Search Cheap Flights to
Windham

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Windham Flights as Low as $102

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

Breeze Airways
Wed, Oct 22 - Wed, Oct 22
MCO
Orlando Intl.
PSM
Portsmouth Intl.
$102 Roundtrip, found 17 hours ago
$102
Roundtrip
found 17 hours ago
Select Breeze Airways flight, departing Wed, Oct 22 from Orlando Intl. to Portsmouth Intl., returning Wed, Oct 22, priced at $102 found 17 hours ago
Breeze Airways
Sat, Aug 30 - Sat, Aug 30
MCO
Orlando Intl.
PSM
Portsmouth Intl.
$107 Roundtrip, found 2 days ago
$107
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Sat, Aug 30 from Orlando Intl. to Portsmouth Intl., returning Sat, Aug 30, priced at $107 found 2 days ago
Spirit Airlines
Wed, Sep 10 - Wed, Sep 24
MCO
Orlando Intl.
BOS
Logan Intl.
$109 Roundtrip, found 1 day ago
$109
Roundtrip
found 1 day ago
Select Spirit Airlines flight, departing Wed, Sep 10 from Orlando Intl. to Logan Intl., returning Wed, Sep 24, priced at $109 found 1 day ago
Breeze Airways
Wed, Oct 22 - Wed, Oct 22
MCO
Orlando Intl.
PSM
Portsmouth Intl.
$112 Roundtrip, found 17 hours ago
$112
Roundtrip
found 17 hours ago
Select Breeze Airways flight, departing Wed, Oct 22 from Orlando Intl. to Portsmouth Intl., returning Wed, Oct 22, priced at $112 found 17 hours ago
Spirit Airlines
Tue, Sep 2 - Tue, Sep 2
MCO
Orlando Intl.
BOS
Logan Intl.
$113 Roundtrip, found 2 days ago
$113
Roundtrip
found 2 days ago
Select Spirit Airlines flight, departing Tue, Sep 2 from Orlando Intl. to Logan Intl., returning Tue, Sep 2, priced at $113 found 2 days ago
Spirit Airlines
Wed, Sep 3 - Wed, Sep 3
MCO
Orlando Intl.
BOS
Logan Intl.
$115 Roundtrip, found 2 days ago
$115
Roundtrip
found 2 days ago
Select Spirit Airlines flight, departing Wed, Sep 3 from Orlando Intl. to Logan Intl., returning Wed, Sep 3, priced at $115 found 2 days ago
Breeze Airways
Wed, Dec 3 - Wed, Dec 10
MCO
Orlando Intl.
PSM
Portsmouth Intl.
$117 Roundtrip, found 5 days ago
$117
Roundtrip
found 5 days ago
Select Breeze Airways flight, departing Wed, Dec 3 from Orlando Intl. to Portsmouth Intl., returning Wed, Dec 10, priced at $117 found 5 days ago
Spirit Airlines
Mon, Sep 15 - Mon, Sep 15
MCO
Orlando Intl.
BOS
Logan Intl.
$120 Roundtrip, found 1 day ago
$120
Roundtrip
found 1 day ago
Select Spirit Airlines flight, departing Mon, Sep 15 from Orlando Intl. to Logan Intl., returning Mon, Sep 15, priced at $120 found 1 day ago
Spirit Airlines
Sun, Aug 31 - Sun, Aug 31
MCO
Orlando Intl.
BOS
Logan Intl.
$121 Roundtrip, found 2 hours ago
$121
Roundtrip
found 2 hours ago
Select Spirit Airlines flight, departing Sun, Aug 31 from Orlando Intl. to Logan Intl., returning Sun, Aug 31, priced at $121 found 2 hours ago
Breeze Airways
Wed, Dec 3 - Wed, Dec 10
MCO
Orlando Intl.
PSM
Portsmouth Intl.
$127 Roundtrip, found 1 day ago
$127
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Wed, Dec 3 from Orlando Intl. to Portsmouth Intl., returning Wed, Dec 10, priced at $127 found 1 day ago
Frontier Airlines
Sun, Aug 24 - Mon, Aug 25
MCO
Orlando Intl.
BOS
Logan Intl.
$148 Roundtrip, found 6 days ago
$148
Roundtrip
found 6 days ago
Select Frontier Airlines flight, departing Sun, Aug 24 from Orlando Intl. to Logan Intl., returning Mon, Aug 25, priced at $148 found 6 days ago
JetBlue Airways
Tue, Sep 9 - Tue, Sep 9
MCO
Orlando Intl.
BOS
Logan Intl.
$152 Roundtrip, found 1 day ago
$152
Roundtrip
found 1 day ago
Select JetBlue Airways flight, departing Tue, Sep 9 from Orlando Intl. to Logan Intl., returning Tue, Sep 9, priced at $152 found 1 day ago
Delta
Tue, Nov 4 - Wed, Nov 12
MCO
Orlando Intl.
BOS
Logan Intl.
$157 Roundtrip, found 15 hours ago
$157
Roundtrip
found 15 hours ago
Select Delta flight, departing Tue, Nov 4 from Orlando Intl. to Logan Intl., returning Wed, Nov 12, priced at $157 found 15 hours ago
Breeze Airways
Wed, Aug 6 - Wed, Aug 13
MCO
Orlando Intl.
MHT
Manchester-Boston Regional
$158 Roundtrip, found 3 days ago
$158
Roundtrip
found 3 days ago
Select Breeze Airways flight, departing Wed, Aug 6 from Orlando Intl. to Manchester-Boston Regional, returning Wed, Aug 13, priced at $158 found 3 days ago
American Airlines
Wed, Oct 22 - Wed, Oct 22
MCO
Orlando Intl.
BOS
Logan Intl.
$171 Roundtrip, found 17 hours ago
$171
Roundtrip
found 17 hours ago
Select American Airlines flight, departing Wed, Oct 22 from Orlando Intl. to Logan Intl., returning Wed, Oct 22, priced at $171 found 17 hours ago
United
Tue, Nov 4 - Wed, Nov 12
MCO
Orlando Intl.
BOS
Logan Intl.
$197 Roundtrip, found 15 hours ago
$197
Roundtrip
found 15 hours ago
Select United flight, departing Tue, Nov 4 from Orlando Intl. to Logan Intl., returning Wed, Nov 12, priced at $197 found 15 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 BOS 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 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 Nashua Municipal 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 $102, 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 $102 right now, why wait?

