Flights To Cumberland County - Cheap Flights Starting at CA $109

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

Portland

Flights
Portland
A brick building with green shutters, a tree with red leaves, and a street with people walking.

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.

Mon, Sep 7 - Fri, Sep 11
CVG
Cincinnati - Northern Kentucky Intl.
PWM
Portland Intl. Jetport
CA $199 Roundtrip, found 3 days ago
CA $199
Roundtrip
found 3 days ago
Select Breeze Airways flight, departing Mon, Sep 7 from Cincinnati - Northern Kentucky Intl. to Portland Intl. Jetport, returning Fri, Sep 11, priced at CA $199 found 3 days ago
Mon, Sep 14 - Fri, Sep 18
CVG
Cincinnati - Northern Kentucky Intl.
PWM
Portland Intl. Jetport
CA $228 Roundtrip, found 4 days ago
CA $228
Roundtrip
found 4 days ago
Select Breeze Airways flight, departing Mon, Sep 14 from Cincinnati - Northern Kentucky Intl. to Portland Intl. Jetport, returning Fri, Sep 18, priced at CA $228 found 4 days ago
Mon, Sep 7 - Mon, Sep 14
CVG
Cincinnati - Northern Kentucky Intl.
PWM
Portland Intl. Jetport
CA $250 Roundtrip, found 3 days ago
CA $250
Roundtrip
found 3 days ago
Select Breeze Airways flight, departing Mon, Sep 7 from Cincinnati - Northern Kentucky Intl. to Portland Intl. Jetport, returning Mon, Sep 14, priced at CA $250 found 3 days ago
Fri, Aug 28 - Mon, Aug 31
CVG
Cincinnati - Northern Kentucky Intl.
PWM
Portland Intl. Jetport
CA $272 Roundtrip, found 4 days ago
CA $272
Roundtrip
found 4 days ago
Select Breeze Airways flight, departing Fri, Aug 28 from Cincinnati - Northern Kentucky Intl. to Portland Intl. Jetport, returning Mon, Aug 31, priced at CA $272 found 4 days ago
Mon, Oct 12 - Mon, Oct 19
CVG
Cincinnati - Northern Kentucky Intl.
PWM
Portland Intl. Jetport
CA $301 Roundtrip, found 3 days ago
CA $301
Roundtrip
found 3 days ago
Select Breeze Airways flight, departing Mon, Oct 12 from Cincinnati - Northern Kentucky Intl. to Portland Intl. Jetport, returning Mon, Oct 19, priced at CA $301 found 3 days ago
Fri, Sep 25 - Mon, Sep 28
CVG
Cincinnati - Northern Kentucky Intl.
PWM
Portland Intl. Jetport
CA $334 Roundtrip, found 4 days ago
CA $334
Roundtrip
found 4 days ago
Select Breeze Airways flight, departing Fri, Sep 25 from Cincinnati - Northern Kentucky Intl. to Portland Intl. Jetport, returning Mon, Sep 28, priced at CA $334 found 4 days ago
Fri, Oct 9 - Mon, Oct 12
CVG
Cincinnati - Northern Kentucky Intl.
PWM
Portland Intl. Jetport
CA $420 Roundtrip, found 14 hours ago
CA $420
Roundtrip
found 14 hours ago
Select Breeze Airways flight, departing Fri, Oct 9 from Cincinnati - Northern Kentucky Intl. to Portland Intl. Jetport, returning Mon, Oct 12, priced at CA $420 found 14 hours ago
Tue, Sep 29 - Fri, Oct 16
YVR
Vancouver Intl.
PWM
Portland Intl. Jetport
CA $428 Roundtrip, found 2 days ago
CA $428
Roundtrip
found 2 days ago
Select United flight, departing Tue, Sep 29 from Vancouver Intl. to Portland Intl. Jetport, returning Fri, Oct 16, priced at CA $428 found 2 days ago
Thu, Sep 10 - Thu, Sep 17
YYZ
Pearson Intl.
PWM
Portland Intl. Jetport
CA $593 Roundtrip, found 4 days ago
CA $593
Roundtrip
found 4 days ago
Select Delta flight, departing Thu, Sep 10 from Pearson Intl. to Portland Intl. Jetport, returning Thu, Sep 17, priced at CA $593 found 4 days ago
OriginDestinationTravel datesFlights from*
RDUPortlandOctober 24 to October 31CA $197
TPAPortlandOctober 31 to November 7CA $225
MCOPortlandNovember 14 to November 16CA $254
JFKPortlandNovember 6 to November 9CA $301
DCAPortlandOctober 3 to October 10CA $364
ATLPortlandNovember 5 to November 11CA $400
*Prices include taxes and fees
OriginDestinationTravel datesFlights from*
JFKPortlandAugust 29 to September 5CA $335
TPAPortlandAugust 30 to September 3CA $930
*Prices include taxes and fees
Price found within the past 48 hours. Click for updated prices.
Boston Harbor Hotel
5.0-star property

