Woodstock Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
Photo by Erik Rowley
Your Woodstock Vacation
With one of our vacation packages to Woodstock, you'll discover infinite opportunities for excitement and adventure. There's tons to experience, including its rich history and spectacular views. You'll want to do some exploring during your trip to Woodstock. Make time for top attractions such as McHenry County College, McHenry County Courthouse and Woodstock Opera House. No matter your travel plans or the size of your budget, putting together the ultimate tailored Woodstock vacation is easy with Expedia.
Top Woodstock Vacation Deals
Price found within the past 48 hours. Click for updated prices.
DoubleTree by Hilton Chicago Schaumburg
Price was CA $878, price is now CA $589 per person
CA $589
per person
Nov 9 - Nov 15
found 23 hours ago
Roundtrip flight included
Montreal (YUL) to Chicago (ORD)
7.4/10 Good! (1,004 reviews)
Quick stay in between traveling. The bed and bedding comfortable. Room is spacious. Staff friendly.
Reviewed on Aug. 30, 2025
Hyatt Centric Chicago Magnificent Mile
Downtown Chicago
Price was CA $1,831, price is now CA $1,198 per person
CA $1,198
per person
Oct 25 - Oct 29
found 8 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (1,028 reviews)
Overall is good but 1 concern we encountered is there is a clicking sound in our room or near our room, that distracts my husband while sleeping.
Reviewed on Aug. 24, 2025
The Langham, Chicago
Downtown Chicago
Price was CA $1,922, price is now CA $1,279 per person
CA $1,279
per person
Oct 22 - Oct 25
found 12 hours ago
Roundtrip non-stop flight included
Québec (YQB) to Chicago (ORD)
9.8/10 Exceptional! (1,003 reviews)
Phenomenal service. Exactly how a 5* hotel should be run. Everything was perfect.
Reviewed on Aug. 12, 2025
Staybridge Suites, Lincolnshire by IHG
Half Day
Price was CA $882, price is now CA $594 per person
CA $594
per person
Nov 9 - Nov 15
found 23 hours ago
Roundtrip flight included
Montreal (YUL) to Chicago (ORD)
9/10 Wonderful! (1,001 reviews)
Very close to grocery stores, restaurants drugstores everything was nearby
Reviewed on Aug. 31, 2025
Level Chicago – Old Town
Downtown Chicago
Price was CA $1,038, price is now CA $699 per person
CA $699
per person
Oct 17 - Oct 19
found 1 day ago
Roundtrip non-stop flight included
Québec (YQB) 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 Aug. 27, 2025
Woodstock Hotel Deals
AmericInn by Wyndham Woodstock IL
990 Lake Avenue, Woodstock, IL
Fully refundableReserve now, pay when you stay
The price is CA $124 per night from Sep 2 to Sep 3
CA $124
CA $137 total
Sep 2 - Sep 3
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 CA $110 per night from Sep 8 to Sep 9
CA $110
CA $122 total
Sep 8 - Sep 9
includes taxes & fees
Super 8 by Wyndham Woodstock
1220 Davis Rd, Woodstock, IL
Fully refundableReserve now, pay when you stay
The price is CA $95 per night from Sep 29 to Sep 30
CA $95
CA $105 total
Sep 29 - Sep 30
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.
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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.