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 9 hours ago
$142
Roundtrip
found 9 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 9 hours ago
Breeze Airways
Wed, Aug 19 - Sat, Aug 22
CMH
John Glenn Columbus Intl.
PWM
Portland Intl. Jetport
$144 Roundtrip, found 9 hours ago
$144
Roundtrip
found 9 hours ago
Select Breeze Airways flight, departing Wed, Aug 19 from John Glenn Columbus Intl. to Portland Intl. Jetport, returning Sat, Aug 22, priced at $144 found 9 hours ago
Breeze Airways
Wed, Sep 16 - Sat, Sep 19
CMH
John Glenn Columbus Intl.
PWM
Portland Intl. Jetport
$147 Roundtrip, found 9 hours ago
$147
Roundtrip
found 9 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 9 hours ago
Breeze Airways
Wed, Aug 19 - Sat, Aug 22
CMH
John Glenn Columbus Intl.
PWM
Portland Intl. Jetport
$149 Roundtrip, found 9 hours ago
$149
Roundtrip
found 9 hours ago
Select Breeze Airways flight, departing Wed, Aug 19 from John Glenn Columbus Intl. to Portland Intl. Jetport, returning Sat, Aug 22, priced at $149 found 9 hours ago
Breeze Airways
Wed, Sep 16 - Sat, Sep 19
CMH
John Glenn Columbus Intl.
PWM
Portland Intl. Jetport
$152 Roundtrip, found 9 hours ago
$152
Roundtrip
found 9 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 9 hours ago
Breeze Airways
Wed, Aug 19 - Sat, Aug 22
CMH
John Glenn Columbus Intl.
PWM
Portland Intl. Jetport
$154 Roundtrip, found 9 hours ago
$154
Roundtrip
found 9 hours ago
Select Breeze Airways flight, departing Wed, Aug 19 from John Glenn Columbus Intl. to Portland Intl. Jetport, returning Sat, Aug 22, priced at $154 found 9 hours ago
Breeze Airways
Wed, Aug 19 - Fri, Aug 21
CMH
John Glenn Columbus Intl.
PWM
Portland Intl. Jetport
$154 Roundtrip, found 9 hours ago
$154
Roundtrip
found 9 hours ago
Select Breeze Airways flight, departing Wed, Aug 19 from John Glenn Columbus Intl. to Portland Intl. Jetport, returning Fri, Aug 21, priced at $154 found 9 hours ago
Breeze Airways
Wed, Aug 19 - Fri, Aug 21
CMH
John Glenn Columbus Intl.
PWM
Portland Intl. Jetport
$159 Roundtrip, found 9 hours ago
$159
Roundtrip
found 9 hours ago
Select Breeze Airways flight, departing Wed, Aug 19 from John Glenn Columbus Intl. to Portland Intl. Jetport, returning Fri, Aug 21, priced at $159 found 9 hours ago
Breeze Airways
Wed, Aug 19 - Fri, Aug 21
CMH
John Glenn Columbus Intl.
PWM
Portland Intl. Jetport
$164 Roundtrip, found 9 hours ago
$164
Roundtrip
found 9 hours ago
Select Breeze Airways flight, departing Wed, Aug 19 from John Glenn Columbus Intl. to Portland Intl. Jetport, returning Fri, Aug 21, priced at $164 found 9 hours ago
Breeze Airways
Sat, Aug 22 - Tue, Aug 25
MCO
Orlando Intl.
PWM
Portland Intl. Jetport
$200 Roundtrip, found 1 day ago
$200
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Sat, Aug 22 from Orlando Intl. to Portland Intl. Jetport, returning Tue, Aug 25, priced at $200 found 1 day ago
Delta
Mon, Aug 17 - Sat, Aug 29
CMH
John Glenn Columbus Intl.
PWM
Portland Intl. Jetport
$201 Roundtrip, found 9 hours ago
$201
Roundtrip
found 9 hours ago
Select Delta flight, departing Mon, Aug 17 from John Glenn Columbus Intl. to Portland Intl. Jetport, returning Sat, Aug 29, priced at $201 found 9 hours ago
Southwest Airlines
Mon, Aug 17 - Sat, Aug 29
CMH
John Glenn Columbus Intl.
PWM
Portland Intl. Jetport
$201 Roundtrip, found 9 hours ago
$201
Roundtrip
found 9 hours ago
