Title: $71 Cheap Flights to Bailey Island, ME - Expedia.com ![Bailey Island featuring rugged coastline and a house](https://images.trvl-media.com/place/6046825/7787ff8e-ec8a-4628-8f3d-1af96a802dbe.jpg?impolicy=fcrop&w=1200&h=500&q=medium) ![](https://images.trvl-media.com/place/6046825/7787ff8e-ec8a-4628-8f3d-1af96a802dbe.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # $71 Cheap Flights to Bailey Island, ME [View $71 flight on Sat, Aug 29, 2026](https://expedia.com/Flights-Search?trip=oneway&leg1=from:TPA,to:PWM,departure:8/29/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:70.65&airProductToken=AQosCioIzbABEgMxMzgY8wMgz2Uot7GWAzD6spYDOEFAAFgBagJOT3IFQU5PMDASCggBEAEYASoCTVgYASIECAEQASgCKAMoBDAN) [Bailey Island Travel Guide](https://expedia.com/Bailey-Island.dx6046825)[Hotels in Bailey Island](https://expedia.com/Bailey-Island-Hotels.d6046825.Travel-Guide-Hotels)[Car Rentals in Bailey Island](https://expedia.com/Car-Rentals-In-Bailey-Island.d6046825.Car-Rental-Guide)[Bailey Island Vacation Packages](https://expedia.com/Bailey-Island.d6046825.Destination-Travel-Guides) ## Popular airlines to Bailey Island - ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_AA.svg) American Airlines [](https://www.expedia.com/Flights-Search?leg1=from:CMH,to:Bailey Island, Maine, United States of America,departure:3/11/2026TANYT&leg2=from:Bailey Island, Maine, United States of America,to:CMH,departure:3/18/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"AA"}}]) - ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_UA.svg) United [](https://www.expedia.com/Flights-Search?leg1=from:CMH,to:Bailey Island, Maine, United States of America,departure:3/11/2026TANYT&leg2=from:Bailey Island, Maine, United States of America,to:CMH,departure:3/18/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"UA"}}]) - ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_WN.svg) Southwest Airlines [](https://www.expedia.com/Flights-Search?leg1=from:CMH,to:Bailey Island, Maine, United States of America,departure:3/11/2026TANYT&leg2=from:Bailey Island, Maine, United States of America,to:CMH,departure:3/18/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"WN"}}]) - ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_DL.svg) Delta [](https://www.expedia.com/Flights-Search?leg1=from:CMH,to:Bailey Island, Maine, United States of America,departure:3/11/2026TANYT&leg2=from:Bailey Island, Maine, United States of America,to:CMH,departure:3/18/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"DL"}}]) - ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_F9.svg) Frontier Airlines [](https://www.expedia.com/Flights-Search?leg1=from:CMH,to:Bailey Island, Maine, United States of America,departure:3/11/2026TANYT&leg2=from:Bailey Island, Maine, United States of America,to:CMH,departure:3/18/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"F9"}}]) - ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_B6.svg) JetBlue Airways [](https://www.expedia.com/Flights-Search?leg1=from:CMH,to:Bailey Island, Maine, United States of America,departure:3/11/2026TANYT&leg2=from:Bailey Island, Maine, United States of America,to:CMH,departure:3/18/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"B6"}}]) - ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_AS.svg) Alaska Airlines [](https://www.expedia.com/Flights-Search?leg1=from:CMH,to:Bailey Island, Maine, United States of America,departure:3/11/2026TANYT&leg2=from:Bailey Island, Maine, United States of America,to:CMH,departure:3/18/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"AS"}}]) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__notification.svg) ### Be in the know Get alerts if flight prices drop or rise\* - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Book smarter Save up to 30% on select hotels after you book a flight\* - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__trophy.svg) ### Earn twice Earn your airline miles on top of our OneKeyCash [Learn about One Key](https://www.expedia.com/welcome-one-key) ## How much is the cheapest flight to Bailey Island? Prices were available within the past 7 days and start at $71 for one-way flights and $147 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply. All deals One way