
Woodstock Vacations from ¥189,118
Book a Hotel + Flight or Car together to unlock savings
Photo by Erik Rowley
- Plan, book, travel with confidence
- Better togetherSave up to ¥45,448 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 Vacation Packages
Price found within the past 48 hours. Click for updated prices.

Arlo Chicago
Downtown Chicago
Price was ¥225,661, price is now ¥189,118 per person
¥189,118
per person
Mar 7 - Mar 12
found 18 hours ago
Roundtrip non-stop flight included
Osaka (KIX) to Chicago (ORD)
9.2/10 Wonderful! (1,862 reviews)
The water handle on the shower fell off. Bed sheets weren’t clean.
Reviewed on Dec 11, 2025

Hilton Chicago O'Hare Airport
O'Hare
Price was ¥289,000, price is now ¥229,086 per person
¥229,086
per person
Mar 7 - Mar 12
found 8 hours ago
Roundtrip non-stop flight included
Osaka (OSA) to Chicago (ORD)
8.2/10 Very Good! (2,158 reviews)
It’s convenient but old features and breakfast was overpriced. Cheap and simple menus. Service person was not friendly.
Reviewed on Dec 6, 2025

Chicago Athletic Association, a Hyatt Hotel
Downtown Chicago
Price was ¥245,555, price is now ¥195,167 per person
¥195,167
per person
Mar 7 - Mar 12
found 18 hours ago
Roundtrip non-stop flight included
Osaka (KIX) to Chicago (ORD)
9/10 Wonderful! (1,002 reviews)
Amazing location. Love this historic hotel and the included room service breakfast is one of the best I’ve ever had.
Reviewed on Dec 8, 2025

Hotel Riu Plaza Chicago
Downtown Chicago
Price was ¥238,617, price is now ¥194,136 per person
¥194,136
per person
Feb 21 - Feb 27
found 15 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (2,790 reviews)
Room was clean and staff members were super friendly
Reviewed on Dec 12, 2025

Kinzie Hotel
Downtown Chicago
Price was ¥233,878, price is now ¥193,500 per person
¥193,500
per person
Mar 7 - Mar 12
found 17 hours ago
Roundtrip non-stop flight included
Osaka (KIX) to Chicago (ORD)
9.2/10 Wonderful! (1,993 reviews)
Room was big and spotless. The reception staff were so amazing and friendly and helpful and the evening reception was a lovely touch especially Jose on the bar so chatty and kind. Shout out to Mickey on reception for always being happy and friendly x and porter in reception for getting us our big taxi back to the airport and helping us with our ten suitcases into the big taxi - 4th visit to Kinzie Hotel would recommend it and will be back soon
Reviewed on Dec 12, 2025
Find the Best Woodstock Vacation Packages
Woodstock Hotel Deals

AmericInn by Wyndham Woodstock IL
990 Lake Avenue Woodstock IL
Fully refundableReserve now, pay when you stay
The price is ¥12,593 per night from Dec 18 to Dec 19
¥12,593
¥13,977 total
Dec 18 - Dec 19
includes taxes & fees
7.8/10 Good! (992 reviews)
The pool area was clean. Great choices for breakfast. Staff was friendly and nice
Reviewed on Dec 5, 2025

Super 8 by Wyndham Woodstock
1220 Davis Rd Woodstock IL
Fully refundableReserve now, pay when you stay
The price is ¥10,441 per night from Jan 1 to Jan 2
¥10,441
¥11,588 total
Jan 1 - Jan 2, 2026
includes taxes & fees
6/10 (533 reviews)
B
Reviewed on Oct 10, 2025

Quality Inn & Suites Woodstock near Lake Geneva
1785 S Eastwood Dr Woodstock IL
Fully refundableReserve now, pay when you stay
The price is ¥10,527 per night from Jan 11 to Jan 12
¥10,527
¥11,684 total
Jan 11 - Jan 12, 2026
includes taxes & fees
5.8/10 (287 reviews)
Management was excellent, property inside was well cared for but outside is run down
Reviewed on Nov 5, 2025
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.
Discover the most popular places to visit in Woodstock
Woodstock Square
4/5(19 reviews)
You can find out about the history of Woodstock with a trip to Woodstock Square. While you're in the area, stroll along the lakeside.
Other vacations you might like
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
