Woodstock Holidays

Top Flight + Hotel Deals in Woodstock

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
Save 100% on your flight
Price was €766, price is now €492 per person
€492
per person
20 Sept - 24 Sept
found 8 hours ago
Return flight included
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
8.2/10 Very good! (2,809 reviews)
decent property - definitely shows better in photos. that was probably my biggest let-down. also, only staying one night, the room cleaner came into our room at 8 am despite check out time not being until noon. my kid was still asleep and I was in the shower. front desk service level definitely elevated the rating.

Reviewed on 17 Jul 2026

Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Downtown Chicago
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Price was €1,014, price is now €663 per person
€663
per person
20 Sept - 24 Sept
found 8 hours ago
Return flight included
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
9/10 Wonderful! (3,435 reviews)

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was €957, price is now €645 per person
€645
per person
20 Sept - 24 Sept
found 8 hours ago
Return flight included
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
9/10 Wonderful! (501 reviews)
Overall, I had a pleasant stay. The room was clean, and the staff were helpful. The property was comfortable and family-friendly. The only improvement would be better Wi-Fi and more breakfast options. I would still recommend this place.

Reviewed on 14 Jul 2026

Hotel Saint Clair- Magnificent Mile

Hotel Saint Clair- Magnificent Mile

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was €770, price is now €554 per person
€554
per person
20 Sept - 24 Sept
found 8 hours ago
Return flight included
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
8.4/10 Very good! (2,006 reviews)
The staff was very hospitable and friendly. I appreciated the fact that the luggage Cart was immediately available to load mine and my family's luggage.

Reviewed on 15 Jul 2026

Hampton Inn & Suites Chicago Medical District UIC

Hampton Inn & Suites Chicago Medical District UIC

2.5 out of 5
Near West Side
Price was €4,797, price is now €3,907 per person
€3,907
per person
8 Oct - 14 Oct
found 24 hours ago
Return flight included
Athens (ATH) to Chicago (ORD)
9.6/10 Exceptional! (657 reviews)
The hotel and room was clean and close to good eating locations. I did not like the bed as it was hard and uncomfortable.

Reviewed on 17 Jul 2026

Top hotels in Woodstock

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 €87 per night from 29 Jul to 30 Jul
€87
29 Jul - 30 Jul
includes taxes & fees
8/10 Very good! (1,000 reviews)
"Pool could use a good cleaning."

Reviewed on 10 Jul 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 €77 per night from 10 Aug to 11 Aug
€77
10 Aug - 11 Aug
includes taxes & fees
6/10 (323 reviews)
"Dirty and run down. Would not recommend"

Reviewed on 12 Jul 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 €197 per night from 21 Jul to 22 Jul
€197
21 Jul - 22 Jul
includes taxes & fees
9.2/10 Wonderful! (1,364 reviews)
"Nice room with beautiful view. Love th sink in room and shower. Balcony is great"

Reviewed on 17 Jul 2026

Harbor Shores on Lake Geneva
See all 1,159 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 holiday package cost?
You'll find cheap prices from €492 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 holiday to Woodstock costs.
What are the cheapest months to go to Woodstock?
If you're hoping to snag a cheap Woodstock holiday package, consider planning a trip in February, March and April. You'll typically find lower prices on flights and accommodation during these quieter months — perfect for travellers wishing to save money.
How many days is enough for Woodstock?
When planning your Woodstock holiday, a handful of days will be enough to tour the top spots. Be sure to check out Old Courthouse Arts Centre — 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 holiday package to Woodstock?
Whether you're looking to check out major attractions like Woodstock Opera House and Old Courthouse Arts Centre on your Woodstock holiday, 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 holiday 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 holiday as a package?
Expedia holiday 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 personalised Woodstock holiday by choosing your favourite accommodation type, airline and car class.
When to book a holiday 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, favourite 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 personalised Woodstock holiday 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.