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Windham

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Windham Flights as Low as $224

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

Bargain Flight
Tue, Jul 7 - Fri, Jul 10
DCA
Ronald Reagan Washington National
PWM
Portland Intl. Jetport
$224 Roundtrip, found 4 hours ago
$224
Roundtrip
found 4 hours ago
Select Bargain Flight flight, departing Tue, Jul 7 from Ronald Reagan Washington National to Portland Intl. Jetport, returning Fri, Jul 10, priced at $224 found 4 hours ago
JetBlue Airways
Wed, Aug 19 - Sat, Aug 22
BNA
Nashville Intl.
PWM
Portland Intl. Jetport
$248 Roundtrip, found 1 day ago
$248
Roundtrip
found 1 day ago
Select JetBlue Airways flight, departing Wed, Aug 19 from Nashville Intl. to Portland Intl. Jetport, returning Sat, Aug 22, priced at $248 found 1 day ago
JetBlue Airways
Tue, Aug 4 - Wed, Aug 12
DCA
Ronald Reagan Washington National
PWM
Portland Intl. Jetport
$251 Roundtrip, found 3 days ago
$251
Roundtrip
found 3 days ago
Select JetBlue Airways flight, departing Tue, Aug 4 from Ronald Reagan Washington National to Portland Intl. Jetport, returning Wed, Aug 12, priced at $251 found 3 days ago
American Airlines
Tue, Aug 4 - Wed, Aug 12
DCA
Ronald Reagan Washington National
PWM
Portland Intl. Jetport
$255 Roundtrip, found 3 days ago
$255
Roundtrip
found 3 days ago
Select American Airlines flight, departing Tue, Aug 4 from Ronald Reagan Washington National to Portland Intl. Jetport, returning Wed, Aug 12, priced at $255 found 3 days ago
JetBlue Airways
Thu, Aug 20 - Tue, Aug 25
BNA
Nashville Intl.
PWM
Portland Intl. Jetport
$259 Roundtrip, found 10 hours ago
$259
Roundtrip
found 10 hours ago
Select JetBlue Airways flight, departing Thu, Aug 20 from Nashville Intl. to Portland Intl. Jetport, returning Tue, Aug 25, priced at $259 found 10 hours ago
Bargain Flight
Mon, Aug 17 - Fri, Aug 28
BNA
Nashville Intl.
PWM
Portland Intl. Jetport
$261 Roundtrip, found 2 days ago
$261
Roundtrip
found 2 days ago
Select Bargain Flight flight, departing Mon, Aug 17 from Nashville Intl. to Portland Intl. Jetport, returning Fri, Aug 28, priced at $261 found 2 days ago
JetBlue Airways
Thu, Aug 20 - Sat, Aug 22
BNA
Nashville Intl.
PWM
Portland Intl. Jetport
$263 Roundtrip, found 1 day ago
$263
Roundtrip
found 1 day ago
Select JetBlue Airways flight, departing Thu, Aug 20 from Nashville Intl. to Portland Intl. Jetport, returning Sat, Aug 22, priced at $263 found 1 day ago
JetBlue Airways
Wed, Aug 19 - Tue, Aug 25
BNA
Nashville Intl.
PWM
Portland Intl. Jetport
$265 Roundtrip, found 10 hours ago
$265
Roundtrip
found 10 hours ago
Select JetBlue Airways flight, departing Wed, Aug 19 from Nashville Intl. to Portland Intl. Jetport, returning Tue, Aug 25, priced at $265 found 10 hours ago
American Airlines
Tue, Aug 4 - Wed, Aug 12
DCA
Ronald Reagan Washington National
PWM
Portland Intl. Jetport
$265 Roundtrip, found 3 days ago
$265
Roundtrip
found 3 days ago
Select American Airlines flight, departing Tue, Aug 4 from Ronald Reagan Washington National to Portland Intl. Jetport, returning Wed, Aug 12, priced at $265 found 3 days ago
American Airlines
Tue, Aug 4 - Wed, Aug 12
DCA
Ronald Reagan Washington National
PWM
Portland Intl. Jetport
$269 Roundtrip, found 3 days ago
$269
Roundtrip
found 3 days ago
Select American Airlines flight, departing Tue, Aug 4 from Ronald Reagan Washington National to Portland Intl. Jetport, returning Wed, Aug 12, priced at $269 found 3 days ago
JetBlue Airways
Sat, Aug 22 - Wed, Aug 26
BNA
Nashville Intl.
PWM
Portland Intl. Jetport
$271 Roundtrip, found 1 day ago
$271
Roundtrip
found 1 day ago
Select JetBlue Airways flight, departing Sat, Aug 22 from Nashville Intl. to Portland Intl. Jetport, returning Wed, Aug 26, priced at $271 found 1 day ago
Delta
Tue, Aug 4 - Wed, Aug 12
DCA
Ronald Reagan Washington National
PWM
Portland Intl. Jetport
$287 Roundtrip, found 3 days ago
$287
Roundtrip
found 3 days ago
Select Delta flight, departing Tue, Aug 4 from Ronald Reagan Washington National to Portland Intl. Jetport, returning Wed, Aug 12, priced at $287 found 3 days ago
JetBlue Airways
Sun, Jul 12 - Thu, Jul 16
ATL
Hartsfield-Jackson Atlanta Intl.
PWM
Portland Intl. Jetport
$297 Roundtrip, found 1 hour ago
$297
Roundtrip
found 1 hour ago
Select JetBlue Airways flight, departing Sun, Jul 12 from Hartsfield-Jackson Atlanta Intl. to Portland Intl. Jetport, returning Thu, Jul 16, priced at $297 found 1 hour ago
Delta
Sat, Oct 31 - Sat, Nov 14
DAL
Love Field
PWM
Portland Intl. Jetport
$381 Roundtrip, found 2 days ago
$381
Roundtrip
found 2 days ago
Select Delta flight, departing Sat, Oct 31 from Love Field to Portland Intl. Jetport, returning Sat, Nov 14, priced at $381 found 2 days ago
American Airlines
Thu, Aug 6 - Mon, Aug 10
TTN
Mercer
PWM
Portland Intl. Jetport
$516 Roundtrip, found 9 hours ago
$516
Roundtrip
found 9 hours ago
Select American Airlines flight, departing Thu, Aug 6 from Mercer to Portland Intl. Jetport, returning Mon, Aug 10, priced at $516 found 9 hours ago
American Airlines
Thu, Aug 6 - Mon, Aug 10
PHL
Philadelphia Intl.
PWM
Portland Intl. Jetport
$519 Roundtrip, found 9 hours ago
$519
Roundtrip
found 9 hours ago
Select American Airlines flight, departing Thu, Aug 6 from Philadelphia Intl. to Portland Intl. Jetport, returning Mon, Aug 10, priced at $519 found 9 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 July, 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 14 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 $224, 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 $224 right now, why wait?

