Flights To Cumberland County - Cheap Flights Starting at CA $151

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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.

Fri, Oct 30 - Mon, Nov 2
JFK
John F. Kennedy Intl.
PWM
Portland Intl. Jetport
CA $301 Roundtrip, found 2 days ago
CA $301
Roundtrip
found 2 days ago
Select Delta flight, departing Fri, Oct 30 from John F. Kennedy Intl. to Portland Intl. Jetport, returning Mon, Nov 2, priced at CA $301 found 2 days ago
Fri, Oct 30 - Mon, Nov 2
JFK
John F. Kennedy Intl.
PWM
Portland Intl. Jetport
CA $301 Roundtrip, found 2 days ago
CA $301
Roundtrip
found 2 days ago
Select JetBlue Airways flight, departing Fri, Oct 30 from John F. Kennedy Intl. to Portland Intl. Jetport, returning Mon, Nov 2, priced at CA $301 found 2 days ago
Fri, Oct 2 - Sun, Oct 4
JFK
John F. Kennedy Intl.
PWM
Portland Intl. Jetport
CA $307 Roundtrip, found 3 days ago
CA $307
Roundtrip
found 3 days ago
Select JetBlue Airways flight, departing Fri, Oct 2 from John F. Kennedy Intl. to Portland Intl. Jetport, returning Sun, Oct 4, priced at CA $307 found 3 days ago
Fri, Oct 30 - Mon, Nov 2
JFK
John F. Kennedy Intl.
PWM
Portland Intl. Jetport
CA $315 Roundtrip, found 2 days ago
CA $315
Roundtrip
found 2 days ago
Select American Airlines flight, departing Fri, Oct 30 from John F. Kennedy Intl. to Portland Intl. Jetport, returning Mon, Nov 2, priced at CA $315 found 2 days ago
Sat, Sep 5 - Sat, Sep 12
JFK
John F. Kennedy Intl.
PWM
Portland Intl. Jetport
CA $321 Roundtrip, found 5 days ago
CA $321
Roundtrip
found 5 days ago
Select JetBlue Airways flight, departing Sat, Sep 5 from John F. Kennedy Intl. to Portland Intl. Jetport, returning Sat, Sep 12, priced at CA $321 found 5 days ago
Fri, Oct 30 - Mon, Nov 2
JFK
John F. Kennedy Intl.
PWM
Portland Intl. Jetport
CA $329 Roundtrip, found 2 days ago
CA $329
Roundtrip
found 2 days ago
Select Delta flight, departing Fri, Oct 30 from John F. Kennedy Intl. to Portland Intl. Jetport, returning Mon, Nov 2, priced at CA $329 found 2 days ago
Sat, Aug 29 - Sat, Sep 5
JFK
John F. Kennedy Intl.
PWM
Portland Intl. Jetport
CA $335 Roundtrip, found 5 days ago
CA $335
Roundtrip
found 5 days ago
Select JetBlue Airways flight, departing Sat, Aug 29 from John F. Kennedy Intl. to Portland Intl. Jetport, returning Sat, Sep 5, priced at CA $335 found 5 days ago
Thu, Sep 10 - Mon, Sep 14
JFK
John F. Kennedy Intl.
PWM
Portland Intl. Jetport
CA $342 Roundtrip, found 2 days ago
CA $342
Roundtrip
found 2 days ago
Select JetBlue Airways flight, departing Thu, Sep 10 from John F. Kennedy Intl. to Portland Intl. Jetport, returning Mon, Sep 14, priced at CA $342 found 2 days ago
Tue, Sep 29 - Fri, Oct 16
YVR
Vancouver Intl.
PWM
Portland Intl. Jetport
CA $428 Roundtrip, found 1 day ago
CA $428
Roundtrip
found 1 day ago
Select United flight, departing Tue, Sep 29 from Vancouver Intl. to Portland Intl. Jetport, returning Fri, Oct 16, priced at CA $428 found 1 day ago
Tue, Sep 22 - Sat, Oct 10
YVR
Vancouver Intl.
PWM
Portland Intl. Jetport
CA $525 Roundtrip, found 5 days ago
CA $525
Roundtrip
found 5 days ago
Select Air Canada flight, departing Tue, Sep 22 from Vancouver Intl. to Portland Intl. Jetport, returning Sat, Oct 10, priced at CA $525 found 5 days ago
Thu, Sep 10 - Thu, Sep 17
YYZ
Pearson Intl.
PWM
Portland Intl. Jetport
CA $593 Roundtrip, found 3 days ago
CA $593
Roundtrip
found 3 days ago
Select Delta flight, departing Thu, Sep 10 from Pearson Intl. to Portland Intl. Jetport, returning Thu, Sep 17, priced at CA $593 found 3 days ago
OriginDestinationTravel datesFlights from*
RDUPortlandOctober 24 to October 31CA $197
TPAPortlandOctober 31 to November 7CA $225
MCOPortlandNovember 14 to November 16CA $254
JFKPortlandOctober 30 to November 2CA $301
DCAPortlandOctober 3 to October 10CA $364
ATLPortlandNovember 5 to November 11CA $400
*Prices include taxes and fees
OriginDestinationTravel datesFlights from*
JFKPortlandAugust 29 to September 5CA $335
*Prices include taxes and fees
Price found within the past 48 hours. Click for updated prices.
Arcadian Hotel
3.5-star property

Arcadian Hotel

Oct 19 - Oct 23

4 night stay

Buffalo (BUF) to Boston (BOS)

JetBlue Airways • Non-stop roundtrip • Coach
Price was CA $1,305, price is now CA $887 per person
CA $887
per person
found 1 day ago
Boston Harbor Hotel
5.0-star property

Boston Harbor Hotel

Oct 28 - Nov 1

4 night stay

Montreal (YUL) to Boston (BOS)

Porter Airlines • Non-stop roundtrip • Coach
Price was CA $3,484, price is now CA $2,171 per person
CA $2,171
per person
found 8 hours ago
Fairmont Copley Plaza, Boston
4.5-star property

Fairmont Copley Plaza, Boston

Sep 18 - Sep 21

3 night stay

Buffalo (BUF) to Boston (BOS)

JetBlue Airways • Non-stop roundtrip • Coach
Price was CA $1,953, price is now CA $1,368 per person
CA $1,368
per person
found 1 day ago
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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 Thompson's Point and Maine Mall are located nearby.
8/10 Very good! (1,632 reviews)
"They had a mini fridge, small keureg in the room, and a microwave so they were useful just wish the gave you a second chair they gave u one comfy chair and a computer chair not useful for us . They have a pool on first floor and hot tub staff , was friendly and if you need anything they gave it to ..."

Reviewed on Aug 21, 2026

Opens in a new windowClarion Hotel Portland Airport ME
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 Thompson's Point are located nearby.
Opens in a new windowFireside Inn & Suites Portland
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 State Theatre and Thompson's Point are located nearby.
9.4/10 Exceptional! (1,748 reviews)
"The most charming hotel in Portland. An old armorh turned into a hotel! Very well kept. Staff was very nice. 2 bars and restaurant are on the premises plus the garden restaurant/bar across the street you can utilize. Would definitely recommend this hotel."

Reviewed on Aug 21, 2026

Opens in a new windowPortland Regency Hotel & Spa
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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 Thompson's Point and Portland Head Light are located nearby.
9/10 Wonderful! (1,006 reviews)
"Friendly welcome staff. Clean room."

Reviewed on Aug 21, 2026

Opens in a new windowThe Westin Portland Harborview
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 $197. 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, 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 $197. 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 $197 and CA $593. 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.