Cheap Flights to Windham County from $41

View $41 flight on Tue, Oct 6, 2026Opens in a new window

Popular airlines to Windham County

  • JetBlue Airways

  • Cape Air

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How much is the cheapest flight to Windham County?

Prices were available within the past 7 days and start at $41 for one-way flights and $82 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

JetBlue Airways
Tue, Oct 6 - Sat, Oct 10
BOS
Boston
LEB
Lebanon
$82 Roundtrip, found 9 hours ago
$82
Roundtrip
found 9 hours ago
Select JetBlue Airways flight, departing Tue, Oct 6 from Boston to Lebanon, returning Sat, Oct 10, priced at $82 found 9 hours ago
JetBlue Airways
Tue, Oct 6 - Sat, Oct 10
BOS
Boston
LEB
Lebanon
$136 Roundtrip, found 9 hours ago
$136
Roundtrip
found 9 hours ago
Select JetBlue Airways flight, departing Tue, Oct 6 from Boston to Lebanon, returning Sat, Oct 10, priced at $136 found 9 hours ago
JetBlue Airways
Tue, Oct 6 - Sat, Oct 10
BOS
Boston
LEB
Lebanon
$141 Roundtrip, found 9 hours ago
$141
Roundtrip
found 9 hours ago
Select JetBlue Airways flight, departing Tue, Oct 6 from Boston to Lebanon, returning Sat, Oct 10, priced at $141 found 9 hours ago
JetBlue Airways
Thu, Jun 11 - Mon, Jun 15
BOS
Boston
LEB
Lebanon
$147 Roundtrip, found 9 hours ago
$147
Roundtrip
found 9 hours ago
Select JetBlue Airways flight, departing Thu, Jun 11 from Boston to Lebanon, returning Mon, Jun 15, priced at $147 found 9 hours ago
JetBlue Airways
Thu, Jun 11 - Mon, Jun 15
BOS
Boston
LEB
Lebanon
$158 Roundtrip, found 9 hours ago
$158
Roundtrip
found 9 hours ago
Select JetBlue Airways flight, departing Thu, Jun 11 from Boston to Lebanon, returning Mon, Jun 15, priced at $158 found 9 hours ago
Cape Air
Thu, May 14 - Sun, May 17
BOS
Boston
RUT
Rutland
$180 Roundtrip, found 16 hours ago
$180
Roundtrip
found 16 hours ago
Select Cape Air flight, departing Thu, May 14 from Boston to Rutland, returning Sun, May 17, priced at $180 found 16 hours ago
Cape Air
Thu, May 14 - Sun, May 17
BOS
Boston
RUT
Rutland
$186 Roundtrip, found 16 hours ago
$186
Roundtrip
found 16 hours ago
Select Cape Air flight, departing Thu, May 14 from Boston to Rutland, returning Sun, May 17, priced at $186 found 16 hours ago
United
Tue, Jul 14 - Tue, Jul 21
IAD
Washington
RUT
Rutland
$354 Roundtrip, found 19 hours ago
$354
Roundtrip
found 19 hours ago
Select United flight, departing Tue, Jul 14 from Washington to Rutland, returning Tue, Jul 21, priced at $354 found 19 hours ago
American Airlines
Wed, Jul 8 - Sun, Jul 12
LGA
New York
RUT
Rutland
$374 Roundtrip, found 15 hours ago
$374
Roundtrip
found 15 hours ago
Select American Airlines flight, departing Wed, Jul 8 from New York to Rutland, returning Sun, Jul 12, priced at $374 found 15 hours ago
Delta
Wed, May 20 - Sat, May 30
TPA
Tampa
RUT
Rutland
$454 Roundtrip, found 5 days ago
$454
Roundtrip
found 5 days ago
Select Delta flight, departing Wed, May 20 from Tampa to Rutland, returning Sat, May 30, priced at $454 found 5 days ago

Trending flights to Windham County

These prices were available within the past 7 days. Prices quoted are per person, round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

JetBlue Airways
Tue, Oct 6 - Sat, Oct 10
BOS
Boston
LEB
Lebanon
$82 Roundtrip, found 9 hours ago
$82
Roundtrip
found 9 hours ago
Select JetBlue Airways flight, departing Tue, Oct 6 from Boston to Lebanon, returning Sat, Oct 10, priced at $82 found 9 hours ago

Frequently asked questions

How do I find cheap flights to Windham County that have flexible change policies?
At Expedia, we've been channeling our inner Olympic gymnast to bring you the most flexible airfares on the market. Just mark the "No change fee" box right under the filter heading "Flexible change policies" to find your ideal flight to Windham County.
Which airlines fly to Windham County?
With a great selection of airlines offering flights into or near Windham County, the choice is all yours:

  • American Airlines - 342 flights to or near Windham County each month, including 342 flights to Albany Intl. Airport (ALB) per month.
  • Delta Air Lines - 281 flights to or near Windham County each month, including 281 flights to Albany Intl. Airport (ALB) per month.
  • Cape Air - 273 flights to or near Windham County each month, including 182 flights to Lebanon Municipal Airport (LEB) per month.

How can I find cheap tickets to Windham County?
In the last seven days, $82 was the lowest price for a flight to Windham County. If you want to save even more, book well ahead of time and be flexible with your dates. Search for your airfare to Windham County, then check out prices for similar time frames by clicking on the "flexible dates" link above.
How much is a flight to Windham County?
If you were traveling one way from Boston (BOS), you could've snapped up a low-cost fare for $41 in the last seven days. Round-trip journeys to Windham County ranged from $82 to $454 over the same period.
What are the most popular airports to fly into in Windham County?
Jet off to Windham County and you'll have a few airports to select from. Below are some of the region's busiest:

  • Albany Intl. Airport (ALB) - 1,101 flights per month.
  • Lebanon Municipal Airport (LEB) - 182 flights per month.
  • Rutland Southern Vermont Regional Airport (RUT) - 91 flights per month.

When is the cheapest time to fly to Windham County?
Depart for Windham County early in the week and you'll usually be rewarded more economical fares. Tuesday is typically the cheapest day to jump on a plane, followed by Monday. If you're hoping to avoid the costliest flights, stay away from Saturdays.
How much is a plane ticket to Windham County?
In the last seven days, airfares to Windham County cost between $82 and $454. Prices depend on multiple things, particularly the time of departure, carrier, cabin class and how early the fare is booked.
What months are the cheapest to book a flight to Windham County?
February is a cheap month to purchase a seat for your Windham County trip. Airfares are at their most expensive throughout the festive month of December, so avoid this time if you can.
How long is a flight to Windham County?
Flight durations can vary for many different reasons, including where you're jetting off from. We've drawn up a list of average flight times for three of the most well-known domestic routes to Windham County:

  • Chicago, IL (ORD-OHare Intl.) to Albany Intl. Airport (ALB) - 2 hours and 2 minutes
  • Washington, DC (DCA-Ronald Reagan Washington National) to Albany Intl. Airport (ALB) - 1 hour and 32 minutes
  • Washington, DC (IAD-Washington Dulles Intl.) to Albany Intl. Airport (ALB) - 1 hour and 37 minutes

What is the best time to go to Windham County?
A fantastic time to visit Londonderry is after June 20 when the summer season starts. In Windham County's leading city, average temperatures fluctuate from 50ºF to 80ºF at this time — wonderful weather for touring around! January, August and December are the most popular months to discover this destination.

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*Flight schedules are subject to change.

*Available to One Key members.

 

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