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Cheap flights to Portland
| Popular in | June | High demand for flights, 8% potential price rise |
| Cheapest in | March | Best time to find cheap flights, 2% potential price drop |
| Average price | $153 | Average for round-trip flights in March 2020 |
| Round-trip from | $41 | From New York to Portland |
Cheapest Prices for Portland flights by month
When is the best time to fly to Portland?
Choose a month below to see average flight price and weather conditions.
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NYC - BOS Price
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$187 - $315
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BOS Temperature
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39.2 - 84.2 °F
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BOS Rainfall
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2.76 - 3.9 inches
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When is the best time to book flights to Portland?
To ensure you get the cheapest price possible for a flight to Portland, you should look to book at least 57 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.
Which day is cheapest to fly to Portland?
Saturday is currently, on average, the cheapest day to fly to Portland. Flying on Sunday will result in higher flight prices.
What time of day is cheapest to fly?
To get the best value, try booking a flight in the afternoon when visiting Portland. Generally the prices will increase for flights at noon as these tend to have higher demand.
Breathe in the crisp, ocean air and feel the essence of the quintessential New England locale when you arrive in Maine’s biggest city, Portland. A fine blend of laid-back environment paired with a lively waterfront and stunning 19th century atmosphere conceives a multi-faceted downtown, perfect for day trips or week-long getaways.
If you are a bohemian traveler, head to the romantic downtown area characterized by the old seaside ports, restored brick buildings, and bustling cafes, shops, and bars. Galleries filled with ocean-inspired art line cobblestone streets, and Victorian neighborhoods bring travelers to Portland straight back to tea parties and parlors. The cobblestones and bricks are here for a reason: In the late 1800’s, fires ravaged the city and left thousands of residents homeless. Vowing to never let it happen again, the community rebuilt Portland completely in stone to safeguard it. Now, beautiful array of cobblestone rock, cobblestone, and brick, establish the feel of New England.
Portland climate
New England has four very distinct seasons that entice travelers to book flights to Portland all year round. Depending on when you plan your trip, you will be in for a unique experience. Between November and March, snow falls and temperatures drop to the 40’s, and sometimes below freezing levels. From April to June, it escalates to between 50-60 degrees F, and after that, June, July, and August roast in the 80’s, which makes for perfect conditions to linger portside. Spanning the length of September – October, fall lures people to book flights to Portland to catch glimpses of the unforgettable vivid views of foliage.
Best Time to Fly to Portland
If you book flights to Portland in June, you’ll experience the Old Port Street Festival, which begun in the 1970’s, and is held annually one the first Sunday in June. Outdoor performances, and musical genres of folk, world, and rock linger on every street corner. Parades, kid rides, and street food are just a few reasons to get outside and enjoy the heat while it lasts.
Peak Season:
Months between June and October are the best times to book flights to Portland. If you’re looking for beachside bliss, go for a sail along the Atlantic Ocean on the 4th of July. If you’re looking for crisper weather and a chance to bundle up among reds, oranges, and yellows, stroll the cobblestone streets during the spectacular fall showcase in September and October.
Off-Peak Season:
Although it’s easy to appreciate the diversity of all of Maine’s four seasons, less travelers book flights to Portland during the winter, as between December and February the freezing temperatures hamper outdoor activity, and snowfall makes getting around a difficult feat.
Getting around Portland
It’s easy to get from Portland to surrounding cities. From the Greyhound Terminal you can get to and from Vermont, Boston, Hartford and New York City every day. Other buses can take you to Brunswick, Lewiston, Augusta, Waterville, Bangor or Bar Harbor. The Amtrak trains also run between Portland and Boston several times a day. Trips take only two and a half hours, which is much quicker than the buses. Ferry cruises leave Portland for Bailey Island or Nova Scotia several times a week in the summer. For travel within Portland, cars and motorcycles are all over the place and it’s easy to rent a car. You’ll want to park in a garage, since metered parking is less available and allows you to stay for only a few hours. If you’d prefer not to drive, you can take the Metro or trains.
Portland Travel Information
Local Art: Portland art galleries mix media to portray the reality and splendor of Portland through paintings and photography. The Domaine Gallery offers fine-art photography, prints about the state’s geography, and jewelry hand-made by artisans. The Fore Street Gallery focuses more on watercolors, oil paintings, and specializes on regional artists. Work also ranges from students to professional. If you decide to take home a painting that suits your style, be sure to pack carefully for your return Portland flight. At the Institute of Contemporary Art, progressive students from the Maine College of Art (MECA) display their work, while in the Portland Museum of Art; American pros like Winslow Homer and Edward Hopper fill the walls. The PMA also gets recognized especially for its temporary exhibits.
Wadsworth-Longfellow House: You’ll see plenty of old, brick homes with lavish gardens and detailed rooftops, but one claims the spotlight more than others: the Henry Wadsworth-Longfellow House. The brick Wadsworth-Longfellow farmhouse sits in the middle of an expansive garden, and is built in the 1788 federal style. The builder, General Peleg Wadsworth, was a hero in the Revolutionary War, and a grandfather to poet Henry Wadsworth Longfellow. The two lived in the house together, and it remains one of New England’s more famous architectural artifacts. Reopened in 2002, the home is part of the Maine Historic Society and is open year-round for travelers.
Harbor side: A mile in length, the Harbor side begins at Casco Bay Lines ferry terminal (at the corner of Commercial and Franklin Streets). For fitness freaks the paved paths allow convenient room for walking, running, and biking with views of the islands. With a 68-acre hillside span of greenery that extends to the water, the Harbor side is your perfect outdoor daytime destination to get the best of the land and the sea.
Portland Sea Dogs: Take in America’s pastime after your flight to Portland lands. The Portland Sea Dogs are a Double A baseball team, affiliated with the World Series Champion Boston Red Sox. Spend an afternoon at the Sea Dogs game for a perfect summertime activity. Park your family on one of Hadlock Field’s aluminum benches, get some game-time grub, and watch as young hopefuls swing their way toward the pros. Pro-players including Josh Beckett, Brad Penny, Alex Gonzalez, and Kevin Millar played for the Portland Sea Dogs – pay close attention to the guys on the field, they might be the next big baseball stars.
