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Bailey Island

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Bailey Island Flights as Low as $215

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

JetBlue Airways
Sat, Jul 5 - Wed, Jul 9
FLL
Fort Lauderdale - Hollywood Intl.
PWM
Portland Intl. Jetport
$215 Roundtrip, found 1 day ago
$215
Roundtrip
found 1 day ago
Select JetBlue Airways flight, departing Sat, Jul 5 from Fort Lauderdale - Hollywood Intl. to Portland Intl. Jetport, returning Wed, Jul 9, priced at $215 found 1 day ago
Delta
Fri, Jul 4 - Tue, Jul 8
PBI
Palm Beach Intl.
PWM
Portland Intl. Jetport
$217 Roundtrip, found 1 day ago
$217
Roundtrip
found 1 day ago
Select Delta flight, departing Fri, Jul 4 from Palm Beach Intl. to Portland Intl. Jetport, returning Tue, Jul 8, priced at $217 found 1 day ago
Delta
Thu, Jul 3 - Fri, Jul 4
FLL
Fort Lauderdale - Hollywood Intl.
PWM
Portland Intl. Jetport
$217 Roundtrip, found 1 day ago
$217
Roundtrip
found 1 day ago
Select Delta flight, departing Thu, Jul 3 from Fort Lauderdale - Hollywood Intl. to Portland Intl. Jetport, returning Fri, Jul 4, priced at $217 found 1 day ago
Delta
Sat, Jul 5 - Sat, Jul 5
LGA
LaGuardia
PWM
Portland Intl. Jetport
$217 Roundtrip, found 1 day ago
$217
Roundtrip
found 1 day ago
Select Delta flight, departing Sat, Jul 5 from LaGuardia to Portland Intl. Jetport, returning Sat, Jul 5, priced at $217 found 1 day ago
JetBlue Airways
Tue, Jul 1 - Wed, Jul 9
FLL
Fort Lauderdale - Hollywood Intl.
PWM
Portland Intl. Jetport
$218 Roundtrip, found 1 day ago
$218
Roundtrip
found 1 day ago
Select JetBlue Airways flight, departing Tue, Jul 1 from Fort Lauderdale - Hollywood Intl. to Portland Intl. Jetport, returning Wed, Jul 9, priced at $218 found 1 day ago
Delta
Sat, Jun 7 - Mon, Jun 9
SRQ
Sarasota-Bradenton Intl.
PWM
Portland Intl. Jetport
$219 Roundtrip, found 1 day ago
$219
Roundtrip
found 1 day ago
Select Delta flight, departing Sat, Jun 7 from Sarasota-Bradenton Intl. to Portland Intl. Jetport, returning Mon, Jun 9, priced at $219 found 1 day ago
Delta
Mon, Jun 30 - Fri, Jul 4
PBI
Palm Beach Intl.
PWM
Portland Intl. Jetport
$220 Roundtrip, found 1 day ago
$220
Roundtrip
found 1 day ago
Select Delta flight, departing Mon, Jun 30 from Palm Beach Intl. to Portland Intl. Jetport, returning Fri, Jul 4, priced at $220 found 1 day ago
Delta
Mon, Jun 9 - Mon, Jun 9
SRQ
Sarasota-Bradenton Intl.
PWM
Portland Intl. Jetport
$222 Roundtrip, found 1 day ago
$222
Roundtrip
found 1 day ago
Select Delta flight, departing Mon, Jun 9 from Sarasota-Bradenton Intl. to Portland Intl. Jetport, returning Mon, Jun 9, priced at $222 found 1 day ago
JetBlue Airways
Sat, Jul 5 - Tue, Jul 8
FLL
Fort Lauderdale - Hollywood Intl.
PWM
Portland Intl. Jetport
$226 Roundtrip, found 1 day ago
$226
Roundtrip
found 1 day ago
Select JetBlue Airways flight, departing Sat, Jul 5 from Fort Lauderdale - Hollywood Intl. to Portland Intl. Jetport, returning Tue, Jul 8, priced at $226 found 1 day ago
JetBlue Airways
Tue, Jul 1 - Tue, Jul 8
FLL
Fort Lauderdale - Hollywood Intl.
PWM
Portland Intl. Jetport
$229 Roundtrip, found 1 day ago
$229
Roundtrip
found 1 day ago
Select JetBlue Airways flight, departing Tue, Jul 1 from Fort Lauderdale - Hollywood Intl. to Portland Intl. Jetport, returning Tue, Jul 8, priced at $229 found 1 day ago
Delta
Sat, Jun 7 - Sun, Jun 8
SRQ
Sarasota-Bradenton Intl.
PWM
Portland Intl. Jetport
$233 Roundtrip, found 1 day ago
$233
Roundtrip
found 1 day ago
Select Delta flight, departing Sat, Jun 7 from Sarasota-Bradenton Intl. to Portland Intl. Jetport, returning Sun, Jun 8, priced at $233 found 1 day ago
Frontier Airlines
Mon, May 19 - Sat, May 24
CVG
Cincinnati - Northern Kentucky Intl.
PWM
Portland Intl. Jetport
$242 Roundtrip, found 3 days ago
$242
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Mon, May 19 from Cincinnati - Northern Kentucky Intl. to Portland Intl. Jetport, returning Sat, May 24, priced at $242 found 3 days ago
Delta
Tue, Aug 5 - Fri, Aug 8
MYR
Myrtle Beach Intl.
PWM
Portland Intl. Jetport
$257 Roundtrip, found 1 day ago
$257
Roundtrip
found 1 day ago
Select Delta flight, departing Tue, Aug 5 from Myrtle Beach Intl. to Portland Intl. Jetport, returning Fri, Aug 8, priced at $257 found 1 day ago
American Airlines
Fri, Jun 6 - Tue, Jun 10
SRQ
Sarasota-Bradenton Intl.
PWM
Portland Intl. Jetport
$293 Roundtrip, found 1 day ago
$293
Roundtrip
found 1 day ago
Select American Airlines flight, departing Fri, Jun 6 from Sarasota-Bradenton Intl. to Portland Intl. Jetport, returning Tue, Jun 10, priced at $293 found 1 day ago
Delta
Tue, Oct 7 - Wed, Oct 15
MEM
Memphis Intl.
PWM
Portland Intl. Jetport
$312 Roundtrip, found 1 day ago
$312
Roundtrip
found 1 day ago
Select Delta flight, departing Tue, Oct 7 from Memphis Intl. to Portland Intl. Jetport, returning Wed, Oct 15, priced at $312 found 1 day ago
Bargain Flight
Fri, Sep 26 - Mon, Sep 29
CVG
Cincinnati - Northern Kentucky Intl.
PWM
Portland Intl. Jetport
$326 Roundtrip, found 1 day ago
$326
Roundtrip
found 1 day ago
Select Bargain Flight flight, departing Fri, Sep 26 from Cincinnati - Northern Kentucky Intl. to Portland Intl. Jetport, returning Mon, Sep 29, priced at $326 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 July, 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 $215, 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 $215 right now, why wait?

