$86 Cheap flights to Cumberland County

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Top places to visit in Cumberland County

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Portland

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Scarborough

Scarborough
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Brunswick

Brunswick

Cheap flights to Cumberland County from $86 One Way, $149 Round Trip

$149 return flights and $86 one-way flights to Cumberland County were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Sat, Aug 22 - Wed, Aug 26
JFK
New York
PWM
Portland
$149 Roundtrip, found 22 hours ago
$149
Roundtrip
found 22 hours ago
Select JetBlue Airways flight, departing Sat, Aug 22 from New York to Portland, returning Wed, Aug 26, priced at $149 found 22 hours ago
Tue, Jul 7 - Sat, Jul 11
JFK
New York
PWM
Portland
$149 Roundtrip, found 1 day ago
$149
Roundtrip
found 1 day ago
Select Delta flight, departing Tue, Jul 7 from New York to Portland, returning Sat, Jul 11, priced at $149 found 1 day ago
Wed, Jul 8 - Wed, Jul 22
JFK
New York
PWM
Portland
$153 Roundtrip, found 21 hours ago
$153
Roundtrip
found 21 hours ago
Select JetBlue Airways flight, departing Wed, Jul 8 from New York to Portland, returning Wed, Jul 22, priced at $153 found 21 hours ago
Fri, Aug 28 - Tue, Sep 1
JFK
New York
PWM
Portland
$157 Roundtrip, found 20 hours ago
$157
Roundtrip
found 20 hours ago
Select Delta flight, departing Fri, Aug 28 from New York to Portland, returning Tue, Sep 1, priced at $157 found 20 hours ago
Tue, Aug 11 - Sat, Aug 15
JFK
New York
PWM
Portland
$159 Roundtrip, found 12 hours ago
$159
Roundtrip
found 12 hours ago
Select JetBlue Airways flight, departing Tue, Aug 11 from New York to Portland, returning Sat, Aug 15, priced at $159 found 12 hours ago
Tue, Sep 1 - Wed, Sep 2
ORD
Chicago
PWM
Portland
$169 Roundtrip, found 2 days ago
$169
Roundtrip
found 2 days ago
Select JetBlue Airways flight, departing Tue, Sep 1 from Chicago to Portland, returning Wed, Sep 2, priced at $169 found 2 days ago
Sat, Aug 22 - Wed, Aug 26
LAX
Los Angeles
PWM
Portland
$271 Roundtrip, found 5 days ago
$271
Roundtrip
found 5 days ago
Select Southwest Airlines flight, departing Sat, Aug 22 from Los Angeles to Portland, returning Wed, Aug 26, priced at $271 found 5 days ago
Tue, Aug 18 - Tue, Sep 1
ONT
Ontario
PWM
Portland
$287 Roundtrip, found 2 days ago
$287
Roundtrip
found 2 days ago
Select Delta flight, departing Tue, Aug 18 from Ontario to Portland, returning Tue, Sep 1, priced at $287 found 2 days ago
Tue, Aug 18 - Tue, Aug 25
LAX
Los Angeles
PWM
Portland
$296 Roundtrip, found 3 days ago
$296
Roundtrip
found 3 days ago
Select JetBlue Airways flight, departing Tue, Aug 18 from Los Angeles to Portland, returning Tue, Aug 25, priced at $296 found 3 days ago
Fri, Aug 28 - Fri, Sep 4
BUR
Burbank
PWM
Portland
$297 Roundtrip, found 2 days ago
$297
Roundtrip
found 2 days ago
Select Southwest Airlines flight, departing Fri, Aug 28 from Burbank to Portland, returning Fri, Sep 4, priced at $297 found 2 days ago
Tue, Aug 18 - Tue, Sep 1
ONT
Ontario
PWM
Portland
$302 Roundtrip, found 2 days ago
$302
Roundtrip
found 2 days ago
Select Delta flight, departing Tue, Aug 18 from Ontario to Portland, returning Tue, Sep 1, priced at $302 found 2 days ago
Tue, Aug 18 - Tue, Sep 1
ONT
Ontario
PWM
Portland
$302 Roundtrip, found 2 days ago
$302
Roundtrip
found 2 days ago
Select American Airlines flight, departing Tue, Aug 18 from Ontario to Portland, returning Tue, Sep 1, priced at $302 found 2 days ago
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Deals For This Weekend's Flights

