
Woodstock Vacations from ¥205,036
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The Latest Woodstock Vacation Packages
Price found within the past 48 hours. Click for updated prices.

Aloft Chicago Downtown River North
Downtown Chicago
Price was ¥243,786, price is now ¥205,036 per person
¥205,036
per person
Nov 27 - Dec 2
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,154 reviews)
Great location, nice size rooms. Beatrix is excellent for breakfast. Noise level from the street was an issue at night.
Reviewed on Oct 24, 2025

Pendry Chicago
Downtown Chicago
Price was ¥287,032, price is now ¥216,994 per person
¥216,994
per person
Nov 27 - Dec 2
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,110 reviews)
Ideal area if it’s your first time visiting Chicago. Hotel staff was very friendly.
Reviewed on Oct 16, 2025

The Emily Hotel
Downtown Chicago
Price was ¥301,025, price is now ¥237,066 per person
¥237,066
per person
Nov 27 - Dec 2
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (1,248 reviews)
We really like The Emily Hotel Chicago. We've stayed a few times this year because the location is very near many great restaurants and bars. The hotel itself has really good dining and lounge options. The staff treats us very well and the rooms and beds are clean and comfortable. A great hotel in a really fun part of town!
Reviewed on Oct 22, 2025

Hilton Grand Vacations Club Chicago Magnificent Mile
Downtown Chicago
Price was ¥317,730, price is now ¥261,747 per person
¥261,747
per person
Dec 3 - Dec 10
found 15 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (303 reviews)
Food price was high but everything was fine
Reviewed on Oct 4, 2025

Springhill Suites by Marriott Chicago Downtown/ River North
Downtown Chicago
Price was ¥244,235, price is now ¥205,307 per person
¥205,307
per person
Nov 27 - Dec 2
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (1,007 reviews)
The room was fantastic! The staff is charming! Loved the breakfast options! I was very impressed!
Reviewed on Oct 11, 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 ¥12,303 per night from Nov 4 to Nov 5
¥12,303
¥13,654 total
Nov 4 - Nov 5
includes taxes & fees
7.8/10 Good! (957 reviews)
Good breakfast, clean room
Reviewed on Oct 13, 2025

Quality Inn & Suites Woodstock near Lake Geneva
1785 S Eastwood Dr, Woodstock, IL
Fully refundableReserve now, pay when you stay
The price is ¥9,039 per night from Oct 30 to Oct 31
¥9,039
¥10,031 total
Oct 30 - Oct 31
includes taxes & fees
5.8/10 (278 reviews)
Very nice staff
Reviewed on Oct 17, 2025

Super 8 by Wyndham Woodstock
1220 Davis Rd, Woodstock, IL
Fully refundableReserve now, pay when you stay
The price is ¥9,339 per night from Nov 5 to Nov 6
¥9,339
¥10,364 total
Nov 5 - Nov 6
includes taxes & fees
6.2/10 (521 reviews)
B
Reviewed on Oct 10, 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
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.