Bailey Island Flight Information
Destination airport
Portland Intl. Jetport
Destination airport IATA code
PWM
Roundtrip price
$214

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 $152 per night from May 26 to May 27
$152
includes taxes & fees
May 26 - May 27
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! (1,003 reviews)
"Loved it!"

Reviewed on May 1, 2025

The Westin Portland Harborview
Portland Harbor Hotel
Portland Harbor Hotel
4 out of 5
468 Fore Street, Portland, ME
The price is $263 per night from May 11 to May 12
$263
includes taxes & fees
May 11 - May 12
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! (1,485 reviews)
"Everything was as expected"

Reviewed on May 1, 2025

Portland Harbor Hotel
Portland Regency Hotel & Spa
Portland Regency Hotel & Spa
3.5 out of 5
20 Milk Street, Portland, ME
The price is $187 per night from May 11 to May 12
$187
includes taxes & fees
May 11 - May 12
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! (1,251 reviews)
Great hotel
"Fantastic hotel very accommodating Exceeded expectations near everything"

Reviewed on May 1, 2025

Portland Regency Hotel & Spa
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 $97 per night from May 5 to May 6
$97
includes taxes & fees
May 5 - May 6
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! (1,004 reviews)
"Very nice people in a very charming hotel, european style, with real keys. Room 108 is on the street, ask for a quieter room if it's possible. The breakfast place is very small but you can bring your plate in your room. Limited menu, no egg no bacon but bagels, muffins, cereals and fresh fruits. ..."

Reviewed on May 1, 2025

Inn at St John Portland In-Town
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 $104 per night from May 6 to May 7
$104
includes taxes & fees
May 6 - May 7
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! (2,141 reviews)
"I love that it’s smoke free and clean."

Reviewed on May 1, 2025

La Quinta Inn & Suites by Wyndham Portland
Cambria Hotel Portland Downtown-Old Port
Cambria Hotel Portland Downtown-Old Port
3 out of 5
25 HANCOCK STREET, Portland, ME
The price is $177 per night from May 11 to May 12
$177
includes taxes & fees
May 11 - May 12
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! (864 reviews)
"Amazing hotel"

Reviewed on May 1, 2025

Cambria Hotel Portland Downtown-Old Port
Clarion Hotel Portland
Clarion Hotel Portland
2.5 out of 5
1230 Congress St, Portland, ME
The price is $103 per night from May 6 to May 7
$103
includes taxes & fees
May 6 - May 7
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! (1,003 reviews)
"Love the pool"

Reviewed on Apr 25, 2025

Clarion Hotel Portland
Holiday Inn Portland-By the Bay by IHG
Holiday Inn Portland-By the Bay by IHG
3 out of 5
88 Spring St, Portland, ME
The price is $131 per night from May 26 to May 27
$131
includes taxes & fees
May 26 - May 27
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! (1,204 reviews)
"Friendly staff, beautiful room, service was wonderful. Really great location. Cannot wait to go back!!"

Reviewed on May 2, 2025

Holiday Inn Portland-By the Bay by IHG
See all 1,737 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.