Cheap Flights to Cumberland County from $72 (2026/2027)

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

Portland

Flights
Portland

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, Oct 28 - Sat, Oct 31
RDU
Raleigh - Durham Intl.
PWM
Portland Intl. Jetport
$142 Roundtrip, found 12 hours ago
$142
Roundtrip
found 12 hours ago
Select Breeze Airways flight, departing Wed, Oct 28 from Raleigh - Durham Intl. to Portland Intl. Jetport, returning Sat, Oct 31, priced at $142 found 12 hours ago
Sat, Sep 26 - Wed, Sep 30
CMH
John Glenn Columbus Intl.
PWM
Portland Intl. Jetport
$142 Roundtrip, just found
$142
Roundtrip
just found
Select Breeze Airways flight, departing Sat, Sep 26 from John Glenn Columbus Intl. to Portland Intl. Jetport, returning Wed, Sep 30, priced at $142 just found
Sat, Aug 22 - Sat, Aug 29
CMH
John Glenn Columbus Intl.
PWM
Portland Intl. Jetport
$145 Roundtrip, just found
$145
Roundtrip
just found
Select Breeze Airways flight, departing Sat, Aug 22 from John Glenn Columbus Intl. to Portland Intl. Jetport, returning Sat, Aug 29, priced at $145 just found
Sat, Sep 26 - Sat, Oct 3
CMH
John Glenn Columbus Intl.
PWM
Portland Intl. Jetport
$147 Roundtrip, found 1 day ago
$147
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Sat, Sep 26 from John Glenn Columbus Intl. to Portland Intl. Jetport, returning Sat, Oct 3, priced at $147 found 1 day ago
Wed, Aug 26 - Sat, Aug 29
CMH
John Glenn Columbus Intl.
PWM
Portland Intl. Jetport
$147 Roundtrip, found 6 hours ago
$147
Roundtrip
found 6 hours ago
Select Breeze Airways flight, departing Wed, Aug 26 from John Glenn Columbus Intl. to Portland Intl. Jetport, returning Sat, Aug 29, priced at $147 found 6 hours ago
Wed, Aug 26 - Sat, Aug 29
CMH
John Glenn Columbus Intl.
PWM
Portland Intl. Jetport
$152 Roundtrip, found 6 hours ago
$152
Roundtrip
found 6 hours ago
Select Breeze Airways flight, departing Wed, Aug 26 from John Glenn Columbus Intl. to Portland Intl. Jetport, returning Sat, Aug 29, priced at $152 found 6 hours ago
Wed, Aug 12 - Wed, Aug 19
CMH
John Glenn Columbus Intl.
PWM
Portland Intl. Jetport
$152 Roundtrip, found 5 days ago
$152
Roundtrip
found 5 days ago
Select Breeze Airways flight, departing Wed, Aug 12 from John Glenn Columbus Intl. to Portland Intl. Jetport, returning Wed, Aug 19, priced at $152 found 5 days ago
Wed, Jul 29 - Wed, Aug 19
CMH
John Glenn Columbus Intl.
PWM
Portland Intl. Jetport
$154 Roundtrip, found 6 days ago
$154
Roundtrip
found 6 days ago
Select Breeze Airways flight, departing Wed, Jul 29 from John Glenn Columbus Intl. to Portland Intl. Jetport, returning Wed, Aug 19, priced at $154 found 6 days ago
Thu, Oct 22 - Sun, Oct 25
JFK
John F. Kennedy Intl.
PWM
Portland Intl. Jetport
$191 Roundtrip, found 2 days ago
$191
Roundtrip
found 2 days ago
Select Delta flight, departing Thu, Oct 22 from John F. Kennedy Intl. to Portland Intl. Jetport, returning Sun, Oct 25, priced at $191 found 2 days ago
OriginDestinationTravel DatesFlights From*
MCOPortlandSeptember 2 to September 9$177
JFKPortlandSeptember 11 to September 15$191
DCAPortlandSeptember 15 to September 16$217
ATLPortlandAugust 18 to August 22$253
CLTPortlandOctober 22 to October 24$323
JFKAugustaOctober 9 to October 11$398
PHLPortlandOctober 6 to October 14$432
PHLAugustaAugust 8 to August 15$452
ATLAugustaOctober 1 to October 6$470
MCOAugustaSeptember 16 to September 19$477
DCAAugustaAugust 9 to August 12$515
TPAAugustaAugust 12 to August 17$545
CLTAugustaAugust 20 to August 25$610
SEAAugustaAugust 12 to August 16$647
FCOPortlandAugust 18 to August 25$1,110
*Prices include taxes and fees
OriginDestinationTravel DatesFlights From*
JFKPortlandJuly 26 to August 20$315
DCAPortlandJuly 25 to July 28$390
CLTPortlandJuly 25 to July 28$420
RDUPortlandJuly 25 to July 29$500
ATLPortlandJuly 26 to August 4$524
TPAPortlandJuly 25 to July 29$527
PHLPortlandJuly 24 to July 25$547
JFKAugustaJuly 25 to July 29$574
SEAPortlandJuly 26 to July 29$609
DCAAugustaJuly 26 to July 30$624
MCOPortlandJuly 26 to July 29$674
*Prices include taxes and fees

