Flights To Cumberland County - Cheap Flights Starting at CA $245

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Portland

Flights
Portland

Freeport

Flights
Freeport

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, Aug 1 - Mon, Aug 24
ORD
O'Hare Intl.
PWM
Portland Intl. Jetport
CA $547 Roundtrip, found 1 day ago
CA $547
Roundtrip
found 1 day ago
Select JetBlue Airways flight, departing Sat, Aug 1 from O'Hare Intl. to Portland Intl. Jetport, returning Mon, Aug 24, priced at CA $547 found 1 day ago
Tue, Jun 16 - Tue, Jun 23
YYZ
Pearson Intl.
PWM
Portland Intl. Jetport
CA $550 Roundtrip, found 2 days ago
CA $550
Roundtrip
found 2 days ago
Select Delta flight, departing Tue, Jun 16 from Pearson Intl. to Portland Intl. Jetport, returning Tue, Jun 23, priced at CA $550 found 2 days ago
Sat, Aug 1 - Mon, Aug 24
ORD
O'Hare Intl.
PWM
Portland Intl. Jetport
CA $554 Roundtrip, found 1 day ago
CA $554
Roundtrip
found 1 day ago
Select JetBlue Airways flight, departing Sat, Aug 1 from O'Hare Intl. to Portland Intl. Jetport, returning Mon, Aug 24, priced at CA $554 found 1 day ago
Thu, Dec 3 - Sun, Dec 6
YVR
Vancouver Intl.
PWM
Portland Intl. Jetport
CA $561 Roundtrip, just found
CA $561
Roundtrip
just found
Select Delta flight, departing Thu, Dec 3 from Vancouver Intl. to Portland Intl. Jetport, returning Sun, Dec 6, priced at CA $561 just found
Wed, Jul 1 - Thu, Jul 2
YHZ
Stanfield Intl.
PWM
Portland Intl. Jetport
CA $583 Roundtrip, found 4 days ago
CA $583
Roundtrip
found 4 days ago
Select Delta flight, departing Wed, Jul 1 from Stanfield Intl. to Portland Intl. Jetport, returning Thu, Jul 2, priced at CA $583 found 4 days ago
Sun, Aug 2 - Mon, Aug 24
ORD
O'Hare Intl.
PWM
Portland Intl. Jetport
CA $636 Roundtrip, found 1 day ago
CA $636
Roundtrip
found 1 day ago
Select JetBlue Airways flight, departing Sun, Aug 2 from O'Hare Intl. to Portland Intl. Jetport, returning Mon, Aug 24, priced at CA $636 found 1 day ago
Wed, Sep 9 - Sun, Sep 13
ORD
O'Hare Intl.
AUG
Augusta State
CA $716 Roundtrip, found 1 day ago
CA $716
Roundtrip
found 1 day ago
Select JetBlue Airways flight, departing Wed, Sep 9 from O'Hare Intl. to Augusta State, returning Sun, Sep 13, priced at CA $716 found 1 day ago
Sat, Aug 1 - Mon, Aug 24
ORD
O'Hare Intl.
PWM
Portland Intl. Jetport
CA $740 Roundtrip, found 1 day ago
CA $740
Roundtrip
found 1 day ago
Select JetBlue Airways flight, departing Sat, Aug 1 from O'Hare Intl. to Portland Intl. Jetport, returning Mon, Aug 24, priced at CA $740 found 1 day ago
Sat, Aug 1 - Mon, Aug 24
ORD
O'Hare Intl.
PWM
Portland Intl. Jetport
CA $746 Roundtrip, found 1 day ago
CA $746
Roundtrip
found 1 day ago
Select JetBlue Airways flight, departing Sat, Aug 1 from O'Hare Intl. to Portland Intl. Jetport, returning Mon, Aug 24, priced at CA $746 found 1 day ago
Sun, Aug 2 - Mon, Aug 24
ORD
O'Hare Intl.
PWM
Portland Intl. Jetport
CA $815 Roundtrip, found 1 day ago
CA $815
Roundtrip
found 1 day ago
Select JetBlue Airways flight, departing Sun, Aug 2 from O'Hare Intl. to Portland Intl. Jetport, returning Mon, Aug 24, priced at CA $815 found 1 day ago
Tue, Jun 9 - Tue, Jun 16
DTW
Detroit Metropolitan Wayne County
AUG
Augusta State
CA $818 Roundtrip, just found
CA $818
Roundtrip
just found
Select JetBlue Airways flight, departing Tue, Jun 9 from Detroit Metropolitan Wayne County to Augusta State, returning Tue, Jun 16, priced at CA $818 just found
OriginDestinationTravel datesFlights from*
JFKPortlandJune 14 to June 23CA $243
TPAPortlandAugust 29 to September 5CA $263
MCOPortlandAugust 29 to August 31CA $333
RDUPortlandJune 10 to June 15CA $372
ATLPortlandJuly 4 to July 11CA $463
SEAPortlandJune 13 to June 15CA $604
ATLAugustaJuly 13 to July 20CA $888
*Prices include taxes and fees
OriginDestinationTravel datesFlights from*
RDUPortlandMay 30 to June 1CA $318
SEAPortlandMay 29 to June 1CA $481
*Prices include taxes and fees
Price found within the past 48 hours. Click for updated prices.
By the Sea Guests Bed & Breakfast & Suites
3.5-star property

