Cheap Flights To Bailey Island 2026

Bailey Island Flights as Low as $163

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.

Breeze Airways
Breeze Airways
Breeze Airways
Delta
Wed, Aug 26 - Wed, Sep 9
JFK
John F. Kennedy Intl.
PWM
Portland Intl. Jetport
$247
Roundtrip
found 12 hours ago
Select Delta flight, departing Wed, Aug 26 from John F. Kennedy Intl. to Portland Intl. Jetport, returning Wed, Sep 9, priced at $247 found 12 hours ago
JetBlue Airways
JetBlue Airways
Delta
Tue, Oct 13 - Fri, Oct 23
CMH
John Glenn Columbus Intl.
PWM
Portland Intl. Jetport
$269
Roundtrip
found 20 hours ago
Select Delta flight, departing Tue, Oct 13 from John Glenn Columbus Intl. to Portland Intl. Jetport, returning Fri, Oct 23, priced at $269 found 20 hours ago
JetBlue Airways
Delta
Thu, Aug 27 - Wed, Sep 9
JFK
John F. Kennedy Intl.
PWM
Portland Intl. Jetport
$282
Roundtrip
found 12 hours ago
Select Delta flight, departing Thu, Aug 27 from John F. Kennedy Intl. to Portland Intl. Jetport, returning Wed, Sep 9, priced at $282 found 12 hours ago
Delta
Tue, Oct 20 - Fri, Oct 30
MCI
Kansas City Intl.
PWM
Portland Intl. Jetport
$331
Roundtrip
found 1 day ago
Select Delta flight, departing Tue, Oct 20 from Kansas City Intl. to Portland Intl. Jetport, returning Fri, Oct 30, priced at $331 found 1 day ago
American Airlines
JetBlue Airways
Southwest Airlines
United
Tue, Sep 22 - Wed, Sep 23
MCI
Kansas City Intl.
PWM
Portland Intl. Jetport
$349
Roundtrip
found 1 day ago
Select United flight, departing Tue, Sep 22 from Kansas City Intl. to Portland Intl. Jetport, returning Wed, Sep 23, priced at $349 found 1 day ago
Delta
Sat, Oct 10 - Tue, Oct 20
TLH
Tallahassee Intl.
PWM
Portland Intl. Jetport
$363
Roundtrip
found 1 day ago
Select Delta flight, departing Sat, Oct 10 from Tallahassee Intl. to Portland Intl. Jetport, returning Tue, Oct 20, priced at $363 found 1 day ago
Delta
Tue, Oct 6 - Thu, Oct 8
GSP
Greenville-Spartanburg Intl.
PWM
Portland Intl. Jetport
$365
Roundtrip
found 6 hours ago
Select Delta flight, departing Tue, Oct 6 from Greenville-Spartanburg Intl. to Portland Intl. Jetport, returning Thu, Oct 8, priced at $365 found 6 hours ago

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.