Flights To Cumberland County - Cheap Flights Starting at CA $113

Wander Wisely with exceptional service, 24/7 supportOpens in a new window

Feel at ease with free flight cancellations within 24 hours of booking

Change your flight without a fee on select flights

Jet to one of Cumberland County's top cities

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.

Sat, Oct 31 - Sat, Nov 7
TPA
Tampa Intl.
PWM
Portland Intl. Jetport
CA $225 Roundtrip, found 5 days ago
CA $225
Roundtrip
found 5 days ago
Select Breeze Airways flight, departing Sat, Oct 31 from Tampa Intl. to Portland Intl. Jetport, returning Sat, Nov 7, priced at CA $225 found 5 days ago
Sat, Oct 31 - Sat, Nov 7
TPA
Tampa Intl.
PWM
Portland Intl. Jetport
CA $278 Roundtrip, found 5 days ago
CA $278
Roundtrip
found 5 days ago
Select Delta flight, departing Sat, Oct 31 from Tampa Intl. to Portland Intl. Jetport, returning Sat, Nov 7, priced at CA $278 found 5 days ago
Sat, Oct 31 - Sat, Nov 7
TPA
Tampa Intl.
PWM
Portland Intl. Jetport
CA $280 Roundtrip, found 5 days ago
CA $280
Roundtrip
found 5 days ago
Select Breeze Airways flight, departing Sat, Oct 31 from Tampa Intl. to Portland Intl. Jetport, returning Sat, Nov 7, priced at CA $280 found 5 days ago
Sat, Oct 31 - Sat, Nov 7
TPA
Tampa Intl.
PWM
Portland Intl. Jetport
CA $283 Roundtrip, found 5 days ago
CA $283
Roundtrip
found 5 days ago
Select Breeze Airways flight, departing Sat, Oct 31 from Tampa Intl. to Portland Intl. Jetport, returning Sat, Nov 7, priced at CA $283 found 5 days ago
Tue, Sep 15 - Wed, Sep 16
TPA
Tampa Intl.
PWM
Portland Intl. Jetport
CA $312 Roundtrip, found 5 days ago
CA $312
Roundtrip
found 5 days ago
Select Breeze Airways flight, departing Tue, Sep 15 from Tampa Intl. to Portland Intl. Jetport, returning Wed, Sep 16, priced at CA $312 found 5 days ago
Thu, Nov 12 - Mon, Nov 16
TPA
Tampa Intl.
PWM
Portland Intl. Jetport
CA $313 Roundtrip, found 4 days ago
CA $313
Roundtrip
found 4 days ago
Select Breeze Airways flight, departing Thu, Nov 12 from Tampa Intl. to Portland Intl. Jetport, returning Mon, Nov 16, priced at CA $313 found 4 days ago
Sat, Oct 31 - Sat, Nov 7
TPA
Tampa Intl.
PWM
Portland Intl. Jetport
CA $330 Roundtrip, found 5 days ago
CA $330
Roundtrip
found 5 days ago
Select Delta flight, departing Sat, Oct 31 from Tampa Intl. to Portland Intl. Jetport, returning Sat, Nov 7, priced at CA $330 found 5 days ago
Sat, Oct 31 - Sat, Nov 7
TPA
Tampa Intl.
PWM
Portland Intl. Jetport
CA $330 Roundtrip, found 5 days ago
CA $330
Roundtrip
found 5 days ago
Select American Airlines flight, departing Sat, Oct 31 from Tampa Intl. to Portland Intl. Jetport, returning Sat, Nov 7, priced at CA $330 found 5 days ago
Thu, Sep 10 - Thu, Sep 17
YYZ
Pearson Intl.
PWM
Portland Intl. Jetport
CA $593 Roundtrip, found 5 days ago
CA $593
Roundtrip
found 5 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 5 days ago
Tue, Sep 22 - Tue, Sep 29
YYZ
Pearson Intl.
PWM
Portland Intl. Jetport
CA $626 Roundtrip, found 4 days ago
CA $626
Roundtrip
found 4 days ago
Select American Airlines flight, departing Tue, Sep 22 from Pearson Intl. to Portland Intl. Jetport, returning Tue, Sep 29, priced at CA $626 found 4 days ago
Sun, Sep 6 - Thu, Sep 10
YHZ
Stanfield Intl.
PWM
Portland Intl. Jetport
CA $712 Roundtrip, found 1 day ago
CA $712
Roundtrip
found 1 day ago
Select WestJet flight, departing Sun, Sep 6 from Stanfield Intl. to Portland Intl. Jetport, returning Thu, Sep 10, priced at CA $712 found 1 day ago
OriginDestinationTravel datesFlights from*
RDUPortlandOctober 24 to October 31CA $197
TPAPortlandOctober 31 to November 7CA $225
MCOPortlandNovember 4 to November 11CA $249
JFKPortlandNovember 6 to November 9CA $300
DCAPortlandOctober 3 to October 10CA $364
ATLPortlandOctober 7 to October 13CA $534
*Prices include taxes and fees
OriginDestinationTravel datesFlights from*
JFKPortlandAugust 28 to September 1CA $543
TPAPortlandAugust 30 to September 3CA $795
*Prices include taxes and fees
Price found within the past 48 hours. Click for updated prices.
Boston Lodge and Suites
4.0-star property

Boston Lodge and Suites

Oct 21 - Oct 23

2 night stay

Toronto (YYZ) to Boston (BOS)

Porter Airlines • Roundtrip • Coach
Price was CA $1,366, price is now CA $810 per person
CA $810
per person
found 17 hours ago
Boston Harbor Hotel
5.0-star property

Boston Harbor Hotel

Oct 29 - Nov 2

4 night stay

Ottawa (YOW) to Boston (BOS)

Porter Airlines • Roundtrip • Coach
Price was CA $3,230, price is now CA $2,072 per person
CA $2,072
per person
found 1 day ago
Luxury Apartments by Hyatus at Boston Everett
5.0-star property

Luxury Apartments by Hyatus at Boston Everett

Oct 1 - Oct 4

3 night stay

Toronto (YYZ) to Boston (BOS)

Porter Airlines • Roundtrip • Coach
Price was CA $2,057, price is now CA $1,374 per person
CA $1,374
per person
found 14 hours ago
Don't see what you're looking for?
See all available trips from Toronto to Cumberland County
View all trips

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.
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! (1,060 reviews)
"Great experience and highly recommend"

Reviewed on Aug 23, 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! (1,752 reviews)
"Great location (near shops, restaurants and bars). The bed was extremely comfortable."

Reviewed on Aug 22, 2026

Opens in a new windowPortland Regency Hotel & Spa
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free
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 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, October 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 $795. 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.