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Windham

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Windham Flights as Low as $178

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Breeze Airways
Sat, Nov 7 - Sat, Nov 14
RDU
Raleigh - Durham Intl.
PWM
Portland Intl. Jetport
$178 Roundtrip, found 8 hours ago
$178
Roundtrip
found 8 hours ago
Select Breeze Airways flight, departing Sat, Nov 7 from Raleigh - Durham Intl. to Portland Intl. Jetport, returning Sat, Nov 14, priced at $178 found 8 hours ago
Breeze Airways
Sat, Nov 7 - Sat, Nov 14
RDU
Raleigh - Durham Intl.
PWM
Portland Intl. Jetport
$183 Roundtrip, found 8 hours ago
$183
Roundtrip
found 8 hours ago
Select Breeze Airways flight, departing Sat, Nov 7 from Raleigh - Durham Intl. to Portland Intl. Jetport, returning Sat, Nov 14, priced at $183 found 8 hours ago
Breeze Airways
Sat, Nov 7 - Sat, Nov 14
RDU
Raleigh - Durham Intl.
PWM
Portland Intl. Jetport
$188 Roundtrip, found 8 hours ago
$188
Roundtrip
found 8 hours ago
Select Breeze Airways flight, departing Sat, Nov 7 from Raleigh - Durham Intl. to Portland Intl. Jetport, returning Sat, Nov 14, priced at $188 found 8 hours ago
Breeze Airways
Wed, Nov 11 - Wed, Dec 2
MCO
Orlando Intl.
PWM
Portland Intl. Jetport
$194 Roundtrip, just found
$194
Roundtrip
just found
Select Breeze Airways flight, departing Wed, Nov 11 from Orlando Intl. to Portland Intl. Jetport, returning Wed, Dec 2, priced at $194 just found
Breeze Airways
Wed, Nov 11 - Wed, Dec 2
MCO
Orlando Intl.
PWM
Portland Intl. Jetport
$204 Roundtrip, just found
$204
Roundtrip
just found
Select Breeze Airways flight, departing Wed, Nov 11 from Orlando Intl. to Portland Intl. Jetport, returning Wed, Dec 2, priced at $204 just found
Breeze Airways
Wed, Nov 11 - Wed, Dec 2
MCO
Orlando Intl.
PWM
Portland Intl. Jetport
$205 Roundtrip, just found
$205
Roundtrip
just found
Select Breeze Airways flight, departing Wed, Nov 11 from Orlando Intl. to Portland Intl. Jetport, returning Wed, Dec 2, priced at $205 just found
Breeze Airways
Tue, Nov 10 - Wed, Nov 18
TPA
Tampa Intl.
PWM
Portland Intl. Jetport
$214 Roundtrip, found 6 hours ago
$214
Roundtrip
found 6 hours ago
Select Breeze Airways flight, departing Tue, Nov 10 from Tampa Intl. to Portland Intl. Jetport, returning Wed, Nov 18, priced at $214 found 6 hours ago
Breeze Airways
Sat, Nov 14 - Wed, Dec 2
MCO
Orlando Intl.
PWM
Portland Intl. Jetport
$214 Roundtrip, found 21 hours ago
$214
Roundtrip
found 21 hours ago
Select Breeze Airways flight, departing Sat, Nov 14 from Orlando Intl. to Portland Intl. Jetport, returning Wed, Dec 2, priced at $214 found 21 hours ago
Breeze Airways
Mon, Nov 9 - Sat, Dec 5
MCO
Orlando Intl.
PWM
Portland Intl. Jetport
$217 Roundtrip, found 21 hours ago
$217
Roundtrip
found 21 hours ago
Select Breeze Airways flight, departing Mon, Nov 9 from Orlando Intl. to Portland Intl. Jetport, returning Sat, Dec 5, priced at $217 found 21 hours ago
United
Tue, Nov 17 - Sat, Dec 5
EWR
Newark Liberty Intl. Airport
PWM
Portland Intl. Jetport
$217 Roundtrip, just found
$217
Roundtrip
just found
Select United flight, departing Tue, Nov 17 from Newark Liberty Intl. Airport to Portland Intl. Jetport, returning Sat, Dec 5, priced at $217 just found
Breeze Airways
Tue, Nov 10 - Wed, Nov 18
TPA
Tampa Intl.
PWM
Portland Intl. Jetport
$219 Roundtrip, found 6 hours ago
$219
Roundtrip
found 6 hours ago
Select Breeze Airways flight, departing Tue, Nov 10 from Tampa Intl. to Portland Intl. Jetport, returning Wed, Nov 18, priced at $219 found 6 hours ago
Delta
Tue, Nov 17 - Sat, Dec 5
EWR
Newark Liberty Intl. Airport
PWM
Portland Intl. Jetport
$237 Roundtrip, just found
$237
Roundtrip
just found
Select Delta flight, departing Tue, Nov 17 from Newark Liberty Intl. Airport to Portland Intl. Jetport, returning Sat, Dec 5, priced at $237 just found
JetBlue Airways
Mon, Nov 9 - Mon, Nov 30
MCO
Orlando Intl.
PWM
Portland Intl. Jetport
$249 Roundtrip, found 4 days ago
$249
Roundtrip
found 4 days ago
Select JetBlue Airways flight, departing Mon, Nov 9 from Orlando Intl. to Portland Intl. Jetport, returning Mon, Nov 30, priced at $249 found 4 days ago
Southwest Airlines
Sat, Nov 14 - Wed, Dec 2
MCO
Orlando Intl.
PWM
Portland Intl. Jetport
$267 Roundtrip, found 21 hours ago
$267
Roundtrip
found 21 hours ago
Select Southwest Airlines flight, departing Sat, Nov 14 from Orlando Intl. to Portland Intl. Jetport, returning Wed, Dec 2, priced at $267 found 21 hours ago
American Airlines
Tue, Nov 10 - Wed, Nov 18
TPA
Tampa Intl.
PWM
Portland Intl. Jetport
$277 Roundtrip, found 6 hours ago
$277
Roundtrip
found 6 hours ago
Select American Airlines flight, departing Tue, Nov 10 from Tampa Intl. to Portland Intl. Jetport, returning Wed, Nov 18, priced at $277 found 6 hours ago
United
Tue, Oct 20 - Sat, Nov 7
IAD
Washington Dulles Intl.
PWM
Portland Intl. Jetport
$397 Roundtrip, found 18 hours ago
$397
Roundtrip
found 18 hours ago
Select United flight, departing Tue, Oct 20 from Washington Dulles Intl. to Portland Intl. Jetport, returning Sat, Nov 7, priced at $397 found 18 hours ago

