Search Cheap Flights to
Windham

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Windham Flights as Low as $126

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

Spirit Airlines
Wed, Aug 20 - Sat, Sep 6
ORD
O'Hare Intl.
BOS
Logan Intl.
$126 Roundtrip, found 1 day ago
$126
Roundtrip
found 1 day ago
Select Spirit Airlines flight, departing Wed, Aug 20 from O'Hare Intl. to Logan Intl., returning Sat, Sep 6, priced at $126 found 1 day ago
JetBlue Airways
Thu, Sep 4 - Mon, Sep 8
ORD
O'Hare Intl.
BOS
Logan Intl.
$129 Roundtrip, found 1 day ago
$129
Roundtrip
found 1 day ago
Select JetBlue Airways flight, departing Thu, Sep 4 from O'Hare Intl. to Logan Intl., returning Mon, Sep 8, priced at $129 found 1 day ago
United
Thu, Sep 4 - Mon, Sep 8
ORD
O'Hare Intl.
BOS
Logan Intl.
$129 Roundtrip, found 1 day ago
$129
Roundtrip
found 1 day ago
Select United flight, departing Thu, Sep 4 from O'Hare Intl. to Logan Intl., returning Mon, Sep 8, priced at $129 found 1 day ago
United
Thu, Sep 4 - Mon, Sep 8
ORD
O'Hare Intl.
BOS
Logan Intl.
$129 Roundtrip, found 1 day ago
$129
Roundtrip
found 1 day ago
Select United flight, departing Thu, Sep 4 from O'Hare Intl. to Logan Intl., returning Mon, Sep 8, priced at $129 found 1 day ago
American Airlines
Thu, Sep 4 - Mon, Sep 8
ORD
O'Hare Intl.
BOS
Logan Intl.
$129 Roundtrip, found 1 day ago
$129
Roundtrip
found 1 day ago
Select American Airlines flight, departing Thu, Sep 4 from O'Hare Intl. to Logan Intl., returning Mon, Sep 8, priced at $129 found 1 day ago
JetBlue Airways
Tue, Sep 2 - Wed, Sep 3
DCA
Ronald Reagan Washington National
BOS
Logan Intl.
$132 Roundtrip, found 5 days ago
$132
Roundtrip
found 5 days ago
Select JetBlue Airways flight, departing Tue, Sep 2 from Ronald Reagan Washington National to Logan Intl., returning Wed, Sep 3, priced at $132 found 5 days ago
JetBlue Airways
Wed, Sep 3 - Wed, Sep 3
DCA
Ronald Reagan Washington National
BOS
Logan Intl.
$134 Roundtrip, found 1 day ago
$134
Roundtrip
found 1 day ago
Select JetBlue Airways flight, departing Wed, Sep 3 from Ronald Reagan Washington National to Logan Intl., returning Wed, Sep 3, priced at $134 found 1 day ago
United
Mon, Sep 1 - Tue, Sep 2
DCA
Ronald Reagan Washington National
BOS
Logan Intl.
$136 Roundtrip, found 3 days ago
$136
Roundtrip
found 3 days ago
Select United flight, departing Mon, Sep 1 from Ronald Reagan Washington National to Logan Intl., returning Tue, Sep 2, priced at $136 found 3 days ago
JetBlue Airways
Sat, Oct 11 - Sat, Oct 18
ORD
O'Hare Intl.
BOS
Logan Intl.
$137 Roundtrip, found 1 day ago
$137
Roundtrip
found 1 day ago
Select JetBlue Airways flight, departing Sat, Oct 11 from O'Hare Intl. to Logan Intl., returning Sat, Oct 18, priced at $137 found 1 day ago
JetBlue Airways
Tue, Aug 26 - Wed, Sep 3
DCA
Ronald Reagan Washington National
BOS
Logan Intl.
$138 Roundtrip, found 3 days ago
$138
Roundtrip
found 3 days ago
Select JetBlue Airways flight, departing Tue, Aug 26 from Ronald Reagan Washington National to Logan Intl., returning Wed, Sep 3, priced at $138 found 3 days ago
Delta
Wed, Aug 20 - Sat, Sep 6
ORD
O'Hare Intl.
BOS
Logan Intl.
$140 Roundtrip, found 1 day ago
$140
Roundtrip
found 1 day ago
Select Delta flight, departing Wed, Aug 20 from O'Hare Intl. to Logan Intl., returning Sat, Sep 6, priced at $140 found 1 day ago
Spirit Airlines
Tue, Sep 9 - Wed, Sep 17
ORD
O'Hare Intl.
BOS
Logan Intl.
$140 Roundtrip, found 6 days ago
$140
Roundtrip
found 6 days ago
Select Spirit Airlines flight, departing Tue, Sep 9 from O'Hare Intl. to Logan Intl., returning Wed, Sep 17, priced at $140 found 6 days ago
United
Sat, Oct 25 - Fri, Oct 31
DEN
Denver Intl.
BOS
Logan Intl.
$198 Roundtrip, found 3 days ago
$198
Roundtrip
found 3 days ago
Select United flight, departing Sat, Oct 25 from Denver Intl. to Logan Intl., returning Fri, Oct 31, priced at $198 found 3 days ago
Frontier Airlines
Fri, Oct 3 - Mon, Oct 6
ORD
O'Hare Intl.
BOS
Logan Intl.
$228 Roundtrip, found 1 day ago
$228
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Fri, Oct 3 from O'Hare Intl. to Logan Intl., returning Mon, Oct 6, priced at $228 found 1 day ago
American Airlines
Sun, Nov 23 - Thu, Nov 27
DCA
Ronald Reagan Washington National
MHT
Manchester-Boston Regional
$229 Roundtrip, found 21 hours ago
$229
Roundtrip
found 21 hours ago
Select American Airlines flight, departing Sun, Nov 23 from Ronald Reagan Washington National to Manchester-Boston Regional, returning Thu, Nov 27, priced at $229 found 21 hours ago
Alaska Airlines
Sat, Sep 27 - Fri, Oct 3
DEN
Denver Intl.
BOS
Logan Intl.
$296 Roundtrip, found 6 days ago
$296
Roundtrip
found 6 days ago
Select Alaska Airlines flight, departing Sat, Sep 27 from Denver Intl. to Logan Intl., returning Fri, Oct 3, priced at $296 found 6 days 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 August, 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 $126, 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 $126 right now, why wait?

