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 $185

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

Breeze Airways
Wed, Oct 28 - Sat, Oct 31
TPA
Tampa Intl.
PWM
Portland Intl. Jetport
$185 Roundtrip, found 4 hours ago
$185
Roundtrip
found 4 hours ago
Select Breeze Airways flight, departing Wed, Oct 28 from Tampa Intl. to Portland Intl. Jetport, returning Sat, Oct 31, priced at $185 found 4 hours ago
Breeze Airways
Wed, Oct 28 - Sat, Oct 31
TPA
Tampa Intl.
PWM
Portland Intl. Jetport
$189 Roundtrip, found 4 hours ago
$189
Roundtrip
found 4 hours ago
Select Breeze Airways flight, departing Wed, Oct 28 from Tampa Intl. to Portland Intl. Jetport, returning Sat, Oct 31, priced at $189 found 4 hours ago
Breeze Airways
Wed, Oct 28 - Sat, Oct 31
TPA
Tampa Intl.
PWM
Portland Intl. Jetport
$191 Roundtrip, found 4 hours ago
$191
Roundtrip
found 4 hours ago
Select Breeze Airways flight, departing Wed, Oct 28 from Tampa Intl. to Portland Intl. Jetport, returning Sat, Oct 31, priced at $191 found 4 hours ago
Breeze Airways
Wed, Oct 28 - Sat, Oct 31
TPA
Tampa Intl.
PWM
Portland Intl. Jetport
$193 Roundtrip, found 4 hours ago
$193
Roundtrip
found 4 hours ago
Select Breeze Airways flight, departing Wed, Oct 28 from Tampa Intl. to Portland Intl. Jetport, returning Sat, Oct 31, priced at $193 found 4 hours ago
Breeze Airways
Wed, Oct 28 - Sat, Oct 31
TPA
Tampa Intl.
PWM
Portland Intl. Jetport
$196 Roundtrip, found 4 hours ago
$196
Roundtrip
found 4 hours ago
Select Breeze Airways flight, departing Wed, Oct 28 from Tampa Intl. to Portland Intl. Jetport, returning Sat, Oct 31, priced at $196 found 4 hours ago
Breeze Airways
Wed, Oct 28 - Sat, Oct 31
TPA
Tampa Intl.
PWM
Portland Intl. Jetport
$197 Roundtrip, found 4 hours ago
$197
Roundtrip
found 4 hours ago
Select Breeze Airways flight, departing Wed, Oct 28 from Tampa Intl. to Portland Intl. Jetport, returning Sat, Oct 31, priced at $197 found 4 hours ago
Breeze Airways
Wed, Oct 28 - Sat, Oct 31
TPA
Tampa Intl.
PWM
Portland Intl. Jetport
$199 Roundtrip, found 4 hours ago
$199
Roundtrip
found 4 hours ago
Select Breeze Airways flight, departing Wed, Oct 28 from Tampa Intl. to Portland Intl. Jetport, returning Sat, Oct 31, priced at $199 found 4 hours ago
Breeze Airways
Tue, Nov 10 - Fri, Nov 13
RDU
Raleigh - Durham Intl.
PWM
Portland Intl. Jetport
$200 Roundtrip, found 13 hours ago
$200
Roundtrip
found 13 hours ago
Select Breeze Airways flight, departing Tue, Nov 10 from Raleigh - Durham Intl. to Portland Intl. Jetport, returning Fri, Nov 13, priced at $200 found 13 hours ago
Bargain Flight
Fri, Nov 13 - Mon, Nov 16
RDU
Raleigh - Durham Intl.
PWM
Portland Intl. Jetport
$201 Roundtrip, found 4 hours ago
$201
Roundtrip
found 4 hours ago
Select Bargain Flight flight, departing Fri, Nov 13 from Raleigh - Durham Intl. to Portland Intl. Jetport, returning Mon, Nov 16, priced at $201 found 4 hours ago
Breeze Airways
Wed, Nov 11 - Wed, Dec 2
MCO
Orlando Intl.
PWM
Portland Intl. Jetport
$223 Roundtrip, found 4 hours ago
$223
Roundtrip
found 4 hours ago
Select Breeze Airways flight, departing Wed, Nov 11 from Orlando Intl. to Portland Intl. Jetport, returning Wed, Dec 2, priced at $223 found 4 hours ago
Southwest Airlines
Fri, Nov 13 - Mon, Nov 16
RDU
Raleigh - Durham Intl.
PWM
Portland Intl. Jetport
$267 Roundtrip, found 4 hours ago
$267
Roundtrip
found 4 hours ago
Select Southwest Airlines flight, departing Fri, Nov 13 from Raleigh - Durham Intl. to Portland Intl. Jetport, returning Mon, Nov 16, priced at $267 found 4 hours ago
American Airlines
Thu, Nov 26 - Wed, Dec 2
RDU
Raleigh - Durham Intl.
PWM
Portland Intl. Jetport
$267 Roundtrip, found 4 hours ago
$267
Roundtrip
found 4 hours ago
Select American Airlines flight, departing Thu, Nov 26 from Raleigh - Durham Intl. to Portland Intl. Jetport, returning Wed, Dec 2, priced at $267 found 4 hours ago
Delta
Fri, Nov 13 - Mon, Nov 16
RDU
Raleigh - Durham Intl.
PWM
Portland Intl. Jetport
$267 Roundtrip, found 4 hours ago
$267
Roundtrip
found 4 hours ago
Select Delta flight, departing Fri, Nov 13 from Raleigh - Durham Intl. to Portland Intl. Jetport, returning Mon, Nov 16, priced at $267 found 4 hours ago
JetBlue Airways
Wed, Nov 11 - Wed, Dec 2
MCO
Orlando Intl.
PWM
Portland Intl. Jetport
$281 Roundtrip, found 4 hours ago
$281
Roundtrip
found 4 hours ago
Select JetBlue Airways flight, departing Wed, Nov 11 from Orlando Intl. to Portland Intl. Jetport, returning Wed, Dec 2, priced at $281 found 4 hours ago
Bargain Flight
Fri, Sep 25 - Tue, Sep 29
PHX
Sky Harbor Intl.
PWM
Portland Intl. Jetport
$363 Roundtrip, found 5 hours ago
$363
Roundtrip
found 5 hours ago
Select Bargain Flight flight, departing Fri, Sep 25 from Sky Harbor Intl. to Portland Intl. Jetport, returning Tue, Sep 29, priced at $363 found 5 hours ago
Delta
Sat, Oct 24 - Fri, Nov 6
MSO
Missoula Intl.
PWM
Portland Intl. Jetport
$404 Roundtrip, found 4 hours ago
$404
Roundtrip
found 4 hours ago
Select Delta flight, departing Sat, Oct 24 from Missoula Intl. to Portland Intl. Jetport, returning Fri, Nov 6, priced at $404 found 4 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 October, 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 $185, 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 $185 right now, why wait?

