Cheap flights To Woodstock (VSF) from $82

Earn rewards on top of your airline miles with Orbitz Rewards

Many airlines offer flexible change policies

Sign up to receive text alerts about your trip

Cheap Flights to Woodstock from $82 One Way, $103 Round Trip

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

Tue, Jul 29 - Fri, Aug 1
BOS
Logan Intl.
RUT
Rutland Southern Vermont Regional
$103 Roundtrip, found 6 days ago
$103
Roundtrip
found 6 days ago
Select JetBlue Airways flight, departing Tue, Jul 29 from Logan Intl. to Rutland Southern Vermont Regional, returning Fri, Aug 1, priced at $103 found 6 days ago
Thu, May 22 - Fri, May 23
BOS
Logan Intl.
RUT
Rutland Southern Vermont Regional
$105 Roundtrip, found 6 days ago
$105
Roundtrip
found 6 days ago
Select JetBlue Airways flight, departing Thu, May 22 from Logan Intl. to Rutland Southern Vermont Regional, returning Fri, May 23, priced at $105 found 6 days ago
Fri, Aug 1 - Fri, Aug 1
BOS
Logan Intl.
RUT
Rutland Southern Vermont Regional
$137 Roundtrip, found 6 days ago
$137
Roundtrip
found 6 days ago
Select JetBlue Airways flight, departing Fri, Aug 1 from Logan Intl. to Rutland Southern Vermont Regional, returning Fri, Aug 1, priced at $137 found 6 days ago
Tue, Jul 29 - Sat, Aug 2
BOS
Logan Intl.
RUT
Rutland Southern Vermont Regional
$143 Roundtrip, found 6 days ago
$143
Roundtrip
found 6 days ago
Select JetBlue Airways flight, departing Tue, Jul 29 from Logan Intl. to Rutland Southern Vermont Regional, returning Sat, Aug 2, priced at $143 found 6 days ago
Wed, Jul 30 - Fri, Aug 1
BOS
Logan Intl.
RUT
Rutland Southern Vermont Regional
$153 Roundtrip, found 6 days ago
$153
Roundtrip
found 6 days ago
Select JetBlue Airways flight, departing Wed, Jul 30 from Logan Intl. to Rutland Southern Vermont Regional, returning Fri, Aug 1, priced at $153 found 6 days ago
Tue, Nov 11 - Tue, Nov 11
BOS
Logan Intl.
LEB
Lebanon Municipal
$154 Roundtrip, found 4 days ago
$154
Roundtrip
found 4 days ago
Select JetBlue Airways flight, departing Tue, Nov 11 from Logan Intl. to Lebanon Municipal, returning Tue, Nov 11, priced at $154 found 4 days ago
Tue, Nov 11 - Tue, Nov 11
BOS
Logan Intl.
LEB
Lebanon Municipal
$159 Roundtrip, found 4 days ago
$159
Roundtrip
found 4 days ago
Select JetBlue Airways flight, departing Tue, Nov 11 from Logan Intl. to Lebanon Municipal, returning Tue, Nov 11, priced at $159 found 4 days ago
Tue, Nov 11 - Tue, Nov 11
BOS
Logan Intl.
LEB
Lebanon Municipal
$171 Roundtrip, found 4 days ago
$171
Roundtrip
found 4 days ago
Select Cape Air flight, departing Tue, Nov 11 from Logan Intl. to Lebanon Municipal, returning Tue, Nov 11, priced at $171 found 4 days ago
Sun, Jul 6 - Mon, Jul 21
ORD
O'Hare Intl.
RUT
Rutland Southern Vermont Regional
$269 Roundtrip, found 6 days ago
$269
Roundtrip
found 6 days ago
Select JetBlue Airways flight, departing Sun, Jul 6 from O'Hare Intl. to Rutland Southern Vermont Regional, returning Mon, Jul 21, priced at $269 found 6 days ago
Sat, Jun 14 - Tue, Jun 17
ORD
O'Hare Intl.
LEB
Lebanon Municipal
$325 Roundtrip, found 2 days ago
$325
Roundtrip
found 2 days ago
Select American Airlines flight, departing Sat, Jun 14 from O'Hare Intl. to Lebanon Municipal, returning Tue, Jun 17, priced at $325 found 2 days ago

