Flights To Cumberland County - Cheap Flights Starting at CA $140

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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.

Wed, Aug 5 - Sat, Aug 8
JFK
John F. Kennedy Intl.
PWM
Portland Intl. Jetport
CA $217 Roundtrip, found 18 hours ago
CA $217
Roundtrip
found 18 hours ago
Select JetBlue Airways flight, departing Wed, Aug 5 from John F. Kennedy Intl. to Portland Intl. Jetport, returning Sat, Aug 8, priced at CA $217 found 18 hours ago
Fri, Jul 31 - Tue, Aug 4
JFK
John F. Kennedy Intl.
PWM
Portland Intl. Jetport
CA $228 Roundtrip, found 15 hours ago
CA $228
Roundtrip
found 15 hours ago
Select JetBlue Airways flight, departing Fri, Jul 31 from John F. Kennedy Intl. to Portland Intl. Jetport, returning Tue, Aug 4, priced at CA $228 found 15 hours ago
Sun, Aug 30 - Fri, Sep 4
JFK
John F. Kennedy Intl.
PWM
Portland Intl. Jetport
CA $240 Roundtrip, found 20 hours ago
CA $240
Roundtrip
found 20 hours ago
Select JetBlue Airways flight, departing Sun, Aug 30 from John F. Kennedy Intl. to Portland Intl. Jetport, returning Fri, Sep 4, priced at CA $240 found 20 hours ago
Sat, Aug 15 - Sun, Aug 16
JFK
John F. Kennedy Intl.
PWM
Portland Intl. Jetport
CA $258 Roundtrip, found 6 days ago
CA $258
Roundtrip
found 6 days ago
Select JetBlue Airways flight, departing Sat, Aug 15 from John F. Kennedy Intl. to Portland Intl. Jetport, returning Sun, Aug 16, priced at CA $258 found 6 days ago
Mon, Jul 27 - Fri, Jul 31
JFK
John F. Kennedy Intl.
PWM
Portland Intl. Jetport
CA $262 Roundtrip, found 2 days ago
CA $262
Roundtrip
found 2 days ago
Select JetBlue Airways flight, departing Mon, Jul 27 from John F. Kennedy Intl. to Portland Intl. Jetport, returning Fri, Jul 31, priced at CA $262 found 2 days ago
Mon, Aug 17 - Fri, Aug 21
JFK
John F. Kennedy Intl.
PWM
Portland Intl. Jetport
CA $269 Roundtrip, found 6 days ago
CA $269
Roundtrip
found 6 days ago
Select JetBlue Airways flight, departing Mon, Aug 17 from John F. Kennedy Intl. to Portland Intl. Jetport, returning Fri, Aug 21, priced at CA $269 found 6 days ago
Mon, Jul 27 - Sat, Aug 1
JFK
John F. Kennedy Intl.
PWM
Portland Intl. Jetport
CA $291 Roundtrip, found 2 days ago
CA $291
Roundtrip
found 2 days ago
Select JetBlue Airways flight, departing Mon, Jul 27 from John F. Kennedy Intl. to Portland Intl. Jetport, returning Sat, Aug 1, priced at CA $291 found 2 days ago
Thu, Sep 3 - Mon, Sep 7
JFK
John F. Kennedy Intl.
PWM
Portland Intl. Jetport
CA $293 Roundtrip, found 21 hours ago
CA $293
Roundtrip
found 21 hours ago
Select JetBlue Airways flight, departing Thu, Sep 3 from John F. Kennedy Intl. to Portland Intl. Jetport, returning Mon, Sep 7, priced at CA $293 found 21 hours ago
Tue, Aug 25 - Mon, Aug 31
YVR
Vancouver Intl.
PWM
Portland Intl. Jetport
CA $449 Roundtrip, found 3 days ago
CA $449
Roundtrip
found 3 days ago
Select American Airlines flight, departing Tue, Aug 25 from Vancouver Intl. to Portland Intl. Jetport, returning Mon, Aug 31, priced at CA $449 found 3 days ago
Tue, Sep 1 - Wed, Sep 2
YVR
Vancouver Intl.
PWM
Portland Intl. Jetport
CA $491 Roundtrip, found 5 days ago
CA $491
Roundtrip
found 5 days ago
Select Delta flight, departing Tue, Sep 1 from Vancouver Intl. to Portland Intl. Jetport, returning Wed, Sep 2, priced at CA $491 found 5 days ago
Tue, Sep 22 - Thu, Sep 24
YYZ
Pearson Intl.
PWM
Portland Intl. Jetport
CA $629 Roundtrip, found 4 days ago
CA $629
Roundtrip
found 4 days ago
Select Delta flight, departing Tue, Sep 22 from Pearson Intl. to Portland Intl. Jetport, returning Thu, Sep 24, priced at CA $629 found 4 days ago
OriginDestinationTravel datesFlights from*
RDUPortlandSeptember 19 to September 26CA $216
JFKPortlandJuly 25 to August 1CA $217
TPAPortlandSeptember 5 to September 9CA $274
DCAPortlandJuly 27 to July 31CA $341
MCOPortlandSeptember 4 to September 7CA $366
ATLPortlandSeptember 17 to September 22CA $420
*Prices include taxes and fees
OriginDestinationTravel datesFlights from*
JFKPortlandJuly 11 to July 13CA $418
MCOPortlandJuly 10 to July 13CA $608
TPAPortlandJuly 11 to October 15CA $646
*Prices include taxes and fees
Price found within the past 48 hours. Click for updated prices.
Clarion Hotel Lewiston
3.0-star property