Best Cumberland County Flight and Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Boston Lodge and Suites
4.0-star property

Boston Lodge and Suites

Oct 1 - Oct 4

3 night stay

Charlotte (CLT) to Boston (BOS)

American Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $1,297, price is now $696 per person
$696
per person
found 1 day ago
By the Sea Guests Bed & Breakfast & Suites
3.5-star property

By the Sea Guests Bed & Breakfast & Suites

Sep 3 - Sep 10

7 night stay

Charlotte (CLT) to Boston (BOS)

JetBlue Airways • Roundtrip • Coach
Save 100% on your flight
Price was $2,900, price is now $1,709 per person
$1,709
per person
found 1 day ago
Iris Hotel Boston
4.0-star property

Iris Hotel Boston

Sep 23 - Sep 30

7 night stay

Charlotte (CLT) to Boston (BOS)

American Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $2,325, price is now $1,394 per person
$1,394
per person
found 18 hours ago
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Travelers ❤️ These Cumberland County 🏨

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 Thompson's Point and Maine Mall are located nearby.
Opens in a new windowFireside Inn & Suites Portland
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.
Opens in a new windowLa Quinta Inn & Suites by Wyndham Portland DT/Maine Med
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 State Theatre are located nearby.
Opens in a new windowClarion Hotel Portland Airport ME
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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 Cross Insurance Arena are located nearby.
9.4/10 Exceptional! (1,709 reviews)
"The property was in a perfect locations and offered a gym and spa along with places to eat. The staff was very helpful and the food was delicious! My sisters and I enjoyed our stay."

Reviewed on Jul 21, 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 $142. 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 16 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 $142. 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 $142 and $1,110. 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.
How long is the average flight to Cumberland County?
Below are a number of preferred direct flights to Cumberland County with their average flight duration:

  • New York, NY (JFK-John F. Kennedy Intl.) to Portland Intl. Jetport Airport (PWM) - 1 hour and 20 minutes
  • Chicago, IL (ORD-O'Hare Intl.) to Portland Intl. Jetport Airport (PWM) - 2 hours and 21 minutes
  • Philadelphia, PA (PHL-Philadelphia Intl.) to Portland Intl. Jetport Airport (PWM) - 1 hour and 32 minutes

What can I expect on a flight to Cumberland County?
The time your flight takes and whether you opt for a budget or full-service carrier will determine what you can expect on board. If you're searching for long-haul flights to Cumberland County, meals, drinks and entertainment are routine inclusions. Chasing cheap flights for family vacations? Check out the deals from budget carriers. Generally, these airlines don't provide as many inclusions, or they'll be available as add-ons.