By the Sea Guests Bed & Breakfast & Suites

Aug 3 - Aug 9

6 night stay

Halifax (YHZ) to Boston (BOS)

Air Canada • Non-stop roundtrip • Coach
Price was CA $2,492, price is now CA $1,530 per person
CA $1,530
per person
found 24 hours ago
Boston Harbor Hotel
5.0-star property

Boston Harbor Hotel

Jul 16 - Jul 20

4 night stay

Halifax (YHZ) to Boston (BOS)

Air Canada • Roundtrip • Coach
Price was CA $3,128, price is now CA $1,795 per person
CA $1,795
per person
found 1 day ago
Nantucket Inn
3.5-star property

Nantucket Inn

Aug 3 - Aug 9

6 night stay

Halifax (YHZ) to Boston (BOS)

Air Canada • Non-stop roundtrip • Coach
Price was CA $5,433, price is now CA $3,175 per person
CA $3,175
per person
found 24 hours ago
Don't see what you're looking for?
See all available trips from Halifax to Cumberland County
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Travelers ❤️ These Cumberland County 🏨

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 Thompson's Point and Maine Mall are located nearby.
9.4/10 Exceptional! (1,783 reviews)
"Staff ensured our room on check in was quiet. Except there was a night club across the street. Then when asked for a new room was told by staff “that they would bet their career it would be quiet”. The room was one floor up on the same side … Couldn’t sleep until after 1am because of the club across ..."

Reviewed on May 22, 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
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 Thompson's Point and Maine Mall are located nearby.
9.4/10 Exceptional! (1,666 reviews)
"We’ve stayed at this hotel 5 times now and have always enjoyed the historic charm and location. Check-in during this stay went smoothly, however we were disappointed when we arrived to find the toilet in our room was dirty. We also asked the front desk if the TVs allowed streaming services like Netflix ..."

Reviewed on May 20, 2026

Opens in a new windowPortland Regency Hotel & Spa
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 Thompson's Point and Maine Mall are located nearby.
9.4/10 Exceptional! (1,216 reviews)
"Clean room, nice location. Wish the tv was a smart tv, and found the $25/room sort of annoying since the restaurant on property was understaffed. But overall we enjoyed it."

Reviewed on May 21, 2026

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

HomeAwhile

2 out of 5
205 Southborough Drive Scarborough ME
Stay at this hotel in Scarborough. Enjoy free WiFi, free parking, and a 24-hour front desk. Popular attractions Maine Mall and Thompson's Point are located nearby.
9.2/10 Wonderful! (47 reviews)
"Room was spacious ( home away from home for sure!) and very clean. The staff was extremely friendly and gave us great suggestions on where to eat since we were visiting! Will definitely come back if I ever visit Portland again."

Reviewed on May 22, 2026

Opens in a new windowHomeAwhile
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 CA $243. 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 20 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 CA $243. 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 CA $243 and CA $888. 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.