Clarion Hotel Lewiston

Jul 31 - Aug 7

7 night stay

Toronto (YYZ) to Portland (PWM)

Porter Airlines • Roundtrip • Coach
Price was CA $1,257, price is now CA $818 per person
CA $818
per person
found 1 day ago
Ogunquit River Inn & Suites
3.0-star property

Ogunquit River Inn & Suites

Sep 12 - Sep 18

6 night stay

Toronto (YYZ) to Portland (PWM)

Porter Airlines • Roundtrip • Coach
Price was CA $1,630, price is now CA $1,077 per person
CA $1,077
per person
found 23 hours ago
Four Seasons Hotel Boston
5.0-star property

Four Seasons Hotel Boston

Jul 23 - Jul 26

3 night stay

Toronto (YYZ) to Boston (BOS)

Air Transat • Non-stop roundtrip • Coach
Price was CA $3,189, price is now CA $2,142 per person
CA $2,142
per person
found 1 day ago
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Travelers ❤️ These Cumberland County 🏨

La Quinta Inn & Suites by Wyndham Portland DT/Maine Med

La Quinta Inn & Suites by Wyndham Portland DT/Maine Med

3 out of 5
340 Park Ave Portland ME
Book a stay at this business-friendly hotel in Portland. Enjoy free breakfast, free WiFi, and an outdoor pool. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Thompson's Point and State Theatre are located nearby.
8.6/10 Excellent! (2,191 reviews)
"Good hotel and helpful staff. Breakfast was pretty terrible."

Reviewed on Jul 7, 2026

Opens in a new windowLa Quinta Inn & Suites by Wyndham Portland DT/Maine Med
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 Casco Bay Lines Ferry Terminal and State Theatre are located nearby.
9.4/10 Exceptional! (1,773 reviews)
"food is good, room is ok, hotel location is good."

Reviewed on Jul 6, 2026

Opens in a new windowPortland Harbor Hotel
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 Cross Insurance Arena and State Theatre are located nearby.
9.4/10 Exceptional! (1,253 reviews)
"This hotel had a great location, large modern clean rooms. We were very impressed with the hotel and the staff."

Reviewed on Jul 7, 2026

Opens in a new windowCambria Hotel Portland Downtown-Old Port
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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 Casco Bay Lines Ferry Terminal and State Theatre are located nearby.
9.4/10 Exceptional! (1,689 reviews)
"Location is amazing!! The garden cafe is such a nice perk and the drinks and food delicious! Staff is very helpful at the hotel. Enjoy the sauna and spa, it’s a nice treat to have onsite. Quiet at night and the beds are so comfy!!! Staff at the armory and garden cafe were wonderful! Chowder at the ..."

Reviewed on Jul 6, 2026

Opens in a new windowPortland Regency Hotel & Spa
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 $216. 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, August 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 $216. 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 $216 and CA $646. 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.