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Windham

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Windham Flights as Low as $201

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

JetBlue Airways
Wed, Aug 19 - Tue, Aug 25
BNA
Nashville Intl.
PWM
Portland Intl. Jetport
$201 Roundtrip, found 5 hours ago
$201
Roundtrip
found 5 hours ago
Select JetBlue Airways flight, departing Wed, Aug 19 from Nashville Intl. to Portland Intl. Jetport, returning Tue, Aug 25, priced at $201 found 5 hours ago
Breeze Airways
Mon, Aug 17 - Tue, Aug 25
MCO
Orlando Intl.
PWM
Portland Intl. Jetport
$210 Roundtrip, found 5 hours ago
$210
Roundtrip
found 5 hours ago
Select Breeze Airways flight, departing Mon, Aug 17 from Orlando Intl. to Portland Intl. Jetport, returning Tue, Aug 25, priced at $210 found 5 hours ago
Breeze Airways
Mon, Aug 17 - Tue, Aug 25
MCO
Orlando Intl.
PWM
Portland Intl. Jetport
$215 Roundtrip, found 5 hours ago
$215
Roundtrip
found 5 hours ago
Select Breeze Airways flight, departing Mon, Aug 17 from Orlando Intl. to Portland Intl. Jetport, returning Tue, Aug 25, priced at $215 found 5 hours ago
American Airlines
Wed, Aug 19 - Tue, Aug 25
MCO
Orlando Intl.
PWM
Portland Intl. Jetport
$217 Roundtrip, found 4 hours ago
$217
Roundtrip
found 4 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 4 hours ago
Delta
Wed, Aug 19 - Tue, Aug 25
MCO
Orlando Intl.
PWM
Portland Intl. Jetport
$217 Roundtrip, found 4 hours ago
$217
Roundtrip
found 4 hours ago
Select Delta flight, departing Wed, Aug 19 from Orlando Intl. to Portland Intl. Jetport, returning Tue, Aug 25, priced at $217 found 4 hours ago
Breeze Airways
Mon, Aug 17 - Tue, Aug 25
MCO
Orlando Intl.
PWM
Portland Intl. Jetport
$218 Roundtrip, found 5 hours ago
$218
Roundtrip
found 5 hours ago
Select Breeze Airways flight, departing Mon, Aug 17 from Orlando Intl. to Portland Intl. Jetport, returning Tue, Aug 25, priced at $218 found 5 hours ago
United
Wed, Aug 19 - Tue, Aug 25
BNA
Nashville Intl.
PWM
Portland Intl. Jetport
$221 Roundtrip, found 5 hours ago
$221
Roundtrip
found 5 hours ago
Select United flight, departing Wed, Aug 19 from Nashville Intl. to Portland Intl. Jetport, returning Tue, Aug 25, priced at $221 found 5 hours ago
American Airlines
Wed, Aug 19 - Tue, Aug 25
BNA
Nashville Intl.
PWM
Portland Intl. Jetport
$221 Roundtrip, found 5 hours ago
$221
Roundtrip
found 5 hours ago
Select American Airlines flight, departing Wed, Aug 19 from Nashville Intl. to Portland Intl. Jetport, returning Tue, Aug 25, priced at $221 found 5 hours ago
JetBlue Airways
Wed, Aug 19 - Tue, Aug 25
MCO
Orlando Intl.
PWM
Portland Intl. Jetport
$223 Roundtrip, found 4 hours ago
$223
Roundtrip
found 4 hours ago
Select JetBlue Airways flight, departing Wed, Aug 19 from Orlando Intl. to Portland Intl. Jetport, returning Tue, Aug 25, priced at $223 found 4 hours ago
Delta
Wed, Aug 12 - Sat, Aug 29
BNA
Nashville Intl.
PWM
Portland Intl. Jetport
$226 Roundtrip, found 9 hours ago
$226
Roundtrip
found 9 hours ago
Select Delta flight, departing Wed, Aug 12 from Nashville Intl. to Portland Intl. Jetport, returning Sat, Aug 29, priced at $226 found 9 hours ago
Breeze Airways
Wed, Aug 19 - Tue, Aug 25
MCO
Orlando Intl.
PWM
Portland Intl. Jetport
$226 Roundtrip, found 4 hours ago
$226
Roundtrip
found 4 hours ago
Select Breeze Airways flight, departing Wed, Aug 19 from Orlando Intl. to Portland Intl. Jetport, returning Tue, Aug 25, priced at $226 found 4 hours ago
Breeze Airways
Mon, Aug 17 - Tue, Aug 25
MCO
Orlando Intl.
PWM
Portland Intl. Jetport
$228 Roundtrip, found 5 hours ago
$228
Roundtrip
found 5 hours ago
Select Breeze Airways flight, departing Mon, Aug 17 from Orlando Intl. to Portland Intl. Jetport, returning Tue, Aug 25, priced at $228 found 5 hours ago
JetBlue Airways
Mon, Jul 27 - Thu, Jul 30
PHX
Sky Harbor Intl.
PWM
Portland Intl. Jetport
$272 Roundtrip, found 5 days ago
$272
Roundtrip
found 5 days ago
Select JetBlue Airways flight, departing Mon, Jul 27 from Sky Harbor Intl. to Portland Intl. Jetport, returning Thu, Jul 30, priced at $272 found 5 days ago
Bargain Flight
Sat, Jul 25 - Tue, Jul 28
DFW
Dallas-Fort Worth Intl.
PWM
Portland Intl. Jetport
$304 Roundtrip, found 5 hours ago
$304
Roundtrip
found 5 hours ago
Select Bargain Flight flight, departing Sat, Jul 25 from Dallas-Fort Worth Intl. to Portland Intl. Jetport, returning Tue, Jul 28, priced at $304 found 5 hours ago
Delta
Sat, Oct 31 - Sat, Nov 14
DAL
Love Field
PWM
Portland Intl. Jetport
$381 Roundtrip, found 5 hours ago
$381
Roundtrip
found 5 hours ago
Select Delta flight, departing Sat, Oct 31 from Love Field to Portland Intl. Jetport, returning Sat, Nov 14, priced at $381 found 5 hours ago
American Airlines
Sat, Jul 25 - Tue, Jul 28
DFW
Dallas-Fort Worth Intl.
PWM
Portland Intl. Jetport
$498 Roundtrip, found 5 hours ago
$498
Roundtrip
found 5 hours ago
Select American Airlines flight, departing Sat, Jul 25 from Dallas-Fort Worth Intl. to Portland Intl. Jetport, returning Tue, Jul 28, priced at $498 found 5 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 August, 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 15 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 $201, 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 $201 right now, why wait?

