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Windham

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Windham Flights as Low as $179

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

Breeze Airways
Wed, May 27 - Sat, May 30
MCO
Orlando Intl.
PWM
Portland Intl. Jetport
$179 Roundtrip, found 12 hours ago
$179
Roundtrip
found 12 hours ago
Select Breeze Airways flight, departing Wed, May 27 from Orlando Intl. to Portland Intl. Jetport, returning Sat, May 30, priced at $179 found 12 hours ago
Breeze Airways
Wed, May 27 - Sat, May 30
MCO
Orlando Intl.
PWM
Portland Intl. Jetport
$182 Roundtrip, found 12 hours ago
$182
Roundtrip
found 12 hours ago
Select Breeze Airways flight, departing Wed, May 27 from Orlando Intl. to Portland Intl. Jetport, returning Sat, May 30, priced at $182 found 12 hours ago
Breeze Airways
Wed, May 27 - Fri, Jun 5
MCO
Orlando Intl.
PWM
Portland Intl. Jetport
$186 Roundtrip, found 20 hours ago
$186
Roundtrip
found 20 hours ago
Select Breeze Airways flight, departing Wed, May 27 from Orlando Intl. to Portland Intl. Jetport, returning Fri, Jun 5, priced at $186 found 20 hours ago
Breeze Airways
Fri, May 29 - Wed, Jun 3
MCO
Orlando Intl.
PWM
Portland Intl. Jetport
$187 Roundtrip, found 1 day ago
$187
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Fri, May 29 from Orlando Intl. to Portland Intl. Jetport, returning Wed, Jun 3, priced at $187 found 1 day ago
Breeze Airways
Wed, May 27 - Sat, May 30
MCO
Orlando Intl.
PWM
Portland Intl. Jetport
$189 Roundtrip, found 12 hours ago
$189
Roundtrip
found 12 hours ago
Select Breeze Airways flight, departing Wed, May 27 from Orlando Intl. to Portland Intl. Jetport, returning Sat, May 30, priced at $189 found 12 hours ago
Breeze Airways
Wed, Aug 19 - Tue, Aug 25
MCO
Orlando Intl.
PWM
Portland Intl. Jetport
$190 Roundtrip, found 11 hours ago
$190
Roundtrip
found 11 hours ago
Select Breeze Airways flight, departing Wed, Aug 19 from Orlando Intl. to Portland Intl. Jetport, returning Tue, Aug 25, priced at $190 found 11 hours ago
Breeze Airways
Fri, May 29 - Wed, Jun 3
MCO
Orlando Intl.
PWM
Portland Intl. Jetport
$192 Roundtrip, found 1 day ago
$192
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Fri, May 29 from Orlando Intl. to Portland Intl. Jetport, returning Wed, Jun 3, priced at $192 found 1 day ago
American Airlines
Tue, Jun 2 - Fri, Jun 5
MCO
Orlando Intl.
PWM
Portland Intl. Jetport
$194 Roundtrip, found 11 hours ago
$194
Roundtrip
found 11 hours ago
Select American Airlines flight, departing Tue, Jun 2 from Orlando Intl. to Portland Intl. Jetport, returning Fri, Jun 5, priced at $194 found 11 hours ago
Delta
Wed, Aug 19 - Tue, Aug 25
MCO
Orlando Intl.
PWM
Portland Intl. Jetport
$217 Roundtrip, found 11 hours ago
$217
Roundtrip
found 11 hours ago
Select Delta flight, departing Wed, Aug 19 from Orlando Intl. to Portland Intl. Jetport, returning Tue, Aug 25, priced at $217 found 11 hours ago
American Airlines
Wed, Aug 19 - Tue, Aug 25
MCO
Orlando Intl.
PWM
Portland Intl. Jetport
$217 Roundtrip, found 11 hours ago
$217
Roundtrip
found 11 hours ago
Select American Airlines flight, departing Wed, Aug 19 from Orlando Intl. to Portland Intl. Jetport, returning Tue, Aug 25, priced at $217 found 11 hours ago
Delta
Tue, Jun 30 - Sat, Jul 4
DFW
Dallas-Fort Worth Intl.
PWM
Portland Intl. Jetport
$217 Roundtrip, found 12 hours ago
$217
Roundtrip
found 12 hours ago
Select Delta flight, departing Tue, Jun 30 from Dallas-Fort Worth Intl. to Portland Intl. Jetport, returning Sat, Jul 4, priced at $217 found 12 hours ago
United
Tue, Jun 2 - Fri, Jun 5
MCO
Orlando Intl.
PWM
Portland Intl. Jetport
$222 Roundtrip, found 11 hours ago
$222
Roundtrip
found 11 hours ago
Select United flight, departing Tue, Jun 2 from Orlando Intl. to Portland Intl. Jetport, returning Fri, Jun 5, priced at $222 found 11 hours ago
Delta
Wed, Jul 8 - Tue, Jul 14
DAL
Love Field
PWM
Portland Intl. Jetport
$237 Roundtrip, found 1 day ago
$237
Roundtrip
found 1 day ago
Select Delta flight, departing Wed, Jul 8 from Love Field to Portland Intl. Jetport, returning Tue, Jul 14, priced at $237 found 1 day ago
Delta
Wed, May 27 - Tue, Jun 2
DAB
Daytona Beach Intl.
PWM
Portland Intl. Jetport
$304 Roundtrip, found 22 hours ago
$304
Roundtrip
found 22 hours ago
Select Delta flight, departing Wed, May 27 from Daytona Beach Intl. to Portland Intl. Jetport, returning Tue, Jun 2, priced at $304 found 22 hours ago
JetBlue Airways
Wed, Jun 17 - Sat, Jun 20
MCO
Orlando Intl.
PWM
Portland Intl. Jetport
$356 Roundtrip, found 1 day ago
$356
Roundtrip
found 1 day ago
Select JetBlue Airways flight, departing Wed, Jun 17 from Orlando Intl. to Portland Intl. Jetport, returning Sat, Jun 20, priced at $356 found 1 day ago
American Airlines
Tue, Apr 28 - Mon, May 4
LAW
Lawton-Fort Sill Regional
PWM
Portland Intl. Jetport
$637 Roundtrip, found 20 hours ago
$637
Roundtrip
found 20 hours ago
Select American Airlines flight, departing Tue, Apr 28 from Lawton-Fort Sill Regional to Portland Intl. Jetport, returning Mon, May 4, priced at $637 found 20 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 May, 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 $179, 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 $179 right now, why wait?

