$71 Cheap Flights to Bailey Island, ME

Popular airlines to Bailey Island

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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 $142 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Breeze Airways
United
American Airlines
JetBlue Airways
Delta

Alternative airports near Bailey Island

Prices were available within the past 7 days. Prices and availability are subject to change.

What you need to know for your flight to Bailey Island

Flights to Bailey Island at a glance

Traveling to Bailey Island is easy—simply explore your options for flights to Bailey Island, whether you're looking for cheap flights to Bailey Island or more traditional choices. Compare travel times to find the best fit for your budget and itinerary as you plan to enjoy the island's iconic sights and charming neighborhoods.

  • Major airport near Bailey Island: Portland International Jetport Airport (PWM)
  • Flights per week: 1,750+ flights arriving at Bailey Island airport
  • Number of airlines that fly to Bailey Island: around 10+ carriers

Popular airport near Bailey Island

Bailey Island is a picturesque destination known for its stunning outdoor landscapes and beautiful beaches, making it ideal for family getaways and romantic escapes. Travelers flock to this charming island for its scenic views and recreational opportunities. The closest airport serving Bailey Island is Port Bailey Airport, which provides convenient access for those seeking domestic flights.

  • Portland International Jetport Airport (PWM): Situated in Cumberland County, Maine, this airport is approximately 17 miles from Bailey Island. It offers connections for both domestic and international travel, facilitating access to over 165 domestic cities and more than 30 international locations. Travelers can opt for enhanced comfort by selecting first class or premium economy class seating, depending on the airline and specific routes. Major carriers at this airport include American Airlines, United, and Delta.

Top routes to Bailey Island

  • Orlando (MCO) to Bailey Island (PWM), with one-way fares starting at around $70
  • New York (JFK/LGA) to Bailey Island (PWM), with one-way tickets available from around $60
  • Washington (IAD/DCA) to Bailey Island (PWM), with one-way flight options from around $90
  • Chicago (ORD/MDW) to Bailey Island (PWM), with one-way airfare from around $90
  • Tampa (TPA) to Bailey Island (PWM), with one-way tickets available from around $65

Cheapest routes to Bailey Island

  • Charleston (CHS/CRW) to Bailey Island (PWM), with low-cost one-way tickets from around $50
  • New York (JFK/LGA) to Bailey Island (PWM), with cheap one-way fares from around $60
  • Raleigh (RDU) to Bailey Island (PWM), with low one-way fares from around $60
  • Tampa (TPA) to Bailey Island (PWM), with cheap one-way fares from around $65
  • Norfolk (ORF) to Bailey Island (PWM), with affordable one-way prices from around $65

*Flight times and fares vary by season and availability and are based on one-way routes

Top airlines with flights to Bailey Island

  • American Airlines: Operating flights to Portland International Jetport Airport (PWM), this airline represents about 36% of arrivals at Bailey Island. One-way tickets average around $270, with premium service possibly including first class, depending on the specific route.
  • United: Also flying to Portland International Jetport Airport (PWM), United accounts for roughly 23% of arrivals at Bailey Island. The typical one-way fare is about $310, and premium service may feature first class based on the route.
  • Delta: Connecting to Portland International Jetport Airport (PWM), Delta comprises approximately 21% of arrivals at Bailey Island. Average one-way fares are around $260, with premium options potentially including both premium economy and first class, depending on the route.
  • Southwest Airlines: Servicing Portland International Jetport Airport (PWM), Southwest Airlines makes up nearly 12% of arrivals to Bailey Island. The average one-way fare is estimated at $270, offering cost-effective travel options.
  • Breeze: Operating flights into Portland International Jetport Airport (PWM), Breeze accounts for about 3% of arrivals to Bailey Island. One-way fares are quite affordable, averaging around $120, making it a budget-friendly choice for travelers.

Best time to fly to Bailey Island

The most popular months for travelers to fly to Bailey Island are March, April, and July, when peak temperatures in Bailey Island can reach up to 68°F in July. If you prefer quieter travel, consider January, the least busy and relatively cheaper time to visit with fewer crowds and temperatures around 26.4°F. For better deals, September usually offers the lowest average one-way fare around $215, roughly 10% cheaper than the yearly average. Looking for additional cheaper months to fly? January, August, and May offer average one-way fares of around $227, making them good options for flexible travelers.

calendar iconMonthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinesscrowd level iconDemandprice iconAverage one-way Fare
January26.4°F (-3.1°C)Light RainMostly SunnyModerately Low$226
February27.1°F (-2.7°C)Light RainMostly CloudyAverage$254
March33.6°F (0.9°C)Light RainMostly SunnyModerately High$259
April43.5°F (6.4°C)Light RainMostly SunnyModerately High$273
May53.2°F (11.8°C)Light RainMostly SunnyAverage$228
June61.2°F (16.2°C)Light RainMostly SunnyAverage$242
July68.0°F (20.0°C)Light RainMostly SunnyModerately High$236
August67.8°F (19.9°C)Light RainMostly SunnyAverage$227
September61.9°F (16.6°C)Light RainMostly SunnyAverage$215
October52.2°F (11.2°C)Light RainMostly SunnyAverage$232
November41.5°F (5.3°C)Light RainMostly SunnyModerately Low$234
December33.1°F (0.6°C)Light RainMostly SunnyModerately Low$251

*Average one-way fare is based on Expedia flight booking data from January 2025 to April 2026 for the specified route and travel class and may change depending on availability, dates, and demand.

