Cheap Flights to Windham County from $76

View $76 flight on Mon, Jan 5, 2026Opens in a new window

Popular airlines to Windham County

  • JetBlue Airways

    JetBlue Airways

  • Cape Air

    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 $76 for one-way flights and $123 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

JetBlue Airways
Sat, Feb 21 - Sat, Feb 28
BOS
Boston
RUT
Rutland
$123 Roundtrip, found 3 hours ago
$123
Roundtrip
found 3 hours ago
Select JetBlue Airways flight, departing Sat, Feb 21 from Boston to Rutland, returning Sat, Feb 28, priced at $123 found 3 hours ago
JetBlue Airways
Thu, Feb 19 - Sat, Feb 28
BOS
Boston
RUT
Rutland
$143 Roundtrip, found 3 hours ago
$143
Roundtrip
found 3 hours ago
Select JetBlue Airways flight, departing Thu, Feb 19 from Boston to Rutland, returning Sat, Feb 28, priced at $143 found 3 hours ago
JetBlue Airways
Sat, Feb 21 - Wed, Feb 25
BOS
Boston
RUT
Rutland
$153 Roundtrip, found 3 hours ago
$153
Roundtrip
found 3 hours ago
Select JetBlue Airways flight, departing Sat, Feb 21 from Boston to Rutland, returning Wed, Feb 25, priced at $153 found 3 hours ago
Cape Air
Mon, Jan 5 - Fri, Jan 9
BOS
Boston
LEB
Lebanon
$155 Roundtrip, found 1 hour ago
$155
Roundtrip
found 1 hour ago
Select Cape Air flight, departing Mon, Jan 5 from Boston to Lebanon, returning Fri, Jan 9, priced at $155 found 1 hour ago
Cape Air
Tue, Feb 3 - Thu, Feb 12
BOS
Boston
LEB
Lebanon
$155 Roundtrip, found 1 hour ago
$155
Roundtrip
found 1 hour ago
Select Cape Air flight, departing Tue, Feb 3 from Boston to Lebanon, returning Thu, Feb 12, priced at $155 found 1 hour ago
JetBlue Airways
Mon, Jan 5 - Fri, Jan 9
BOS
Boston
LEB
Lebanon
$159 Roundtrip, found 1 hour ago
$159
Roundtrip
found 1 hour ago
Select JetBlue Airways flight, departing Mon, Jan 5 from Boston to Lebanon, returning Fri, Jan 9, priced at $159 found 1 hour ago
JetBlue Airways
Mon, Jan 5 - Fri, Jan 9
BOS
Boston
LEB
Lebanon
$159 Roundtrip, found 1 hour ago
$159
Roundtrip
found 1 hour ago
Select JetBlue Airways flight, departing Mon, Jan 5 from Boston to Lebanon, returning Fri, Jan 9, priced at $159 found 1 hour ago
JetBlue Airways
Thu, Feb 19 - Tue, Feb 24
BOS
Boston
RUT
Rutland
$163 Roundtrip, found 3 hours ago
$163
Roundtrip
found 3 hours ago
Select JetBlue Airways flight, departing Thu, Feb 19 from Boston to Rutland, returning Tue, Feb 24, priced at $163 found 3 hours ago
Delta
Wed, Jan 28 - Sat, Feb 7
EWR
New York
LEB
Lebanon
$300 Roundtrip, found 1 day ago
$300
Roundtrip
found 1 day ago
Select Delta flight, departing Wed, Jan 28 from New York to Lebanon, returning Sat, Feb 7, priced at $300 found 1 day ago
Accessrail
Tue, Jan 6 - Fri, Jan 9
WPT
West Palm Beach
RUT
Rutland
$584 Roundtrip, just found
$584
Roundtrip
just found
Select Accessrail flight, departing Tue, Jan 6 from West Palm Beach to Rutland, returning Fri, Jan 9, priced at $584 just found

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. Cheapest option available. Flights from $489
RUT
Rutland Southern Vermont Regional
Cheapest
Flights from $489

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, Feb 21 - Sat, Feb 28
BOS
Boston
RUT
Rutland
$123 Roundtrip, found 3 hours ago
$123
Roundtrip
found 3 hours ago
Select JetBlue Airways flight, departing Sat, Feb 21 from Boston to Rutland, returning Sat, Feb 28, priced at $123 found 3 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, $123 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 $123 to $584 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 $123 and $584. 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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Travel information

Windham County Flights Information

Airlines serving
Cape Air, JetBlue Airways, American Airlines, Delta, Accessrail
Roundtrip price
from $123
Windham County Flights Information

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