Windham Flight Information
Destination airport
Logan Intl.
Destination airport IATA code
BOS
Roundtrip price
$98

Last Minute Hotel Deals in Windham

DoubleTree by Hilton Manchester Downtown

DoubleTree by Hilton Manchester Downtown

4 out of 5
700 Elm St., Manchester, NH
Stay at this 4-star hotel in Manchester. Enjoy breakfast (surcharge), room service, and a fitness center. Our guests praise the helpful staff and the clean rooms ...
8.8/10 Excellent! (1,003 reviews)
"Although I was only there for 1 night I I availed myself of the snack/drinks area in the lobby & the bar. Staff were knowledgeable & friendly. I will definitely go again."

Reviewed on Jul 30, 2025

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DoubleTree by Hilton Manchester Downtown
Even Hotels Manchester Airport by IHG

Even Hotels Manchester Airport by IHG

3.5 out of 5
55 John E. Devine Drive, Manchester, NH
Stay at this 3.5-star business-friendly hotel in Manchester. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and ...
8.8/10 Excellent! (842 reviews)
"Hotel was very clean, front desk staff very helpful, busy area around hotel would definitely stay again"

Reviewed on Jul 28, 2025

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Even Hotels Manchester Airport by IHG
La Quinta Inn & Suites by Wyndham Boston-Andover

La Quinta Inn & Suites by Wyndham Boston-Andover

3 out of 5
131 River Rd, Andover, MA
Stay at this 3-star business-friendly hotel in Andover. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our ...
8/10 Very Good! (1,815 reviews)
"Cimfortable bed, good shower, clean."

Reviewed on Jul 31, 2025

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La Quinta Inn & Suites by Wyndham Boston-Andover
Seabrook Inn

Seabrook Inn

2.5 out of 5
9 Stard Rd, Seabrook, NH
Book a stay at this business-friendly motel in Seabrook. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the clean rooms in our reviews. ...
6.4/10 (1,003 reviews)
clean room
"One night stay, clean room, ez check in and out"

Reviewed on Jul 28, 2025

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Seabrook Inn
Homewood Suites by Hilton Boston/Billerica

Homewood Suites by Hilton Boston/Billerica

3 out of 5
35 Middlesex Turnpike, Billerica, MA
Stay at this 3-star business-friendly hotel in Billerica. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
8/10 Very Good! (1,005 reviews)
"Staff was extremely helpful, food was fresh and delicious"

Reviewed on Aug 1, 2025

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Homewood Suites by Hilton Boston/Billerica
Best Western Plus Executive Court Inn & Conference Center

Best Western Plus Executive Court Inn & Conference Center

3 out of 5
13500 S Willow St, Manchester, NH
Stay at this 3-star business-friendly hotel in Manchester. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
8.2/10 Very Good! (1,222 reviews)
"This was our second time staying here the rooms are nice and the breakfast is very good. Our 4yo loves the pool and the game room. Staff has been very nice each time we've stayed."

Reviewed on Aug 1, 2025

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Best Western Plus Executive Court Inn & Conference Center
Holiday Inn Express Andover North-Lawrence by IHG

Holiday Inn Express Andover North-Lawrence by IHG

2.5 out of 5
224 Winthrop Ave, Lawrence, MA
Book a stay at this business-friendly hotel in Lawrence. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
8.2/10 Very Good! (1,003 reviews)
"Good property for family and friends."

Reviewed on Jul 30, 2025

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Holiday Inn Express Andover North-Lawrence by IHG
Hilton Garden Inn Tewksbury Andover

Hilton Garden Inn Tewksbury Andover

3 out of 5
4 Highwood Drive, Tewksbury, MA
Stay at this 3-star business-friendly hotel in Tewksbury. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the ...
8.8/10 Excellent! (693 reviews)
"Just love being at this Hilton!!!"

Reviewed on Jul 31, 2025

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Hilton Garden Inn Tewksbury Andover
See all 422 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.