OriginDestinationTravel DatesFlights From*
JFKPortlandJune 21 to June 30$290
MCOPortlandJune 19 to June 22$308
RDUPortlandJune 20 to June 22$424
DCAPortlandJune 20 to June 20$436
CLTPortlandJune 20 to June 26$458
TPAPortlandJune 21 to June 24$476
TTNPortlandJune 20 to June 24$504
EWRAugustaJune 19 to June 22$595
DCAAugustaJune 19 to June 22$679
ATLPortlandJune 19 to June 22$681
SEAPortlandJune 19 to June 21$748
*Prices include taxes and fees

Find The Perfect Hotel For After Your Flight

Score Epic Cumberland County Accommodation Deals

Clarion Hotel Portland Airport ME

Clarion Hotel Portland Airport ME

2.5 out of 5
1230 Congress St Portland ME
The price is $140 total per night from Jun 22 to Jun 23
$140 total
per night
Jun 22 - Jun 23
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 ...
8/10 Very Good! (1,506 reviews)
"Stayed at the Clarion a couple nights and even though the main lobby/pool area was clean, our room was not. When we first went into the room, there was a used bar of soap on the floor as well as the shampoo and conditioners being half way full, showing that they were used. I told the front desk and ..."

Reviewed on Jun 15, 2026

Opens in a new windowClarion Hotel Portland Airport ME
Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
468 Fore Street Portland ME
The price is $386 total per night from Jul 5 to Jul 6
$386 total
per night
Jul 5 - Jul 6
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 ...
9.4/10 Exceptional! (1,785 reviews)
"We had a great stay! Everyone was so nice, helpful, and efficient! We loved the location. Portland is an amazing city! Wasn’t aware of the $35 a day charges but it worked out!"

Reviewed on Jun 12, 2026

Opens in a new windowPortland Harbor Hotel
Portland Regency Hotel & Spa

Portland Regency Hotel & Spa

3.5 out of 5
20 Milk Street Portland ME
The price is $302 total per night from Jun 21 to Jun 22
$302 total
per night
Jun 21 - Jun 22
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 ...
9.4/10 Exceptional! (1,697 reviews)
"R"

Reviewed on Jun 16, 2026

Opens in a new windowPortland Regency Hotel & Spa
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Cambria Hotel Portland Downtown-Old Port

Cambria Hotel Portland Downtown-Old Port

3 out of 5
25 HANCOCK STREET Portland ME
Fully refundableReserve now, pay when you stay
The price is $335 total per night from Jun 21 to Jun 22
$335 total
per night
Jun 21 - Jun 22
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 ...
9.4/10 Exceptional! (1,254 reviews)
"The Cambria is a perfect location to everything is the Old Portland area. You can walk with ease to restaurants, shopping, bike rentals, bars, etc. The property is updated, immaculate and the attendants are friendly. My only issue was the people above us kept me from sleeping. It was as if someone ..."

Reviewed on Jun 15, 2026

Opens in a new windowCambria Hotel Portland Downtown-Old Port
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.

Need a Car For After Your Flight?