Woodstock Flight Information

Traveling To
Woodstock
Destination Airport IATA Code
VSF
Number of Airlines Serving
Airlines
JetBlue Airways, Cape Air, American Airlines
Flight Price
$103
Earliest Departing Flight
Latest Departing Flight

Book Your Flight & Hotel Together & Save

Woodstock economy flight packages

Price found within the past 48 hours. Click for updated prices.
Jackson Gore Village
3.0-star property

Jackson Gore Village

Jun 20 - Jun 22

2 night stay

Chicago (ORD) to Springfield (VSF)

American Airlines • Roundtrip • Coach
per person
found 15 hours ago
The Shire Woodstock
3.0-star property

The Shire Woodstock

Jun 9 - Jun 12

3 night stay

Chicago (ORD) to Springfield (VSF)

American Airlines • Non-stop • Coach

Springfield (VSF) to Chicago (ORD)

Cape Air • Non-stop • Coach
per person
found 10 hours ago
Don't see what you're looking for?
See all available trips from Chicago to Woodstock
View all trips

Woodstock

Get the absolute lowest prices on flights to Woodstock by shopping with Orbitz. Orbitz is the most efficient travel planner around, allowing you to search, compare and book discount domestic and international flights fast. With cutting-edge mobile tools and access to frequent flier rewards programs, we have everything you need for both your routine and holiday excursions.

Book Your Flight To Woodstock Using Your Mobile Device

New mobile app tools enable those with hand-held devices to scout out the best bargains and to secure tickets from any location. If you have an iPhone, iPad or Android device, you may take advantage of special discounts, only available to mobile device customers, when you book hotel rooms or car rentals on the same day as booking Woodstock flights.

Avoid Check-In Hassles When Traveling On Flights to Woodstock

Orbitz also provides an array of resources that can help you eliminate most check-in hassles. Detailed baggage information is continually available for Woodstock flights. Mobile apps can also be used to share travel itineraries with family members or business associates.

Keeping Everyone Up To Date

When you download the free Orbitz mobile phone app, you can get regular and free flight updates. These will keep you informed of important scheduling changes. Updates can even be sent to several contacts, helping to keep everyone current on anticipated arrival times and all other relevant flight details.

Orbitz makes traveling on a budget very easy to do. We provide everything you need to plan your ideal trip from start to finish. Getting there and back again is a snap when you book your Woodstock flight using Orbitz.

Frequently asked questions

What is the best airport to fly to in Woodstock?
Lebanon Municipal Airport (LEB), around 10 miles east of central Woodstock, is one choice. Rutland Southern Vermont Regional Airport (RUT) will also get you to this city’s doorstep. Compare the flight deals to both airports, as well as which terminal is closer to wherever you’re staying.
How much is a flight to Woodstock?
Travelers from far and wide landed round-trip deals ranging between $103 and $325 this week. Starting your journey from Boston (BOS)? The lowest one-way tickets started at just $82.
How to book the cheapest flight to Woodstock?
With some of the most incredible flight deals around, bagging a bargain is easy with Orbitz. The following tips and hints will help you find cheap flights to Woodstock — and leave you with more money in your pocket:

  • Consider departing from or arriving at nearby airports to save money. Enter your preferred departure and arrival airports in the form fields, then choose the ‘Nearby airports’ function below. It will list your options, if any.
  • If your plans aren’t written in stone, click on the ‘Show flexible dates’ option to scan the flight deals for different departure dates. You may find a cheaper fare.
  • To fine tune your results, hit ‘Show options.’ You can search based on seating class, airlines, nonstop flights and refundable flights. You can also select whether you want to fly in the morning, afternoon or evening under ‘Sort & Filter’ to the left.
  • If you’ve sorted your travel dates, don’t delay booking your flight. Ticket prices usually climb as the departure date gets closer.
  • Make even more savings on your adventure by bundling your flights, hotels and car rentals into one convenient package deal. Your wallet will thank you for it.
  • If you can, avoid traveling in peak seasons. Airfares are often at their most expensive during school breaks, summer and around other vacation times like Easter, Thanksgiving and Christmas.