Roundtrip ![JetBlue Airways](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/b6.gif) Tue, Apr 7 - Mon, Apr 13 JFK New York PWM Portland $147 Roundtrip found 7 hours ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:JFK,to:PWM,departure:4/7/2026TANYT&leg2=from:PWM,to:JFK,departure:4/13/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:146.79&airProductToken=AQouCiwIwmwSAzMwOBipUSDPZSiR4YkDMO7hiQM4TEAAWAFqAkROcghVSTJRVVNMMQouCiwIwmwSAzUwNxjPZSCpUSj4nIoDMMWdigM4TEAAWAFqAkROcghVSTJRVVNMMRIKCAEQARgBKgJCNhgBIgQIARABKAIoBCgGMAE) ![Breeze Airways](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/MX.gif) Sat, Sep 5 - Sat, Sep 12 MCO Orlando PWM Portland $152 Roundtrip found 1 day ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:MCO,to:PWM,departure:9/5/2026TANYT&leg2=from:PWM,to:MCO,departure:9/12/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:151.68&airProductToken=AQosCioIzbABEgM3MzgYzHAgz2UomPyWAzDY_ZYDOEJAAFgBagJOT3IFQk5PMDAKLAoqCM2wARIDNzM5GM9lIMxwKODMlwMwrc6XAzhCQABYAWoCTk9yBUJOTzAwEgoIARABGAEqAk1YGAEiBAgBEAEoAigDKAQwDQ) ![American Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AA.gif) Fri, Apr 3 - Mon, Apr 6 DCA Washington PWM Portland $189 Roundtrip found 4 hours ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:DCA,to:PWM,departure:4/3/2026TANYT&leg2=from:PWM,to:DCA,departure:4/6/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:188.80&airProductToken=AQoyCjAIwYIBEgQxMjU1GEMgz2UojLSJAzDrtIkDOEJAAFgBagVCQVNJQ3IIT1ZGSFpOQlgKMgowCMGCARIEMzAzMBjPZSBDKJjOiQMwhs-JAzhCQABYAWoFQkFTSUNyCE9WRkhaTkJYEgoIARABGAEqAkFBGAEiBAgBEAEoAigDKAQwCw) ![United](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/UA.gif) Sat, Jul 11 - Sat, Jul 18 IAD Washington PWM Portland $189 Roundtrip just found [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:IAD,to:PWM,departure:7/11/2026TANYT&leg2=from:PWM,to:IAD,departure:7/18/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:188.80&airProductToken=AQo4CjYI1YIBEgQyMDY0GIgYIM9lKOKNkgMwx46SAzhOQABYAWoKMV9iYXNpY2Vjb3IIS0ZBMkFEQk4KOAo2CNWCARIEMTkyNhjPZSCIGCjL1JIDMLTVkgM4TkAAWAFqCjFfYmFzaWNlY29yCEtGQTJBREJOEgoIARABGAEqAlVBGAEiBAgBEAEoAigDKAQwCw) ![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif) Wed, May 6 - Wed, May 13 ORD Chicago PWM Portland $197 Roundtrip found 19 hours ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:ORD,to:PWM,departure:5/6/2026TANYT&leg2=from:PWM,to:ORD,departure:5/13/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:196.40&airProductToken=AQpuCjUIxJgBEgQ0OTM1GK4cIKlRKPmljAMwmKeMAzhFQABYAWoJTUFJTkJBU0lDcghWQVZXQTVCQwo1CMSYARIENTQxMRipUSDPZSjTp4wDML6ojAM4RUABWAFqCU1BSU5CQVNJQ3IIVkFWV0E1QkMSDAgBEAEYASoCREwyABgBIgQIARABKAIoAygEMAE) ## Alternative airports near Bailey Island Prices were available within the past 7 days. Prices and availability are subject to change. [](https://www.expedia.com/Flights-Search?leg1=from:CMH,to:PWM,departure:3/11/2026TANYT&leg2=from:PWM,to:CMH,departure:3/18/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&sortOrder=INCREASING&sortType=PRICE) PWM Portland Intl. Jetport Cheapest [Flights from $372 ](https://www.expedia.com/Flights-Search?leg1=from:CMH,to:PWM,departure:3/11/2026TANYT&leg2=from:PWM,to:CMH,departure:3/18/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&sortOrder=INCREASING&sortType=PRICE) ![](https://forever.travel-assets.com/flex/flexmanager/images/2026/02/06/expedia-sale-2026-desktop-us-ca.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh) ## The Annual Vacation Sale Members save up to 40% on hotels and homes. Plan this year’s big trip and save. [Book now](https://expedia.com/deals?rfrr=FTG_SPRING_PROMO_) ## Frequently asked questions ### What month is the cheapest to fly to Bailey Island? ### Which US cities have the cheapest flights to Bailey Island? > - Orlando (MCO) > - Raleigh (RDU) > - Fort Myers (FMY, RSW) > - Boston (BOS) > - New York (JFK, LGA) > > > with prices usually starting around $51. ### Which US cities fly direct to Bailey Island? > - Washington (DCA, IAD) > - Newark (EWR) > - New York (JFK, LGA) > - Chicago (MDW, ORD) > - Philadelphia (PHL) > > > To Portsmouth Intl. (PSM) > - Orlando (MCO) > - Raleigh (RDU) > - Fort Myers (RSW) > > > To Manchester-Boston Regional (MHT) > - Orlando (MCO) > - Baltimore (BWI) > - Charlotte (CLT) > - Washington (DCA, IAD) > - Philadelphia (PHL) ### How to find a cheap flight to Bailey Island? ### Which airlines fly to Bailey Island? > - American Airlines > - Delta > - Delta Air Lines > - JetBlue Airways > - United > - United Airlines ### Where do you fly into Bailey Island? > - The closest major airport is Portland, ME (PWM-Portland Intl. Jetport), about 23 miles from the city center, which is a hub for United, Delta, and American Airlines, with other airlines like WN, JetBlue Airways also operating here. > - Manchester, NH (MHT-Manchester-Boston Regional) is another option, about 114 miles away, serving as a hub for American Airlines, WN, and United, with JetBlue Airways, MX also operating here. > - Portsmouth, NH (PSM-Portsmouth Intl.), about 73 miles away, serving as a hub for MX. > - Augusta, ME (AUG-Augusta State), about 42 miles away, serving as a hub for 9K. > - Rockland, ME (RKD-Knox County Regional), about 66 miles away, serving as a hub for 9K and JetBlue Airways. ### What is the cheapest airport to fly to in Bailey Island? ### Which budget airlines fly to Bailey Island? > - Southwest Airlines: serves Portland (PWM), Manchester (MHT) > - Breeze: serves Portland (PWM), Portsmouth (PSM), Manchester (MHT) > - JetBlue Airways: serves Portland (PWM), Augusta (AUG), Rockland (RKD), Manchester (MHT) > - Sun Country Airlines: flies to Portland (PWM) > - Frontier Airlines: flies to Portland (PWM) > - WestJet: flies to Portland (PWM) ### What is the best month to visit Bailey Island? ### How far in advance should I book a flight to Bailey Island? ### What day of the week is cheapest day to buy a plane ticket to Bailey Island? ### What is the most expensive month to fly to Bailey Island? ### How far is the airport from central Bailey Island? ### How can I track flight prices to Bailey Island? ### How to get a cheap last-minute flight to Bailey Island? ### Can I earn miles booking a flight to Bailey Island with Expedia? ### Can I save money by booking a Bailey Island trip package? ### Can I change or cancel my flight to Bailey Island? \*Flight schedules are subject to change. ## Book with confidence # Tips to find the cheapest flights to Bailey Island **The cheapest day to fly** Get started finding a cheap flight to Bailey Island on Expedia by either choosing a deal on this page or entering into the search bar your travel dates, origin airport, and whether you want roundtrip or one-way airfare. You can filter for flexibility, number of stops, airline, and departure/arrival times to find the best flight for you. **The cheapest month to fly** April is the cheapest month to fly to Bailey Island. This coincides with the low season when fewer people travel. Whichever month you travel in, though, be sure to book at least a month in advance if you want to score cheap tickets to Bailey Island. ARC's data shows that domestic flights booked 28 days or more before departure are typically 24% cheaper than those booked last minute. **The most affordable time to book a flight** Typically, a Sunday can be the cheapest time to book a flight to Bailey Island, according to ARC’s data. On average, you could save between 6% and 13% by booking on a Sunday instead of a Friday, which is the most expensive day to make a reservation. **The cheapest round-trip tickets to Bailey Island** The lowest price for round-trip flights to Bailey Island in 2026 starts from from $147, while one-way tickets start from from $71\. Expedia's effective search tool is one of the best ways to find a budget airfare. Simply enter your dates, and within seconds, it'll show you a vast selection of the cheapest flights to Bailey Island. If you have a preferred departure time or airline, you can use the handy filters to customize your search. **The cheapest airlines flying to Bailey Island** Breeze Airways, JetBlue Airways, American Airlines, Southwest Airlines, Delta, United are just some of the airlines that can typically offer cheap tickets to Bailey Island. You can find their most affordable flights by using the “airline” search filter and then sorting prices from low to high. As a trusted partner of the world's leading airlines, Expedia offers you some of the best airfare deals to Bailey Island and countless