$119 Cheap flights to Cumberland County

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Top places to visit in Cumberland County

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

Portland
A crowded beach with people sunbathing and swimming, surrounded by houses and lush green hills.
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Scarborough

Scarborough
A red car driving on a street with a brick building and a church in the background.
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Brunswick

Brunswick

Cheap flights to Cumberland County from $119 One Way, $237 Round Trip

$237 return flights and $119 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, Oct 17 - Tue, Oct 20
JFK
New York
PWM
Portland
$237 Roundtrip, found 1 day ago
$237
Roundtrip
found 1 day ago
Select JetBlue Airways flight, departing Sat, Oct 17 from New York to Portland, returning Tue, Oct 20, priced at $237 found 1 day ago
Sat, Oct 17 - Tue, Oct 20
JFK
New York
PWM
Portland
$237 Roundtrip, found 1 day ago
$237
Roundtrip
found 1 day ago
Select Delta flight, departing Sat, Oct 17 from New York to Portland, returning Tue, Oct 20, priced at $237 found 1 day ago
Tue, Oct 27 - Wed, Nov 4
DCA
Washington
PWM
Portland
$249 Roundtrip, found 6 hours ago
$249
Roundtrip
found 6 hours ago
Select American Airlines flight, departing Tue, Oct 27 from Washington to Portland, returning Wed, Nov 4, priced at $249 found 6 hours ago
Sat, Sep 5 - Sat, Sep 12
ORD
Chicago
PWM
Portland
$256 Roundtrip, found 3 days ago
$256
Roundtrip
found 3 days ago
Select American Airlines flight, departing Sat, Sep 5 from Chicago to Portland, returning Sat, Sep 12, priced at $256 found 3 days ago
Mon, Sep 7 - Fri, Sep 11
ORD
Chicago
PWM
Portland
$266 Roundtrip, found 7 hours ago
$266
Roundtrip
found 7 hours ago
Select United flight, departing Mon, Sep 7 from Chicago to Portland, returning Fri, Sep 11, priced at $266 found 7 hours ago
Fri, Oct 30 - Mon, Nov 2
DEN
Denver
PWM
Portland
$328 Roundtrip, found 6 days ago
$328
Roundtrip
found 6 days ago
Select JetBlue Airways flight, departing Fri, Oct 30 from Denver to Portland, returning Mon, Nov 2, priced at $328 found 6 days ago

Deals For This Weekend's Flights

OriginDestinationTravel DatesFlights From*
DCAPortlandAugust 15 to August 22$323
MCOPortlandAugust 14 to August 18$326
RDUPortlandAugust 15 to August 22$344
EWRPortlandAugust 16 to August 23$347
TPAPortlandAugust 15 to August 18$414
CLTPortlandAugust 15 to August 22$427
TTNPortlandAugust 15 to August 16$540
DCAAugustaAugust 15 to August 29$543
EWRAugustaAugust 16 to August 26$546
ATLPortlandAugust 14 to August 17$668
SEAPortlandAugust 15 to August 22$891
*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
Fully refundable
$131 nightly
The price is $145 total per night from Sep 1 to Sep 2
$145 total
Sep 1 - Sep 2
Total with taxes and fees
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 ...
8.2/10 Very Good! (1,611 reviews)
"The wallpaper coming off the walls. Dust at every corner, my throat was inching from mold I believe. The ceiling was stained from water leak."

Reviewed on Aug 8, 2026

Opens in a new windowClarion Hotel Portland Airport ME
Portland Regency Hotel & Spa

Portland Regency Hotel & Spa

3.5 out of 5
20 Milk Street Portland ME
Fully refundableReserve now, pay when you stay
$355 nightly
The price is $393 total per night from Aug 30 to Aug 31
$393 total
Aug 30 - Aug 31
Total with taxes and fees
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! (1,725 reviews)
"Great location. Beautiful historic property. I felt updated and modernized. Definitely recommend."

Reviewed on Aug 8, 2026

Opens in a new windowPortland Regency Hotel & Spa
Fireside Inn & Suites Portland

Fireside Inn & Suites Portland

3 out of 5
81 Riverside St Portland ME
Fully refundableReserve now, pay when you stay
$106 nightly
The price is $117 total per night from Sep 8 to Sep 9
$117 total
Sep 8 - Sep 9
Total with taxes and fees
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 ...
Opens in a new windowFireside Inn & Suites Portland
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Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
468 Fore Street Portland ME
Fully refundableReserve now, pay when you stay
$357 nightly
The price is $395 total per night from Sep 8 to Sep 9
$395 total
Sep 8 - Sep 9
Total with taxes and fees
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 ...
9.2/10 Wonderful! (1,801 reviews)
"We had a shower that leaked all the way out to the foyer. We called and reported it. They sent a repair person. They caulked around the edge which helped but didn’t fix the whole problem. It still leaked, just not as bad. No one followed up to see if it was fixed. They have a pantry on each floor ..."

Reviewed on Aug 7, 2026

Opens in a new windowPortland Harbor Hotel
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?

Mini Van

Chrysler Pacifica
  • 7 people
  • Unlimited mileage
Portland, Maine, USA
Chrysler Pacifica

$79

$306 total
found 10 hours ago
Mini Van Chrysler Pacifica

Economy

Mitsubishi Mirage
  • 4 people
  • Unlimited mileage
Portland, Maine, USA
Mitsubishi Mirage

$80

$289 total
found 10 hours ago
Economy Mitsubishi Mirage

Compact

Nissan Versa
  • 5 people
  • Unlimited mileage
Portland, Maine, USA
Nissan Versa

$81

$292 total
found 10 hours ago
Compact Nissan Versa

Special

Vehicle determined upon pick-up Compact or Larger
  • 5 people
  • Unlimited mileage
Portland, Maine, USA
Vehicle determined upon pick-up Compact or Larger

$81

$292 total
found 10 hours ago
Special Vehicle determined upon pick-up Compact or Larger
Lowest prices found within the past 10 hours. Prices and availability subject to change. Additional terms may apply.

Cumberland County

If you are looking for discount prices on flights to Cumberland County then look no further than Orbitz. With some of the best deals available, cutting-edge technology, and great customer service, Orbitz makes booking Cumberland County flights easy and affordable.

Booking Made Easy

With Orbitz’s Display Matrix, booking flights to Cumberland County is simple. Just one glance gives you all the pricing information you need, including your discounts and savings. View all your options before selecting and booking your perfect Cumberland County flights.

Manage Travel Plans on the Move

By using Orbitz’s free apps for iPhone and Android, and an easy-to-use mobile browser at m.orbitz.com, booking flights to Cumberland County has never been so convenient. Check for updates and alerts wherever you are, or manage your booking quickly. And we also offer mobile exclusive deals on hotels, so don’t delay—book right away.

The Complete Package

Orbitz makes it stress-free to book Cumberland County flights, and we can also help you figure out the rest of your trip just as easily. If you need great deals on hotels and car rentals following your flights to Cumberland County, just add the details to your booking and search for the cheapest deals out there. And why waste time lining up for admission to attractions and events? With Orbitz, you can book tickets in advance and waltz straight in.

Low Price Guarantee

Booking your Cumberland County flights with Orbitz guarantees low prices every day, all day—no matter when and where you book. You will always find the best deals available, coupled with extra great savings and discounts for all around great value.

Frequently asked questions

Which airlines fly to Cumberland County?
There are 12 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 $237 and $891 this week. Starting your journey from Chicago (ORD)? The cheapest one-way fares started at just $119.
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.