Cheap Flights to Windham County from $77 (2026/2027)

Wander Wisely with exceptional service, 24/7 supportOpens in a new window

Feel at ease with free flight cancellations within 24 hours of booking

Change your flight without a fee on select flights

Jet to one of Windham County's top cities

A calm lake reflecting a forest with autumn foliage.

Brattleboro

Flights
Brattleboro

How Much Does it Cost To Fly To Windham County?

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

Fri, Mar 5 - Sat, Mar 13
BOS
Logan Intl.
LEB
Lebanon Municipal
$155 Roundtrip, found 10 hours ago
$155
Roundtrip
found 10 hours ago
Select Cape Air flight, departing Fri, Mar 5 from Logan Intl. to Lebanon Municipal, returning Sat, Mar 13, priced at $155 found 10 hours ago
Sun, Nov 1 - Sat, Nov 7
BOS
Logan Intl.
LEB
Lebanon Municipal
$165 Roundtrip, found 16 hours ago
$165
Roundtrip
found 16 hours ago
Select Cape Air flight, departing Sun, Nov 1 from Logan Intl. to Lebanon Municipal, returning Sat, Nov 7, priced at $165 found 16 hours ago
Wed, Nov 25 - Sun, Nov 29
BOS
Logan Intl.
LEB
Lebanon Municipal
$175 Roundtrip, found 16 hours ago
$175
Roundtrip
found 16 hours ago
Select Cape Air flight, departing Wed, Nov 25 from Logan Intl. to Lebanon Municipal, returning Sun, Nov 29, priced at $175 found 16 hours ago
Mon, Sep 7 - Sun, Sep 13
BOS
Logan Intl.
LEB
Lebanon Municipal
$178 Roundtrip, found 17 hours ago
$178
Roundtrip
found 17 hours ago
Select Cape Air flight, departing Mon, Sep 7 from Logan Intl. to Lebanon Municipal, returning Sun, Sep 13, priced at $178 found 17 hours ago
Thu, Oct 22 - Thu, Oct 22
BOS
Logan Intl.
LEB
Lebanon Municipal
$180 Roundtrip, found 5 days ago
$180
Roundtrip
found 5 days ago
Select Cape Air flight, departing Thu, Oct 22 from Logan Intl. to Lebanon Municipal, returning Thu, Oct 22, priced at $180 found 5 days ago
Sat, Nov 21 - Sat, Nov 28
BOS
Logan Intl.
RUT
Rutland Southern Vermont Regional
$180 Roundtrip, found 12 hours ago
$180
Roundtrip
found 12 hours ago
Select Cape Air flight, departing Sat, Nov 21 from Logan Intl. to Rutland Southern Vermont Regional, returning Sat, Nov 28, priced at $180 found 12 hours ago
Wed, Sep 2 - Wed, Sep 2
BOS
Logan Intl.
LEB
Lebanon Municipal
$182 Roundtrip, found 11 hours ago
$182
Roundtrip
found 11 hours ago
Select Cape Air flight, departing Wed, Sep 2 from Logan Intl. to Lebanon Municipal, returning Wed, Sep 2, priced at $182 found 11 hours ago
Wed, Nov 25 - Sun, Nov 29
BOS
Logan Intl.
LEB
Lebanon Municipal
$185 Roundtrip, found 16 hours ago
$185
Roundtrip
found 16 hours ago
Select Cape Air flight, departing Wed, Nov 25 from Logan Intl. to Lebanon Municipal, returning Sun, Nov 29, priced at $185 found 16 hours ago
Mon, Sep 21 - Fri, Sep 25
DEN
Denver Intl.
LEB
Lebanon Municipal
$490 Roundtrip, found 3 days ago
$490
Roundtrip
found 3 days ago
Select United flight, departing Mon, Sep 21 from Denver Intl. to Lebanon Municipal, returning Fri, Sep 25, priced at $490 found 3 days ago
OriginDestinationTravel DatesFlights From*
DCAWest LebanonDecember 3 to December 6$310
DCANorth ClarendonSeptember 7 to September 9$386
DENWest LebanonSeptember 21 to September 25$490
DENNorth ClarendonOctober 29 to November 1$522
TPANorth ClarendonOctober 3 to October 6$534
LAXNorth ClarendonNovember 6 to November 9$544
MCONorth ClarendonOctober 9 to October 13$546
CLTWest LebanonNovember 13 to November 18$562
CLTNorth ClarendonSeptember 5 to September 6$573
FLLNorth ClarendonSeptember 10 to September 15$584
LAXWest LebanonSeptember 20 to October 3$586
ATLWest LebanonSeptember 17 to October 30$591
ATLNorth ClarendonSeptember 24 to September 27$626
FLLWest LebanonSeptember 24 to September 27$770
TPAWest LebanonSeptember 25 to September 27$775
*Prices include taxes and fees
OriginDestinationTravel DatesFlights From*
ORDWest LebanonAugust 30 to September 2$896
*Prices include taxes and fees

