Woodstock Holidays from AU$3,264
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to AU$2,500 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Your Woodstock Holiday
There's plenty to like about Woodstock, from its rich history to its spectacular views and beyond. When you're ready to spend a bit of time in this fascinating city, our Woodstock holiday packages are calling your name. Like to explore your surroundings? McHenry County Courthouse, McHenry County College and Bull Valley Golf Club are among the top-rated places to visit during a trip to Woodstock. Whoever you're travelling with and whatever your bank balance, your dream Woodstock holiday is just a few clicks away with Expedia.
The Latest Woodstock Holiday Deals
Price found within the past 48 hours. Click for updated prices.
Level Chicago Fulton Market
Downtown Chicago
Price was AU$4,641, price is now AU$3,264 per person
AU$3,264
per person
10 July - 17 July
found 24 hours ago
Return direct flight included
Melbourne (MEL) to Chicago (ORD)
9.2/10 Wonderful! (488 reviews)
Room was not cleaned/ towels weren't replaced for the duration of our 3 night stay which I found rather peculiar. They also only provided 1 key for our room. I had believed it was common practice to provide 2. Other than that, the room was clean when we arrived, the bedding was comfortable, and the gym was lovely.
Reviewed on 22 May 2026
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was AU$6,048, price is now AU$4,393 per person
AU$4,393
per person
10 July - 17 July
found 24 hours ago
Return direct flight included
Melbourne (MEL) to Chicago (ORD)
9.4/10 Exceptional! (1,872 reviews)
I really can’t say any thing negative.
It was one of the cleanest hotel I ever stayed.
Super nice staff.and location was excellent.
Reviewed on 30 May 2026
LondonHouse Chicago, Curio Collection by Hilton
Downtown Chicago
Price was AU$5,196, price is now AU$3,776 per person
AU$3,776
per person
10 July - 17 July
found 24 hours ago
Return direct flight included
Melbourne (MEL) to Chicago (ORD)
9.4/10 Exceptional! (3,727 reviews)
Extraordinarily lovely and helpful staff. This hotel manages to promote a staff and facility that beautifully balance solid upscale services with a true sence of welcome and connection, with a warm but unintrusive vibe and clear consideration of it's guests.
Reviewed on 31 May 2026
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Price was AU$4,869, price is now AU$3,599 per person
AU$3,599
per person
10 July - 17 July
found 24 hours ago
Return direct flight included
Melbourne (MEL) to Chicago (ORD)
9.4/10 Exceptional! (2,511 reviews)
Without a doubt, the view of the pier and city skyline was the BEST part of this hotel experience. The room was pretty large and had a great sitting area to read, gaze at the water, people watch, and relax. The hotel staff was nice and helpful. Everything I needed and wanted to do for this trip was at the Navy Pier so the Sable Hotel checked all my boxes.
Reviewed on 28 May 2026
Woodstock Holiday
Woodstock Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Population | 25,200 |
Max Temp Winter | -1.11ºC |
Max Temp Summer | 24ºC |
Top Sights | Main Beach, Woodstock Opera House and McHenry Shores Beach Park |
Our pick of the best Woodstock Hotel Deals
AmericInn by Wyndham Woodstock IL
990 Lake Avenue Woodstock IL
Fully refundableReserve now, pay when you stay
The price is AU$139 per night from 7 June to 8 June
AU$139
7 June - 8 June
includes taxes & fees
8/10 Very Good! (1,001 reviews)
"Worst hotel I’ve stayed in"
Reviewed on 25 May 2026
Quality Inn & Suites Woodstock near Lake Geneva
1785 S Eastwood Dr Woodstock IL
Fully refundable
The price is AU$124 per night from 21 June to 22 June
AU$124
21 June - 22 June
includes taxes & fees
6/10 (312 reviews)
"Breakfast is included???? Only waffles. Coffee??? Bad quality. Rooms okay. Bathroom not the best. Only stay for one night and check out"
Reviewed on 25 May 2026
Harbor Shores on Lake Geneva
300 Wrigley Dr Lake Geneva WI
Fully refundableReserve now, pay when you stay
The price is AU$285 per night from 4 June to 5 June
AU$285
4 June - 5 June
includes taxes & fees
9.2/10 Wonderful! (1,348 reviews)
"Clean rooms. Excellent location. But it would be nice if rooms have screen doors or sheer curtains to keep balcony doors open for fresh air and prevent bugs flying into rooms . Coffee machine in the lobby was out of order through duration of our trip"
Reviewed on 30 May 2026
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.
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.
