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Bailey Island

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Bailey Island Flights as Low as $212

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

Breeze Airways
Wed, Apr 30 - Wed, May 7
RSW
Southwest Florida Intl.
PWM
Portland Intl. Jetport
$212 Roundtrip, found 11 hours ago
$212
Roundtrip
found 11 hours ago
Select Breeze Airways flight, departing Wed, Apr 30 from Southwest Florida Intl. to Portland Intl. Jetport, returning Wed, May 7, priced at $212 found 11 hours ago
American Airlines
Wed, Apr 30 - Wed, May 7
RSW
Southwest Florida Intl.
PWM
Portland Intl. Jetport
$230 Roundtrip, found 11 hours ago
$230
Roundtrip
found 11 hours ago
Select American Airlines flight, departing Wed, Apr 30 from Southwest Florida Intl. to Portland Intl. Jetport, returning Wed, May 7, priced at $230 found 11 hours ago
Breeze Airways
Wed, Apr 30 - Tue, May 6
RSW
Southwest Florida Intl.
PWM
Portland Intl. Jetport
$236 Roundtrip, found 11 hours ago
$236
Roundtrip
found 11 hours ago
Select Breeze Airways flight, departing Wed, Apr 30 from Southwest Florida Intl. to Portland Intl. Jetport, returning Tue, May 6, priced at $236 found 11 hours ago
Breeze Airways
Wed, Apr 30 - Tue, May 6
RSW
Southwest Florida Intl.
PWM
Portland Intl. Jetport
$241 Roundtrip, found 11 hours ago
$241
Roundtrip
found 11 hours ago
Select Breeze Airways flight, departing Wed, Apr 30 from Southwest Florida Intl. to Portland Intl. Jetport, returning Tue, May 6, priced at $241 found 11 hours ago
American Airlines
Tue, Jul 15 - Wed, Jul 23
RSW
Southwest Florida Intl.
PWM
Portland Intl. Jetport
$251 Roundtrip, found 1 day ago
$251
Roundtrip
found 1 day ago
Select American Airlines flight, departing Tue, Jul 15 from Southwest Florida Intl. to Portland Intl. Jetport, returning Wed, Jul 23, priced at $251 found 1 day ago
American Airlines
Wed, Apr 30 - Tue, May 6
RSW
Southwest Florida Intl.
PWM
Portland Intl. Jetport
$254 Roundtrip, found 11 hours ago
$254
Roundtrip
found 11 hours ago
Select American Airlines flight, departing Wed, Apr 30 from Southwest Florida Intl. to Portland Intl. Jetport, returning Tue, May 6, priced at $254 found 11 hours ago
JetBlue Airways
Fri, May 2 - Sun, May 4
RSW
Southwest Florida Intl.
PWM
Portland Intl. Jetport
$259 Roundtrip, found 11 hours ago
$259
Roundtrip
found 11 hours ago
Select JetBlue Airways flight, departing Fri, May 2 from Southwest Florida Intl. to Portland Intl. Jetport, returning Sun, May 4, priced at $259 found 11 hours ago
United
Wed, Jan 1 - Mon, Jan 6
RIC
Richmond Intl.
PWM
Portland Intl. Jetport
$262 Roundtrip, found 20 hours ago
$262
Roundtrip
found 20 hours ago
Select United flight, departing Wed, Jan 1 from Richmond Intl. to Portland Intl. Jetport, returning Mon, Jan 6, priced at $262 found 20 hours ago
American Airlines
Wed, Apr 30 - Wed, May 7
RSW
Southwest Florida Intl.
PWM
Portland Intl. Jetport
$263 Roundtrip, found 11 hours ago
$263
Roundtrip
found 11 hours ago
Select American Airlines flight, departing Wed, Apr 30 from Southwest Florida Intl. to Portland Intl. Jetport, returning Wed, May 7, priced at $263 found 11 hours ago
American Airlines
Wed, Jan 1 - Mon, Jan 6
RIC
Richmond Intl.
PWM
Portland Intl. Jetport
$266 Roundtrip, found 20 hours ago
$266
Roundtrip
found 20 hours ago
Select American Airlines flight, departing Wed, Jan 1 from Richmond Intl. to Portland Intl. Jetport, returning Mon, Jan 6, priced at $266 found 20 hours ago
American Airlines
Tue, Jul 15 - Wed, Jul 23
RSW
Southwest Florida Intl.
PWM
Portland Intl. Jetport
$268 Roundtrip, found 1 day ago
$268
Roundtrip
found 1 day ago
Select American Airlines flight, departing Tue, Jul 15 from Southwest Florida Intl. to Portland Intl. Jetport, returning Wed, Jul 23, priced at $268 found 1 day ago
Breeze Airways
Tue, Jul 15 - Wed, Jul 23
RSW
Southwest Florida Intl.
PWM
Portland Intl. Jetport
$270 Roundtrip, found 1 day ago
$270
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Tue, Jul 15 from Southwest Florida Intl. to Portland Intl. Jetport, returning Wed, Jul 23, priced at $270 found 1 day ago
American Airlines
Wed, Apr 30 - Wed, May 7
RSW
Southwest Florida Intl.
PWM
Portland Intl. Jetport
$277 Roundtrip, found 11 hours ago
$277
Roundtrip
found 11 hours ago
Select American Airlines flight, departing Wed, Apr 30 from Southwest Florida Intl. to Portland Intl. Jetport, returning Wed, May 7, priced at $277 found 11 hours ago
American Airlines
Tue, Jul 15 - Wed, Jul 23
RSW
Southwest Florida Intl.
PWM
Portland Intl. Jetport
$278 Roundtrip, found 1 day ago
$278
Roundtrip
found 1 day ago
Select American Airlines flight, departing Tue, Jul 15 from Southwest Florida Intl. to Portland Intl. Jetport, returning Wed, Jul 23, priced at $278 found 1 day ago
JetBlue Airways
Tue, Apr 29 - Mon, May 5
RSW
Southwest Florida Intl.
PWM
Portland Intl. Jetport
$284 Roundtrip, found 11 hours ago
$284
Roundtrip
found 11 hours ago
Select JetBlue Airways flight, departing Tue, Apr 29 from Southwest Florida Intl. to Portland Intl. Jetport, returning Mon, May 5, priced at $284 found 11 hours ago
Delta
Tue, Dec 31 - Tue, Jan 7
RIC
Richmond Intl.
PWM
Portland Intl. Jetport
$292 Roundtrip, found 4 days ago
$292
Roundtrip
found 4 days ago
Select Delta flight, departing Tue, Dec 31 from Richmond Intl. to Portland Intl. Jetport, returning Tue, Jan 7, priced at $292 found 4 days 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 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 $212, 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 $212 right now, why wait?