Windham Flight Information
Destination airport
Portland Intl. Jetport
Destination airport IATA code
PWM
Roundtrip price
$178

Last Minute Hotel Deals in Windham

Dormir

Dormir

3 out of 5
965 Roosevelt Trail Windham ME
Book a stay at this business-friendly hotel in Windham. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
8.8/10 Excellent! (999 reviews)
Parking was convenient. Room was clean and comfortable

Reviewed on Apr 19, 2026

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Dormir
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 ...
8.8/10 Excellent! (1,003 reviews)
The rooms are always great. We stay here every time we go to Portland. THE MOST COMFORTABLE BEDS AND PILLOWS I EVER HAD IN A HOTEL! Great experience, as always!

Reviewed on Apr 23, 2026

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The Westin Portland Harborview
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 ...
9.2/10 Wonderful! (1,746 reviews)
Portland Harbor Hotel was in a great location to explore the downtown and harbor area. It’s very close to lots of shops and restaurants.

Reviewed on Apr 23, 2026

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Portland Harbor Hotel
HomeAwhile

HomeAwhile

4 out of 5
205 Southborough Drive Scarborough ME
Stay at this aparthotel in Scarborough. Enjoy free WiFi, free parking, and laundry facilities. Popular attractions Maine Mall and Thompson's Point are located ...
9.6/10 Exceptional! (26 reviews)
Nice and quiet

Reviewed on Apr 25, 2026

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HomeAwhile
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 ...
9.4/10 Exceptional! (1,192 reviews)
View was nice from room. Otherwise the heating system was loud, the food was meh at best (I can see why they give a credit) and parking was confusing. The staff was friendly and engaging however and the location was nice

Reviewed on Apr 21, 2026

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Cambria Hotel Portland Downtown-Old Port
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 ...
9.4/10 Exceptional! (1,627 reviews)
We were upgraded upon arrival to a lovely executive king. The shuttle service from the airport was convenient. Bed, bedding and pillows were very comfy and towels were good quality. Excellent location!

Reviewed on Apr 24, 2026

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Portland Regency Hotel & Spa
Holiday Inn Portland-By the Bay by IHG

Holiday Inn Portland-By the Bay by IHG

4 out of 5
88 Spring St Portland ME
Book a stay at this business-friendly hotel in Portland. Enjoy free WiFi, breakfast (surcharge), and a free airport shuttle. Our guests praise the helpful staff ...
9/10 Wonderful! (1,518 reviews)
Overall stay was good. The clock alarm went off at 6 am. I never thought of checking to see if the alarm clock was set...just assumed it wasn't. Walking distance to Old Port and good restaurants. Beds/bedding was ok. Staff was friendly. I'd stay again.

Reviewed on Apr 25, 2026

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Holiday Inn Portland-By the Bay by IHG
Hyatt Place Portland Downtown - Old Port Square

Hyatt Place Portland Downtown - Old Port Square

3 out of 5
433 Fore St Portland ME
Book a stay at this business-friendly hotel in Portland. Enjoy free WiFi, breakfast (surcharge), and a free airport shuttle. Our guests praise the breakfast ...
9/10 Wonderful! (1,319 reviews)
The hotel was clean and in a great spot. The staff was helpful. I was disappointed in some of the tech. You are asked to text to retrieve your car. Our car was “not recognized by the system”. We also were unable to cast to the TV in our room with a streaming app. The service kept on recognizing an ...

Reviewed on Apr 24, 2026

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Hyatt Place Portland Downtown - Old Port Square
See all 3,197 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.