
Woodstock Holidays
Photo by Erik Rowley
Top Flight + Hotel Deals in Woodstock
Price found within the past 48 hours. Click for updated prices.

The Allegro Royal Sonesta Hotel Chicago Loop
Downtown Chicago
per person
6 Nov - 10 Nov
found 1 day ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
8.8/10 Excellent! (1,925 reviews)
My husband and I stayed at The Allegro for a weekend getaway to celebrate our anniversary. It was my husband’s first time in Chicago and we could not have asked for a better stay. The location is perfect and the staff is amazing. We had a late flight after the 11am check-out time and the hotel let us check our bags for a few hours so we could fit in a little more exploration before heading home. We will definitely be visiting again!
Reviewed on 16 Aug 2025



The Royal Sonesta Chicago River North
Downtown Chicago
per person
6 Nov - 10 Nov
found 1 day ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.2/10 Wonderful! (1,980 reviews)
so I gotta say The royal sonesta river north in particular is amazing it feels more like a hotel, it feels like a small community and all the staff and guest know each other. The front desk woman Gabby is amazing and dope as heck. Shaunda is a travel guide there, shes hilarious and gave us wonderful recommendations in the area. Antwonne is a dope Bellman great service and attitude. Every detail was perfect Jessenia apart of the housekeeping staff has such good attention to detail when it came to fixing up and cleaning the room everything was so organized and neat. Now to the room it couldn't have been more perfect they upgraded us to the luxury suite and it was beautiful (use the tub as much as you can)
Reviewed on 15 Aug 2025

The Peninsula Chicago
Downtown Chicago
Save 100% on your flight
per person
6 Nov - 10 Nov
found 1 day ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.8/10 Exceptional! (1,004 reviews)
Peninsula is simply the best. Top notch service, amenities and everything in between.
Reviewed on 14 Aug 2025
Top hotels in Woodstock

AmericInn by Wyndham Woodstock IL
990 Lake Avenue, Woodstock, IL
Fully refundableReserve now, pay when you stay
The price is €85 per night from 18 Aug to 19 Aug
€85
18 Aug - 19 Aug
includes taxes & fees
7.8/10 Good! (919 reviews)
"Very convenient and relaxing for our family trip."
Reviewed on 15 Aug 2025

Quality Inn & Suites Woodstock near Lake Geneva
1785 S Eastwood Dr, Woodstock, IL
Fully refundableReserve now, pay when you stay
The price is €73 per night from 24 Aug to 25 Aug
€73
24 Aug - 25 Aug
includes taxes & fees
5.8/10 (245 reviews)
"Outside not well kept. But room was clean"
Reviewed on 6 Aug 2025

Harbor Shores on Lake Geneva
300 Wrigley Dr, Lake Geneva, WI
Fully refundableReserve now, pay when you stay
9/10 Wonderful! (1,213 reviews)
"Location is perfect. Lake Geneva is not a place to be using the car, everything is walking distance, so this hotel by the lake and main walking area was perfect for us. It was surprisingly quiet for the location, we have a 3 year old so that worked out pretty well. Highly recommended."
Reviewed on 15 Aug 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.
Popular places to visit
Crystal Woods Golf Club
Enjoy a round of golf in Woodstock at Crystal Woods Golf Club. Amble around the area's lakeside or attend a sporting event.
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.