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.

Sat, Oct 24 - Sat, Oct 31
RDU
Raleigh - Durham Intl.
PWM
Portland Intl. Jetport
$142 Roundtrip, found 17 hours ago
$142
Roundtrip
found 17 hours ago
Select Breeze Airways flight, departing Sat, Oct 24 from Raleigh - Durham Intl. to Portland Intl. Jetport, returning Sat, Oct 31, priced at $142 found 17 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
Wed, Aug 19 - Sat, Aug 22
JFK
John F. Kennedy Intl.
PWM
Portland Intl. Jetport
$149 Roundtrip, found 9 hours ago
$149
Roundtrip
found 9 hours 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 9 hours ago
Sat, Aug 29 - Sat, Sep 5
JFK
John F. Kennedy Intl.
PWM
Portland Intl. Jetport
$153 Roundtrip, just found
$153
Roundtrip
just found
Select JetBlue Airways flight, departing Sat, Aug 29 from John F. Kennedy Intl. to Portland Intl. Jetport, returning Sat, Sep 5, priced at $153 just found
Wed, Aug 19 - Sun, Aug 23
JFK
John F. Kennedy Intl.
PWM
Portland Intl. Jetport
$157 Roundtrip, found 1 hour ago
$157
Roundtrip
found 1 hour ago
Select JetBlue Airways flight, departing Wed, Aug 19 from John F. Kennedy Intl. to Portland Intl. Jetport, returning Sun, Aug 23, priced at $157 found 1 hour ago
Wed, Oct 7 - Wed, Oct 7
BOS
Logan Intl.
AUG
Augusta State
$174 Roundtrip, found 21 hours ago
$174
Roundtrip
found 21 hours ago
Select Cape Air flight, departing Wed, Oct 7 from Logan Intl. to Augusta State, returning Wed, Oct 7, priced at $174 found 21 hours ago
Mon, Oct 26 - Thu, Oct 29
JFK
John F. Kennedy Intl.
PWM
Portland Intl. Jetport
$181 Roundtrip, just found
$181
Roundtrip
just found
Select Delta flight, departing Mon, Oct 26 from John F. Kennedy Intl. to Portland Intl. Jetport, returning Thu, Oct 29, priced at $181 just found
Wed, Oct 21 - Sat, Oct 24
BOS
Logan Intl.
PWM
Portland Intl. Jetport
$237 Roundtrip, found 10 hours ago
$237
Roundtrip
found 10 hours ago
Select JetBlue Airways flight, departing Wed, Oct 21 from Logan Intl. to Portland Intl. Jetport, returning Sat, Oct 24, priced at $237 found 10 hours ago
Thu, Aug 27 - Wed, Sep 2
DEN
Denver Intl.
PWM
Portland Intl. Jetport
$271 Roundtrip, found 6 days ago
$271
Roundtrip
found 6 days ago
Select JetBlue Airways flight, departing Thu, Aug 27 from Denver Intl. to Portland Intl. Jetport, returning Wed, Sep 2, priced at $271 found 6 days ago
Tue, Sep 1 - Sat, Sep 5
JFK
John F. Kennedy Intl.
PWM
Portland Intl. Jetport
$316 Roundtrip, found 22 hours ago
$316
Roundtrip
found 22 hours ago
Select American Airlines flight, departing Tue, Sep 1 from John F. Kennedy Intl. to Portland Intl. Jetport, returning Sat, Sep 5, priced at $316 found 22 hours ago
OriginDestinationTravel DatesFlights From*
JFKPortlandAugust 5 to August 8$149
MCOPortlandSeptember 23 to September 30$167
ATLPortlandAugust 29 to September 5$193
DCAPortlandJuly 27 to July 31$240
PHLPortlandAugust 17 to August 20$298
CLTPortlandAugust 22 to August 29$330
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
MCOPortlandJuly 11 to July 14$353
RDUPortlandJuly 12 to July 15$378
TPAPortlandJuly 12 to July 13$425
DCAPortlandJuly 11 to July 12$441
JFKAugustaJuly 11 to July 25$466
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 12 to July 15$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.
Boston Harbor Hotel
5.0-star property

Boston Harbor Hotel

Sep 4 - Sep 7

3 night stay

Dallas (DAL) to Boston (BOS)

Southwest Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $2,079, price is now $1,209 per person
$1,209
per person
found 1 day ago
The Atlas Hotel
4.5-star property

The Atlas Hotel

Sep 23 - Sep 30

7 night stay

Dallas (DAL) to Boston (BOS)

Delta • Coach

Boston (BOS) to Dallas (DAL)

Frontier Airlines • Coach
Save 100% on your flight
Price was $2,339, price is now $1,344 per person
$1,344
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
Don't see what you're looking for?
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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 $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 19 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 $1,187. 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.