Select Southwest Airlines flight, departing Mon, Aug 17 from John Glenn Columbus Intl. to Portland Intl. Jetport, returning Sat, Aug 29, priced at $201 found 9 hours ago
American Airlines
Mon, Aug 17 - Sat, Aug 29
CMH
John Glenn Columbus Intl.
PWM
Portland Intl. Jetport
$201 Roundtrip, found 9 hours ago
$201
Roundtrip
found 9 hours ago
Select American Airlines flight, departing Mon, Aug 17 from John Glenn Columbus Intl. to Portland Intl. Jetport, returning Sat, Aug 29, priced at $201 found 9 hours ago
Bargain Flight
Tue, Aug 25 - Wed, Aug 26
CLT
Charlotte-Douglas Intl.
PWM
Portland Intl. Jetport
$258 Roundtrip, found 8 hours ago
$258
Roundtrip
found 8 hours ago
Select Bargain Flight flight, departing Tue, Aug 25 from Charlotte-Douglas Intl. to Portland Intl. Jetport, returning Wed, Aug 26, priced at $258 found 8 hours ago
Bargain Flight
Tue, Aug 11 - Wed, Aug 19
DFW
Dallas-Fort Worth Intl.
PWM
Portland Intl. Jetport
$304 Roundtrip, found 8 hours ago
$304
Roundtrip
found 8 hours ago
Select Bargain Flight flight, departing Tue, Aug 11 from Dallas-Fort Worth Intl. to Portland Intl. Jetport, returning Wed, Aug 19, priced at $304 found 8 hours ago
Southwest Airlines
Tue, Aug 25 - Fri, Sep 11
DAL
Love Field
PWM
Portland Intl. Jetport
$333 Roundtrip, found 8 hours ago
$333
Roundtrip
found 8 hours ago
Select Southwest Airlines flight, departing Tue, Aug 25 from Love Field to Portland Intl. Jetport, returning Fri, Sep 11, priced at $333 found 8 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 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 $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! (1,595 reviews)
"We needed a budget-friendly stay that was clean for a young family. This met our expectations. I will say it was much better than most other Choice Hotel properties and was decently maintained. The pool was in especislly decent shape, and the shuttle to Old Port and Airport was VERY convenient. Perhaps ..."

Reviewed on Aug 2, 2026

Get rates
Clarion Hotel Portland Airport ME
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 ...
Get rates
Fireside Inn & Suites 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! (627 reviews)
"It needs some updating, but other than that we enjoyed the stay"

Reviewed on Aug 2, 2026

Get rates
Clarion Pointe South Portland
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! (625 reviews)
"No complaints, everything was perfect"

Reviewed on Aug 2, 2026

Get rates
Waves Oceanfront Resort
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! (1,786 reviews)
"Great location, lovely patio/courtyard. The only complaint is that we visited at a peak time (camp visiting weekend) so we paid at least 2x what would otherwise feel like appropriate price for the quality of hotel. All in all,though, definitely recommend the hotel!"

Reviewed on Aug 2, 2026

Get rates
Portland Harbor Hotel
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 ...
Get rates
Portland Regency Hotel & Spa
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 ...
Get rates
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! (1,007 reviews)
"there was no complimentary breakfast the bathroom did not have any safety bars in case of falls plus it was so small the staff was very friendly and professional the hotel was clean"

Reviewed on Aug 2, 2026

Get rates
Ramada Plaza by Wyndham Portland
See all 3,291 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.