Flights To Cumberland County - Cheap Flights Starting at CA $105

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Portland

Flights
Portland

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.

Thu, Sep 10 - Tue, Sep 15
RDU
Raleigh - Durham Intl.
PWM
Portland Intl. Jetport
CA $290 Roundtrip, found 6 days ago
CA $290
Roundtrip
found 6 days ago
Select Breeze Airways flight, departing Thu, Sep 10 from Raleigh - Durham Intl. to Portland Intl. Jetport, returning Tue, Sep 15, priced at CA $290 found 6 days ago
Fri, Sep 11 - Tue, Sep 15
RDU
Raleigh - Durham Intl.
PWM
Portland Intl. Jetport
CA $337 Roundtrip, found 6 days ago
CA $337
Roundtrip
found 6 days ago
Select JetBlue Airways flight, departing Fri, Sep 11 from Raleigh - Durham Intl. to Portland Intl. Jetport, returning Tue, Sep 15, priced at CA $337 found 6 days ago
Fri, Sep 11 - Tue, Sep 15
RDU
Raleigh - Durham Intl.
PWM
Portland Intl. Jetport
CA $351 Roundtrip, found 6 days ago
CA $351
Roundtrip
found 6 days ago
Select Breeze Airways flight, departing Fri, Sep 11 from Raleigh - Durham Intl. to Portland Intl. Jetport, returning Tue, Sep 15, priced at CA $351 found 6 days ago
Mon, Aug 17 - Wed, Aug 19
FLL
Fort Lauderdale - Hollywood Intl.
PWM
Portland Intl. Jetport
CA $403 Roundtrip, found 1 day ago
CA $403
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Mon, Aug 17 from Fort Lauderdale - Hollywood Intl. to Portland Intl. Jetport, returning Wed, Aug 19, priced at CA $403 found 1 day ago
Thu, Sep 10 - Tue, Sep 15
RDU
Raleigh - Durham Intl.
PWM
Portland Intl. Jetport
CA $404 Roundtrip, found 6 days ago
CA $404
Roundtrip
found 6 days ago
Select Breeze Airways flight, departing Thu, Sep 10 from Raleigh - Durham Intl. to Portland Intl. Jetport, returning Tue, Sep 15, priced at CA $404 found 6 days ago
Sat, Jun 13 - Mon, Jun 15
RDU
Raleigh - Durham Intl.
PWM
Portland Intl. Jetport
CA $412 Roundtrip, found 5 days ago
CA $412
Roundtrip
found 5 days ago
Select Breeze Airways flight, departing Sat, Jun 13 from Raleigh - Durham Intl. to Portland Intl. Jetport, returning Mon, Jun 15, priced at CA $412 found 5 days ago
Wed, Jun 3 - Mon, Jun 8
RDU
Raleigh - Durham Intl.
PWM
Portland Intl. Jetport
CA $420 Roundtrip, found 5 days ago
CA $420
Roundtrip
found 5 days ago
Select Breeze Airways flight, departing Wed, Jun 3 from Raleigh - Durham Intl. to Portland Intl. Jetport, returning Mon, Jun 8, priced at CA $420 found 5 days ago
Wed, Sep 16 - Sun, Sep 20
RDU
Raleigh - Durham Intl.
PWM
Portland Intl. Jetport
CA $421 Roundtrip, found 23 hours ago
CA $421
Roundtrip
found 23 hours ago
Select Breeze Airways flight, departing Wed, Sep 16 from Raleigh - Durham Intl. to Portland Intl. Jetport, returning Sun, Sep 20, priced at CA $421 found 23 hours ago
Wed, Sep 30 - Wed, Oct 14
YVR
Vancouver Intl.
PWM
Portland Intl. Jetport
CA $526 Roundtrip, found 5 hours ago
CA $526
Roundtrip
found 5 hours ago
Select Delta flight, departing Wed, Sep 30 from Vancouver Intl. to Portland Intl. Jetport, returning Wed, Oct 14, priced at CA $526 found 5 hours ago
Fri, Oct 23 - Fri, Oct 30
YVR
Vancouver Intl.
PWM
Portland Intl. Jetport
CA $544 Roundtrip, found 2 days ago
CA $544
Roundtrip
found 2 days ago
Select WestJet flight, departing Fri, Oct 23 from Vancouver Intl. to Portland Intl. Jetport, returning Fri, Oct 30, priced at CA $544 found 2 days ago
Tue, Jun 16 - Tue, Jun 23
YYZ
Pearson Intl.
PWM
Portland Intl. Jetport
CA $550 Roundtrip, found 6 days ago
CA $550
Roundtrip
found 6 days ago
Select Delta flight, departing Tue, Jun 16 from Pearson Intl. to Portland Intl. Jetport, returning Tue, Jun 23, priced at CA $550 found 6 days ago
OriginDestinationTravel datesFlights from*
JFKPortlandJuly 25 to August 1CA $250
RDUPortlandJune 13 to June 17CA $302
MCOPortlandAugust 31 to September 6CA $339
TPAPortlandSeptember 1 to September 9CA $354
ATLPortlandJune 27 to July 4CA $475
SEAPortlandJuly 13 to July 22CA $632
PHLPortlandJuly 25 to August 1CA $741
ATLAugustaJune 21 to June 23CA $991
*Prices include taxes and fees
Price found within the past 48 hours. Click for updated prices.
The Atlas Hotel
4.5-star property