What is the best time to book a flight to Woodstock?
Book in January, February or August for the lowest airfares to Woodstock. Once you’ve found a bargain, buy it — cheap flights are known to appear and vanish at the tap of a button.
What day of the week is the cheapest to book a flight to Woodstock?
To pick up a great flight deal, make a booking on a Tuesday, Wednesday or Saturday. These are usually the cheapest days to book tickets to Woodstock.
What is the cheapest day of the week to fly to Woodstock?
If you’re after cheap flights to Woodstock, depart at the start of the week. Orbitz data from 2020 shows Monday is the cheapest day to set off, followed by Tuesday. Saturday has the most expensive fares, so avoid flying on this day and do your wallet a favor.
What is the cheapest month to fly to Woodstock?
To book cheap flights to Woodstock, you should depart in August. If getting a good deal on your ticket is your top priority, Orbitz data has found that this is generally the best month to take a trip. June is when fares are the most expensive.
Which airlines allow free cancellation?
Life changes, and your ticket should be able to do the same. That’s why Orbitz makes it a cinch to search for flights with free cancellation and no change fees. Just enter your travel details and then choose “Filter by flexible change policies.” How’s that for peace of mind?
What do I need for the flight to Woodstock?
There’s nothing more enjoyable than flying off on an adventure, but it’s good to be prepared. These top tips will help get your trip off to a smooth start:

  • Your travel documents are the most important items you’ll need to carry on your flight. To avoid any delays when checking in, make sure that the name on your ticket corresponds with your government-issued photo ID.
  • Take some activities to keep you busy on your journey to Woodstock. Books, magazines and electronic gadgets like laptops and tablets are perfect. Make sure you take a bottle of water with you as well. Even on a short flight, it’s important to keep hydrated.
  • It can get chilly on the plane. If you’d rather not shiver your way through the flight, layer up.

How do I get cheap first-class/business deals to Woodstock?
If you think a business or first-class airfare is beyond your reach, you may want to think again. Here are some tips to help you score a premium flight to Woodstock for less:

  • Flexibility is important. By being open to different travel dates, you’ll have more chances of landing a great deal on your airfares.
  • Search for a budget carrier that offers seats in business class. They often come with more space and a glass of Champagne — but at a more affordable price.
  • Make the most of your airline’s rewards program and use points to upgrade your seat. Alternatively, you can try bidding for an upgrade in online auctions.

How to get into Woodstock from the airport?
Walk off the plane at Lebanon Municipal Airport (LEB) and then collect the keys from one of two Lebanon Municipal Airport (LEB) car rental outlets on-site, Avis or Hertz. With a sweet set of wheels, getting to the heart of Woodstock from LEB will be a snap. All you have to do is set your GPS and cruise 10 miles to the west. You could also use public transportation or take a taxi into town and rent some wheels directly from the city center. Check out the deals available on our Woodstock car rentals.
What is the best time to go to Woodstock?
There’s never a bad time to go to Woodstock, but January, June and August are the liveliest months. As with most of the Northern Hemisphere, the summer season kicks off June 20. If you’d rather get around in a short-sleeved top than a big winter jacket, this time of year may be perfect for you. Expect average daytime highs of 75 ºF and nighttime lows around 50 ºF.

Nearby

Flights To

Fare, taxes & fees: Fares include all taxes and fees, except baggage fees. Rates shown reflect fares found by other Orbitz users over the past 7 days. Due to rapidly changing airline prices & seat availability, these fares may no longer be available.

Refunds/changes/cancellations: Itinerary changes, if permitted for the fare, will have a $30 service fee charged by Orbitz. Additional airline charges may apply.

Other conditions: Schedules, fares and rules are subject to change without notice. Seats are limited and may not be available on all flights/dates or in all markets. Lower fares may be available. Fares will not be honored retroactively or in exchange for any wholly/partially unused ticket. Tickets are non-transferable and non-refundable. Fare rules are provided for the selected itinerary before booking.