Cheap Flights To Bailey Island 2026

Bailey Island Flights as Low as $355

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
Tue, Oct 13 - Tue, Oct 20
JAX
Jacksonville Intl.
PWM
Portland Intl. Jetport
$355
Roundtrip
found 1 day ago
Select United flight, departing Tue, Oct 13 from Jacksonville Intl. to Portland Intl. Jetport, returning Tue, Oct 20, priced at $355 found 1 day ago
Delta
Tue, Oct 13 - Tue, Oct 20
JAX
Jacksonville Intl.
PWM
Portland Intl. Jetport
$372
Roundtrip
found 1 day ago
Select Delta flight, departing Tue, Oct 13 from Jacksonville Intl. to Portland Intl. Jetport, returning Tue, Oct 20, priced at $372 found 1 day ago
United
Tue, Oct 13 - Tue, Oct 20
JAX
Jacksonville Intl.
PWM
Portland Intl. Jetport
$377
Roundtrip
found 1 day ago
Select United flight, departing Tue, Oct 13 from Jacksonville Intl. to Portland Intl. Jetport, returning Tue, Oct 20, priced at $377 found 1 day ago
Delta
Sat, Oct 31 - Mon, Nov 16
BNA
Nashville Intl.
PWM
Portland Intl. Jetport
$379
Roundtrip
found 1 day ago
Select Delta flight, departing Sat, Oct 31 from Nashville Intl. to Portland Intl. Jetport, returning Mon, Nov 16, priced at $379 found 1 day ago
United
Tue, Oct 13 - Tue, Oct 20
JAX
Jacksonville Intl.
PWM
Portland Intl. Jetport
$382
Roundtrip
found 1 day ago
Select United flight, departing Tue, Oct 13 from Jacksonville Intl. to Portland Intl. Jetport, returning Tue, Oct 20, priced at $382 found 1 day ago
United
Delta
Fri, Oct 30 - Mon, Nov 16
BNA
Nashville Intl.
PWM
Portland Intl. Jetport
$398
Roundtrip
found 1 day ago
Select Delta flight, departing Fri, Oct 30 from Nashville Intl. to Portland Intl. Jetport, returning Mon, Nov 16, priced at $398 found 1 day ago
American Airlines
American Airlines
United
Sat, Oct 31 - Sun, Nov 8
LIT
Clinton National Airport
PWM
Portland Intl. Jetport
$406
Roundtrip
found 1 day ago
Select United flight, departing Sat, Oct 31 from Clinton National Airport to Portland Intl. Jetport, returning Sun, Nov 8, priced at $406 found 1 day ago
Delta
Tue, Oct 20 - Tue, Oct 27
DTW
Detroit Metropolitan Wayne County
PWM
Portland Intl. Jetport
$429
Roundtrip
found 1 hour ago
Select Delta flight, departing Tue, Oct 20 from Detroit Metropolitan Wayne County to Portland Intl. Jetport, returning Tue, Oct 27, priced at $429 found 1 hour ago
Delta
Wed, Oct 14 - Wed, Oct 21
DTW
Detroit Metropolitan Wayne County
PWM
Portland Intl. Jetport
$439
Roundtrip
found 1 hour ago
Select Delta flight, departing Wed, Oct 14 from Detroit Metropolitan Wayne County to Portland Intl. Jetport, returning Wed, Oct 21, priced at $439 found 1 hour ago
Southwest Airlines
JetBlue Airways
Breeze 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.