Woodstock Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
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.
Hotel Riu Plaza Chicago
Downtown Chicago
Price was CA $1,125, price is now CA $689 per person
CA $689
per person
Apr 2 - Apr 5
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (2,790 reviews)
Clean rooms, excellent shower, but most importantly the best, friendly, helpful staff. Really enjoyed our stay.
Reviewed on Feb 26, 2026
Level Chicago Fulton Market
Downtown Chicago
Price was CA $1,955, price is now CA $1,149 per person
CA $1,149
per person
May 4 - May 8
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (347 reviews)
Room smelled like food but overall very clean, very great service and staff both night and morning shift.
Reviewed on Feb 16, 2026
La Banque Hotel
Price was CA $1,406, price is now CA $853 per person
CA $853
per person
Apr 23 - Apr 28
found 3 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to Chicago (ORD)
9.4/10 Exceptional! (447 reviews)
Courteous Staff, clean, one of the most beautiful and interesting hotel. The history is amazing. The restaurant is delicious and the community is outstanding. Plan to return in the spring.
Reviewed on Jan 26, 2026
Chicago Athletic Association, a Hyatt Hotel
Downtown Chicago
Price was CA $1,317, price is now CA $951 per person
CA $951
per person
May 5 - May 8
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (1,002 reviews)
This was a trendy aesthetic hotel. It is in a great location. Had a good time.
Reviewed on Feb 26, 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 Mar 5 to Mar 6
CA $123
CA $137 total
Mar 5 - Mar 6
includes taxes & fees
8/10 Very Good! (1,001 reviews)
.
Reviewed on Feb 24, 2026
Abbey Resort and Avani Spa
269 Fontana Boulevard Fontana WI
Fully refundableReserve now, pay when you stay
The price is CA $135 per night from Mar 1 to Mar 2
CA $135
CA $184 total
Mar 1 - Mar 2
includes taxes & fees
8.6/10 Excellent! (1,755 reviews)
I want to give the resort 5 stars but I’m very disappointed on how there facilities has in my opinion lost its luster. The Spa
Reviewed on Feb 25, 2026
Timber Ridge Lodge and Waterpark
7020 Grand Geneva Way Lake Geneva WI
Fully refundableReserve now, pay when you stay
The price is CA $192 per night from Mar 3 to Mar 4
CA $192
CA $268 total
Mar 3 - Mar 4
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.
