
Woodstock Vacations from $483
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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.
The Latest Woodstock vacation packages
Price found within the past 48 hours. Click for updated prices.

The Whitehall Hotel, BW Premier Collection
Downtown Chicago
Save 100% on your flight
Price was $712, price is now $483 per person
$483
per person
Sep 3 - Sep 6
found 2 days ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.4/10 Very Good! (3,950 reviews)
The Whitehall is “my Go To” when I am traveling solo, or with a girlfriend! Location is best in the city, for high end shopping and restaurants! Lake Michigan and Oak Street Beach are a “stones throw” away.
This is one of the Real Classic Hotels. It is a bit dated, yet; all of my needs are met, with awesome beds, crisp clean linens, luggage racks, a safe for your valuables, along with marble bathrooms, really Hot Showers! The staff is always polite and helpful. The rooms are spacious and views can be awesome!😎
As a 25 year Chicagoan, whom no longer lives here, I Love 💕 this place… 👏 👏 👏
Reviewed on Jun 26, 2026

Hotel Felix River North/Magnificent Mile
Downtown Chicago
Save 100% on your flight
Price was $1,186, price is now $747 per person
$747
per person
Sep 17 - Sep 21
found 2 days ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.2/10 Very Good! (2,767 reviews)
Great location, we were able to walk everywhere we wanted to see. The red line is about a 10 minute walk if you are heading to Wrigley.
Reviewed on Jun 26, 2026

Pendry Chicago
Downtown Chicago
Save 100% on your flight
Price was $1,074, price is now $699 per person
$699
per person
Sep 3 - Sep 6
found 2 days ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (1,134 reviews)
The staff was very welcoming! The bellman greeted us by name the entire trip. Great location for shopping and the riverwalk. Highly recommend!
Reviewed on Jun 23, 2026

Level Chicago – Old Town
Downtown Chicago
Save 100% on your flight
Price was $1,216, price is now $797 per person
$797
per person
Sep 13 - Sep 16
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (495 reviews)
We love where this is property is located and all the amenities. The pool was closed the 2 days we were there which was disappointing but the weather didn't really cooperate either. The staff is very accomodating and attentive.
Reviewed on Jun 11, 2026

Hotel Riu Plaza Chicago
Downtown Chicago
Save 100% on your flight
Price was $1,162, price is now $764 per person
$764
per person
Sep 3 - Sep 6
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (4,518 reviews)
The hotel room cleanliness is of a very high standard. The complementary breakfast is extraordinary with a different majority of food and with a good procedure to take care of guests. The rooftop bar was sophisticated and attracts high class clientele. The room space is big enough to feel comfortable. There is individual Wi-Fi for each room that allows you to connect your phone to the TV. And the location downtown was excellent.
Reviewed on Jun 25, 2026
Stay near popular Woodstock attractions
Woodstock Hotel Deals

AmericInn by Wyndham Woodstock IL
990 Lake Avenue Woodstock IL
Fully refundableReserve now, pay when you stay
$88 nightly
The price is $98 total per night from Jul 14 to Jul 15
$98 total
Jul 14 - Jul 15
Total with taxes and fees
8/10 Very Good! (1,001 reviews)
"clean room mstaff was nice bed was confortable"
Reviewed on Jun 23, 2026

Quality Inn & Suites Woodstock near Lake Geneva
1785 S Eastwood Dr Woodstock IL
Fully refundable
$77 nightly
The price is $86 total per night from Jul 19 to Jul 20
$86 total
Jul 19 - Jul 20
Total with taxes and 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
$178 nightly
The price is $197 total per night from Jun 29 to Jun 30
$197 total
Jun 29 - Jun 30
Total with taxes and fees
8.6/10 Excellent! (1,906 reviews)
"There was so much walking. It was like a maze at the resort.!! also booked our trip on Expedia did not get the room that we were told we were gonna get with the continental breakfast. There was no continental breakfast however they did put us in a different room but we lost half a day.!"
Reviewed on Jun 25, 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.
Find the Best Woodstock Vacation Packages
Woodstock Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Population | 25,200 |
Max Temp Winter | 30ºF |
Max Temp Summer | 75ºF |
Top Sights | McHenry Shores Beach Park, Petersen Park Beach and Main Beach |
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- Hotels near Woodstock Opera House
- Hotels near Woodstock Square
- Hotels near Woodstock Station
- Hotels near McHenry County Fairgrounds
- Hotels near Emricson Park
- Hotels near McHenry County Courthouse
- Hotels near Bull Valley Golf Club
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- Hotels near McHenry County College
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- Woodstock Opera House
- Woodstock Square
- Woodstock City Hall
- Emricson Park
- Mchenry County Courthouse
- Craig Woods Golf Club
- Crystal Woods Golf Club
- Wonder Lake Vacations
- Visit Wonder Lake
- Main Beach
- Veterans Acres Park
- Crystal Lake City Hall
- Crystal Lake Vacations
- Visit Crystal Lake
- Visit Village of Lakewood
- Car rentals near Woodstock Square
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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.





