more destinations worldwide. **The most affordable airports to fly into** To view the cheapest airports to fly into for Bailey Island, simply order your search results from lowest to highest price. Expedia's search tool compares flight prices for all airports close to your destination, so you don't have to manually search them one by one to find the cheapest flight to Bailey Island. If you have a preferred place to fly into, take advantage of the “arrival airport” filter to narrow down your search on Expedia. **Save with a package** With Expedia's amazing [package deals](https://www.expedia.com/package-deals), you could save hundreds of dollars by booking your Bailey Island plane tickets together with your accommodations, car rental, or activities. Just select the search wizard's “package” option to view some of the cheapest deals. Look out for the green savings label to see how much you're saving. **Date flexibility for the cheapest flights to Bailey Island** If you can be flexible with your travel dates, it's a good idea to broaden your search by comparing prices on different days. This will open up more options, meaning you could uncover a less expensive flight to Bailey Island. **Stopover savings** The cheapest tickets to Bailey Island are sometimes those with a stopover. Book one of these flights, and you'll change planes at an airport en route to Bailey Island. While the overall travel time might be longer than a non-stop flight, you may decide it's worth it for the money saved. **Get Expedia's Price Drop Protection** Price Drop Protection means that if your flight gets cheaper after booking, you'll be credited the difference\*. This gives you peace of mind that you're getting one of the cheapest flights to Bailey Island for your chosen departure. Expedia's Price Drop Protection is available for a small fee but is free to One Key Gold and Platinum tier members. \*Terms apply. **Use our Price Tracking feature** Expedia's Price Tracking feature is another great tool that removes the guesswork from finding cheap flights to Bailey Island. Simply download the free Expedia app to your smart device and activate Bailey Island flight price alerts for your travel dates. There's even a price predictor tool that uses historical data to indicate the best time to book, giving you peace of mind that you'll nab the lowest prices. **Book with Expedia** As well as Price Drop Protection and Price Tracking, Expedia's close partnership with a vast selection of the world's leading airlines means you're sure to find cheap flights to Bailey Island. Plus, the One Key rewards program lets you earn real cash rewards on most bookings that you can use to save money on future trips. Best of all, it's free to join, and members often unlock exclusive discounts, too. Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023\. The percentages you see are averages. ## Travel information | Destination airport | Portland Intl. Jetport | | ----------------------------- | ---------------------- | | Destination airport IATA code | PWM | | Destination city name | Portland | | Roundtrip price | $147 | ## Trending flights to Bailey Island Prices were available within the past 7 days and start at $71 for one-way flights and $147 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply. All deals One way Roundtrip ![JetBlue Airways](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/b6.gif) Tue, Apr 7 - Mon, Apr 13 JFK New York PWM Portland $147 Roundtrip found 7 hours ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:JFK,to:PWM,departure:4/7/2026TANYT&leg2=from:PWM,to:JFK,departure:4/13/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:146.79&airProductToken=AQouCiwIwmwSAzMwOBipUSDPZSiR4YkDMO7hiQM4TEAAWAFqAkROcghVSTJRVVNMMQouCiwIwmwSAzUwNxjPZSCpUSj4nIoDMMWdigM4TEAAWAFqAkROcghVSTJRVVNMMRIKCAEQARgBKgJCNhgBIgQIARABKAIoBCgGMAE) ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rentals - Other - [Hotels near Cobwork Bridge ](https://www.expedia.com/Cobwork-Bridge-Hotels.0-l553248621532668105-0.Travel-Guide-Filter-Hotels) - [Hotels near Land's End Gift Shop ](https://www.expedia.com/Lands-End-Gift-Shop-Hotels.0-l553248621532668102-0.Travel-Guide-Filter-Hotels) - 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