Search Cheap Flights to
Windham

Search 400 airlines and 321,000 hotels worldwide.

Stop Planning & Start Exploring

FREE 24 hour cancellation on most flights

Windham Flights as Low as $142

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
$142 Roundtrip, found 16 hours ago
$142
Roundtrip
found 16 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 $142 found 16 hours ago
Breeze Airways
Wed, Sep 16 - Sat, Sep 19
CMH
John Glenn Columbus Intl.
PWM
Portland Intl. Jetport
$147 Roundtrip, found 16 hours ago
$147
Roundtrip
found 16 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 $147 found 16 hours ago
Breeze Airways
Wed, Sep 16 - Sat, Sep 19
CMH
John Glenn Columbus Intl.
PWM
Portland Intl. Jetport
$152 Roundtrip, found 16 hours ago
$152
Roundtrip
found 16 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 $152 found 16 hours ago
Breeze Airways
Tue, Aug 25 - Mon, Aug 31
CHS
Charleston Intl.
PWM
Portland Intl. Jetport
$178 Roundtrip, found 17 hours ago
$178
Roundtrip
found 17 hours ago
Select Breeze Airways flight, departing Tue, Aug 25 from Charleston Intl. to Portland Intl. Jetport, returning Mon, Aug 31, priced at $178 found 17 hours ago
Breeze Airways
Tue, Aug 25 - Mon, Aug 31
CHS
Charleston Intl.
PWM
Portland Intl. Jetport
$183 Roundtrip, found 17 hours ago
$183
Roundtrip
found 17 hours ago
Select Breeze Airways flight, departing Tue, Aug 25 from Charleston Intl. to Portland Intl. Jetport, returning Mon, Aug 31, priced at $183 found 17 hours ago
Breeze Airways
Tue, Aug 25 - Mon, Aug 31
CHS
Charleston Intl.
PWM
Portland Intl. Jetport
$189 Roundtrip, found 17 hours ago
$189
Roundtrip
found 17 hours ago
Select Breeze Airways flight, departing Tue, Aug 25 from Charleston Intl. to Portland Intl. Jetport, returning Mon, Aug 31, priced at $189 found 17 hours ago
JetBlue Airways
Thu, Aug 20 - Mon, Aug 24
BNA
Nashville Intl.
PWM
Portland Intl. Jetport
$234 Roundtrip, found 3 days ago
$234
Roundtrip
found 3 days ago
Select JetBlue Airways flight, departing Thu, Aug 20 from Nashville Intl. to Portland Intl. Jetport, returning Mon, Aug 24, priced at $234 found 3 days ago
Breeze Airways
Tue, Aug 25 - Mon, Aug 31
CHS
Charleston Intl.
PWM
Portland Intl. Jetport
$240 Roundtrip, found 17 hours ago
$240
Roundtrip
found 17 hours ago
Select Breeze Airways flight, departing Tue, Aug 25 from Charleston Intl. to Portland Intl. Jetport, returning Mon, Aug 31, priced at $240 found 17 hours ago
JetBlue Airways
Wed, Aug 26 - Thu, Sep 17
BNA
Nashville Intl.
PWM
Portland Intl. Jetport
$241 Roundtrip, found 2 days ago
$241
Roundtrip
found 2 days ago
Select JetBlue Airways flight, departing Wed, Aug 26 from Nashville Intl. to Portland Intl. Jetport, returning Thu, Sep 17, priced at $241 found 2 days ago
Breeze Airways
Tue, Aug 25 - Mon, Aug 31
CHS
Charleston Intl.
PWM
Portland Intl. Jetport
$245 Roundtrip, found 17 hours ago
$245
Roundtrip
found 17 hours ago
Select Breeze Airways flight, departing Tue, Aug 25 from Charleston Intl. to Portland Intl. Jetport, returning Mon, Aug 31, priced at $245 found 17 hours ago
Delta
Mon, Sep 14 - Tue, Sep 22
CMH
John Glenn Columbus Intl.
PWM
Portland Intl. Jetport
$249 Roundtrip, found 3 days ago
$249
Roundtrip
found 3 days ago
Select Delta flight, departing Mon, Sep 14 from John Glenn Columbus Intl. to Portland Intl. Jetport, returning Tue, Sep 22, priced at $249 found 3 days ago
Breeze Airways
Tue, Aug 25 - Mon, Aug 31
CHS
Charleston Intl.
PWM
Portland Intl. Jetport
$250 Roundtrip, found 17 hours ago
$250
Roundtrip
found 17 hours ago
Select Breeze Airways flight, departing Tue, Aug 25 from Charleston Intl. to Portland Intl. Jetport, returning Mon, Aug 31, priced at $250 found 17 hours ago
American Airlines
Wed, Aug 26 - Thu, Sep 17
BNA
Nashville Intl.
PWM
Portland Intl. Jetport
$277 Roundtrip, found 2 days ago
$277
Roundtrip
found 2 days ago
Select American Airlines flight, departing Wed, Aug 26 from Nashville Intl. to Portland Intl. Jetport, returning Thu, Sep 17, priced at $277 found 2 days ago
United
Wed, Sep 16 - Fri, Sep 18
CMH
John Glenn Columbus Intl.
PWM
Portland Intl. Jetport
$291 Roundtrip, found 3 days ago
$291
Roundtrip
found 3 days ago
Select United flight, departing Wed, Sep 16 from John Glenn Columbus Intl. to Portland Intl. Jetport, returning Fri, Sep 18, priced at $291 found 3 days ago
Delta
Tue, Sep 22 - Wed, Sep 30
RIC
Richmond Intl.
PWM
Portland Intl. Jetport
$307 Roundtrip, found 21 hours ago
$307
Roundtrip
found 21 hours ago
Select Delta flight, departing Tue, Sep 22 from Richmond Intl. to Portland Intl. Jetport, returning Wed, Sep 30, priced at $307 found 21 hours ago
Delta
Tue, Sep 22 - Fri, Oct 2
CHO
Charlottesville-Albemarle
PWM
Portland Intl. Jetport
$309 Roundtrip, found 21 hours ago
$309
Roundtrip
found 21 hours ago
Select Delta flight, departing Tue, Sep 22 from Charlottesville-Albemarle to Portland Intl. Jetport, returning Fri, Oct 2, priced at $309 found 21 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 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 $142, 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 $142 right now, why wait?

