$133 Find Cheap Flights to Woodstock

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight to Woodstock departing on 8/1. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy

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Cheap Flights to Woodstock

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights to Woodstock that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals to Woodstock

Sat, Sep 27 - Wed, Oct 1
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7:05 am - 2:58 pmPIT-LEB
7h 53m1 stop
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10:43 am - 3:31 pmLEB-PIT
4h 48m1 stop
Sat, Sep 27 - Wed, Oct 1
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11:04 am - 9:48 amPIT-LEB
22h 44m2 stops
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7:08 am - 3:42 pmLEB-PIT
8h 34m2 stops
Tue, Aug 5 - Tue, Aug 12
JetBlue Logo
11:45 am - 6:53 pmDCA-LEB
7h 08m1 stop
JetBlue Logo
7:08 am - 11:37 amLEB-DCA
4h 29m1 stop
$395JetBlue
Find Deal
Fri, Sep 26 - Mon, Sep 29
JetBlue Logo
1:35 pm - 6:53 pmDCA-LEB
5h 18m1 stop
JetBlue Logo
10:43 am - 3:31 pmLEB-DCA
4h 48m1 stop
$400JetBlue
Find Deal
Wed, Jul 16 - Mon, Jul 21
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8:29 am - 2:58 pmDCA-LEB
6h 29m1 stop
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2:14 pm - 7:54 amLEB-DCA
17h 40m1 stop
Fri, Jul 4 - Tue, Jul 8
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5:50 pm - 1:44 pmPIT-LEB
19h 54m1 stop
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10:43 am - 11:58 amLEB-PIT
25h 15m1 stop
Sat, Aug 16 - Sat, Aug 30
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7:45 pm - 2:58 pmORD-LEB
18h 13m1 stop
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4:08 pm - 11:33 amLEB-ORD
20h 25m1 stop
Thu, Jul 17 - Thu, Jul 24
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10:59 pm - 2:58 pmJFK-LEB
15h 59m1 stop
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10:43 am - 9:04 pmLEB-JFK
10h 21m1 stop
Sun, Sep 7 - Fri, Sep 12
JetBlue Logo
6:30 am - 9:48 amJFK-LEB
3h 18m1 stop
JetBlue Logo
7:08 am - 11:18 amLEB-JFK
4h 10m1 stop
$415JetBlue
Find Deal
Fri, Jul 4 - Tue, Jul 8
JetBlue Logo
12:28 pm - 6:53 pmPIT-LEB
6h 25m1 stop
JetBlue Logo
10:43 am - 5:09 pmLEB-PIT
6h 26m1 stop
$415JetBlue
Find Deal
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Good to know - Book Cheap Woodstock Plane Tickets

Low seasonFebruary
High seasonAugust
Cheapest flight$133
Best time to beat the crowds with an average 32% drop in price.
Most popular time to fly and prices are also 8% lower on average.
Flight from Chicago to Lebanon

FAQs - booking Woodstock flights

  • How long is the flight to Woodstock?

    Flights from White Plains1h 33m
    Flights from Boston1h 07m
  • What is the cheapest flight to Lebanon?

    In the last 3 days, the cheapest flight deal to Lebanon was found on the route from Chicago, at $381 return. The most popular connection is from Boston to Lebanon and KAYAK users have found round-trip deals for as low as $179 in the last 3 days.

  • How to fly to Woodstock?

    You cannot fly directly to Woodstock. KAYAK recommends you fly to Lebanon Municipal (LEB) (10.48 miles from Woodstock). From there you can rent a car or get a taxi.

  • What airports are near Woodstock?

    The closest airport is Lebanon Municipal (LEB) (10.48 mi). Other nearby airports are Rutland (RUT) (22.41 mi), Morristown Morrisville-Stowe (MVL) (63.24 mi), Burlington (BTV) (66.41 mi) or Manchester (MHT) (72.58 mi). KAYAK recommends you fly to Lebanon Municipal.

  • How far is Lebanon Municipal Airport from central Lebanon?

    The city center of Lebanon is 3 miles from Lebanon Municipal Airport.

  • What is the name of Lebanon’s airport?

    Lebanon is served by Lebanon Municipal Airport, also commonly referred to as Lebanon Municipal or Lebanon Rgnl. The airport code is LEB.

