
Woodstock Vacations from ¥104,548
Book a Hotel + Flight or Car together to unlock savings
Photo by Erik Rowley
- Plan, book, travel with confidence
Better together
Save up to ¥45,448 when you book a flight and hotel together*
Find the right fit
With over 300,000 hotels worldwide, it's easy to create a perfect package
Rest easy
Plan, 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.

The Chicago Hotel Collection River North
Downtown Chicago
Price was ¥129,674, price is now ¥104,548 per person
¥104,548
per person
Oct 8 - Oct 11
found 23 hours ago
Roundtrip flight included
Los Angeles (QLA) to Chicago (ORD)
7.2/10 Good! (583 reviews)
I really like the location and the place. I really recomend it
Reviewed on Sep 3, 2025

Hotel Riu Plaza Chicago
Downtown Chicago
Save 100% on your flight
Price was ¥250,708, price is now ¥142,392 per person
¥142,392
per person
Oct 8 - Oct 11
found 1 day ago
Roundtrip flight included
Los Angeles (QLA) to Chicago (ORD)
9.4/10 Exceptional! (2,373 reviews)
World class breakfast buffet
Reviewed on Sep 8, 2025

The Talbott, Autograph Collection
Downtown Chicago
Save 100% on your flight
Price was ¥159,337, price is now ¥116,406 per person
¥116,406
per person
Oct 8 - Oct 11
found 23 hours ago
Roundtrip flight included
Los Angeles (QLA) to Chicago (ORD)
9.2/10 Wonderful! (33 reviews)
Everything was great except only one elevator was working and my room was poorly lite even with all of the lights on.
Reviewed on Aug 30, 2025

LondonHouse Chicago, Curio Collection by Hilton
Downtown Chicago
Price was ¥235,502, price is now ¥196,520 per person
¥196,520
per person
Nov 19 - Nov 24
found 19 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (3,363 reviews)
The staff was great. The room was well appointed but the ventilation was off - the room was stuffy or cold and clammy.
Reviewed on Sep 8, 2025

The Allegro Royal Sonesta Hotel Chicago Loop
Downtown Chicago
Price was ¥216,916, price is now ¥182,124 per person
¥182,124
per person
Nov 19 - Nov 24
found 19 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9/10 Wonderful! (1,992 reviews)
The staff were very friendly and helpful, and the location in the city is excellent. My only complaint is that the walls are quite thin, so you can easily hear noise from the surrounding rooms.
Reviewed on Sep 8, 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 ¥13,266 per night from Sep 22 to Sep 23
¥13,266
¥14,723 total
Sep 22 - Sep 23
includes taxes & fees

Quality Inn & Suites Woodstock near Lake Geneva
1785 S Eastwood Dr, Woodstock, IL
Fully refundableReserve now, pay when you stay
The price is ¥8,625 per night from Sep 14 to Sep 15
¥8,625
¥9,572 total
Sep 14 - Sep 15
includes taxes & fees

Super 8 by Wyndham Woodstock
1220 Davis Rd, Woodstock, IL
Fully refundableReserve now, pay when you stay
The price is ¥9,900 per night from Sep 15 to Sep 16
¥9,900
¥10,987 total
Sep 15 - Sep 16
includes taxes & fees
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.