$71 Cheap flight deals from Pittsburgh (PIT) to Casco Bay Islands (PWM)

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This Weekend's Flight Deals from Pittsburgh to Casco Bay Islands

This weekend's flight prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Sun, Oct 11 - Thu, Oct 15
PIT
Pittsburgh Intl.
PWM
Portland Intl. Jetport
$739 Roundtrip, found 2 days ago
$739
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Sun, Oct 11 from Pittsburgh Intl. to Portland Intl. Jetport, returning Thu, Oct 15, priced at $739 found 2 days ago

Airfares from $71 One Way, $142 Round Trip from Pittsburgh to Casco Bay Islands

Prices starting at $142 for return flights and $71 for one-way flights to Casco Bay Islands were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Sun, Nov 1 - Thu, Nov 5
PIT
Pittsburgh
PWM
Portland
$142 Roundtrip, found 1 hour ago
$142
Roundtrip
found 1 hour ago
Select Breeze Airways flight, departing Sun, Nov 1 from Pittsburgh to Portland, returning Thu, Nov 5, priced at $142 found 1 hour ago
Sun, Nov 1 - Thu, Nov 5
PIT
Pittsburgh
PWM
Portland
$147 Roundtrip, found 1 hour ago
$147
Roundtrip
found 1 hour ago
Select Breeze Airways flight, departing Sun, Nov 1 from Pittsburgh to Portland, returning Thu, Nov 5, priced at $147 found 1 hour ago
Sun, Nov 1 - Thu, Nov 5
PIT
Pittsburgh
PWM
Portland
$152 Roundtrip, found 1 hour ago
$152
Roundtrip
found 1 hour ago
Select Breeze Airways flight, departing Sun, Nov 1 from Pittsburgh to Portland, returning Thu, Nov 5, priced at $152 found 1 hour ago
Sun, Nov 1 - Sun, Nov 8
PIT
Pittsburgh
PWM
Portland
$152 Roundtrip, found 4 hours ago
$152
Roundtrip
found 4 hours ago
Select Breeze Airways flight, departing Sun, Nov 1 from Pittsburgh to Portland, returning Sun, Nov 8, priced at $152 found 4 hours ago
Thu, Oct 29 - Thu, Nov 5
PIT
Pittsburgh
PWM
Portland
$157 Roundtrip, found 1 hour ago
$157
Roundtrip
found 1 hour ago
Select Breeze Airways flight, departing Thu, Oct 29 from Pittsburgh to Portland, returning Thu, Nov 5, priced at $157 found 1 hour ago

Casco Bay Islands economy flight packages

Price found within the past 48 hours. Click for updated prices.
Evalina Hotel
2.5-star property

Evalina Hotel

10/10 Exceptional! (13 reviews)

Dec 1 - Dec 4

3 night stay

Pittsburgh (PIT) to Portland (PWM)

Southwest Airlines • Non-stop roundtrip • Coach
Price was $830, price is now $673 per person
$673
per person
found 16 hours ago
Centrally located in the Old Port, with views of the harbor, this was a last minute — therefore pricey — excellent find for a fall weekend getaway. Stylish, elegant rehab of 19th century granite industrial building. Whimsical decor notes referring to 19th century owner Evalina Fox. Nicely appointed kitchenette — though if you came to Portland for the foodie scene, you might end up just using it for breakfast, as we did. Only sour note was the disco music (coming in via the ventilation system?) from a nearby establishment audible during business hours. Well, if you pick a hotel in the middle of things, you get the noise and bustle that comes from being in the middle of things. That said, we’d come again, but shoot for a penthouse/upper floor unit farther from the street-level mania.

Reviewed on Oct 5, 2026

The Docent's Collection at 178 Middle Street
3.5-star property

The Docent's Collection at 178 Middle Street

9.6/10 Exceptional! (70 reviews)

Dec 1 - Dec 4

3 night stay

Pittsburgh (PIT) to Portland (PWM)

Southwest Airlines • Non-stop roundtrip • Coach
Price was $934, price is now $746 per person
$746
per person
found 16 hours ago
This place was wonderful! The staff was incredibly helpful and it was a time location for things to do and places to eat, all within walking distance. Would definitely recommend and stay again

Reviewed on Oct 7, 2026

The Docent's Collection at 121 Middle Street
3.5-star property

The Docent's Collection at 121 Middle Street

9.6/10 Exceptional! (400 reviews)

Dec 1 - Dec 4

3 night stay

Pittsburgh (PIT) to Portland (PWM)

Southwest Airlines • Non-stop roundtrip • Coach
Price was $808, price is now $696 per person
$696
per person
found 16 hours ago

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More About Flying To Casco Bay Islands from Pittsburgh

Route Information for Flights from Pittsburgh to Casco Bay Islands

Origin Airport IATA Code
PIT
Destination Airport IATA Code
PWM
Distance
Direct Flight Airlines
Earliest Flight Arrival
Latest Flight Arrival

Pittsburgh to Casco Bay Islands

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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.