We work with more than 300 partners to bring you better travel deals
Cheap Flights to Portland
| Popular in | July | High demand for flights, 15% potential price rise |
| Cheapest in | February | Best time to find cheap flights, 3% potential price drop |
| Average price | C$ 365 | Average for round-trip flights in May 2020 |
| Round-trip from | C$ 189 | From Toronto 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.
|
YTO - BOS Price
|
C$ 325 - C$ 545
|
|
BOS Temperature
|
4 - 29 °C
|
|
BOS Rainfall
|
70 - 99 mm
|
When is the best time to book a flight to Portland?
The price you pay for your flight to Portland may vary depending on when you book. For the best chance of a lower fare, look to book 33 days in advance of your trip. Fares are likely to increase in the final two weeks or so before your departure date.
Which day is cheapest to fly to Portland?
Friday is currently, on average, the cheapest day to fly to Portland. Flying on Monday will result in higher flight prices.
What time of day is cheapest to fly?
Portland flights can be made cheaper if you choose a flight in the afternoon. Booking a flight at noon will likely mean higher prices.
Breathe in the crisp, ocean air, and feel the essence of the quintessential New England locale when you arrive in Portland. Flights to Portland land travellers in Maine’s biggest city. 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.
For the 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 booking flights to Portland straight back to tea parties and parlours. The cobblestones and bricks are here for a reason: In the late 1800s, 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 offers four very distinct seasons that entice travellers to book flights to Portland all year round. Depending on when you plan your Portland flights, you will be in for a unique experience. Between November and March, snow falls and temperatures drop to around 7 degrees Celsius, and sometimes below freezing levels. From April to June, it escalates to around 13 degrees C, and after that, June, July, and August roast in over 30 degrees, 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.
When is the 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 1970s, 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:
Summer and fall 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.
Off-Peak Season:
Although it’s easy to appreciate the diversity of all of Maine’s four seasons, less travellers book flights to Portland during the winter, since 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 Harbour. The Amtrak trains also run between Portland and Boston several times a day. Trips take only two 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. If you’re heading into Canada, don’t forget to bring your passport. 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 allow you to stay for only a few hours. If you’d prefer not to drive, you can take the Metro or trains.
