Woodstock Holidays from NZ$4,270
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to NZ$616 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
The Latest Woodstock Holiday Deals
Price found within the past 48 hours. Click for updated prices.
Eurostars Magnificent Mile
Downtown Chicago
Price was NZ$5,697, price is now NZ$4,568 per person
NZ$4,568
per person
30 May - 4 June
found 1 day ago
Return flight included
Auckland (AKL) to Chicago (ORD)
9/10 Wonderful! (3,314 reviews)
The staff was super helpful and very welcoming. The room had an amazing view for us, beings it was our first time being in Chicago. It’s was so close to everything we wanted to visit and super convenient. I will most definitely stay at this hotel again for future stays in the city.!! Thank you so much for taking pride in your establishment, and your employees, as both we’re definitely deserving of a 5 star rating and review.!
Reviewed on 17 Mar 2026
Sports Illustrated Resorts Chicago
Downtown Chicago
Price was NZ$5,628, price is now NZ$4,551 per person
NZ$4,551
per person
30 May - 4 June
found 1 day ago
Return flight included
Auckland (AKL) to Chicago (ORD)
9.2/10 Wonderful! (1,414 reviews)
Check in was quick and easy, room was clean and spacious
Reviewed on 9 Mar 2026
Staypineapple, An Iconic Hotel, The Loop
Downtown Chicago
Price was NZ$5,406, price is now NZ$4,541 per person
NZ$4,541
per person
30 May - 4 June
found 1 day ago
Return flight included
Auckland (AKL) to Chicago (ORD)
9.4/10 Exceptional! (1,021 reviews)
I would have rated all 5 star but the restaurant Atwood was closed and we weren’t notified in time to change plans!
The staff and (Mr.Brown ) were extremely accommodating! It was my bday and they decorated our room with all sorts of goodies including a hand made stuffed wash cloth doggie! Our housekeeper was amazing too!
The room decor is such fun and extremely clean! The only drawback is the rooms are very small and some not configured well!
All and all it’s a wonderful place to experience!!!!🍍
Reviewed on 18 Mar 2026
Hilton Garden Inn Chicago Downtown South Loop
Downtown Chicago
Price was NZ$5,177, price is now NZ$4,393 per person
NZ$4,393
per person
30 May - 4 June
found 1 day ago
Return flight included
Auckland (AKL) to Chicago (ORD)
8.8/10 Excellent! (1,894 reviews)
I’ve asked for a room with bathtub but they gave me room with shower instead. It’s my way of taking bathe and relaxing in the bathtub but I was disappointed.
Reviewed on 18 Mar 2026
Woodstock Holiday
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 NZ$153 per night from 26 Mar to 27 Mar
NZ$153
26 Mar - 27 Mar
includes taxes & fees
8/10 Very Good! (1,001 reviews)
There are no drapes on the windows and the blinds don’t block out the parking lot lights. Made the room too bright.
Reviewed on 17 Mar 2026
Quality Inn & Suites Woodstock near Lake Geneva
1785 S Eastwood Dr Woodstock IL
Fully refundableReserve now, pay when you stay
The price is NZ$129 per night from 25 Mar to 26 Mar
NZ$129
25 Mar - 26 Mar
includes taxes & fees
6/10 (301 reviews)
The bed was comfortable. Not a bad place if you're looking to go cheap.
Reviewed on 11 Mar 2026
Abbey Resort and Avani Spa
269 Fontana Boulevard Fontana WI
Fully refundableReserve now, pay when you stay
The price is NZ$237 per night from 19 Apr to 20 Apr
NZ$237
19 Apr - 20 Apr
includes taxes & fees
8.6/10 Excellent! (1,770 reviews)
The atmosphere is very relaxing.
Reviewed on 18 Mar 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.
