$230 Cheap Flights from New Haven (HVN) to Portland (PWM)

View $230 flight on Fri, Oct 17, 2025Opens in a new window

Popular airlines from New Haven, CT (HVN-Tweed - New Haven Regional) to Portland Intl. Jetport Airport (PWM)

Cheap Flights from New Haven to Portland (HVN-PWM)

Prices were available within the past 7 days and start at $230 for one-way flights and $458 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Breeze Airways
Fri, Oct 17 - Wed, Oct 29
HVN
New Haven
PWM
Portland
$458 Roundtrip, found 5 days ago
$458
Roundtrip
found 5 days ago
Select Breeze Airways flight, departing Fri, Oct 17 from New Haven to Portland, returning Wed, Oct 29, priced at $458 found 5 days ago
Breeze Airways
Fri, Oct 17 - Sat, Nov 1
HVN
New Haven
PWM
Portland
$468 Roundtrip, found 5 hours ago
$468
Roundtrip
found 5 hours ago
Select Breeze Airways flight, departing Fri, Oct 17 from New Haven to Portland, returning Sat, Nov 1, priced at $468 found 5 hours ago
Breeze Airways
Fri, Nov 14 - Fri, Dec 5
HVN
New Haven
PWM
Portland
$469 Roundtrip, found 2 days ago
$469
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Fri, Nov 14 from New Haven to Portland, returning Fri, Dec 5, priced at $469 found 2 days ago
Breeze Airways
Fri, Oct 10 - Wed, Oct 29
HVN
New Haven
PWM
Portland
$477 Roundtrip, found 4 days ago
$477
Roundtrip
found 4 days ago
Select Breeze Airways flight, departing Fri, Oct 10 from New Haven to Portland, returning Wed, Oct 29, priced at $477 found 4 days ago
Breeze Airways
Fri, Nov 14 - Fri, Dec 5
HVN
New Haven
PWM
Portland
$478 Roundtrip, found 5 hours ago
$478
Roundtrip
found 5 hours ago
Select Breeze Airways flight, departing Fri, Nov 14 from New Haven to Portland, returning Fri, Dec 5, priced at $478 found 5 hours ago
Breeze Airways
Thu, Nov 20 - Mon, Dec 8
HVN
New Haven
PWM
Portland
$479 Roundtrip, found 4 days ago
$479
Roundtrip
found 4 days ago
Select Breeze Airways flight, departing Thu, Nov 20 from New Haven to Portland, returning Mon, Dec 8, priced at $479 found 4 days ago
Breeze Airways
Thu, Nov 13 - Fri, Dec 5
HVN
New Haven
PWM
Portland
$483 Roundtrip, found 2 days ago
$483
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Thu, Nov 13 from New Haven to Portland, returning Fri, Dec 5, priced at $483 found 2 days ago
Breeze Airways
Fri, Oct 10 - Wed, Oct 29
HVN
New Haven
PWM
Portland
$486 Roundtrip, found 3 days ago
$486
Roundtrip
found 3 days ago
Select Breeze Airways flight, departing Fri, Oct 10 from New Haven to Portland, returning Wed, Oct 29, priced at $486 found 3 days ago
Breeze Airways
Fri, Nov 14 - Sun, Dec 7
HVN
New Haven
PWM
Portland
$488 Roundtrip, found 5 days ago
$488
Roundtrip
found 5 days ago
Select Breeze Airways flight, departing Fri, Nov 14 from New Haven to Portland, returning Sun, Dec 7, priced at $488 found 5 days ago
Breeze Airways
Thu, Feb 26 - Mon, Mar 16
HVN
New Haven
PWM
Portland
$489 Roundtrip, found 1 hour ago
$489
Roundtrip
found 1 hour ago
Select Breeze Airways flight, departing Thu, Feb 26 from New Haven to Portland, returning Mon, Mar 16, priced at $489 found 1 hour ago

