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Windham

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Windham Flights as Low as $127

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

Breeze Airways
Wed, Sep 16 - Sat, Sep 19
CMH
John Glenn Columbus Intl.
PWM
Portland Intl. Jetport
$127 Roundtrip, found 11 hours ago
$127
Roundtrip
found 11 hours ago
Select Breeze Airways flight, departing Wed, Sep 16 from John Glenn Columbus Intl. to Portland Intl. Jetport, returning Sat, Sep 19, priced at $127 found 11 hours ago
Breeze Airways
Wed, Sep 16 - Sat, Sep 19
CMH
John Glenn Columbus Intl.
PWM
Portland Intl. Jetport
$132 Roundtrip, found 11 hours ago
$132
Roundtrip
found 11 hours ago
Select Breeze Airways flight, departing Wed, Sep 16 from John Glenn Columbus Intl. to Portland Intl. Jetport, returning Sat, Sep 19, priced at $132 found 11 hours ago
Breeze Airways
Wed, Sep 16 - Sat, Sep 19
CMH
John Glenn Columbus Intl.
PWM
Portland Intl. Jetport
$137 Roundtrip, found 11 hours ago
$137
Roundtrip
found 11 hours ago
Select Breeze Airways flight, departing Wed, Sep 16 from John Glenn Columbus Intl. to Portland Intl. Jetport, returning Sat, Sep 19, priced at $137 found 11 hours ago
Breeze Airways
Tue, Sep 1 - Tue, Sep 8
ORF
Norfolk Intl.
PWM
Portland Intl. Jetport
$199 Roundtrip, found 6 hours ago
$199
Roundtrip
found 6 hours ago
Select Breeze Airways flight, departing Tue, Sep 1 from Norfolk Intl. to Portland Intl. Jetport, returning Tue, Sep 8, priced at $199 found 6 hours ago
Breeze Airways
Tue, Sep 1 - Tue, Sep 8
ORF
Norfolk Intl.
PWM
Portland Intl. Jetport
$201 Roundtrip, found 6 hours ago
$201
Roundtrip
found 6 hours ago
Select Breeze Airways flight, departing Tue, Sep 1 from Norfolk Intl. to Portland Intl. Jetport, returning Tue, Sep 8, priced at $201 found 6 hours ago
Breeze Airways
Tue, Sep 1 - Tue, Sep 8
ORF
Norfolk Intl.
PWM
Portland Intl. Jetport
$204 Roundtrip, found 6 hours ago
$204
Roundtrip
found 6 hours ago
Select Breeze Airways flight, departing Tue, Sep 1 from Norfolk Intl. to Portland Intl. Jetport, returning Tue, Sep 8, priced at $204 found 6 hours ago
Breeze Airways
Tue, Sep 1 - Tue, Sep 8
ORF
Norfolk Intl.
PWM
Portland Intl. Jetport
$206 Roundtrip, found 6 hours ago
$206
Roundtrip
found 6 hours ago
Select Breeze Airways flight, departing Tue, Sep 1 from Norfolk Intl. to Portland Intl. Jetport, returning Tue, Sep 8, priced at $206 found 6 hours ago
Breeze Airways
Tue, Sep 1 - Tue, Sep 8
ORF
Norfolk Intl.
PWM
Portland Intl. Jetport
$208 Roundtrip, found 6 hours ago
$208
Roundtrip
found 6 hours ago
Select Breeze Airways flight, departing Tue, Sep 1 from Norfolk Intl. to Portland Intl. Jetport, returning Tue, Sep 8, priced at $208 found 6 hours ago
Breeze Airways
Tue, Sep 1 - Tue, Sep 8
ORF
Norfolk Intl.
PWM
Portland Intl. Jetport
$211 Roundtrip, found 6 hours ago
$211
Roundtrip
found 6 hours ago
Select Breeze Airways flight, departing Tue, Sep 1 from Norfolk Intl. to Portland Intl. Jetport, returning Tue, Sep 8, priced at $211 found 6 hours ago
Breeze Airways
Wed, Sep 23 - Wed, Sep 30
MCO
Orlando Intl.
PWM
Portland Intl. Jetport
$229 Roundtrip, found 13 hours ago
$229
Roundtrip
found 13 hours ago
Select Breeze Airways flight, departing Wed, Sep 23 from Orlando Intl. to Portland Intl. Jetport, returning Wed, Sep 30, priced at $229 found 13 hours ago
Delta
Thu, Oct 29 - Fri, Nov 13
ROC
Greater Rochester Intl.
PWM
Portland Intl. Jetport
$267 Roundtrip, found 6 hours ago
$267
Roundtrip
found 6 hours ago
Select Delta flight, departing Thu, Oct 29 from Greater Rochester Intl. to Portland Intl. Jetport, returning Fri, Nov 13, priced at $267 found 6 hours ago
United
Mon, Oct 5 - Wed, Oct 7
ROC
Greater Rochester Intl.
PWM
Portland Intl. Jetport
$271 Roundtrip, found 17 hours ago
$271
Roundtrip
found 17 hours ago
Select United flight, departing Mon, Oct 5 from Greater Rochester Intl. to Portland Intl. Jetport, returning Wed, Oct 7, priced at $271 found 17 hours ago
American Airlines
Mon, Oct 5 - Wed, Oct 7
ROC
Greater Rochester Intl.
PWM
Portland Intl. Jetport
$271 Roundtrip, found 17 hours ago
$271
Roundtrip
found 17 hours ago
Select American Airlines flight, departing Mon, Oct 5 from Greater Rochester Intl. to Portland Intl. Jetport, returning Wed, Oct 7, priced at $271 found 17 hours ago
Southwest Airlines
Thu, Oct 29 - Fri, Nov 13
ROC
Greater Rochester Intl.
PWM
Portland Intl. Jetport
$303 Roundtrip, found 6 hours ago
$303
Roundtrip
found 6 hours ago
Select Southwest Airlines flight, departing Thu, Oct 29 from Greater Rochester Intl. to Portland Intl. Jetport, returning Fri, Nov 13, priced at $303 found 6 hours ago
JetBlue Airways
Wed, Feb 24 - Sat, Feb 27
MCO
Orlando Intl.
PWM
Portland Intl. Jetport
$367 Roundtrip, found 2 hours ago
$367
Roundtrip
found 2 hours ago
Select JetBlue Airways flight, departing Wed, Feb 24 from Orlando Intl. to Portland Intl. Jetport, returning Sat, Feb 27, priced at $367 found 2 hours ago
Delta
Thu, Nov 19 - Fri, Dec 4
MOB
Mobile Regional
PWM
Portland Intl. Jetport
$383 Roundtrip, found 1 day ago
$383
Roundtrip
found 1 day ago
Select Delta flight, departing Thu, Nov 19 from Mobile Regional to Portland Intl. Jetport, returning Fri, Dec 4, priced at $383 found 1 day 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 September, 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 $127, 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 $127 right now, why wait?