Windham Flight Information
Destination airport
Portland Intl. Jetport
Destination airport IATA code
PWM
Roundtrip price
$141

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! (1,550 reviews)
"Could use an update"

Reviewed on Jul 12, 2026

Get rates
Clarion Hotel Portland Airport ME
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! (2,202 reviews)
"I would rate this hotel as just OK. Nothing was great. Everything was just fine. The bed was nice and everything was clean.it was a little noisy. The staff was efficient but not super friendly or even courteous. I really expected a little more for $395."

Reviewed on Jul 11, 2026

Get rates
La Quinta Inn & Suites by Wyndham Portland DT/Maine Med
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! (1,263 reviews)
"Clean room, great location."

Reviewed on Jul 12, 2026

Get rates
Cambria Hotel Portland Downtown-Old Port
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! (1,781 reviews)
"Very helpful staff and had snacks, coffee and water available 24/7"

Reviewed on Jul 11, 2026

Get rates
Portland Harbor Hotel
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! (544 reviews)
"The lady who cked us in never once smiled. And our room was not too clean. We got to be by all the barking dogs. I had spilled so water on the floor and wiped it up and the cloth was so dirty. When we checked out I asked the young lady for a receipt and she said she would email it, well that never ..."

Reviewed on Jul 12, 2026

Get rates
Clarion Pointe South 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! (1,708 reviews)
"Some amenities were not available at the time of my stay."

Reviewed on Jul 11, 2026

Get rates
Portland Regency Hotel & Spa
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! (2,213 reviews)
"Room was clean, parking was convenient, many dining options close by, friendly staff, would definitely stay here again."

Reviewed on Jul 12, 2026

Get rates
Comfort Inn South Portland Airport
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! (1,630 reviews)
"Staff was friendly. Room was pretty clean.asked for a room with sofa but did not get that. Asked for more pillows since had to watch TV from bed but Did not get those. Room was not serviced, and did not get clean towels even when we asked for them. They did not even empty the trash. Front desk did ..."

Reviewed on Jul 10, 2026

Get rates
Holiday Inn Portland-By the Bay by IHG
See all 3,351 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.