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Cheap Vacations in Woodstock

Choose two or more items and save on your trip:

3-night Woodstock vacations

Hotel Zachary Chicago, a Tribute Portfolio Hotel
Four Points by Sheraton Mt Prospect O'Hare
The Langham, Chicago
The Peninsula Chicago
The Gwen, a Luxury Collection Hotel, Michigan Avenue Chicago
The Godfrey Hotel Chicago
Renaissance Chicago Downtown Hotel
Courtyard by Marriott Chicago Magnificent Mile
Swissotel - Chicago
Virgin Hotels Chicago
Nobu Hotel Chicago
Hyatt Centric Chicago Magnificent Mile

Woodstock Vacation Deal FAQ's

Where to find Woodstock package deals?

On CheapTickets, you can find package deals in Woodstock as low as $180!

When is peak season in Woodstock?

are very popular times to visit Woodstock.

When is the best time to visit Woodstock?

If you're looking for cheap vacations to Woodstock, is the best time to visit Woodstock.

When is the worst time time to visit Woodstock?

Prices for Woodstock vacations can peak during .

When is low season in Woodstock?

We have found to be the least-crowded time of the year to visit Woodstock.

Where is Woodstock?

Well hello there, proud penny-pinchers. We know you're itching to make the most out of your Woodstock adventure for the least amount of cash. But first, let's learn a bit about this awesome destination!

It's the national capital of United States of America and located about 53 miles to the north-west of the significant city of Chicago.

The population of this area of Chicago is approximately 24,800.

Cheap Things to do in Woodstock

When planning your days, it's easy to gravitate towards the obvious tourist attractions (which can often cost a bundle). Utilize some of our suggestions for free things to do in or near Woodstock, and discover a thriftier and more genuine local experience:

  • Art and culture are best without a price tag. The Old Courthouse Arts Center is an excellent place to catch a few free or inexpensive events — check out the program to find something that interests you!
  • Turn your next sightseeing outing into a captivating history lesson at McHenry County Courthouse. This free age-old landmark is well worth making an extra effort to visit.
  • If you're stopping by Three Oaks Recreation Area, Crystal Lake Park, Emricson Park and Veterans Acres Park, it's well worth pulling out your smartphone and reading a few things about the plant life there.

Cheap Woodstock Vacation Package Deals

Don't let any unnecessary fears of having to sleep in a small, sad room stop you from embarking on that extraordinary vacation. When you organize your travels with CheapTickets, you won't be asked to hand over too much money or sacrifice quality and comfort.

Personalize your cheap trip by mixing and matching from more than 500 airline partners and 500,000 worldwide properties. If you want to save up to $290^, simply combine your booking with a hotel and flight package.

You can let your inner cheapaholic breathe a sigh of relief with the CheapTickets Price Guarantee. Here's how it works — if within 48 hours you discover your package for less, we'll meet it and refund you the difference. Thrifty is our middle name!

Get CheapCash

The best deals and handsome rewards — it doesn't get much better than that, does it fellow cheapster? Simply book your flight with us and you'll save heaps on your next qualifying CheapTickets hotel stay.

Taking advantage of our CheapCash loyalty program couldn't be easier. Sign up (for free!) or log in, and you'll immediately qualify to save on eligible bookings, as well as being first in line for other amazing bonus offers and penny-pinching perks!

Cheap Car Rentals in Woodstock

We know you're into cheap, so why not rent a car in Woodstock? It's not only a great way to get around, it'll save you precious money too.

Arriving in the city? Enterprise can be found 2 miles from the middle of town at 760 S EASTWOOD DR. Another convenient outlet located 2 miles from the middle of the city is Enterprise at 760 S Eastwood Dr.

Cheap Hotel Accommodations in Woodstock

After a cheap and chic escape? At present, CheapTickets only lists 3 hotels in Woodstock. If you're eager to stay, book a room soon.

We'll try to make organizing your vacation as easy as possible. Recommended accommodations include the Quality Inn and Best Western Woodstock Inn.

Flight deals to Woodstock

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

Wed, Feb 17
LAX
Los Angeles
ORD
Chicago
$24
Spirit Airlines
Tue, Mar 2 - Wed, Mar 3
LAX
Los Angeles
ORD
Chicago
$48
Spirit Airlines
Thu, Mar 11
FCO
Rome
ORD
Chicago
$276
Delta
Thu, Oct 28 - Tue, Nov 30
FCO
Rome
ORD
Chicago
$400
TAP Portugal
Tue, Apr 27
HKG
Hong Kong
ORD
Chicago
$462
Japan Airlines
Thu, Jul 15 - Sun, Aug 15
HKG
Hong Kong
ORD
Chicago
$637
United

Top rated hotels for your Woodstock vacation

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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.

^Savings based on all package bookings with Flight + Hotel made on CheapTickets.com from 2019-04-01 - 2020-03-31 as compared to the price of the same components booked separately. Savings will vary based on origin/destination, length of trip, stay dates and selected travel supplier(s). Savings not available on all packages.