Boston Harbor Hotel

Nov 11 - Nov 13

2 night stay

Montreal (YMQ) to Boston (BOS)

Porter Airlines • Non-stop roundtrip • Coach
Price was CA $1,804, price is now CA $1,246 per person
CA $1,246
per person
found 16 hours ago
By the Sea Guests Bed & Breakfast & Suites
3.5-star property

By the Sea Guests Bed & Breakfast & Suites

Aug 27 - Sep 1

5 night stay

Toronto (YYZ) to Boston (BOS)

Porter Airlines • Roundtrip • Coach
Price was CA $4,780, price is now CA $3,348 per person
CA $3,348
per person
found 1 day ago
Four Seasons Hotel Boston
5.0-star property

Four Seasons Hotel Boston

Sep 4 - Sep 7

3 night stay

Montreal (YMQ) to Boston (BOS)

Porter Airlines • Roundtrip • Coach
Price was CA $3,051, price is now CA $2,191 per person
CA $2,191
per person
found 1 day ago
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Travelers ❤️ These Cumberland County 🏨

Clarion Hotel Portland Airport ME

Clarion Hotel Portland Airport ME

2.5 out of 5
1230 Congress St Portland ME
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 clean rooms in our reviews. Popular attractions Thompson's Point and Maine Mall are located nearby.
8/10 Very good! (1,634 reviews)
"Parking was convenient. Close to the place we needed to be."

Reviewed on Aug 21, 2026

Opens in a new windowClarion Hotel Portland Airport ME
Fireside Inn & Suites Portland

Fireside Inn & Suites Portland

3 out of 5
81 Riverside St Portland ME
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 rooms in our reviews. Popular attractions Maine Mall and Thompson's Point are located nearby.
8.2/10 Very good! (1,056 reviews)
"The room is clean"

Reviewed on Aug 22, 2026

Opens in a new windowFireside Inn & Suites Portland
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 State Theatre and Thompson's Point are located nearby.
9.4/10 Exceptional! (1,751 reviews)
"The location was perfect. However, the front desk staff wasn’t overly helpful-friendly. Also, we had 4 adults sharing one room, the room had two double beds and was really crowded."

Reviewed on Aug 22, 2026

Opens in a new windowPortland Regency Hotel & Spa
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The Westin Portland Harborview

The Westin Portland Harborview

4 out of 5
157 High St Portland ME
Book a stay at this spa hotel in Portland. Enjoy free WiFi, a full-service spa, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Thompson's Point and Portland Head Light are located nearby.
9/10 Wonderful! (1,006 reviews)
"Friendly welcome staff. Clean room."

Reviewed on Aug 21, 2026

Opens in a new windowThe Westin Portland Harborview
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 $197. 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 17 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, September 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 $197. 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 $197 and CA $930. 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.