  • How does KAYAK find such low prices on flights to Woodstock?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights to Woodstock.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket to Woodstock?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Woodstock is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights to Woodstock?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Woodstock with an airline and back with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight to Woodstock?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Woodstock up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Top tips for finding cheap flights to Woodstock

  • There is no major airport in Woodstock. It is instead served by Lebanon Municipal Airport.
  • Looking for cheap airfare to Woodstock? 25% of our users found round-trip tickets to Woodstock for the following prices or less: From Boston $156
  • Enter your preferred departure airport and travel dates into the search form above to unlock the latest Woodstock flight deals.

Reviews of the top airlines flying to Woodstock

 
Need help choosing which airline to fly with from the United States to Woodstock? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
9.1
Cape AirOverall score based on 35 reviews
9.3Crew
8.7Food
8.7Comfort
8.9Entertainment
8.9Boarding
Airline reviews

It was good. It was convenient and frequent enough to be a very useful flight to reach more regional hubs. I felt comfortable enough to sleep. During the flight but loved seeing the countryside when I was awake.

10.0 ExcellentAnonymous, Jun 2025SDY - BIL
Read more Cape Air reviews

It was good. It was convenient and frequent enough to be a very useful flight to reach more regional hubs. I felt comfortable enough to sleep. During the flight but loved seeing the countryside when I was awake.

It’s less complicated from Culebra to SJU airport. Next time I will prefer to leave from Isla Grande airport to Culebra !!

10 seat Cesna. Equal parts transportation and adventure. 20 minute hop at 10000 feet and 160 mph, sitting 10 feet from the pilot. Panoramic views of the island. Very simple boarding, very low stress. VQS airport tiny, undeveloped. Highly recommended flight, Cape Air doing a great job here.

We traveled in a small Cesna so there was no food or entertainment. The pilot was excellent enjoy being able to see the places we were flying above. It was an OK flight.

Very smooth flight and landing. Pilot delivered his safety instruction in such a monotone that it wasn’t easily understandable. Words were said but he didn't communicate to us. If he was communicating to someone he cared about, he would have used inflection and other nuances of speaking. Virtually all emphasis was removed so it was just blah blah blah (really fast, like the end of a Pharma commercial)

My pilot on Cape Air was AMAZING!!!! I hoping that next time I fly I have him as my pilot. He made me feel safe and secure in his skills.

I so appreciate this service into and out of Glendive. Always a good experience with crew and support team.

It was not what I had expected but it was a great way to see the landscape.

Pros: "ground crew, pilot, flight was smooth and gate connections to Jet Blue in Boston were fantastic!"
Cons: "leg room"

Seats were not too comfortable; it was impossible to locate the underseat power outlet.

You get what you pay for with JetBlue. Every little thing costs more, you are nickel and dimed until the end. Entertainment doesn’t function. Flight attendants do the bare minimum.

The check in and boarding process was a bit of a cluster. Two people at the counter to check in, three random lines that nobody knew which was for what, and people kept getting shuffled from one line to another for no apparent reason because then they’d get shuffled back and end up getting out further back in the line than they were originally. I only had to hand my already checked bag over and it took 45 minutes. I was never assigned a seat so when I tried to board I was pulled out of line again while someone had to try to manually assign me a seat. During the flight I got up to go to the bathroom, and there was an attendant in the aisle offering pillows etc and it was a 30 min wait unbuckled standing by the bathrooms because she said I couldn’t go past her. First and last time flying jet blue to be honest.

Communication since no reason or explanation was given for 3 hrs delay

Flight was delayed several 3 hours - no reason was given and no communication what so ever.

No overhead baggage room even though I was seated in row 2. Consequently had to check in my carry on bag. Baggage carousel was jammed. Took 45 min to get my bag.

Excellent. Although they used to greet me as a mosaic member and provide a free drink, early boarding helps me to keep coming back to JetBlue.

Cancelled flight with no specific instructions to get a boarding pass for another flight. The whole flight of people were in line for an hour because there was only 1 person to help at the desk. This was unusual for JetBlue.

It was too hot in the cabin. The AC did not help.

Except for the 28 minute delay leaving and the earlier reschedule to a later takeoff time the flight was good.

Everything you need to know for your flight to Woodstock

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