Cheap Flights to Windham

Fall in love at first flight with your vacation to Windham by saving a ton of cash on your last-minute cheap flight. There’s no more scouring the internet for a good deal—book your flight to Windham on Hotwire, and you’ll be up, up, and on a getaway in no time.

Because once the wheels are down in Windham, the good times start rolling. So buckle up, you’re in for a fun ride.

Frequently Asked Questions About flights to Windham

Don’t waste your time on endless searches for cheap airline tickets oneway or roundtrip. We’ll have you on your way to Windham with a tiny bag of pretzels in your hand before you can say “tray tables in the upright position”—and for a ticket price that works for your vacay budget.

So all you have to worry about is where you’re headed after the PWM airport.

What is the cheapest month to fly to Windham?

Airline ticket prices fluctuate all the time, depending on the day of the week or the month of the year. The cheapest round trip flights to Windham are in November, but when you book your flight on Hotwire, savings are always in season.

How many airlines fly to Windham?

Variety is the spice of life, even when it comes to booking your next trip. Want options for airlines? You’ll find 16 to choose from for your flight to Windham.

What airport is best to fly into Windham?

When you’re planning your trip to Windham, convenience is the name of the game. Luckily, Windham Portland Intl. Jetport Airport is nearby so you can deplane and get going on checking off everything on your Windham must-do list.

How much are flights to Windham?

Got very cheap flights on your vacation itinerary? When you book your airline tickets to Windham on Hotwire, you may just get what’s on your getaway wish list. With tickets as low as $178, you’ll have leftover cash for at least a magazine and a bottle of water at the airport book store.

How to get cheap flights to Windham?

The trick to saving a stack of cash on your flight to Windham? Snatch up that Hotwire flight deal when you see a killer rate because it could be gone in a flash. And with flights as low as $178 right now, why wait?

Windham Flight Information
Destination airport
Portland Intl. Jetport
Destination airport IATA code
PWM
Roundtrip price
$177

Last Minute Hotel Deals in Windham

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 ...
8.2/10 Very Good! (1,785 reviews)
"Check in staff was professional and courteous. We did not need an accessible room, but had one, the shower was terrible. Water leaked all over the bathroom floor because the base wasn’t sloped properly towards the drain and bump/seal didn’t work so the water ran right under it. Bed comfy. Easy to ..."

Reviewed on Oct 18, 2026

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Clarion Hotel Portland Airport ME
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 ...
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The Westin Portland Harborview
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 ...
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Fireside Inn & Suites Portland
Quality Inn & Suites South Portland

Quality Inn & Suites South Portland

2.5 out of 5
738 Main Street South Portland ME
Book a stay at this business-friendly hotel in South Portland. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
6.2/10 (1,189 reviews)
"The place was easy to find, easy on and off the interstate. Plenty of parking. Rooms were quiet. Breakfast was normal for a motel- sausage, waffles, French toast, eggs one morning, cereal, breads, yogurt. Can tell they have been doing some updating in the rooms. Some stuff has been changed, other ..."

Reviewed on Oct 18, 2026

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Quality Inn & Suites South Portland
Inn at St John Portland In-Town

Inn at St John Portland In-Town

2.5 out of 5
939 Congress St Portland ME
Stay at this B&B in Portland. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular ...
8.6/10 Excellent! (1,161 reviews)
"This is a lovely place. Not a standard all the same hotel. It has charm. However - there is no elevator so be prepared to do steps."

Reviewed on Oct 18, 2026

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Inn at St John Portland In-Town
Clarion Pointe South Portland

Clarion Pointe South Portland

2 out of 5
675 Main Street I-95 South Portland ME
Book a stay at this business-friendly hotel in South Portland. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Maine Mall and Cross Insurance ...
7.2/10 Good! (972 reviews)
"The price was very reasonable for the season and compared to other hotels in the area."

Reviewed on Oct 18, 2026

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Clarion Pointe South Portland
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 ...
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Portland Harbor Hotel
Casco Bay Hotel Portland Airport - Maine Mall, an Ascend Collection Hotel

Casco Bay Hotel Portland Airport - Maine Mall, an Ascend Collection Hotel

3.5 out of 5
80 John Roberts Rd. South Portland ME
Book a stay at this business-friendly hotel in South Portland. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
8.4/10 Very Good! (2,984 reviews)
"Overall, I would stay here again, but I really hope the rooms are cleaner and better maintained. The bed was extremely comfy, and the room was well insulated from noise outside/hallway. The room at first glance looked overall good, but quickly we realized it wasn't very clean. The room was dusty ..."

Reviewed on Oct 18, 2026

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Casco Bay Hotel Portland Airport - Maine Mall, an Ascend Collection Hotel
See all 3,315 properties in Windham
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.