Woodstock Vacations from ￥280,564

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The Latest Woodstock Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Price was ￥338,731, price is now ￥280,564 per person
￥280,564
per person
Sep 18 - Sep 22
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
8.2/10 Very Good! (2,809 reviews)
I thoroughly enjoyed my stay at Hotel Felix! While it may not technically be a five-star luxury chain, it definitely gave us five-star hotel vibes thanks to the incredible staff and the fantastic extra perks.The location is absolutely awesome. It puts you about a mile or so from all the major hotspots, including Navy Pier, the Riverwalk, and the Magnificent Mile. There are tons of excellent places to eat right nearby, and having a Divvy bike rental station right down the street made exploring the city incredibly easy.The service from the staff was top-notch from start to finish. I highly recommend this hotel for anyone looking for a stylish, perfectly located, and highly accommodating place to stay in Chicago!

Reviewed on Jul 13, 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Price was ￥417,913, price is now ￥311,530 per person
￥311,530
per person
Sep 18 - Sep 22
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (4,586 reviews)
Great location, clean, rooftop bar and great staff.

Reviewed on Jul 13, 2026

Omni Chicago Hotel

Omni Chicago Hotel

4.5 out of 5
Downtown Chicago
Price was ￥382,081, price is now ￥300,700 per person
￥300,700
per person
Sep 18 - Sep 22
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (1,819 reviews)
Main area was nice. Hotel room was outdated

Reviewed on Jul 13, 2026

LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 out of 5
Downtown Chicago
Price was ￥379,612, price is now ￥309,040 per person
￥309,040
per person
Sep 18 - Sep 22
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (3,764 reviews)
Probably the best hotel I ever stayed at next time. Make sure I get a room with a view of the lake for five stars.

Reviewed on Jul 12, 2026

Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Downtown Chicago
Price was ￥379,093, price is now ￥316,714 per person
￥316,714
per person
Sep 18 - Sep 22
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9/10 Wonderful! (3,435 reviews)
The staff was so nice and they even upgraded me to a suite for my daughter's sweet 16. A suite for a sweet. Very appreciative. I have stayed at a few hotels downtown, but I keep going back for the views! Thank you Swissotel.

Reviewed on Jul 13, 2026

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
The price is ￥14,549 per night from Jul 19 to Jul 20
￥14,549
￥16,147 total
Jul 19 - Jul 20
includes taxes & fees
8/10 Very Good! (1,008 reviews)
"Pool could use a good cleaning."

Reviewed on Jul 10, 2026

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 ￥12,918 per night from Aug 3 to Aug 4
￥12,918
￥14,336 total
Aug 3 - Aug 4
includes taxes & fees
6/10 (323 reviews)
"Dirty and run down. Would not recommend"

Reviewed on Jul 12, 2026

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 ￥28,957 per night from Jul 20 to Jul 21
￥28,957
￥36,451 total
Jul 20 - Jul 21
includes taxes & fees
9.2/10 Wonderful! (1,375 reviews)
"The property is clean and well run. Staff very nice and helpful. The view of Lake Geneva from our room balcony is beautiful and hard to beat!"

Reviewed on Jul 12, 2026

Harbor Shores on Lake Geneva
See all 1,171 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 ￥280,564 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.

Explore a world of travel with Expedia

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