Windham Flight Information
Destination airport
Logan Intl.
Destination airport IATA code
BOS
Roundtrip price
$116

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! (1,031 reviews)
"Ok"

Reviewed on Jul 25, 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! (826 reviews)
"Rooms have good space and comfortable beds. The facilities need some attention. Only one elevator is functioning, broken . Also the carpets on the halls must be cleaned or changed."

Reviewed on Jul 24, 2025

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Even Hotels Manchester Airport by IHG
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 (1,012 reviews)
"Good"

Reviewed on Jul 24, 2025

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Seabrook Inn
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! (1,224 reviews)
"5 out of 5 stars all around!"

Reviewed on Jul 24, 2025

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Best Western Plus Executive Court Inn & Conference Center
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! (1,819 reviews)
"All good except for the hair in the pool. Kinda skeeved my wife out. Our room didn’t have a shower curtain when we checked in but they delivered one within a few hours."

Reviewed on Jul 24, 2025

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La Quinta Inn & Suites by Wyndham Boston-Andover
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! (1,018 reviews)
"clean, nice staff"

Reviewed on Jul 25, 2025

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Homewood Suites by Hilton Boston/Billerica
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)
"Glad that the service was good, though it was a little confusing on how to get to the hotel."

Reviewed on Jul 24, 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! (684 reviews)
"Very nice"

Reviewed on Jul 25, 2025

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Hilton Garden Inn Tewksbury Andover
See all 423 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.