Woodstock Vacation Packages
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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.
Fairmont Chicago at Millennium Park
Downtown Chicago
Price was CA $1,003, price is now CA $755 per person
CA $755
per person
Jun 22 - Jun 24
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.8/10 Excellent! (2,144 reviews)
Keep an eye that nothing is added from the minibar but great property and can't wait to stay again!
Reviewed on May 5, 2026
Pendry Chicago
Downtown Chicago
Price was CA $1,968, price is now CA $1,453 per person
CA $1,453
per person
Jun 25 - Jun 29
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,122 reviews)
Great staff and perfect place to be in the middle of everything!
Reviewed on Apr 27, 2026
Hilton Chicago O'Hare Airport
O'Hare
Price was CA $1,123, price is now CA $834 per person
CA $834
per person
Jul 11 - Jul 14
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.4/10 Very Good! (2,281 reviews)
Wonderful location, staff were very helpful and room was clean. Older hotel but well maintained. Pricey but worthwhile for convenience sake.
Reviewed on May 5, 2026
Woodstock Hotel Deals
AmericInn by Wyndham Woodstock IL
990 Lake Avenue Woodstock IL
Fully refundableReserve now, pay when you stay
The price is CA $123 per night from May 25 to May 26
CA $123
CA $136 total
May 25 - May 26
includes taxes & fees
8/10 Very Good! (1,003 reviews)
Super sketchy. Would not recommend
Reviewed on May 4, 2026
Abbey Resort and Avani Spa
269 Fontana Boulevard Fontana WI
Fully refundableReserve now, pay when you stay
The price is CA $148 per night from May 13 to May 14
CA $148
CA $200 total
May 13 - May 14
includes taxes & fees
8.6/10 Excellent! (1,874 reviews)
The place was ok but definitely needs a better upkeep. The front desk could use some etiquette training and a smile could be helpful when greeting guests!
Reviewed on May 8, 2026
Harbor Shores on Lake Geneva
300 Wrigley Dr Lake Geneva WI
Fully refundableReserve now, pay when you stay
The price is CA $135 per night from May 10 to May 11
CA $135
CA $183 total
May 10 - May 11
includes taxes & fees
9.2/10 Wonderful! (1,340 reviews)
Clean room and friendly staff room head air conditioning and was comfortable. Loved the view of the lake
Reviewed on May 7, 2026
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.