How to save money on a flight to Bailey Island

Getting some of the best deals on flights to Bailey Island is all about timing and flexibility. Here are some key tips to help you save:

  1. Compare flight options—use Expedia's search tool to compare airlines, routes, direct vs. non-direct flights, and flight times. You can also sort by price to find the most affordable options.
  2. Set up price alerts—as an Expedia member you can use Price Tracking to receive notifications when flight prices change.
  3. Bundle and save—book a flight and unlock a hotel deal on Expedia*, or explore our Bailey Island hotel and flight deals.
  4. Think about luggage-nowadays, it's important to check the airline's baggage policies to find the best value. That may be paying for an additional carry-on bag or booking a ticket with checked luggage included. Either way, double-check your baggage allowance before confirming your booking to avoid excess baggage fees at the airport.
  5. Earn miles—you can earn airline miles when you book your Bailey Island flight with Expedia. Just select your frequent flyer program and enter your program number when confirming your booking.

*For members. Select hotels.

Arriving in Bailey Island

Bailey Island welcomes travelers through its range of transport options based on price, convenience, and proximity. Here's how to reach Bailey Island efficiently:

  • Public transportation: From Portland International Jetport Airport, travelers can conveniently access several key transport links by car: Portland Transportation Center, a train station, is located about 2.4 miles away, while Portland Seaport, a seaport, is about 4.2 miles from the airport. Additionally, Casco Bay Lines Ferry Terminal, a ferry terminal, is situated approximately 4.9 miles away.
  • Hotel transfer: Transfers offer a convenient way to reach your hotel in Bailey Island, with private rides that can be arranged in advance.
  • Car rental: Renting a car in Bailey Island is a good option if you plan to explore and sightsee beyond the city. Browse cheap car rentals in Bailey Island on Expedia.
  • Taxi/ride-hailing: Taxis and ride-hailing services may be available from designated pickup areas outside the terminal, check locally on arrival.

Where to stay around Bailey Island

  • Freeport: Freeport is located 28 miles drive away from Bailey Island and is a vibrant city known for its combination of outdoor activities and scenic beauty. Here, families can enjoy a variety of experiences, from exploring Wolfe's Neck Woods State Park to relaxing at local beaches and lakes. The area also features shopping centers and cultural sites like Bowdoin College and the historic Harrington House, making it a great spot for both adventure seekers and culture enthusiasts alike.
  • Brunswick: Brunswick is located 12 miles drive away from Bailey Island and offers a charming mix of outdoor scenery and romantic settings. With its lovely beaches and historic college, it’s an ideal destination for couples and families. Popular spots include Thomas Point Beach for sunbathing and Maine Street for shopping and dining. The town’s picturesque surroundings and vibrant community make it a delightful place to explore.
  • Harpswell: Harpswell is located 7 miles drive away from Bailey Island and is a picturesque coastal town perfect for outdoor enthusiasts. Known for its stunning scenery, Harpswell beckons visitors to its beautiful beaches and the tranquil Casco Bay. With recreational areas for hiking and water activities, it’s an excellent destination for romance and family outings alike. Don’t miss Popham Beach for a relaxing day by the ocean, where you can soak in the natural beauty of the Maine coastline.

Tips for short-haul flights to Bailey Island

For quick getaways, efficiency is key. Here is how to make your short-haul journey smoother:

  • Pack light and skip checked bags—when flying with budget airlines, it's often more economical to travel with just a carry-on. Maximize your space by using mini toiletries, wearing your heaviest clothing, and coordinating your outfits effectively. This approach also eliminates the hassle of waiting at baggage claim upon arrival.
  • Bring your own entertainment—many short-haul flights do not provide in-flight entertainment options. To keep yourself entertained, download TV shows, movies, music, or podcasts ahead of time, and consider bringing a book. Remember to charge your devices fully before you board.
  • Arrive at the airport in plenty of time—even for short or domestic flights, it’s advisable to reach the airport at least 1.5 to 2 hours before your departure, taking into account traffic and potential security lines.
  • Bring your own snacks and water—pack snacks and a refillable water bottle to stay hydrated and save money while at the airport.

Tips for long-haul flights to Bailey Island

Flying long-haul sometimes requires extra planning to ensure a comfortable journey:

  • Select your seat in advance—for longer flights, choosing your seat is crucial for comfort. Full-service airlines often allow free seat selection once online check-in begins, typically 24–48 hours before your flight. Some airlines may offer seat selection even earlier than that.
  • Arrive at the airport in plenty of time—aim to arrive at the airport at least 3 hours before your international flight's departure to accommodate check-in, security, and immigration processes.
  • Relax at the airport—if you find yourself with extra time, take the opportunity to browse the shops, visit a coffee shop, or unwind at the gate or in a departure lounge if you have access. Airport Wi-Fi is generally free and available.
  • Adjust to the new time zone mid-flight—begin syncing your body clock by setting your watch and modifying your sleep schedule to align with your destination's time zone. Try to sleep or stay awake during the flight according to the local time of your arrival to help minimize jet lag.

