip, found 11 hours ago
$170
Roundtrip
found 11 hours ago
Select Bargain Flight flight, departing Tue, Sep 30 from Ronald Reagan Washington National to Portland Intl. Jetport, returning Sat, Oct 4, priced at $170 found 11 hours ago
Frontier Airlines
Sat, Jul 26 - Sat, Aug 2
MCO
Orlando Intl.
PWM
Portland Intl. Jetport
$171 Roundtrip, found 4 hours ago
$171
Roundtrip
found 4 hours ago
Select Frontier Airlines flight, departing Sat, Jul 26 from Orlando Intl. to Portland Intl. Jetport, returning Sat, Aug 2, priced at $171 found 4 hours ago
American Airlines
Tue, Sep 30 - Sat, Oct 4
DCA
Ronald Reagan Washington National
PWM
Portland Intl. Jetport
$173 Roundtrip, found 11 hours ago
$173
Roundtrip
found 11 hours ago
Select American Airlines flight, departing Tue, Sep 30 from Ronald Reagan Washington National to Portland Intl. Jetport, returning Sat, Oct 4, priced at $173 found 11 hours ago
American Airlines
Mon, Aug 4 - Fri, Aug 15
DCA
Ronald Reagan Washington National
PWM
Portland Intl. Jetport
$176 Roundtrip, found 1 day ago
$176
Roundtrip
found 1 day ago
Select American Airlines flight, departing Mon, Aug 4 from Ronald Reagan Washington National to Portland Intl. Jetport, returning Fri, Aug 15, priced at $176 found 1 day ago
Delta
Tue, Sep 30 - Wed, Oct 1
DCA
Ronald Reagan Washington National
PWM
Portland Intl. Jetport
$177 Roundtrip, found 10 hours ago
$177
Roundtrip
found 10 hours ago
Select Delta flight, departing Tue, Sep 30 from Ronald Reagan Washington National to Portland Intl. Jetport, returning Wed, Oct 1, priced at $177 found 10 hours ago
Delta
Mon, Aug 11 - Tue, Aug 19
DCA
Ronald Reagan Washington National
PWM
Portland Intl. Jetport
$179 Roundtrip, found 10 hours ago
$179
Roundtrip
found 10 hours ago
Select Delta flight, departing Mon, Aug 11 from Ronald Reagan Washington National to Portland Intl. Jetport, returning Tue, Aug 19, priced at $179 found 10 hours ago
Frontier Airlines
Sat, Aug 16 - Sat, Aug 23
MCO
Orlando Intl.
PWM
Portland Intl. Jetport
$183 Roundtrip, found 3 days ago
$183
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Sat, Aug 16 from Orlando Intl. to Portland Intl. Jetport, returning Sat, Aug 23, priced at $183 found 3 days ago
United
Mon, Sep 29 - Tue, Sep 30
DCA
Ronald Reagan Washington National
PWM
Portland Intl. Jetport
$185 Roundtrip, found 3 days ago
$185
Roundtrip
found 3 days ago
Select United flight, departing Mon, Sep 29 from Ronald Reagan Washington National to Portland Intl. Jetport, returning Tue, Sep 30, priced at $185 found 3 days ago
Bargain Flight
Sat, Jul 12 - Sat, Jul 19
CLT
Charlotte-Douglas Intl.
PWM
Portland Intl. Jetport
$242 Roundtrip, found 5 hours ago
$242
Roundtrip
found 5 hours ago
Select Bargain Flight flight, departing Sat, Jul 12 from Charlotte-Douglas Intl. to Portland Intl. Jetport, returning Sat, Jul 19, priced at $242 found 5 hours ago
United
Tue, Sep 16 - Tue, Sep 23
ONT
Los Angeles - Ontario Intl.
PWM
Portland Intl. Jetport
$256 Roundtrip, found 9 hours ago
$256
Roundtrip
found 9 hours ago
Select United flight, departing Tue, Sep 16 from Los Angeles - Ontario Intl. to Portland Intl. Jetport, returning Tue, Sep 23, priced at $256 found 9 hours ago
Delta
Mon, Aug 4 - Thu, Sep 4
SAN
San Diego Intl.
PWM
Portland Intl. Jetport
$335 Roundtrip, found 2 hours ago
$335
Roundtrip
found 2 hours ago
Select Delta flight, departing Mon, Aug 4 from San Diego Intl. to Portland Intl. Jetport, returning Thu, Sep 4, priced at $335 found 2 hours 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 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 14 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 $157, 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 $157 right now, why wait?

Bailey Island Flight Information
Destination airport
Portland Intl. Jetport
Destination airport IATA code
PWM
Roundtrip price
$157

Last Minute Hotel Deals in Bailey Island

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! (1,013 reviews)
"This is my go to spot when I stay in Portland!"

Reviewed on Jul 1, 2025

Get rates
Clarion Hotel Portland
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
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 ...
7.8/10 Good! (1,003 reviews)
"Staff were great"

Reviewed on Jul 2, 2025

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Days Inn by Wyndham Airport/Maine Mall
Ramada Plaza by Wyndham Portland
Ramada Plaza by Wyndham Portland
3 out of 5
155 Riverside St, Portland, ME
Stay at this 3-star business-friendly hotel in Portland. Enjoy free WiFi, free parking, and 2 hot tubs. Our guests praise the restaurant and the helpful staff ...
7.6/10 Good! (1,027 reviews)
Great staff
"Staff was very friendly and helpful"

Reviewed on Jun 29, 2025

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Ramada Plaza by Wyndham Portland
Hyatt Place Portland Downtown - Old Port Square
Hyatt Place Portland Downtown - Old Port Square
3 out of 5
433 Fore St, Portland, ME
Stay at this 3-star business-friendly hotel in Portland. Enjoy free WiFi, 2 bars/lounges, and breakfast (surcharge). Our guests praise the breakfast and the ...
8.8/10 Excellent! (1,148 reviews)
"Great stay!"

Reviewed on Jul 4, 2025

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Hyatt Place Portland Downtown - Old Port Square
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! (1,334 reviews)
Wonderful hotel
"Great front desk staff. Rooms nice/beds very comfortable. Breakfast was delicious. Cannot beat location. Spa treatments excellent but the spa receptionist was full of herself and unwelcoming"

Reviewed on Jun 29, 2025

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Portland Regency Hotel & Spa
Canopy by Hilton Portland Waterfront
Canopy by Hilton Portland Waterfront
4 out of 5
9 Center Street, Portland, ME
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 ...
9.4/10 Exceptional! (1,002 reviews)
"This is probably one of most favorite hotels I’ve ever stayed at. I love the rooftop bar in the location is great along the waterfront which has a lot of old historic buildings. The hotel lobby is amazing. It is so beautiful and so are the rooms. Very modern and comfortable. The breakfast Café and ..."

Reviewed on Jul 4, 2025

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Canopy by Hilton Portland Waterfront
Comfort Inn Airport
Comfort Inn Airport
2.5 out of 5
90 Maine Mall Rd, South Portland, ME
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 ...
8.4/10 Very Good! (1,357 reviews)
Great stay
"Nice room, clean, quiet. Has a great breakfast."

Reviewed on Jul 2, 2025

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Comfort Inn Airport
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 ...
9.2/10 Wonderful! (1,520 reviews)
"Lovely hotel in a perfect location - some elements of the room hadn’t been cleaned that well but made up for by the complimentary coffee and cookie station."

Reviewed on Jul 3, 2025

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Portland Harbor Hotel
See all 1,803 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.