Economy

Chevrolet Spark
  • 4 people
Chevrolet Spark
Economy Chevrolet Spark

Compact

Ford Focus
  • 4 people
Ford Focus
Compact Ford Focus

Midsize

Toyota Corolla
  • 5 people
Toyota Corolla
Midsize Toyota Corolla

SUV

Jeep Compass
  • 5 people
Jeep Compass
SUV Jeep Compass

Cumberland County

Finding cheap flights to Cumberland County is easy when you have Orbitz at your fingertips. Not only does Orbitz offer great deals on Cumberland County flights, but we also include some special extras to make booking a breeze. Just check out our:

Mobile Site and Apps

With Orbitz’s mobile site, m.orbitz.com, you can book your flights to Cumberland County through your smartphone or tablet’s Web browser. Plus, our free downloadable apps for Android and iPhone mean it’s just a simple click to access your flight updates and alerts. You can even book exclusive mobile-only deals on hotels to go with your flights to Cumberland County—even on the same day.

Pick and Choose or Book Full Vacation Packages

Don’t just be satisfied with great deals on Cumberland County flights—go for the full package! With Orbitz, you can also find fantastic savings on the perfect hotel, car rental, cruise, and even activities, so you don’t waste your trip waiting in line but have the time to enjoy your trip. Pick and choose the add-ons you need, or book an entire vacation package for greater overall discounts.

Rewards That Are Miles Better

Booking directly with an airline earns you air miles or points, and you can get those same rewards with booking on Orbitz too. When you book qualifying flights to Cumberland County with Orbitz, just add in your frequent flyer number during your online booking and your details will be sent to your program.

Great Deals Every Day

Add in our extra savings on packages, free nights, and other discounts, and you know you are in good hands.

Frequently asked questions

Which airlines fly to Cumberland County?
There are 24 airlines that travel to Portland Intl. Jetport Airport (PWM). With this many to select from, there's a great chance you'll land a low-cost flight! Your Cumberland County vacation awaits with one of these leading carriers:

  • Delta - 168 flights to Cumberland County per month
  • American Airlines - 136 flights to Cumberland County per month
  • United Airlines - 114 flights to Cumberland County per month

What is the best airport to fly to in Cumberland County?
Touch down at Portland Intl. Jetport Airport (PWM), the main entry point to Cumberland County. Organizing your flight to this region doesn't get much easier.
How much is a flight to Cumberland County?
Travelers from near and far picked up round-trip deals ranging between $149 and $748 this week. Starting your journey from Chicago (ORD)? The cheapest one-way fares started at just $86.
How to book the cheapest flight to Cumberland County?
Using Orbitz, you'll find some of the best flight deals around from a terrific range of airlines. But if you'd love to improve your chances of snapping up cheap flights to Cumberland County, here are some tips to follow:

  • Consider taking off from or landing at other airports to save on your flight. Enter your preferred departure and arrival airports in the form fields, then click on the 'Nearby airports' function below. It will list your options, if any.
  • If your travel plans aren't cast in stone, click on the 'Show flexible dates' link to see the flight deals for alternative departure dates. You may find a cheaper fare.
  • You can also select the 'Show options' function to filter results for your preferred carrier, seating class, and nonstop and refundable flights. Under 'Sort & Filter' to the left, you can even choose the time of day you want to fly.
  • Once you've worked out your travel dates, don't wait to book. Ticket prices normally climb as the departure date gets closer.
  • Make serious savings on your adventure by combining your flights, hotels and car rentals into a package. Your budget will thank you for it.
  • If it's an option, avoid flying in peak seasons. Airfares significantly increase during school breaks, summer and around other vacation times like Easter and Christmas.

How long is a flight to Cumberland County?
You could have time to read a few chapters or more of your novel, or you might plow through the entire thing! The length of a flight depends on the place of departure, but these well-known routes to Cumberland County will give you some insight:

  • New York, NY (LGA-LaGuardia) to Portland Intl. Jetport Airport (PWM) - 1 hour and 29 minutes
  • New York, NY (JFK-John F. Kennedy Intl.) to Portland Intl. Jetport Airport (PWM) - 1 hour and 22 minutes
  • Newark, NJ (EWR-Liberty Intl.) to Portland Intl. Jetport Airport (PWM) - 1 hour and 20 minutes