Frequently asked questions

What month is the cheapest to fly to Bailey Island?
November is the cheapest month to travel to Bailey Island. There's less demand then, so fares are usually more affordable. Organizing your trip outside of major holidays and school breaks can also help you save.
Which US cities have the cheapest flights to Bailey Island?
Get cheap flights to Bailey Island from Washington, New York and Philadelphia. These cities generally offer the lowest fares to this popular destination. But keep in mind that stopovers, seasonality and demand will also have an impact on rates, so remain flexible and book when you spot a bargain.
Which US cities fly direct to Bailey Island?
Choose from 12 US destinations that have direct flights to Bailey Island. While booking on Expedia, select the "Direct flights only" filter to find nonstop itineraries. Fly to Bailey Island from any of these top cities:

  • Washington
  • New York
  • Philadelphia
  • Baltimore
  • Newark

How to find a cheap flight to Bailey Island?
To secure cheap flights to Bailey Island, book in advance and travel during the low season. Want an insider tip? Fly on a Thursday and save around 16% on average compared to those who jet off on a Sunday.* Sign up for price tracking on the Expedia app and we'll let you know the moment prices drop.*Best day of the week to book, depart and ideal booking window recommendations based on average round-trip ticket prices for January through August 2023, sourced from Airline Reporting Corporation's (ARC) global airline sales database. Percentages noted are averages.
How to get a cheap last-minute flight to Bailey Island?
Although booking in advance is generally the easiest way to save cash, don't panic if your Bailey Island vacation is last minute. You can still get cheap flights to Bailey Island, especially if your plans have a little wiggle room. Try switching up your travel dates, exploring different ticket options or departing from an alternative hub.
How far in advance should I book a flight to Bailey Island?
To nab some of the biggest savings on domestic journeys, book your flight to Bailey Island 28 days ahead of your travel dates. For international flights, it's two to four months in advance. This increases your chances of locking in the departure dates and seats you want.**Best day of the week to book, depart and ideal booking window recommendations based on average round-trip ticket prices for January through August 2023, sourced from Airline Reporting Corporation's (ARC) global airline sales database. Percentages noted are averages.
Which day of the week is the cheapest day to buy a plane ticket to Bailey Island?
Sundays are generally the best day to book a cheap flight to Bailey Island, with savings of about 8% on average compared to Fridays. If you purchase tickets on a Friday, expect to pay a higher price as this is typically the most expensive day.**Best day of the week to book, depart and ideal booking window recommendations based on average round-trip ticket prices for January through August 2023, sourced from Airline Reporting Corporation's (ARC) global airline sales database. Percentages noted are averages.
Which airlines fly to Bailey Island?
Dig out your passport, pack your bags and select from these leading airlines that have flights to Bailey Island:

  • American Airlines - 260 flights to Bailey Island each month, including 260 flights to Portland Intl. Jetport Airport (PWM) per month.
  • United Airlines - 234 flights to Bailey Island each month, including 234 flights to Portland Intl. Jetport Airport (PWM) per month.
  • Delta Air Lines - 212 flights to Bailey Island each month, including 212 flights to Portland Intl. Jetport Airport (PWM) per month.

Where do you fly into Bailey Island?
If you're flying to Bailey Island, the main airport to land at is Portland Intl. Jetport Airport (PWM). You can also jet into nearby hubs like Augusta State Airport (AUG), Knox County Regional Airport (RKD) or Brunswick, ME (NHZ-Brunswick Executive). Another option worth keeping in mind when you fly to Bailey Island is Wiscasset, ME (ISS).
Can I save money by booking a Bailey Island trip package?
Bundle your flights and accommodations and you could save hundreds of dollars. Better still, you can add extras like activities and car rentals to your Bailey Island flight and hotel package deal. With Expedia, it's easy to organize all your Bailey Island travel arrangements in the same place.
Can I change or cancel my flight to Bailey Island?
It's often possible to cancel or change your flight to Bailey Island. Many airlines allow you to cancel your flights for free within 24 hours of making your booking. However, some flights are non-refundable, and airlines may offer you a credit toward a future flight rather than a direct refund. To reserve cheap flights to Bailey Island with flexible change policies, select "Changes included" or "No cancel fee" during your search. Looking for more information? Visit our Customer Service Portal.

*Flight schedules are subject to change.

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Travel information

Destination airport
Portland Intl. Jetport
Destination airport IATA code
PWM
Destination city name
Portland
Roundtrip price
$141

Trending flights to Bailey Island

Prices were available within the past 7 days and start at $71 for one-way flights and $142 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Breeze Airways

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