Woodstock Vacations from NT$19,606

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The Latest Woodstock Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Chicago Marriott Downtown Magnificent Mile

Chicago Marriott Downtown Magnificent Mile

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was NT$27,267, price is now NT$19,606 per person
NT$19,606
per person
Aug 27 - Aug 30
found 6 hours ago
Roundtrip flight included
Detroit (DTW) to Chicago (ORD)
8.8/10 Excellent! (1,008 reviews)

Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was NT$32,521, price is now NT$22,380 per person
NT$22,380
per person
Aug 27 - Aug 30
found 6 hours ago
Roundtrip flight included
Detroit (DTW) to Chicago (ORD)
8.2/10 Very Good! (2,854 reviews)

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was NT$51,728, price is now NT$36,532 per person
NT$36,532
per person
Aug 27 - Aug 30
found 6 hours ago
Roundtrip flight included
Detroit (DTW) to Chicago (ORD)
9.6/10 Exceptional! (1,934 reviews)
Great location !! Great hotel !! Great service

Reviewed on 2026/7/27

Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was NT$31,482, price is now NT$22,427 per person
NT$22,427
per person
Aug 27 - Aug 30
found 6 hours ago
Roundtrip flight included
Detroit (DTW) to Chicago (ORD)
8.8/10 Excellent! (2,271 reviews)
This hotel it’s a 10/10 I stayed in this place before and I totally love it. Rooms are super spacious,clean,good view,etc. Staff always helpful and very friendly. The only thing I wish they need is a pool but overall it’s an excellent place to stay.

Reviewed on 2026/7/26

Eurostars Magnificent Mile

Eurostars Magnificent Mile

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was NT$35,273, price is now NT$25,507 per person
NT$25,507
per person
Aug 27 - Aug 30
found 6 hours ago
Roundtrip flight included
Detroit (DTW) to Chicago (ORD)
9/10 Wonderful! (3,725 reviews)
Couldn’t check in but nice

Reviewed on 2026/7/27

Find the Best Woodstock Vacation Packages

Woodstock Hotel Deals

AmericInn by Wyndham Woodstock IL

AmericInn by Wyndham Woodstock IL

3 out of 5
990 Lake Avenue Woodstock IL
Fully refundableReserve now, pay when you stay
The price is NT$2,914 per night from Jul 28 to Jul 29
NT$2,914
NT$3,233 total
Jul 28 - Jul 29
includes taxes & fees
AmericInn by Wyndham Woodstock IL
Quality Inn & Suites Woodstock near Lake Geneva

Quality Inn & Suites Woodstock near Lake Geneva

2.5 out of 5
1785 S Eastwood Dr Woodstock IL
Fully refundable
The price is NT$2,587 per night from Aug 17 to Aug 18
NT$2,587
NT$2,871 total
Aug 17 - Aug 18
includes taxes & fees
6/10 (327 reviews)
"ceiling in shower peeling paint"

Reviewed on 2026/7/25

Quality Inn & Suites Woodstock near Lake Geneva
Harbor Shores on Lake Geneva

Harbor Shores on Lake Geneva

3.5 out of 5
300 Wrigley Dr Lake Geneva WI
Fully refundableReserve now, pay when you stay
The price is NT$5,799 per night from Jul 30 to Jul 31
NT$5,799
NT$7,299 total
Jul 30 - Jul 31
includes taxes & fees
Harbor Shores on Lake Geneva
See all 1,166 properties in Woodstock
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.

Stay near popular Woodstock attractions

A historic building with a clock tower, a theater, and a street with cars and pedestrians.

Woodstock Opera House

8.2/10 (27 reviews)
This historic 1889 venue blends Victorian elegance with cultural significance as a "Groundhog Day" filming location. Experience performances surrounded by meticulously restored architectural details.
See properties

Frequently asked questions

How much does a Woodstock vacation package cost?
You'll find cheap prices from NT$19,606 on Expedia for your Woodstock getaway. However, factors like the length of stay, the season and your choice of hotel will influence how much your vacation to Woodstock costs.
What are the cheapest months to go to Woodstock?
If you're hoping to snag a cheap Woodstock vacation package, consider planning a trip in February, March and April. You'll typically find lower prices on flights and accommodations during these quieter months — perfect for travelers wishing to save money.
How many days is enough for Woodstock?
When planning your Woodstock vacation, a handful of days will be enough to tour the top spots. Be sure to check out Old Courthouse Arts Center — it's one of the leading sights in this destination. If you're looking for more adventure, think about basing yourself here and heading off on some tours from Woodstock.
Is it worth booking a vacation package to Woodstock?
Whether you're looking to check out major attractions like Woodstock Opera House and Old Courthouse Arts Center on your Woodstock vacation, or coming for its great golfing, festivals and history, there's something for everyone here. With so many things to do, you'll soon discover why so many visitors think Woodstock is a good vacation destination.
How to find the best Woodstock package deals?
Start your search for a Woodstock package deal by entering your preferred trip dates and destination under our "Packages" tab. Then add some filters, like "Property type" and "Guest rating," to fine-tune the results to your exact style. You can also sort by "Package discount" and browse offers that come with huge savings. If you don't find the ideal Woodstock package deal straight away, simply change your dates and search again. Bear in mind that deals are only available for a limited time, so book early and get your Woodstock escape underway.
Is it cheaper to book a Woodstock vacation as a package?
Expedia vacation packages are designed to help you keep more cash in your pocket. Bundle your hotel, flight and car rental into one great-value price and you could save hundreds of dollars. You'll typically land a better deal than booking each component individually. And you'll still enjoy the flexibility to create a personalized Woodstock vacation by choosing your favorite accommodation type, airline and car class.
When to book a vacation package to Woodstock?
Land fantastic discounts by reserving your flights early with Expedia. If spontaneity is more your thing, grab one of our last-minute deals for a spur-of-the-moment Woodstock escape.
How to plan a trip to Woodstock?

  1. Choose the best time to travel: Your schedule, favorite season and the type of weather you like can all impact your decision on when to visit Woodstock.
  2. Plan your budget wisely: In addition to the cost of your hotel, you should factor in other expenses. These include transportation, food and flights. Also, put aside some extra funds for unexpected costs that may crop up during your trip to Woodstock.
  3. Decide your trip length: Consider how long you want to spend discovering Woodstock. Plan your days so you can get to all the attractions and experiences you're interested in without rushing.
  4. Bundle your bookings: With your travel dates in order, you can combine your car rental, flights, hotels and more into a personalized Woodstock vacation package.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.