Cheap Flights to Windsor County from $40

View $40 flight on Fri, Oct 23, 2026Opens in a new window

Popular airlines to Windsor County

  • JetBlue Airways

  • Cape Air

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How much is the cheapest flight to Windsor County?

Prices were available within the past 7 days and start at $40 for one-way flights and $79 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

JetBlue Airways
Fri, Oct 23 - Sun, Oct 25
BOS
Boston
LEB
Lebanon
$79 Roundtrip, found 7 hours ago
$79
Roundtrip
found 7 hours ago
Select JetBlue Airways flight, departing Fri, Oct 23 from Boston to Lebanon, returning Sun, Oct 25, priced at $79 found 7 hours ago
JetBlue Airways
Tue, Feb 24 - Wed, Mar 4
BOS
Boston
LEB
Lebanon
$99 Roundtrip, found 1 day ago
$99
Roundtrip
found 1 day ago
Select JetBlue Airways flight, departing Tue, Feb 24 from Boston to Lebanon, returning Wed, Mar 4, priced at $99 found 1 day ago
JetBlue Airways
Sat, Feb 14 - Sun, Feb 15
BOS
Boston
LEB
Lebanon
$119 Roundtrip, found 5 hours ago
$119
Roundtrip
found 5 hours ago
Select JetBlue Airways flight, departing Sat, Feb 14 from Boston to Lebanon, returning Sun, Feb 15, priced at $119 found 5 hours ago
JetBlue Airways
Mon, Mar 2 - Tue, Mar 10
BOS
Boston
RUT
Rutland
$123 Roundtrip, found 11 hours ago
$123
Roundtrip
found 11 hours ago
Select JetBlue Airways flight, departing Mon, Mar 2 from Boston to Rutland, returning Tue, Mar 10, priced at $123 found 11 hours ago
Cape Air
Sat, Feb 14 - Sun, Feb 15
BOS
Boston
LEB
Lebanon
$125 Roundtrip, found 5 hours ago
$125
Roundtrip
found 5 hours ago
Select Cape Air flight, departing Sat, Feb 14 from Boston to Lebanon, returning Sun, Feb 15, priced at $125 found 5 hours ago
JetBlue Airways
Fri, Oct 23 - Sun, Oct 25
BOS
Boston
LEB
Lebanon
$129 Roundtrip, found 7 hours ago
$129
Roundtrip
found 7 hours ago
Select JetBlue Airways flight, departing Fri, Oct 23 from Boston to Lebanon, returning Sun, Oct 25, priced at $129 found 7 hours ago
JetBlue Airways
Sat, Feb 14 - Sun, Feb 15
BOS
Boston
LEB
Lebanon
$129 Roundtrip, found 5 hours ago
$129
Roundtrip
found 5 hours ago
Select JetBlue Airways flight, departing Sat, Feb 14 from Boston to Lebanon, returning Sun, Feb 15, priced at $129 found 5 hours ago
Cape Air
Fri, Oct 23 - Sun, Oct 25
BOS
Boston
LEB
Lebanon
$135 Roundtrip, found 7 hours ago
$135
Roundtrip
found 7 hours ago
Select Cape Air flight, departing Fri, Oct 23 from Boston to Lebanon, returning Sun, Oct 25, priced at $135 found 7 hours ago
Delta
Tue, Mar 10 - Sat, Mar 14
DCA
Washington
LEB
Lebanon
$330 Roundtrip, found 4 days ago
$330
Roundtrip
found 4 days ago
Select Delta flight, departing Tue, Mar 10 from Washington to Lebanon, returning Sat, Mar 14, priced at $330 found 4 days ago
American Airlines
Thu, Feb 26 - Sat, Feb 28
TTN
Trenton
RUT
Rutland
$441 Roundtrip, found 2 days ago
$441
Roundtrip
found 2 days ago
Select American Airlines flight, departing Thu, Feb 26 from Trenton to Rutland, returning Sat, Feb 28, priced at $441 found 2 days ago

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*Flight schedules are subject to change.

*Flight schedules are subject to change.

Trending flights to Windsor 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
Thu, Feb 26 - Sat, Feb 28
ORD
Chicago
LEB
Lebanon
$254 Roundtrip, found 1 day ago
$254
Roundtrip
found 1 day ago
Select JetBlue Airways flight, departing Thu, Feb 26 from Chicago to Lebanon, returning Sat, Feb 28, priced at $254 found 1 day ago
*Available to One Key members.