What is the best time to book a flight to Cumberland County?
Generally speaking, January is the cheapest month to book your airfare. This is followed by February and August. Keep this in mind while tracking down a cheap flight to Cumberland County.
What day of the week is the cheapest to book a flight to Cumberland County?
When it comes to cheap airfares to Cumberland County, the best days to book are generally Tuesdays, Wednesdays and Saturdays. A fantastic flight deal is just a few clicks away with Orbitz.
What is the cheapest day of the week to fly to Cumberland County?
According to Orbitz data from 2020, Monday is usually the best day of the week for cheap flights to Cumberland County. Tuesday also has more affordable fares, whereas Saturday has the highest ticket rates. Even though leaving at the weekend may be more convenient, you'll have more money to play with if you set off earlier in the week.
What is the cheapest month to fly to Cumberland County?
If you have some flexibility with your travel dates, think about departing in August. Orbitz data shows that this is generally the best month to take a trip if you want cheap flights to Cumberland County. As you might imagine, airfares get pricier in June and flights sell out quickly.
Which airlines allow free cancellation?
If you suspect your travel plans may change, Orbitz will help you find a flexible ticket. All you need to do is choose "Filter by flexible change policies" when searching for your perfect flight. We'll show you airlines that include free cancellation and no change fees — in addition to our awesome low prices.
What do I need for the flight to Cumberland County?
There is so much to plan for any big journey, so it's good to get a little bit of help along the way. Here are a few suggestions to ensure that you're ready for your flight:

  • Make sure you've packed your travel papers and identification. For international trips, you'll need to take your passport. When reserving your tickets, always use the same name, birth date and gender as indicated on your government-issued ID.
  • A well-packed carry-on bag is just the ticket for a comfortable flight experience. Given this journey to Cumberland County is no quick hop, take enough snacks and things to keep you occupied. A book, magazine or e-reader will help the hours pass.
  • Regardless what the season is at your destination, plane cabins can feel a little chilly. Bring a sweater on your journey to stay cozy and warm.

How many direct flights are there to Cumberland County?
At the moment, there are 92 direct flights every month to Cumberland County. When it comes to airlines that will take you there, you have loads of options. American Airlines, Delta Air Lines and United Airlines are among the most well-known. Southwest Airlines, JetBlue Airways and Sun Country Airlines are some other dependable carriers that offer nonstop services.
How do I get cheap first-class/business deals to Cumberland County?
Experienced travelers have mastered the art of finding first or business-class airfares to Cumberland County that don't cost a packet. Take their lead with these helpful hints:

  • Be flexible. By being open to a range of travel dates, you'll have more chances of picking up a great deal on first or business-class airfares.
  • Many low-cost airlines nowadays have terrific business or premium-class seating that doesn't cost the earth.
  • Make a bid for an upgrade. Some airlines hold online auctions that let you offer a price for a seat at the front of the plane. You may also be able to upgrade with points earned through a loyalty scheme.

What is the best time to go to Cumberland County?
Cumberland County is a lively place in March, July and August. If you plan to visit during these months, it may be an idea to book early to ensure you score the greatest deals. Wondering what the summer's like in Cumberland County? Average daily temperatures typically range between 55 ºF and 75 ºF. Like most destinations in the Northern Hemisphere, summer begins June 20 here.

Fare, taxes & fees: Fares include all taxes and fees, except baggage fees. Rates shown reflect fares found by other Orbitz users over the past 7 days. Due to rapidly changing airline prices & seat availability, these fares may no longer be available.

Refunds/changes/cancellations: Itinerary changes, if permitted for the fare, will have a $30 service fee charged by Orbitz. Additional airline charges may apply.

Other conditions: Schedules, fares and rules are subject to change without notice. Seats are limited and may not be available on all flights/dates or in all markets. Lower fares may be available. Fares will not be honored retroactively or in exchange for any wholly/partially unused ticket. Tickets are non-transferable and non-refundable. Fare rules are provided for the selected itinerary before booking.