
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
Save 100% on your flight
per person
6 Nov - 10 Nov
found 8 hours ago
Return flight included
Philadelphia (PHL) to Chicago (ORD)
8.8/10 Excellent! (1,925 reviews)
Overall the staff were very prompt and helpful. My only complaints with the hotel is the rooms are smaller than I expected, the 4 of us had a hard time fitting into a double bed room. It would have been nice to know that most of the food places around the hotel close on the weekend. Definitely not the best choice for a family. Proximity to activities were doable , but a little far. Wells street at night was a little scary over the weekend. Parking in Chicago is really crazy but I found parking for $18 a night on the same block without in and out access. We parked and left the car the whole time. Overall staff was amazing, nothing bad to say there, but I was disappointed as a first time visitor with the size of the hotel rooms, the cleanliness was fair, dark room, windows you couldn’t see out of well. The room temp was set at 65 but we were all swearing overnight and had to purchase a fan to help.
Reviewed on 13 Aug 2025

The Royal Sonesta Chicago River North
Downtown Chicago
Save 100% on your flight
per person
6 Nov - 10 Nov
found 8 hours ago
Return flight included
Philadelphia (PHL) 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



Hilton Grand Vacations Club Chicago Magnificent Mile
Downtown Chicago
Save 100% on your flight
per person
6 Nov - 10 Nov
found 8 hours ago
Return flight included
Philadelphia (PHL) to Chicago (ORD)
9.2/10 Wonderful! (277 reviews)
Ran into some confusion with my credit card. It was used at check in and then they said they didn’t have it
Reviewed on 9 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! (1,220 reviews)
"Wonderful AC. Relaxing pool time. Excellent location to lake, walking path, shopping, and restaurants."
Reviewed on 12 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.
Frequently asked questions
More trip options
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.