Windham Flight Information
Destination airport
Portland Intl. Jetport
Destination airport IATA code
PWM
Roundtrip price
$200

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 ...
8/10 Very Good! (1,496 reviews)
"One elevator was out of order. The other elevator did not stop at my floor. Carpet is threadbare. There were stains in the sink and tub."

Reviewed on Jun 13, 2026

Get rates
Clarion Hotel Portland Airport ME
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! (1,785 reviews)
"We had a great stay! Everyone was so nice, helpful, and efficient! We loved the location. Portland is an amazing city! Wasn’t aware of the $35 a day charges but it worked out!"

Reviewed on Jun 12, 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! (1,250 reviews)
"Great area, very walkable, the staff was excellent! Would definitely stay again."

Reviewed on Jun 13, 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! (1,691 reviews)
"We loved the hotel. The location is great and convenient to the best parts of Portland. The room was perfect with a comfortable bed a great bathroom. Staff was friendly and helpful. We would happily stay again at your hotel."

Reviewed on Jun 13, 2026

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Portland Regency Hotel & Spa
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 (1,010 reviews)
"tv in the room didn’t work. carpet near the a/c was soaked. items from last person’s stay were left in the bathroom (NyQuil packets, hair clips, etc)."

Reviewed on Jun 13, 2026

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Quality Inn & Suites South Portland
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! (482 reviews)
"N/a"

Reviewed on Jun 14, 2026

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Clarion Pointe South Portland
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! (2,226 reviews)
"The hotel was in a good location. Front desk was helpful and pleasant. Amenities were average. Breakfast was horrible. Had to wait for food that was inedible."

Reviewed on Jun 14, 2026

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La Quinta Inn & Suites by Wyndham Portland DT/Maine Med
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! (2,114 reviews)
"Friendly, helpful staff. Comfy bed. Water was clean tasting from faucet. Tv was excellent…but wifi was spoty. I will stay again. Close to transportation center and airport, and affordable."

Reviewed on Jun 12, 2026

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Comfort Inn South Portland Airport
See all 3,267 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.