Flights To Cumberland County - Cheap Flights Starting at CA $101

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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, Nov 14 - Mon, Nov 16
RDU
Raleigh - Durham Intl.
PWM
Portland Intl. Jetport
CA $225 Roundtrip, found 5 days ago
CA $225
Roundtrip
found 5 days ago
Select Breeze Airways flight, departing Sat, Nov 14 from Raleigh - Durham Intl. to Portland Intl. Jetport, returning Mon, Nov 16, priced at CA $225 found 5 days ago
Tue, Nov 3 - Fri, Nov 6
RDU
Raleigh - Durham Intl.
PWM
Portland Intl. Jetport
CA $246 Roundtrip, found 7 hours ago
CA $246
Roundtrip
found 7 hours ago
Select Breeze Airways flight, departing Tue, Nov 3 from Raleigh - Durham Intl. to Portland Intl. Jetport, returning Fri, Nov 6, priced at CA $246 found 7 hours ago
Sat, Nov 14 - Mon, Nov 16
RDU
Raleigh - Durham Intl.
PWM
Portland Intl. Jetport
CA $315 Roundtrip, found 5 days ago
CA $315
Roundtrip
found 5 days ago
Select American Airlines flight, departing Sat, Nov 14 from Raleigh - Durham Intl. to Portland Intl. Jetport, returning Mon, Nov 16, priced at CA $315 found 5 days ago
Sat, Nov 14 - Mon, Nov 16
RDU
Raleigh - Durham Intl.
PWM
Portland Intl. Jetport
CA $342 Roundtrip, found 5 days ago
CA $342
Roundtrip
found 5 days ago
Select Southwest Airlines flight, departing Sat, Nov 14 from Raleigh - Durham Intl. to Portland Intl. Jetport, returning Mon, Nov 16, priced at CA $342 found 5 days ago
Sat, Nov 14 - Mon, Nov 16
RDU
Raleigh - Durham Intl.
PWM
Portland Intl. Jetport
CA $350 Roundtrip, found 5 days ago
CA $350
Roundtrip
found 5 days ago
Select Southwest Airlines flight, departing Sat, Nov 14 from Raleigh - Durham Intl. to Portland Intl. Jetport, returning Mon, Nov 16, priced at CA $350 found 5 days ago
Sat, Nov 14 - Mon, Nov 16
RDU
Raleigh - Durham Intl.
PWM
Portland Intl. Jetport
CA $379 Roundtrip, found 5 days ago
CA $379
Roundtrip
found 5 days ago
Select American Airlines flight, departing Sat, Nov 14 from Raleigh - Durham Intl. to Portland Intl. Jetport, returning Mon, Nov 16, priced at CA $379 found 5 days ago
Sat, Nov 14 - Mon, Nov 16
RDU
Raleigh - Durham Intl.
PWM
Portland Intl. Jetport
CA $387 Roundtrip, found 5 days ago
CA $387
Roundtrip
found 5 days ago
Select American Airlines flight, departing Sat, Nov 14 from Raleigh - Durham Intl. to Portland Intl. Jetport, returning Mon, Nov 16, priced at CA $387 found 5 days ago
Sat, Nov 14 - Mon, Nov 16
RDU
Raleigh - Durham Intl.
PWM
Portland Intl. Jetport
CA $395 Roundtrip, found 5 days ago
CA $395
Roundtrip
found 5 days ago
Select United flight, departing Sat, Nov 14 from Raleigh - Durham Intl. to Portland Intl. Jetport, returning Mon, Nov 16, priced at CA $395 found 5 days ago
Sat, Oct 24 - Tue, Oct 27
YYZ
Pearson Intl.
PWM
Portland Intl. Jetport
CA $659 Roundtrip, found 6 days ago
CA $659
Roundtrip
found 6 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 6 days ago
Sat, Oct 24 - Tue, Oct 27
YYZ
Pearson Intl.
PWM
Portland Intl. Jetport
CA $669 Roundtrip, found 6 days ago
CA $669
Roundtrip
found 6 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 6 days ago
Wed, Mar 10 - Wed, Mar 17
YYZ
Pearson Intl.
PWM
Portland Intl. Jetport
CA $924 Roundtrip, found 1 hour ago
CA $924
Roundtrip
found 1 hour ago
Select WestJet flight, departing Wed, Mar 10 from Pearson Intl. to Portland Intl. Jetport, returning Wed, Mar 17, priced at CA $924 found 1 hour 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
*Prices include taxes and fees
Price found within the past 48 hours. Click for updated prices.
Raffles Boston
5.0-star property

Raffles Boston

Nov 20 - Nov 23

3 night stay

Toronto (YYZ) to Boston (BOS)

Delta • Non-stop roundtrip • Coach
Save 100% on your flight
Price was CA $2,365, price is now CA $1,683 per person
CA $1,683
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 1 day ago
Hotel AKA Boston Common
4.0-star property

Hotel AKA Boston Common

Nov 2 - Nov 9

7 night stay

Calgary (YYC) to Boston (BOS)

Porter Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
Price was CA $3,333, price is now CA $2,416 per person
CA $2,416
per person
found 24 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.
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.
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! (1,017 reviews)
"Decent value for the money. Clean room, just look very tired and dated."

Reviewed on Oct 7, 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.
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 20 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, November 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 $967. 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.