Best Windham County Flight and Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Holiday Inn Club Vacations Mount Ascutney Resort by IHG
3.0-star property

Holiday Inn Club Vacations Mount Ascutney Resort by IHG

Oct 15 - Oct 19

4 night stay

Chicago (CHI) to Rutland (RUT)

United • Roundtrip • Coach
Save 100% on your flight
Price was $932, price is now $641 per person
$641
per person
found 1 day ago
My Place Hotel-Randolph VT
2.0-star property

My Place Hotel-Randolph VT

Oct 15 - Oct 19

4 night stay

Chicago (CHI) to Rutland (RUT)

United • Roundtrip • Coach
Price was $891, price is now $651 per person
$651
per person
found 1 day ago
The Shire Woodstock
3.0-star property

The Shire Woodstock

Oct 15 - Oct 19

4 night stay

Philadelphia (PHL) to Springfield (VSF)

American Airlines • Coach

Springfield (VSF) to Philadelphia (PHL)

Southwest Airlines • Coach
Save 100% on your flight
Price was $2,086, price is now $1,565 per person
$1,565
per person
just found
Don't see what you're looking for?
See all available trips from Chicago to Windham County
View all trips

Travelers ❤️ These Windham County 🏨

Colonial Motel

Colonial Motel

3 out of 5
889 Putney Rd Brattleboro VT
Book a stay at this business-friendly motel in Brattleboro. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Brattleboro Bowl and New England Center for Circus Arts are located nearby.
Opens in a new windowColonial Motel
Latchis Hotel

Latchis Hotel

2.5 out of 5
50 Main Street Brattleboro VT
Stay at this hotel in Brattleboro. Enjoy free WiFi, free parking, and conference space. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Latchis Theatre and Brattleboro Museum & Art Center are located nearby.
8.6/10 Excellent! (963 reviews)
"The art deco building is gorgeous. I applaud the non-profit organization that saved, renovated and maintains this exceptional building. I very much appreciated the original bathroom fixtures. The hotel really gives you a taste of what it might have been like to travel back in the 1930-40s. On the ..."

Reviewed on Aug 22, 2026

Opens in a new windowLatchis Hotel
Hampton Inn Brattleboro

Hampton Inn Brattleboro

2.5 out of 5
1378 Putney Road Brattleboro VT
Book a stay at this business-friendly hotel in Brattleboro. Enjoy free breakfast, free parking, and a fitness center. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions United States Navy Seabee Bridge and Brattleboro Bowl are located nearby.
8.2/10 Very Good! (1,015 reviews)
"Staff were extremely friendly. The whole place was clean. Hit tub was really a whirlpool..movement but no bubbles. So nice and warm though. Great stay!!"

Reviewed on Aug 21, 2026

Opens in a new windowHampton Inn Brattleboro
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free
Comfort Inn & Suites Brattleboro I-91

Comfort Inn & Suites Brattleboro I-91

2.5 out of 5
1186 Putney Road Brattleboro VT
Book a stay at this business-friendly hotel in Brattleboro. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions United States Navy Seabee Bridge and Brattleboro Bowl are located nearby.
8.6/10 Excellent! (849 reviews)
"Breakfast was fine."

