Cheap Flights to Woodstock from $82

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

Change your flight without a fee on select flights

How Much Does it Cost To Fly To Woodstock?

The cheapest prices found with in the last 7 days for return flights were $157 and $82 for one-way flights to Woodstock for the period specified. Prices and availability are subject to change. Additional terms apply

OriginDestinationTravel DatesFlights From*
DCANorth ClarendonAugust 1 to August 4$319
DCAWest LebanonJuly 15 to July 21$351
JFKWest LebanonAugust 18 to August 21$355
ATLWest LebanonAugust 12 to August 19$402
TPANorth ClarendonJuly 14 to July 22$402
PHLWest LebanonAugust 9 to August 23$408
JFKNorth ClarendonAugust 16 to August 18$414
TPAWest LebanonSeptember 4 to September 7$415
EWRWest LebanonAugust 14 to August 16$421
ATLNorth ClarendonJuly 3 to July 7$440
DENWest LebanonAugust 5 to August 18$451
DENNorth ClarendonJuly 31 to August 11$463
PHLNorth ClarendonJuly 8 to July 12$501
LAXWest LebanonSeptember 27 to October 3$510
LAXNorth ClarendonAugust 9 to August 16$529
*Prices include taxes and fees
OriginDestinationTravel DatesFlights From*
DCANorth ClarendonJune 29 to July 1$495
ATLWest LebanonJune 29 to July 9$530
DENNorth ClarendonJune 29 to July 11$578
JFKWest LebanonJune 29 to July 3$606
TPAWest LebanonJune 28 to June 30$672
LAXWest LebanonJune 29 to July 19$688
JFKNorth ClarendonJune 27 to June 29$2,205
EWRNorth ClarendonJune 27 to June 29$2,246
*Prices include taxes and fees

Woodstock Flight Information

Traveling to
Woodstock
Lowest Price
$157
Number of Airlines Serving
Airlines Serving
JetBlue Airways
Number of Daily Flights
Airlines with Direct Flights

Find The Perfect Hotel For After Your Flight

Amazing Woodstock Accommodation Deals

Sleep Woodstock Motel

Sleep Woodstock Motel

2 out of 5
4324 West Woodstock Road, Woodstock, VT
Stay at this motel in Woodstock. Enjoy free WiFi, free parking, and a picnic area. Our guests praise the helpful staff and the clean rooms in our reviews. Popular ...
9.6/10 Exceptional! (491 reviews)
"Nice room"

Reviewed on Jun 19, 2025

Sleep Woodstock Motel
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.

Luxury Hotels in Woodstock

On The River Inn

On The River Inn

4 out of 5
1653 West Woodstock Road, Woodstock, VT
Stay at this 4-star family-friendly hotel in Woodstock. Enjoy free WiFi, free parking, and a fitness center. Our guests praise the breakfast and the helpful ...
9.2/10 Wonderful! (1,003 reviews)
"Great hotel with a clean pool a good breakfast. The Resturant needs more help that was the only flaw, food was great but the employees where running crazy."

Reviewed on Jun 22, 2025

On The River Inn
Woodstock Inn & Resort

Woodstock Inn & Resort

4.5 out of 5
Fourteen The Green, Woodstock, VT
Stay at this 4.5-star luxury resort in Woodstock. Enjoy free WiFi, free valet parking, and an outdoor pool. Our guests praise the helpful staff in our reviews. ...
9.2/10 Wonderful! (520 reviews)
"Nice, historic vibe, a centerpiece of Woodstock."

Reviewed on Jun 20, 2025

Woodstock Inn & Resort
Sleep Woodstock Motel

Sleep Woodstock Motel

2 out of 5
4324 West Woodstock Road, Woodstock, VT
Stay at this motel in Woodstock. Enjoy free WiFi, free parking, and a picnic area. Our guests praise the helpful staff and the clean rooms in our reviews. Popular ...
9.6/10 Exceptional! (491 reviews)
"Nice room"

Reviewed on Jun 19, 2025

Sleep Woodstock Motel
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.