Windham Flight Information
Destination airport
Portland Intl. Jetport
Destination airport IATA code
PWM
Roundtrip price
$224

Last Minute Hotel Deals in Windham

La Quinta Inn & Suites by Wyndham Portland DT/Maine Med

La Quinta Inn & Suites by Wyndham Portland DT/Maine Med

3 out of 5
340 Park Ave Portland ME
Book a stay at this business-friendly hotel in Portland. Enjoy free breakfast, free WiFi, and an outdoor pool. Our guests praise the breakfast and the helpful ...
8.6/10 Excellent! (2,198 reviews)
"The property was very clean and quiet. The outside parking was ample and the surface had just been re-paved. The room was clean and comfortable, the a/c worked great and we had plenty of hot water with adequate water pressure. Breakfast was simple (bagels, waffle, cereal, eggs/sausage)but adequate. ..."

Reviewed on Jun 19, 2026

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La Quinta Inn & Suites by Wyndham Portland DT/Maine Med
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 ...
9.4/10 Exceptional! (1,769 reviews)
"Beautiful hotel, great location, friendly associates, but would not return to this location. Unfortunately many negatives.They offer what they call is a “kitchen” on every floor- coffee maker did not work and the ice machine did not work- spoke to an associate and was told coffee machine has been ..."

Reviewed on Jun 20, 2026

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Portland Harbor Hotel
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! (1,249 reviews)
"I loved staying at Cambria in Portland. The location was perfect; the rooms were spacious and clean. The pillows were really comfortable. The staff was excellent."

Reviewed on Jun 20, 2026

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Cambria Hotel Portland Downtown-Old Port
Ramada Plaza by Wyndham Portland

Ramada Plaza by Wyndham Portland

3 out of 5
155 Riverside St Portland ME
Book a stay at this business-friendly hotel in Portland. Enjoy free WiFi, free parking, and 2 restaurants. Our guests praise the restaurant and the helpful staff ...
7.8/10 Good! (1,010 reviews)
"Nice clean stay, shower had good pressures"

Reviewed on Jun 20, 2026

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Ramada Plaza by Wyndham 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 ...
9.4/10 Exceptional! (1,670 reviews)
"Clean, staff very professional and friendly. Conveniently located"

Reviewed on Jun 20, 2026

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Portland Regency Hotel & Spa
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 Thompson's ...
7.4/10 Good! (500 reviews)
"Basic but did as described. Room okay but had a dripping shower. Breakfast, again basic but sufficient."

Reviewed on Jun 20, 2026

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Clarion Pointe South Portland
Comfort Inn South Portland Airport

Comfort Inn South Portland Airport

2.5 out of 5
90 Maine Mall Rd South Portland ME
Book a stay at this business-friendly hotel in South Portland. Enjoy free breakfast, free WiFi, and a free airport shuttle. Our guests praise the breakfast and ...
8.6/10 Excellent! (2,139 reviews)
"Welcoming staff, good breakfast, nice beds and fluffy pillows. Everything we were looking for."

Reviewed on Jun 20, 2026

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Comfort Inn South Portland Airport
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 ...
6.6/10 (1,007 reviews)
"This hotel was disgusting. Nothing was cleaned and there were bugs everywhere. The shower and bathroom sink did not drain, there was no soap or shampoo in the shower or soap at the bathroom sink. The sheets were dirty, the carpet was damp and smelt like mold. Do not stay here"

Reviewed on Jun 20, 2026

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Quality Inn & Suites South Portland
See all 3,284 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.