Cheap Flights to Portland

Portland overview

When is the best time to fly

New England has four very distinct seasons that entice travellers 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 an average of 4 and sometimes below freezing levels. From April to June, it escalates to between 10-15 degrees, and after that, June, July, and August roast in the mid-20’s, which makes for perfect conditions to linger portside. Spanning the length of September – October, fall lures people to book a flight to Portland to catch glimpses of the unforgettable vivid views of foliage.

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 autumn showcase in September and October. 

Off-Peak Season: 

Although it’s easy to appreciate the diversity of all of Maine’s four seasons, less travellers take up cheap flights to Portland offers during the winter, as between December and February the freezing temperatures hamper outdoor activity, and snowfall makes getting around a difficult feat.

City Overview

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 traveller, 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 neighbourhoods bring travellers to Portland straight back to tea parties and parlours. 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.

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,


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 insider information

Local Art: Portland art galleries mix media to portray the reality and splendour of Portland through paintings and photography. The Domaine Gallery offers fine-art photography, prints about the state’s geography, and jewellery hand-made by artisans. The Fore Street Gallery focuses more on watercolours, 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 artefacts. Reopened in 2002, the home is part of the Maine Historic Society and is open year-round for travellers. 

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 aluminium 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 the next big baseball stars.

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Prices found by our users for local departures to Portland

How much do things cost in Portland?

Clothing & Shoes
Pair of jeans
$ 53.86
Pair of Nike shoes
$ 90.88
Coke/Pepsi (0.33 litre)
$ 2.47
Local draught beer (0.5 litre)
$ 5.24
Small bottle of water (0.33 litre)
$ 2.23
Imported beer (0.33 litre)
$ 6.55
1 km taxi journey
$ 1.93
Taxi - fixed fee
$ 2.49
Petrol (1 litre)
$ 0.79
One-way ticket (local transport)
$ 1.97
Bottle of local beer (0.5 litre)
$ 1.70
Pack of Marlboro cigarettes
$ 10.24
Bottle of wine
$ 17.03
Large bottle of water
$ 2.57
How much does an apartment cost in Portland?
1 bedroom apartment in city centre
$ 1451
3 bedroom apartment in city centre
$ 2739
1 bedroom apartment outside of centre
$ 1146
3 bedroom apartment outside of centre
$ 2074

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