Family Friendly Hotels in Woodstock

On The River Inn
Great for families

On The River Inn

4 out of 5
1653 West Woodstock Road, Woodstock, VT
Stay at this 4-star family-friendly hotel in Woodstock. Enjoy free WiFi, free parking, and a fitness center. Our guests praise the breakfast and the helpful ...
9.2/10 Wonderful! (1,003 reviews)

Families like: Kids pool, playground, game room, skiing nearby

Travelers say...
"Great hotel with a clean pool a good breakfast. The Resturant needs more help that was the only flaw, food was great but the employees where running crazy."

Reviewed on Jun 22, 2025

On The River Inn
Sleep Woodstock Motel

Sleep Woodstock Motel

2 out of 5
4324 West Woodstock Road, Woodstock, VT
Stay at this motel in Woodstock. Enjoy free WiFi, free parking, and a picnic area. Our guests praise the helpful staff and the clean rooms in our reviews. Popular ...
9.6/10 Exceptional! (491 reviews)
"Nice room"

Reviewed on Jun 19, 2025

Sleep Woodstock Motel
The Shire Woodstock

The Shire Woodstock

3 out of 5
46 Pleasant St., Woodstock, VT
Stay at this 3-star hotel in Woodstock. Enjoy free WiFi, free parking, and free bicycles on site. Our guests praise the helpful staff and the clean rooms in ...
8.6/10 Excellent! (758 reviews)
"Surprisingly my room had a fireplace and a patio with a lovely river view. Get the river view! I didn’t want to leave after one night, so just before checkout I asked for another night."

Reviewed on Jun 20, 2025

The Shire Woodstock
Save an average of 15% on thousands of hotels when you're signed in
Woodstock Inn & Resort

Woodstock Inn & Resort

4.5 out of 5
Fourteen The Green, Woodstock, VT
Stay at this 4.5-star luxury resort in Woodstock. Enjoy free WiFi, free valet parking, and an outdoor pool. Our guests praise the helpful staff in our reviews. ...
9.2/10 Wonderful! (520 reviews)
"Nice, historic vibe, a centerpiece of Woodstock."

Reviewed on Jun 20, 2025

Woodstock Inn & Resort
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.

Best Woodstock Flight and Hotel Packages

Woodstock flight + hotel packages - economy flights

Price found within the past 48 hours. Click for updated prices.
Solitude Village at Okemo
Winterplace at Okemo
Jackson Gore Village
Don't see what you're looking for?
See all available trips from Chicago to Woodstock
View all trips

Need a Car For After Your Flight?

Plane Tickets To Woodstock

Although you may try and resist the urge, you know that when the travel bug comes, there is only one way to get rid of it. Thankfully, Travelocity is here to help nip that travel bug in the bud with great deals on flights to Woodstock. Browse through our inventory to explore a wide range of cheap flights to Woodstock to solidify your next big trip out of town. Whether you are heading out on a business trip, exploring a place you have never been for pleasure or are bringing the family on the annual vacation, we have the perfect getaway waiting for you. In no time, you will be day dreaming of your plane landing in Woodstock as you anxiously await to exit the plane and explore what Woodstock has to offer. Considering all the amazing local food and culture in Woodstock, we won't hold this against you.

When you are ready to embark on your next big adventure, Travelocity will be right here waiting to open the doors to the garden so that you can go and smell the roses. When you decide to book and travel is entirely up to you, but don't wait too long because we have some of the best deals on the web and they won't last long. Take time to go through our huge selection of cheap flights to Woodstock to find the best deals that fit into your budget. If browsing on your phone while your boss isn't looking is more your thing (we promise we won't tell), consider checking out Travelocity's mobile app which allows you to take advantage of all our flights to Woodstock without having to compromise your work computer's search history. If you are looking to save even more, you can easily save up to $537 when you bundle one of our cheap flights to Woodstock with one of our hotels. So why are you waiting around? There is no better time than now to start booking that next trip. Start your search now to book one of our flights to Woodstock today!

*Price based on the lowest price found within past 24 hours and based upon one night stay for two adults over the next thirty days. Prices and availability subject to change. Additional terms may apply.