Flights To Cumberland County - Cheap Flights Starting at CA $361

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A lighthouse, a white house with a red roof, and rocky coastline at sunset.

Portland

Flights
Portland
A brick building with green shutters, a tree with red leaves, and a street with people walking.

Freeport

Flights
Freeport

How Much Does it Cost To Fly To Cumberland County?

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Sat, Oct 24 - Tue, Oct 27
YYZ
Pearson Intl.
PWM
Portland Intl. Jetport
CA $659 Roundtrip, found 5 days ago
CA $659
Roundtrip
found 5 days ago
Select Delta flight, departing Sat, Oct 24 from Pearson Intl. to Portland Intl. Jetport, returning Tue, Oct 27, priced at CA $659 found 5 days ago
Sat, Oct 24 - Tue, Oct 27
YYZ
Pearson Intl.
PWM
Portland Intl. Jetport
CA $669 Roundtrip, found 5 days ago
CA $669
Roundtrip
found 5 days ago
Select American Airlines flight, departing Sat, Oct 24 from Pearson Intl. to Portland Intl. Jetport, returning Tue, Oct 27, priced at CA $669 found 5 days ago
Thu, Nov 5 - Thu, Nov 12
YYZ
Pearson Intl.
PWM
Portland Intl. Jetport
CA $674 Roundtrip, found 14 hours ago
CA $674
Roundtrip
found 14 hours ago
Select Delta flight, departing Thu, Nov 5 from Pearson Intl. to Portland Intl. Jetport, returning Thu, Nov 12, priced at CA $674 found 14 hours ago
Sat, Oct 24 - Tue, Oct 27
YYZ
Pearson Intl.
PWM
Portland Intl. Jetport
CA $677 Roundtrip, found 5 days ago
CA $677
Roundtrip
found 5 days ago
Select Delta flight, departing Sat, Oct 24 from Pearson Intl. to Portland Intl. Jetport, returning Tue, Oct 27, priced at CA $677 found 5 days ago
Sat, Oct 24 - Tue, Oct 27
YYZ
Pearson Intl.
PWM
Portland Intl. Jetport
CA $687 Roundtrip, found 5 days ago
CA $687
Roundtrip
found 5 days ago
Select Delta flight, departing Sat, Oct 24 from Pearson Intl. to Portland Intl. Jetport, returning Tue, Oct 27, priced at CA $687 found 5 days ago
Thu, Oct 29 - Sun, Nov 1
YYZ
Pearson Intl.
PWM
Portland Intl. Jetport
CA $705 Roundtrip, found 4 days ago
CA $705
Roundtrip
found 4 days ago
Select American Airlines flight, departing Thu, Oct 29 from Pearson Intl. to Portland Intl. Jetport, returning Sun, Nov 1, priced at CA $705 found 4 days ago
Wed, Oct 28 - Mon, Nov 2
YYZ
Pearson Intl.
PWM
Portland Intl. Jetport
CA $740 Roundtrip, found 1 day ago
CA $740
Roundtrip
found 1 day ago
Select Delta flight, departing Wed, Oct 28 from Pearson Intl. to Portland Intl. Jetport, returning Mon, Nov 2, priced at CA $740 found 1 day ago
Wed, Oct 28 - Mon, Nov 2
YYZ
Pearson Intl.
PWM
Portland Intl. Jetport
CA $745 Roundtrip, found 1 day ago
CA $745
Roundtrip
found 1 day ago
Select Delta flight, departing Wed, Oct 28 from Pearson Intl. to Portland Intl. Jetport, returning Mon, Nov 2, priced at CA $745 found 1 day ago
OriginDestinationTravel datesFlights from*
RDUPortlandNovember 14 to November 16CA $225
MCOPortlandNovember 11 to November 18CA $249
JFKPortlandOctober 29 to November 4CA $324
TPAPortlandOctober 31 to November 3CA $349
SEAAugustaNovember 7 to November 9CA $967
*Prices include taxes and fees
OriginDestinationTravel datesFlights from*
JFKPortlandOctober 10 to October 12CA $458
SEAPortlandOctober 9 to October 13CA $902
RDUPortlandOctober 9 to October 9CA $1,272
TPAPortlandOctober 9 to October 12CA $1,562
*Prices include taxes and fees
Price found within the past 48 hours. Click for updated prices.
The Cove at Yarmouth by Westgate Resorts
3.0-star property

The Cove at Yarmouth by Westgate Resorts

Oct 24 - Oct 30

6 night stay

Toronto (YYZ) to Boston (BOS)

Porter Airlines • Roundtrip • Coach
Save 100% on your flight
Price was CA $1,421, price is now CA $953 per person
CA $953
per person
found 1 day ago
The Cape Club Resort
2.0-star property

The Cape Club Resort

Oct 24 - Oct 30

6 night stay

Toronto (YYZ) to Boston (BOS)

Porter Airlines • Roundtrip • Coach
Save 100% on your flight
Price was CA $1,641, price is now CA $1,008 per person
CA $1,008
per person
found 1 day ago
Boston Harbor Hotel
5.0-star property

Boston Harbor Hotel

Nov 20 - Nov 24

4 night stay

Calgary (YYC) to Boston (BOS)

Delta • Non-stop roundtrip • Coach
Save 100% on your flight
Price was CA $2,831, price is now CA $1,754 per person
CA $1,754
per person
found 13 hours ago
Don't see what you're looking for?
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Travelers ❤️ These Cumberland County 🏨

Clarion Hotel Portland Airport ME

Clarion Hotel Portland Airport ME

2.5 out of 5
1230 Congress St Portland ME
Book a stay at this business-friendly hotel in Portland. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Cross Insurance Arena and Maine Mall are located nearby.
8.2/10 Very good! (1,755 reviews)
"Clean room, just very outdated building/room. Small elevator. Floor in room by door was warped (?) door hard to open /close."

