Cheap Flights to Portland

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.

Back to top

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.

Back to top