Bailey Island Flight Information
Destination airport
Portland Intl. Jetport
Destination airport IATA code
PWM
Roundtrip price
$212

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 $110 per night from Jan 7 to Jan 8
$110
includes taxes & fees
Jan 7 - Jan 8, 2025
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 ...
8.6/10 Excellent! (1,004 reviews)
"This is our second time staying here. It's conveniently located. The room is clean & very spacious. Staff is very welcoming. A free shuttle service from the bus terminal was very helpful!"

Reviewed on Dec 23, 2024

The Westin Portland Harborview
Ramada Plaza by Wyndham Portland
Ramada Plaza by Wyndham Portland
3 out of 5
155 Riverside St, Portland, ME
The price is $103 per night from Dec 26 to Dec 27
$103
includes taxes & fees
Dec 26 - Dec 27
Stay at this 3-star business-friendly hotel in Portland. Enjoy free WiFi, free parking, and 2 spa tubs. Our guests praise the restaurant and the helpful staff ...
7.6/10 Good! (1,010 reviews)
"The property was excellent. The only issue was the shower in the room. Also the vending machines were a bit tricky to operate. The staff was excellent. The room was clean and comfortable."

Reviewed on Dec 23, 2024

Ramada Plaza by Wyndham Portland
Portland Harbor Hotel
Portland Harbor Hotel
4 out of 5
468 Fore Street, Portland, ME
The price is $183 per night from Dec 26 to Dec 27
$183
includes taxes & fees
Dec 26 - Dec 27
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! (1,427 reviews)
"Nice hotel in a great location!"

Reviewed on Dec 22, 2024

Portland Harbor Hotel
Canopy by Hilton Portland Waterfront
Canopy by Hilton Portland Waterfront
4 out of 5
9 Center Street, Portland, ME
The price is $159 per night from Jan 5 to Jan 6
$159
includes taxes & fees
Jan 5 - Jan 6, 2025
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! (871 reviews)
"Friendly service and convenient location. Property well maintained."

Reviewed on Dec 23, 2024

Canopy by Hilton Portland Waterfront
Casco Bay Hotel, Ascend Hotel Collection
Casco Bay Hotel, Ascend Hotel Collection
3.5 out of 5
80 John Roberts Rd., South Portland, ME
The price is $92 per night from Jan 6 to Jan 7
$92
includes taxes & fees
Jan 6 - Jan 7, 2025
Stay at this 3.5-star 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! (2,414 reviews)
"Staff helpful and friendly. Would highly recommend this Hotel! ⭐️⭐️⭐️⭐️⭐️"

Reviewed on Dec 22, 2024

Casco Bay Hotel, Ascend Hotel Collection
Tru by Hilton Portland Airport Area
Tru by Hilton Portland Airport Area
2.5 out of 5
369 Maine Mall Road, South Portland, ME
The price is $88 per night from Jan 2 to Jan 3
$88
includes taxes & fees
Jan 2 - Jan 3, 2025
Stay at this hotel in South Portland. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. ...
8.8/10 Excellent! (1,238 reviews)
"This is a very good mid-range property in an area seriously lacking in mid-range. The included breakfast is serviceable and what you'd expect out of an included breakfast. Starbucks is across the parking lot and I'd go there for your caffeine fix. The hotel is quiet, staff is friendly. I'd prefer ..."

Reviewed on Dec 16, 2024

Tru by Hilton Portland Airport Area
Cambria Hotel Portland Downtown-Old Port
Cambria Hotel Portland Downtown-Old Port
3 out of 5
25 HANCOCK STREET, Portland, ME
The price is $134 per night from Jan 5 to Jan 6
$134
includes taxes & fees
Jan 5 - Jan 6, 2025
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! (729 reviews)
"Good location for walking the city, quiet hotel"

Reviewed on Dec 17, 2024

Cambria Hotel Portland Downtown-Old Port
Portland Regency Hotel & Spa
Portland Regency Hotel & Spa
3.5 out of 5
20 Milk Street, Portland, ME
The price is $165 per night from Jan 1 to Jan 2
$165
includes taxes & fees
Jan 1 - Jan 2, 2025
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! (1,226 reviews)
"Beautiful hotel with great staff!"

Reviewed on Dec 13, 2024

Portland Regency Hotel & Spa
See all 1,602 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.