Windham Flight Information
Destination airport
Portland Intl. Jetport
Destination airport IATA code
PWM
Roundtrip price
$185

Last Minute Hotel Deals in Windham

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! (3,017 reviews)
"Already contacted the hotel and left a bad review. Issue was with a guest screaming at midnight, but the staff failed and let her back in so she was screaming and carrying on again at 12:30. Would not recommend."

Reviewed on Sep 13, 2026

Get rates
Casco Bay Hotel Portland Airport - Maine Mall, an Ascend Collection Hotel
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 ...
6.4/10 (1,125 reviews)
"The entire hotel was filthy and outdated. The bathroom was disgusting, especially the shower. In addition, it was not pointed out to me in advance, but when I checked in, the gentleman at the desk said there was a $50 incidental fee to cover things that we might do to the room. He said it was refundable ..."

Reviewed on Sep 13, 2026

Get rates
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 ...
8.2/10 Very Good! (1,686 reviews)
"Nice rooms just a short distance from the airport"

Reviewed on Sep 13, 2026

Get rates
Clarion Hotel Portland Airport ME
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! (802 reviews)
"It was a little more run down than the pictures showed online. The bed was clean. The bathroom had a ceiling tile missing and somethings stained the floor. The lobby was ok - a little tired looking."

Reviewed on Sep 13, 2026

Get rates
Clarion Pointe South Portland
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 ...
Get rates
Portland Harbor Hotel
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! (2,389 reviews)
"Shuttle was great"

Reviewed on Sep 13, 2026

Get rates
Comfort Inn South Portland Airport
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! (1,007 reviews)
"The property was clean, well maintained and the staff was helpful. It is an older property and is a bit tired."

Reviewed on Sep 13, 2026

Get rates
Fireside Inn & Suites Portland
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 ...
9.2/10 Wonderful! (1,312 reviews)
"Stayed here 4 nights. Pros-Clean, Good location with restaurants and Old Port easily walkable. Cons-Our room was very far from the elevator. If you have mobility issues check first. On our last night we headed back to have a drink at the hotel after a long day of adventures only to find the bar and ..."

Reviewed on Sep 13, 2026

Get rates
Cambria Hotel Portland Downtown-Old Port
See all 3,274 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.