Cheap Flights to Cumberland County from $78 (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.

Wed, Aug 5 - Sat, Aug 8
JFK
John F. Kennedy Intl.
PWM
Portland Intl. Jetport
$149 Roundtrip, found 6 hours ago
$149
Roundtrip
found 6 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 $149 found 6 hours ago
Tue, Sep 1 - Wed, Sep 2
JFK
John F. Kennedy Intl.
PWM
Portland Intl. Jetport
$153 Roundtrip, found 4 hours ago
$153
Roundtrip
found 4 hours ago
Select JetBlue Airways flight, departing Tue, Sep 1 from John F. Kennedy Intl. to Portland Intl. Jetport, returning Wed, Sep 2, priced at $153 found 4 hours ago
Wed, Aug 19 - Fri, Aug 21
JFK
John F. Kennedy Intl.
PWM
Portland Intl. Jetport
$157 Roundtrip, found 5 hours ago
$157
Roundtrip
found 5 hours ago
Select JetBlue Airways flight, departing Wed, Aug 19 from John F. Kennedy Intl. to Portland Intl. Jetport, returning Fri, Aug 21, priced at $157 found 5 hours ago
Wed, Aug 19 - Fri, Aug 21
JFK
John F. Kennedy Intl.
PWM
Portland Intl. Jetport
$161 Roundtrip, found 5 hours ago
$161
Roundtrip
found 5 hours ago
Select JetBlue Airways flight, departing Wed, Aug 19 from John F. Kennedy Intl. to Portland Intl. Jetport, returning Fri, Aug 21, priced at $161 found 5 hours ago
Fri, Aug 21 - Sun, Aug 23
JFK
John F. Kennedy Intl.
PWM
Portland Intl. Jetport
$165 Roundtrip, found 19 hours ago
$165
Roundtrip
found 19 hours ago
Select JetBlue Airways flight, departing Fri, Aug 21 from John F. Kennedy Intl. to Portland Intl. Jetport, returning Sun, Aug 23, priced at $165 found 19 hours ago
Wed, Oct 7 - Wed, Oct 7
BOS
Logan Intl.
AUG
Augusta State
$174 Roundtrip, found 1 day ago
$174
Roundtrip
found 1 day ago
Select Cape Air flight, departing Wed, Oct 7 from Logan Intl. to Augusta State, returning Wed, Oct 7, priced at $174 found 1 day ago
Mon, Oct 26 - Thu, Oct 29
JFK
John F. Kennedy Intl.
PWM
Portland Intl. Jetport
$181 Roundtrip, found 17 hours ago
$181
Roundtrip
found 17 hours ago
Select Delta flight, departing Mon, Oct 26 from John F. Kennedy Intl. to Portland Intl. Jetport, returning Thu, Oct 29, priced at $181 found 17 hours ago
Wed, Sep 23 - Sat, Sep 26
DCA
Ronald Reagan Washington National
PWM
Portland Intl. Jetport
$207 Roundtrip, found 3 hours ago
$207
Roundtrip
found 3 hours ago
Select American Airlines flight, departing Wed, Sep 23 from Ronald Reagan Washington National to Portland Intl. Jetport, returning Sat, Sep 26, priced at $207 found 3 hours ago
OriginDestinationTravel DatesFlights From*
RDUPortlandAugust 25 to September 1$145
JFKPortlandAugust 5 to August 8$149
TPAPortlandSeptember 19 to September 23$178
DCAPortlandSeptember 23 to September 26$207
ATLPortlandSeptember 10 to September 15$295
PHLPortlandAugust 17 to August 20$298
CLTPortlandSeptember 16 to September 21$313
JFKAugustaJuly 30 to August 6$432
PHLAugustaSeptember 18 to September 21$432
TPAAugustaJuly 28 to July 29$470
RDUAugustaAugust 12 to August 26$487
ATLAugustaSeptember 4 to September 8$492
MCOAugustaOctober 2 to October 6$493
DCAAugustaAugust 1 to August 8$662
SEAAugustaAugust 20 to August 25$675
*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
MCOPortlandJuly 11 to July 13$456
JFKAugustaJuly 11 to July 25$466
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.
The Groton Inn
3.5-star property

The Groton Inn

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 $975, price is now $620 per person
$620
per person
found 1 day ago
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
Meco Hotel - Hostel
2.0-star property

Meco Hotel - Hostel

Jul 16 - Jul 20

4 night stay

Dallas (DAL) to Boston (BOS)

Southwest Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $2,087, price is now $1,329 per person
$1,329
per person
found 1 day ago
Don't see what you're looking for?
See all available trips from Detroit to Cumberland County
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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! (2,193 reviews)
"Overall a fine place to stay but nothing special. Fridge was turned off when we arrived, coffee at breakfast was cold, and parking was a $10 daily charge. The humidity was also so bad the toilet bowl had constant condensation and dripped so much it created a puddle. The bed and pillows were comfortable ..."

Reviewed on Jul 8, 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! (1,777 reviews)
"The stay itself was quite nice, and the room was mostly cleaned, except there was an errant pill from a previous guest in the sofa. The location was very convenient, but for how much we spent... to have an additional $45 daily valet parking (in a parking lot where I can literally see my car 50 feet ..."

Reviewed on Jul 8, 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! (1,258 reviews)
"Pros: The rooms are big and spacious. Clean rooms. Well maintained Good location. Central Part of downtown. Easy access to restaurants. Gym Good size gym . All necessary equipments available. Good weights range. Cons No smart TV, was hoping to relax and watch Netflix or HBO, or HDMI port to connect ..."

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! (1,696 reviews)
"Highly recommend . The rate dropped a lot and Expedia would do nothing to match it . So search with Expedia but book directly to hotel . I wish I had done that , I would have saved a lot of money by not booking w Expedia . Hotel was great , Expedia was not my friend ."

Reviewed on Jul 8, 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 $145. 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, 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 $145. 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 $145 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.