Cheap Flights to Windham County from $76

View $76 flight on Thu, Mar 19, 2026Opens in a new window

Flight 1

Flight 2

Popular airlines to Windham County

  • JetBlue Airways

  • Cape Air

  • Be in the know

    Get alerts if flight prices drop or rise*

  • Book smarter

    Save up to 30% on select hotels after you book a flight*

  • Earn twice

    Earn your airline miles on top of our OneKeyCash
    Learn about One Key

How much is the cheapest flight to Windham County?

Prices were available within the past 7 days and start at $76 for one-way flights and $153 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

JetBlue Airways
Sat, Mar 21 - Sat, Apr 11
BOS
Boston
RUT
Rutland
$153 Roundtrip, found 6 days ago
$153
Roundtrip
found 6 days ago
Select JetBlue Airways flight, departing Sat, Mar 21 from Boston to Rutland, returning Sat, Apr 11, priced at $153 found 6 days ago
Cape Air
Thu, Mar 19 - Mon, Mar 23
BOS
Boston
LEB
Lebanon
$156 Roundtrip, found 5 hours ago
$156
Roundtrip
found 5 hours ago
Select Cape Air flight, departing Thu, Mar 19 from Boston to Lebanon, returning Mon, Mar 23, priced at $156 found 5 hours ago
Cape Air
Thu, Mar 19 - Mon, Mar 23
BOS
Boston
LEB
Lebanon
$160 Roundtrip, found 5 hours ago
$160
Roundtrip
found 5 hours ago
Select Cape Air flight, departing Thu, Mar 19 from Boston to Lebanon, returning Mon, Mar 23, priced at $160 found 5 hours ago
Cape Air
Mon, Mar 16 - Thu, Mar 19
BOS
Boston
RUT
Rutland
$160 Roundtrip, found 2 hours ago
$160
Roundtrip
found 2 hours ago
Select Cape Air flight, departing Mon, Mar 16 from Boston to Rutland, returning Thu, Mar 19, priced at $160 found 2 hours ago
JetBlue Airways
Fri, Mar 20 - Sat, Apr 11
BOS
Boston
RUT
Rutland
$163 Roundtrip, found 6 days ago
$163
Roundtrip
found 6 days ago
Select JetBlue Airways flight, departing Fri, Mar 20 from Boston to Rutland, returning Sat, Apr 11, priced at $163 found 6 days ago
JetBlue Airways
Thu, Mar 19 - Mon, Mar 23
BOS
Boston
LEB
Lebanon
$164 Roundtrip, found 5 hours ago
$164
Roundtrip
found 5 hours ago
Select JetBlue Airways flight, departing Thu, Mar 19 from Boston to Lebanon, returning Mon, Mar 23, priced at $164 found 5 hours ago
Cape Air
Thu, Mar 19 - Mon, Mar 23
BOS
Boston
LEB
Lebanon
$166 Roundtrip, found 5 hours ago
$166
Roundtrip
found 5 hours ago
Select Cape Air flight, departing Thu, Mar 19 from Boston to Lebanon, returning Mon, Mar 23, priced at $166 found 5 hours ago
United
Wed, Apr 8 - Sat, Apr 25
EWR
New York
LEB
Lebanon
$350 Roundtrip, found 5 days ago
$350
Roundtrip
found 5 days ago
Select United flight, departing Wed, Apr 8 from New York to Lebanon, returning Sat, Apr 25, priced at $350 found 5 days ago
Delta
Wed, Apr 22 - Sun, Apr 26
LGA
New York
RUT
Rutland
$354 Roundtrip, found 1 day ago
$354
Roundtrip
found 1 day ago
Select Delta flight, departing Wed, Apr 22 from New York to Rutland, returning Sun, Apr 26, priced at $354 found 1 day ago
American Airlines
Mon, Mar 23 - Mon, Mar 30
LGA
New York
LEB
Lebanon
$435 Roundtrip, found 3 hours ago
$435
Roundtrip
found 3 hours ago
Select American Airlines flight, departing Mon, Mar 23 from New York to Lebanon, returning Mon, Mar 30, priced at $435 found 3 hours ago

The Annual Vacation Sale

Members save up to 40% on hotels and homes. Plan this year’s big trip and save.
Book now

Airports in Windham County

Prices were available within the past 7 days. Prices and availability are subject to change.

Select flight to Rutland Southern Vermont Regional RUT. Flights from $519
RUT
Rutland Southern Vermont Regional
Flights from $519
Select flight to Lebanon Municipal LEB. Cheapest option available. Flights from $510
LEB
Lebanon Municipal
Cheapest
Flights from $510

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
Sat, Mar 21 - Sat, Apr 11
BOS
Boston
RUT
Rutland
$153 Roundtrip, found 6 days ago
$153
Roundtrip
found 6 days ago
Select JetBlue Airways flight, departing Sat, Mar 21 from Boston to Rutland, returning Sat, Apr 11, priced at $153 found 6 days 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, $153 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 $76 in the last seven days. Round-trip journeys to Windham County ranged from $153 to $435 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 $153 and $435. 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.

Book with confidence

Enjoy extra legroom, flight flexibility, and a seamless travel experience.

Travel information

*Flight schedules are subject to change.

*Flight schedules are subject to change.

Explore a world of travel with Expedia

*Available to One Key members.