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

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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.

Fri, Oct 30 - Mon, Nov 2
CMH
John Glenn Columbus Intl.
PWM
Portland Intl. Jetport
$138 Roundtrip, found 1 hour ago
$138
Roundtrip
found 1 hour ago
Select Breeze Airways flight, departing Fri, Oct 30 from John Glenn Columbus Intl. to Portland Intl. Jetport, returning Mon, Nov 2, priced at $138 found 1 hour ago
Tue, Nov 10 - Wed, Nov 18
RDU
Raleigh - Durham Intl.
PWM
Portland Intl. Jetport
$142 Roundtrip, found 3 hours ago
$142
Roundtrip
found 3 hours ago
Select Breeze Airways flight, departing Tue, Nov 10 from Raleigh - Durham Intl. to Portland Intl. Jetport, returning Wed, Nov 18, priced at $142 found 3 hours ago
Sat, Sep 12 - Sat, Sep 19
CMH
John Glenn Columbus Intl.
PWM
Portland Intl. Jetport
$142 Roundtrip, just found
$142
Roundtrip
just found
Select Breeze Airways flight, departing Sat, Sep 12 from John Glenn Columbus Intl. to Portland Intl. Jetport, returning Sat, Sep 19, priced at $142 just found
Sat, Aug 22 - Wed, Aug 26
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 Wed, Aug 26, priced at $145 just found
Wed, Sep 16 - Wed, Sep 30
CMH
John Glenn Columbus Intl.
PWM
Portland Intl. Jetport
$147 Roundtrip, found 8 hours ago
$147
Roundtrip
found 8 hours ago
Select Breeze Airways flight, departing Wed, Sep 16 from John Glenn Columbus Intl. to Portland Intl. Jetport, returning Wed, Sep 30, priced at $147 found 8 hours ago
Wed, Aug 19 - Sat, Aug 22
JFK
John F. Kennedy Intl.
PWM
Portland Intl. Jetport
$149 Roundtrip, found 1 hour ago
$149
Roundtrip
found 1 hour ago
Select JetBlue Airways flight, departing Wed, Aug 19 from John F. Kennedy Intl. to Portland Intl. Jetport, returning Sat, Aug 22, priced at $149 found 1 hour ago
Wed, Aug 26 - Tue, Sep 1
MCO
Orlando Intl.
PWM
Portland Intl. Jetport
$158 Roundtrip, found 5 days ago
$158
Roundtrip
found 5 days ago
Select Breeze Airways flight, departing Wed, Aug 26 from Orlando Intl. to Portland Intl. Jetport, returning Tue, Sep 1, priced at $158 found 5 days ago
Thu, Aug 13 - Thu, Aug 20
RDU
Raleigh - Durham Intl.
PWM
Portland Intl. Jetport
$171 Roundtrip, found 1 hour ago
$171
Roundtrip
found 1 hour ago
Select American Airlines flight, departing Thu, Aug 13 from Raleigh - Durham Intl. to Portland Intl. Jetport, returning Thu, Aug 20, priced at $171 found 1 hour ago
OriginDestinationTravel DatesFlights From*
JFKPortlandAugust 5 to August 8$149
MCOPortlandSeptember 23 to September 30$167
TPAPortlandSeptember 19 to September 26$180
DCAPortlandAugust 10 to August 13$212
PHLPortlandAugust 17 to August 20$298
CLTPortlandJuly 21 to August 4$326
JFKAugustaJuly 30 to August 6$432
PHLAugustaSeptember 18 to September 21$432
TPAAugustaJuly 28 to July 29$470
ATLAugustaSeptember 4 to September 8$492
MCOAugustaOctober 2 to October 6$493
RDUAugustaAugust 14 to August 16$494
DCAAugustaJuly 21 to July 25$510
SEAAugustaAugust 20 to August 25$675
FCOPortlandAugust 18 to August 25$982
*Prices include taxes and fees
OriginDestinationTravel DatesFlights From*
EWRPortlandJuly 12 to August 1$224
TPAPortlandJuly 11 to July 13$425
DCAPortlandJuly 11 to July 12$441
JFKAugustaJuly 11 to July 25$466
MCOPortlandJuly 11 to July 13$467
RDUPortlandJuly 11 to July 13$487
TTNPortlandJuly 10 to July 17$552
RDUAugustaJuly 12 to July 13$594
SEAPortlandJuly 12 to July 25$648
CLTPortlandJuly 11 to July 18$686
ATLPortlandJuly 11 to July 16$700
FCOPortlandJuly 10 to July 14$1,187
*Prices include taxes and fees

Best Cumberland County Flight and Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Four Seasons Hotel Boston
5.0-star property

Four Seasons Hotel Boston

Sep 24 - Sep 27

3 night stay

Detroit (DTW) to Boston (BOS)

JetBlue Airways • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $2,561, price is now $1,528 per person
$1,528
per person
found 1 day ago
Nantucket Inn
3.5-star property

Nantucket Inn

Aug 12 - Aug 16

4 night stay

Dallas (DFW) to Boston (BOS)

Southwest Airlines • Non-stop • Coach

Boston (BOS) to Dallas (DFW)

Frontier Airlines • Non-stop • Coach
Save 100% on your flight
Price was $2,563, price is now $1,566 per person
$1,566
per person
found 1 day ago
Blind Tiger Portland - Danforth Street.
3.5-star property

Blind Tiger Portland - Danforth Street.

Sep 10 - Sep 15

5 night stay

Denver (DEN) to Portland (PWM)

United • Roundtrip • Coach
Save 100% on your flight
Price was $2,794, price is now $1,754 per person
$1,754
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! (2,192 reviews)
"The room smelled like moldy water. The sink only had a trickle of water due to the placement of the faucet flush up against the mirror which did not allow the handle to fully extend. Room 405"

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! (1,776 reviews)
"We really enjoyed our stay at the hotel. The location was great. The things that knocked off a star from the rating are as follows: they don’t have bellhop service. When you arrive at the hotel, they lend you a luggage cart and then you’re on your own. Same thing for checking out. For an upscale ..."

Reviewed on Jul 7, 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! (1,257 reviews)
"Restaurant was understaffed. Good location."

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! (1,691 reviews)
"Great Location , excellent staff and clean rooms, comfortable rooms."

Reviewed on Jul 7, 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 $138. 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 15 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 $138. 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 $138 and $1,187. 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.