The Atlas Hotel

Aug 16 - Aug 21

5 night stay

Toronto (YYZ) to Boston (BOS)

Porter Airlines • Roundtrip • Coach
Price was CA $1,519, price is now CA $1,047 per person
CA $1,047
per person
found 1 day ago
Boston Harbor Hotel
5.0-star property

Boston Harbor Hotel

Aug 1 - Aug 8

7 night stay

Toronto (YYZ) to Boston (BOS)

Porter Airlines • Roundtrip • Coach
Price was CA $5,296, price is now CA $2,658 per person
CA $2,658
per person
found 1 day ago
Fairmont Copley Plaza, Boston
4.5-star property

Fairmont Copley Plaza, Boston

Aug 23 - Aug 27

4 night stay

Toronto (YYZ) to Boston (BOS)

Porter Airlines • Roundtrip • Coach
Price was CA $1,570, price is now CA $1,076 per person
CA $1,076
per person
found 1 day ago
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Travelers ❤️ These Cumberland County 🏨

Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
468 Fore Street Portland ME
Book a stay at this business-friendly hotel in Portland. Enjoy free WiFi, 3 coffee shops/cafes, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Thompson's Point and Cross Insurance Arena are located nearby.
9.4/10 Exceptional! (1,768 reviews)
"An attractive city hotel with contemporary rooms and a lux feeling lobby area. Ed and pillow were very good; a/c was robust. Downside: The one working elevator to the guest rooms made transit up and downstairs slow."

Reviewed on May 25, 2026

Opens in a new windowPortland Harbor Hotel
Portland Regency Hotel & Spa

Portland Regency Hotel & Spa

3.5 out of 5
20 Milk Street Portland ME
Book a stay at this spa hotel in Portland. Enjoy free WiFi, a full-service spa, and 2 bars/lounges. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Thompson's Point and Maine Mall are located nearby.
9.4/10 Exceptional! (1,652 reviews)
"Just okay, guest services staff a bit aloof. Can’t beat the location in the heart of the old port. Comfortable bed. Room service closed too early. Nothing in the minibar fridge. Walls are surprisingly thin. I expected more from the Regency."

Reviewed on May 25, 2026

Opens in a new windowPortland Regency Hotel & Spa
Cambria Hotel Portland Downtown-Old Port

Cambria Hotel Portland Downtown-Old Port

3 out of 5
25 HANCOCK STREET Portland ME
Book a stay at this business-friendly hotel in Portland. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Thompson's Point and Maine Mall are located nearby.
9.4/10 Exceptional! (1,222 reviews)
"Beautiful room, perfect location , nice staff"

Reviewed on May 26, 2026

Opens in a new windowCambria Hotel Portland Downtown-Old Port
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HomeAwhile

HomeAwhile

2 out of 5
205 Southborough Drive Scarborough ME
Stay at this hotel in Scarborough. Enjoy free WiFi, free parking, and a 24-hour front desk. Popular attractions Maine Mall and Thompson's Point are located nearby.
9.4/10 Exceptional! (52 reviews)
"This was my second stay at this hotel, and the staff was so nice and accommodating. If you need a place to stay while in the area, I highly recommend it. The staff was friendly, and the hotel was clean."

Reviewed on May 25, 2026

Opens in a new windowHomeAwhile
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 $250. 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, September 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 $250. 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 $250 and CA $991. 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.