Reviewed on Aug 18, 2026

Opens in a new windowComfort Inn & Suites Brattleboro I-91
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.

Frequently asked questions

How much is the cheapest flight to Windham County?
Some thrifty travelers booked a roundtrip flight to Windham County for as little as $155 in the last seven days. If you spot a bargain, act fast. Cheap deals don't hang around for long! This price was available on Travelocity for flights to Windham County departing within the next year. Prices and availability are subject to change. Additional terms apply.
Which airlines fly to Windham County?
You can choose from 16 airlines when you're ready to lock in your flight to Windham County. Let Cape Air fly you there. This favorite air carrier offers 182 services per month to Bellows Falls, Windham County's primary city.
What is the cheapest month to fly to Windham County?
For the greatest chance at landing a terrific flight deal, time your break sometime in March. Based on Travelocity's direct flight demand from January to December last year, it's the cheapest time to journey to Windham County.
How can I check my flight status to Windham County?
Check out our helpful portal, Trips. You'll find just about everything related to your flight to Windham County here, including important information about the status of your flight and more. Trips is found at the top right of the Travelocity homepage. Simply sign up, log in and get the answers you need. Alternatively, you can access your itinerary while you're on the go and get real-time travel updates through the Travelocity app. You'll find all your itineraries in one place, making it a snap to share details with any members of your family flying with you.
How do I find the best deals on flights to Windham County?
Be flexible with your dates and there's a strong chance you'll find an amazing deal. After you've searched for flights on Travelocity, hit the "Flexible dates" box at the top of the page to compare prices with nearby days. Also try to book ahead of schedule and avoid the busy tourist season. In the last seven days, the best price for a return flight to Windham County was $155. This price was available on Travelocity for flights departing within the next year. Prices and availability are subject to change. Additional terms apply.
Why should I book my flight to Windham County with Travelocity?
Look for cheap flights to Windham County with Travelocity and begin packing for your next vacation. With 24/7 customer service throughout every step of the process and our Price Match Guarantee, we take the stress out of booking cheap family flights, hotels, activities and more. Snag a great deal now and prepare for an epic adventure.
What are the most popular flight routes to Windham County?
As a renowned vacation destination, you'll find excellent connections to Windham County. Check out this sample of popular routes:

  • Chicago, IL (ORD-O'Hare Intl.) to Albany Intl. Airport (ALB) - 1,122 flights a month.
  • Detroit, MI (DTW-Detroit Metropolitan Wayne County) to Albany Intl. Airport (ALB) - 706 flights a month.
  • Philadelphia, PA (PHL-Philadelphia Intl.) to Albany Intl. Airport (ALB) - 689 flights a month.

How much is a flight to Windham County on average?
Based on prices found on Travelocity over the last seven days, roundtrip flights to Windham County were between $155 and $896. Whenever you're ready to go, Travelocity will help you find a fare that won't blow your budget. These prices were available on Travelocity for flights departing within the next year. Prices and availability are subject to change. Additional terms apply.
How long is the average flight to Windham County?
The length of your direct flight to Windham County is typically dependent on your starting point. If you'd like an idea of what to expect, here are the average travel times for a handful of leading routes to Windham County:

  • Chicago, IL (ORD-O'Hare Intl.) to Albany Intl. Airport (ALB) - 2 hours and 1 minute
  • Detroit, MI (DTW-Detroit Metropolitan Wayne County) to Albany Intl. Airport (ALB) - 1 hour and 32 minutes
  • Philadelphia, PA (PHL-Philadelphia Intl.) to Albany Intl. Airport (ALB) - 1 hour and 16 minutes

What can I expect on a flight to Windham County?
This mainly depends on where you're departing from and which carrier you fly with. You're likely to find all kinds of flights to Windham County, from first class trips to cheap flights for family vacations. If you're traveling long haul, your airline will typically provide hot meals and entertainment as well as games to amuse the kids.