Frequently asked questions

How much does a flight from Tweed - New Haven Regional Airport (HVN) to Portland Intl. Jetport Airport (PWM) cost?
Grab a cheap one-way flight from $230 or cheap return flight from $458 from Tweed - New Haven Regional Airport (HVN) to Portland Intl. Jetport Airport (PWM) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to find our cheapest flight offers on this route.
What is the cheapest month to fly from Tweed - New Haven Regional Airport (HVN) to Portland Intl. Jetport Airport (PWM)?
The cheapest month to fly from HVN to PWM is October, when demand is low. Off-peak season is often when better flight deals are available between these airports.
What is the cheapest airline that flies from Tweed - New Haven Regional Airport (HVN) to Portland Intl. Jetport Airport (PWM)?
Use the filters on Expedia to compare airlines and find the cheapest carrier that'll fly you from HVN to PWM. Then, sort your results by "Price (lowest to highest)" to pick up a good deal.
How many flights per day from Tweed - New Haven Regional Airport (HVN) to Portland Intl. Jetport Airport (PWM)?
You'll have to hop on a flight with a layover if you're traveling from Tweed - New Haven Regional Airport (HVN) to Portland Intl. Jetport Airport (PWM). Direct flights don't operate daily on this route. However, just filter your search to include one or more stops to find the best option for your trip.
What day of the week has the most flights from HVN to PWM?
Friday is usually the busiest day for flights, while Tuesday tends to be the quietest.* Keep in mind that flight schedules can change depending on various factors, including the airline and season.*Busiest/quietest day to travel is based on Expedia flight demand through January to December 2024.
What is the best time to fly from Tweed - New Haven Regional Airport (HVN) to Portland Intl. Jetport Airport (PWM)?
Book a flight from Tweed - New Haven Regional Airport (HVN) to Portland Intl. Jetport Airport (PWM) that leaves before 3 PM to reduce the risk of cancellations. Departures later than this are on average 22% more likely to be canceled.**Most reliable time of the day and month to travel recommendation is based on January through August 2024 flight status data sourced from OAG's global flight data platform.
Is it cheaper to buy a plane ticket from Tweed - New Haven Regional Airport (HVN) to Portland Intl. Jetport Airport (PWM) last-minute?
Holding off until just before your trip to book your flight from HVN to PWM often results in higher prices. Although you may find some last-minute discounts, they're not always guaranteed. Keep your travel plans flexible to maximize your chances of getting a bargain.
Is it cheaper to book a HVN to PWM flight and hotel package?
You'll generally save money by booking a HVN to PWM flight and hotel package compared to booking separately. In fact, you could save hundreds of dollars by bundling with Expedia. And it's easy to manage everything in one convenient place. After choosing your ideal flights and accommodations, consider adding extras such as tours, activities and car rentals.
Can I cancel or change the date of my flight from Tweed - New Haven Regional Airport (HVN) to Portland Intl. Jetport Airport (PWM)?
If you reserved your HVN to PWM flight in the last 24 hours, you may be able to modify or cancel it without any fees. Depending on the airline and the type of ticket you purchased, additional charges may apply for changes beyond this timeframe. Airline policies and contact information can be found in your itinerary or confirmation email. Or, visit our Customer Service portal for more details.

Travel information

Travel information

Origin airport
Tweed - New Haven Regional
Destination airport
Portland Intl. Jetport
Airlines serving
Breeze Airways
Roundtrip price
$458
Distance
210 mi

Book with confidence

Book with confidence

New Haven to Portland Flights

The cheapest times to fly from New Haven to Portland

On average, Thursday can be the cheapest time to fly, according to data from the Airlines Reporting Corporation (ARC), one of the world's biggest databases for global airline sales. The data reveals that you could save up to 16% by flying on a Thursday—the cheapest day to travel on average—instead of a Sunday—the most expensive. Some of the most affordable flights from New Haven to Portland are during the month of October. You can find some of the cheapest flights from New Haven to Portland with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from New Haven to Portland

Sunday is one of the best days to book for cheap flights from New Haven to Portland: Tickets reserved on a Sunday cost between 6% and 13% less than those reserved on a Friday, according to ARC data. The data also suggests booking early can also lead to cheaper airfares. You could save 24% by buying your tickets for domestic flights at least a month in advance and 10% by booking international flights 2 months in advance.

 

How to find cheap round-trip tickets from New Haven to Portland

Being flexible with your dates and using Expedia's Price Drop Protection and Price Tracking features are some of the best ways of finding a cheap ticket from New Haven to Portland in 2025. You can also book with separate airlines for your outbound and return journeys, from $230 one-way. Expedia also offers Price Drop Protection, so if the cost of your airfare goes down after booking, you'll receive a credit for the difference*. This is available for a small fee, and is free to One Key Gold and Platinum tier members.

 

Expedia's Price Tracking feature means you can stay on top of airfares without manually checking every day. It sends you automated price alerts for cheap New Haven to Portland flights and uses historical data to indicate when the best time to book is. Download Expedia's free app to activate this handy tool in a few easy taps.

 

You could also save big by booking one of Expedia's vacation packages. Bundling together your New Haven to Portland airfare with your accommodations and car rental is often cheaper than booking everything separately. There’s also One Key, Expedia's generous rewards program. Join for free and you could earn One Key cash on most bookings to save on future adventures.

 

*Terms apply.

 

Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023. The percentages you see are averages.

 

New Haven to Portland Flights

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*Available to One Key members.