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.
The Royal Sonesta Chicago River North
Downtown Chicago
Save 100% on your flight
Price was €998, price is now €576 per person
€576
per person
31 Oct - 6 Nov
found 9 hours ago
Return flight included
Nashville (BNA) to Chicago (ORD)
9.2/10 Wonderful! (2,052 reviews)
Excellent staff very friendly
Reviewed on 29 Aug 2025
The Emily Hotel
Downtown Chicago
Price was €1,487, price is now €781 per person
€781
per person
31 Oct - 6 Nov
found 9 hours ago
Return flight included
Nashville (BNA) to Chicago (ORD)
9.2/10 Wonderful! (1,192 reviews)
The staff here are absolutely the most helpful and sweetest. The hotel is perfect for a boutique hotel. The night life seemed to quite popular as well and right around Fulton market! I definitely recommend.
Also the coffee bags ? PERFECTION. Just had to add that
Reviewed on 22 Aug 2025
Level Chicago – Old Town
Downtown Chicago
Save 100% on your flight
Price was €1,099, price is now €603 per person
€603
per person
31 Oct - 6 Nov
found 9 hours ago
Return flight included
Nashville (BNA) to Chicago (ORD)
9/10 Wonderful! (343 reviews)
It was fine but nit as good as I had expected. Staff were un friendly and un helpful fur an expensive stay.
Reviewed on 27 Aug 2025
Trump International Hotel & Tower Chicago
Downtown Chicago
Save 100% on your flight
Price was €2,381, price is now €1,344 per person
€1,344
per person
31 Oct - 6 Nov
found 7 hours ago
Return direct flight included
Nashville (BNA) to Chicago (ORD)
9.4/10 Exceptional! (1,694 reviews)
5 star hotel that goes above and beyond. My family loved staying at the Trump
Reviewed on 29 Aug 2025
Park Hyatt Chicago
Downtown Chicago
Save 100% on your flight
Price was €2,650, price is now €1,559 per person
€1,559
per person
31 Oct - 6 Nov
found 7 hours ago
Return direct flight included
Nashville (BNA) to Chicago (ORD)
9.6/10 Exceptional! (1,000 reviews)
Nothing beats a stay at the Park Hyatt when in Chicago!
Reviewed on 10 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 7 Sept to 8 Sept
€85
7 Sept - 8 Sept
includes taxes & fees
Super 8 by Wyndham Woodstock
1220 Davis Rd, Woodstock, IL
Fully refundableReserve now, pay when you stay
The price is €65 per night from 29 Sept to 30 Sept
€65
29 Sept - 30 Sept
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 €76 per night from 7 Sept to 8 Sept
€76
7 Sept - 8 Sept
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.
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.
More trip options
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.