Windham Flight Information
Destination airport
Portland Intl. Jetport
Destination airport IATA code
PWM
Roundtrip price
$126

Last Minute Hotel Deals in Windham

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 ...
7.2/10 Good! (715 reviews)
"We stayed in the hotel for 2 days in two different rooms on two different occasions a few days apart. On the first occasion we were on the first floor, one of the first rooms. This room was very clean and very well maintained. On the second occasion, we were on the second floor in a room far away ..."

Reviewed on Aug 22, 2026

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Clarion Pointe South 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 ...
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Quality Inn & Suites South Portland
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! (1,640 reviews)
"Really a pleasant place to stay. And a great price!"

Reviewed on Aug 23, 2026

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Clarion Hotel Portland Airport ME
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! (2,368 reviews)
"Staff was great, every one of them we encountered. Location is central to a lot around the airport area. Only negative is bathroom was small and cramped."

Reviewed on Aug 22, 2026

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Comfort Inn South Portland Airport
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! (1,753 reviews)
"The check in staff were very friendly. The room was clean and the bed very comfortable. Great central location for walking around Portland."

Reviewed on Aug 23, 2026

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Portland Regency Hotel & Spa
Waves Oceanfront Resort

Waves Oceanfront Resort

3 out of 5
87 W Grand Ave Old Orchard Beach ME
Book a stay at this beach hotel in Old Orchard Beach. Enjoy free parking, an outdoor pool, and a beach locale. Our guests praise the helpful staff and the clean ...
8.4/10 Very Good! (655 reviews)
"The only negative was that the WiFi was very spotty and we couldn't use our Roku with the tv. The hotel itself was very clean and spacious. The staff were wonderful, and the amenities were wonderful as well."

Reviewed on Aug 22, 2026

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Waves Oceanfront Resort
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! (3,023 reviews)
"Clean, comfortable bed and conveniently located."

Reviewed on Aug 23, 2026

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Casco Bay Hotel Portland Airport - Maine Mall, an Ascend Collection Hotel
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 ...
8.2/10 Very Good! (1,060 reviews)
"Great experience and highly recommend"

Reviewed on Aug 23, 2026

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Fireside Inn & Suites Portland
See all 3,327 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.