Reviewed on Oct 7, 2026

Opens in a new windowClarion Hotel Portland Airport ME
The Westin Portland Harborview

The Westin Portland Harborview

4 out of 5
157 High St Portland ME
Book a stay at this spa hotel in Portland. Enjoy free WiFi, a full-service spa, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Cross Insurance Arena and Maine Mall are located nearby.
9/10 Wonderful! (1,009 reviews)
"Wonderful, historic building. Clean room. Great staff. Design starting to look a bit dated."

Reviewed on Oct 6, 2026

Opens in a new windowThe Westin Portland Harborview
Fireside Inn & Suites Portland

Fireside Inn & Suites Portland

3 out of 5
81 Riverside St Portland ME
Book a stay at this business-friendly hotel in Portland. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Maine Mall and Cross Insurance Arena are located nearby.
8.2/10 Very good! (1,015 reviews)
"S for"

Reviewed on Oct 6, 2026

Opens in a new windowFireside Inn & Suites Portland
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Inn at St John Portland In-Town

Inn at St John Portland In-Town

2.5 out of 5
939 Congress St Portland ME
Stay at this B&B in Portland. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Cross Insurance Arena and Maine Mall are located nearby.
8.6/10 Excellent! (1,146 reviews)
"The inn itself was beautifully kept. The water pressure was great. There was plenty of hot water except very early in the morning (before 6am). I didn’t walk in the area but if I had too, I wouldn’t feel comfortable in the evening. There was parking behind the hotel and I was lucky to get a spot ..."

Reviewed on Oct 6, 2026

Opens in a new windowInn at St John Portland In-Town
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Frequently asked questions

How much is the cheapest flight to Cumberland County?
The next trip you take doesn't have to make a huge dent in your budget. During the last seven days, the cheapest return flight to Cumberland County cost CA $225. Find a cheap seat and spend the dollars you save on cool experiences. This price was available on Travelocity for flights to Cumberland County departing within the next year. Prices and availability are subject to change. Additional terms apply.
Which airlines fly to Cumberland County?
Lock in a seat with one of the 15 airlines that operate flights to Cumberland County. If you're staying in Portland, let American Airlines take you to this buzzing city to explore its iconic sights. This well-known carrier offers 416 flights there per month.
What is the cheapest month to fly to Cumberland County?
According to Travelocity's direct return flight demand from January to December last year, October is the cheapest month to board a plane to Cumberland County. Browse for flights throughout this month and snap up a terrific deal today.
How can I check my flight status to Cumberland County?
"Trips" will clue you in when it comes to the finer details of your flight to Cumberland County. This handy customer portal lets you do everything in the one place, from looking up your flight status to making updates to your itinerary. Click on Trips at the top of the Travelocity homepage and then sign in. You can also download the Travelocity app and access your travel itinerary while you're on the go. Whether you have the family flying with you or you're riding solo, all your bookings are right at your fingertips.
How do I find the best deals on flights to Cumberland County?
Being flexible with your dates is a simple way to nab an incredible deal. Travelocity makes it a piece of cake to find your ideal fare through the "Flexible dates" function. Search for your flight to Cumberland County, then compare prices for surrounding dates by clicking the Flexible dates dropdown box above. Booking in advance and avoiding peak season are other ways to save on fares. In the last seven days, the best price for a return flight to Cumberland County was CA $225. This price was available on Travelocity for flights departing within the next year. Prices and availability are subject to change. Additional terms apply.
Why should I book my flight to Cumberland County with Travelocity?
Seek out cheap flights to Cumberland County with Travelocity and begin packing for your next break. With round-the-clock personal assistance along every step of your trip and a Price Match Guarantee, we take the stress out of reserving cheap family flights, places to stay and more. Snag a great deal today and brace yourself for the adventure of a lifetime.
What are the most popular flight routes to Cumberland County?
As a renowned tourist destination, you'll find excellent connections to Cumberland County. Here are some of the major routes:

  • New York, NY (JFK-John F. Kennedy Intl.) to Portland Intl. Jetport Airport (PWM) - 949 flights a month.
  • Chicago, IL (ORD-O'Hare Intl.) to Portland Intl. Jetport Airport (PWM) - 676 flights a month.
  • Philadelphia, PA (PHL-Philadelphia Intl.) to Portland Intl. Jetport Airport (PWM) - 645 flights a month.

How much is a flight to Cumberland County on average?
Get your next break off to the best start by snapping up a terrific deal with Travelocity. In the last seven days, roundtrip flights to Cumberland County cost between CA $225 and CA $1,562. Have a look at our site and secure a ticket that works with your budget. These prices were available on Travelocity for flights departing within the next year. Prices and availability are subject to change. Additional terms apply.