Cheap Flights To Bailey Island 2026

Bailey Island Flights as Low as $309

These prices were available within the past 7 days. Prices quoted are per person, round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

American Airlines
United
Southwest Airlines
Delta
Tue, Jan 26 - Wed, Jan 27
CLE
Hopkins Intl.
PWM
Portland Intl. Jetport
$309
Roundtrip
found 15 hours ago
Select Delta flight, departing Tue, Jan 26 from Hopkins Intl. to Portland Intl. Jetport, returning Wed, Jan 27, priced at $309 found 15 hours ago
Southwest Airlines
Southwest Airlines
American Airlines
United
American Airlines
American Airlines
United
Delta
Fri, Nov 27 - Sat, Dec 12
ATL
Hartsfield-Jackson Atlanta Intl.
PWM
Portland Intl. Jetport
$417
Roundtrip
found 14 hours ago
Select Delta flight, departing Fri, Nov 27 from Hartsfield-Jackson Atlanta Intl. to Portland Intl. Jetport, returning Sat, Dec 12, priced at $417 found 14 hours ago
Delta
Tue, Oct 27 - Tue, Nov 3
LAS
Harry Reid Intl.
PWM
Portland Intl. Jetport
$433
Roundtrip
found 1 day ago
Select Delta flight, departing Tue, Oct 27 from Harry Reid Intl. to Portland Intl. Jetport, returning Tue, Nov 3, priced at $433 found 1 day ago
Delta
Fri, Nov 27 - Sat, Dec 12
ATL
Hartsfield-Jackson Atlanta Intl.
PWM
Portland Intl. Jetport
$459
Roundtrip
found 14 hours ago
Select Delta flight, departing Fri, Nov 27 from Hartsfield-Jackson Atlanta Intl. to Portland Intl. Jetport, returning Sat, Dec 12, priced at $459 found 14 hours ago
United
Sat, Oct 17 - Tue, Oct 20
COU
Columbia Regional
PWM
Portland Intl. Jetport
$498
Roundtrip
found 14 hours ago
Select United flight, departing Sat, Oct 17 from Columbia Regional to Portland Intl. Jetport, returning Tue, Oct 20, priced at $498 found 14 hours ago
JetBlue Airways

Flights to Bailey Island

No matter how much you fight the travel bug, sometimes there's only one solution—to hop on the next plane to Bailey Island. AARP Travel Center Powered by Expedia® is here to help you cure that bug with great deals on flights and activities. AARP Travel combines their members-only discount with the best rates from Expedia, giving members the best price in travel, guaranteed.

AARP members get exclusive rates on:

  • Hotels
  • Car rentals
  • Flights
  • Waived booking fees on flights

Once you have got your trip scheduled, we will show you a full list of deals for your route. Don't forget to look at flights to alternative airports nearby, which can help you find a lower rate.

Transportation at the Bailey Island Airport

Once you have reserved plane tickets to Bailey Island, you may want to book a car so you can get around on your own. You can schedule a Bailey Island rental car under our cars tab and hop in the car right when you step out of the airport. For more information, check out the Bailey Island Car Rentals Guide.

Bailey Island Activities

Not sure where to start? Not to worry—there's lots to do in this city. Bailey Island has so much to do, and we can help you get started.

If you're looking for some fun activities to do in Bailey Island, make sure you look at our "Things to Do in Bailey Island" page for activities and excursions for the whole clan.

Book Your Hotel in Bailey Island

Bailey Island has accommodation to choose from, make sure you check out our hotel listings tab for some great recommendations from past visitors. Remember that you will get the best for your trip to to Bailey Island when you book with AARP Travel.

Booking Your Visit to Bailey Island

Whether you are heading out on an exploration to a place you have never been for pleasure, bringing the family on the annual vacation, or a business trip, we have the perfect getaway waiting for you. There is no better time than now to start booking that next trip. Book one of our flights today.