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

Hotel Felix River North/Magnificent Mile
Downtown Chicago
per person
28 Oct - 2 Nov
found 1 day ago
Return direct flight included
Shannon (SNN) to Chicago (ORD)
8.2/10 Very Good! (1,991 reviews)
Convenient. Can stroll to locations within 30 mins. Train 4 blocks away, bus to riverwalk around the corner, restaurants, and the Mile a short walk away.
Reviewed on 14 Aug 2025


Trump International Hotel & Tower Chicago
Downtown Chicago
Save 100% on your flight
per person
30 Oct - 2 Nov
found 1 day ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (1,679 reviews)
Beautiful views and incredibly clean environment. Perfect location for the lake, shopping, park, eating, you name it!
Reviewed on 14 Aug 2025

Level Chicago - River North
Downtown Chicago
per person
28 Oct - 2 Nov
found 1 day ago
Return direct flight included
Shannon (SNN) to Chicago (ORD)
9/10 Wonderful! (654 reviews)
Quick and easy check in. Parking in their private garage was breeze. Plenty of space, mostly empty, and our vehicle could stay in the garage until 2:00 PM the next day. Beautiful 1 BR condo. Full kitchen, beautiful views of the city on the balcony and from the living room, and very clean space overall. Need your key card for just about everything (pool, lounge, some of the outdoor bathrooms, elevators, etc.).
Reviewed on 27 Jul 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 17 Aug to 18 Aug
€85
17 Aug - 18 Aug
includes taxes & fees
7.8/10 Good! (917 reviews)
Great stay
"Great customer service, great breakfast, comfortable beds , awesome pool"
Reviewed on 12 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
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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.