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.
The Talbott, Autograph Collection
Downtown Chicago
Price was CA $1,271, price is now CA $892 per person
CA $892
per person
Aug 31 - Sep 4
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (120 reviews)
The hotel is fresh and clean. Very nice facility. Staff anre wonderful. Only comment is there should be free water in the rooms, at least for Marriott members. For the rates charged, water should be included. Water pressure is a bit low.
Reviewed on Jun 21, 2026
Hotel Felix River North/Magnificent Mile
Downtown Chicago
Price was CA $1,474, price is now CA $997 per person
CA $997
per person
Sep 18 - Sep 21
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Chicago (ORD)
8.2/10 Very good! (2,767 reviews)
Overall, the hotel was okay for the price, but pretty basic. The room was very simple and lacked some expected amenities—there were no slippers provided, which was a bit disappointing. Also, the area around the bed wasn’t very clean, which affected the overall experience.
I paid $170 per night, and for that price, I expected a bit more attention to cleanliness and comfort. It’s not terrible, but definitely not great either.
Reviewed on Jun 22, 2026
Level Chicago - River North
Downtown Chicago
Price was CA $1,871, price is now CA $1,383 per person
CA $1,383
per person
Aug 15 - Aug 20
found 1 day ago
Roundtrip flight included
Montreal (YMQ) to Chicago (ORD)
9.2/10 Wonderful! (1,034 reviews)
Really plan ahead when it comes to parking. You’ll get ticketed for just trying to put your things in your vehicle.
Reviewed on Jun 19, 2026
Level Chicago Fulton Market
Downtown Chicago
Price was CA $1,850, price is now CA $1,372 per person
CA $1,372
per person
Aug 19 - Aug 23
found 1 day ago
Roundtrip flight included
Montreal (YMQ) to Chicago (ORD)
9.2/10 Wonderful! (498 reviews)
The place was serene,close proximity to Fulton market and had amazing views
Reviewed on Jun 22, 2026
Hampton Inn & Suites Chicago Medical District UIC
Near West Side
Price was CA $1,290, price is now CA $958 per person
CA $958
per person
Sep 14 - Sep 17
found 23 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
9.6/10 Exceptional! (622 reviews)
James at the front desk was absolutely incredible. It was a quick stay due to storms in the area, but James' professionalism and care added some positivity to an otherwise stressful travel experience.
Reviewed on Jun 22, 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 $127 per night from Jun 25 to Jun 26
CA $127
CA $141 total
Jun 25 - Jun 26
includes taxes & fees
8/10 Very good! (1,003 reviews)
"Check in was great day 1. The main area looked clean. The biggest issue that really made a huge impact to our stay was that our room smelled SO BAD of urine. Whether it was human or animal- it was HORRIBLE. We let the front desk know and the only resolution was “we will look into it” Wouldn’t stay ..."
Reviewed on Jun 21, 2026
Quality Inn & Suites Woodstock near Lake Geneva
1785 S Eastwood Dr Woodstock IL
Fully refundable
The price is CA $109 per night from Jul 14 to Jul 15
CA $109
CA $121 total
Jul 14 - Jul 15
includes taxes & fees
6/10 (318 reviews)
"Disgusting, nasty and filthy, smells horrible! Worst experience ever! Didn’t even stay left as soon as I seen the room!"
Reviewed on Jun 15, 2026
Abbey Resort and Avani Spa
269 Fontana Boulevard Fontana WI
Fully refundableReserve now, pay when you stay
The price is CA $190 per night from Jun 28 to Jun 29
CA $190
CA $248 total
Jun 28 - Jun 29
includes taxes & fees
8.6/10 Excellent! (1,917 reviews)
"All good, very nice"
Reviewed on Jun 21, 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.
