Deals on vacations and trips to Woodstock

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Woodstock flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.
Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Price was $605, price is now $407 per person
$407
per person
Mar 13 - Mar 15
found 1 day ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Enjoy the a rooftop terrace and perks like free WiFi. Valet parking, a coffee shop, and a terrace are also offered.
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,052, price is now $630 per person
$630
per person
Mar 14 - Mar 18
found 13 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Chicago (ORD)
This aparthotel features a 24-hour gym and a seasonal outdoor pool. There's fun for all ages with a playground and an arcade/game room, and barbecue grills are available on site. Enjoy the a rooftop terrace and perks like free WiFi.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $763, price is now $466 per person
$466
per person
Mar 13 - Mar 15
found 1 day ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
This hotel features 2 bars/lounges and a 24-hour gym. Business travelers can take advantage of the free WiFi in public areas. Enjoy a meal from the restaurant and free buffet breakfast each morning.
Hilton Chicago O'Hare Airport

Hilton Chicago O'Hare Airport

4 out of 5
O'Hare
Save 100% on your flight
Price was $839, price is now $553 per person
$553
per person
Mar 12 - Mar 16
found 1 day ago
Roundtrip flight included
Charlotte (CLT) to Chicago (ORD)
This hotel features 2 restaurants, a bar/lounge, and A 24-hour gym. Traveling on business? Take advantage of the business center, free WiFi in public areas, and free airport shuttle. You'll appreciate the area shuttle, valet parking, and coffee shop/cafe.
The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $674, price is now $448 per person
$448
per person
Mar 13 - Mar 15
found 1 day ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the free WiFi in public areas, laundry service, and valet parking. A coffee shop, a snack bar/deli, and luggage storage are also on offer.

Top Woodstock hotels deals

AmericInn by Wyndham Woodstock IL

AmericInn by Wyndham Woodstock IL

2.5 out of 5
990 Lake Avenue Woodstock IL
Free Cancellation
Reserve now, pay when you stay
$81 nightly
The price is $90 total per night
$90 total
Dec 29 - Dec 30
Total with taxes and fees
A casino, a 24-hour gym, and a restaurant are all featured at this smoke-free hotel. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the indoor pool and free perks like continental breakfast and free self parking.
Pool
Breakfast included
Quality Inn & Suites Woodstock near Lake Geneva

Quality Inn & Suites Woodstock near Lake Geneva

2.5 out of 5
1785 S Eastwood Dr Woodstock IL
Free Cancellation
Reserve now, pay when you stay
$68 nightly
The price is $75 total per night
$75 total
Dec 29 - Dec 30
Total with taxes and fees
This hotel doesn't skimp on freebies - guests receive free continental breakfast, free WiFi, and free self parking. Business travelers can take advantage of the business center. Enjoy the gym and conveniences like a 24-hour front desk and laundry facilities.
Breakfast included
Parking included
Super 8 by Wyndham Woodstock

Super 8 by Wyndham Woodstock

2 out of 5
1220 Davis Rd Woodstock IL
Free Cancellation
Reserve now, pay when you stay
$69 nightly
The price is $76 total per night
$76 total
Jan 1 - Jan 2, 2026
Total with taxes and fees
This motel features free WiFi in public areas, laundry facilities, and free self parking. Enjoy the free on-the-go breakfast each morning. The front desk is staffed around-the-clock and free newspapers are on offer.
Breakfast included
Pet friendly
Abbey Resort and Avani Spa

Abbey Resort and Avani Spa

3.5 out of 5
269 Fontana Boulevard Fontana WI
Free Cancellation
Reserve now, pay when you stay
$142 nightly
The price is $157 total per night
$157 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
This smoke-free resort features a full-service spa, a marina, and 2 restaurants. Bring the family and enjoy the children's pool, waterslide, and kid-friendly dining. Relax with a drink at one of the 2 bars/lounges and enjoy perks like free self parking.
Pool
Hot Tub
Timber Ridge Lodge and Waterpark

Timber Ridge Lodge and Waterpark

3.5 out of 5
7020 Grand Geneva Way Lake Geneva WI
Free Cancellation
Reserve now, pay when you stay
$194 nightly
The price is $216 total per night
$216 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
This smoke-free aparthotel features a golf course, free water park access, and a full-service spa. Take advantage of ski lessons, ski rentals and ski storage on site, and enjoy downhill skiing. Bring the family and enjoy the lazy river, mini golf, and kid-friendly dining.
Pool
Hot Tub
Hyatt Place Chicago/Hoffman Estates

Hyatt Place Chicago/Hoffman Estates

3 out of 5
2750 Greenspoint Pkwy Hoffman Estates IL
Free Cancellation
Reserve now, pay when you stay
$109 nightly
The price is $123 total per night
$123 total
Dec 24 - Dec 25
Total with taxes and fees
This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the 24-hour gym and free perks like continental breakfast and free self parking.
Pool
Breakfast included
Don't see what you're looking for?
See all available properties in Woodstock
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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.

Popular places to visit

Highlighted in the movie Groundhog Day, also housed plays that featured famous actors Orson Welles and Paul Newman.

Woodstock Opera House

You can enjoy a show at Woodstock Opera House during your trip to Woodstock. While you're in the area, stroll along the lakeside.

Woodstock Opera House

Woodstock Square

You can find out about the history of Woodstock with a trip to Woodstock Square. While you're in the area, stroll along the lakeside.

Woodstock Square

McHenry County Fairgrounds

Enjoy an outing to McHenry County Fairgrounds during your stay in Woodstock. While you're in the area, stroll along the lakeside.

McHenry County Fairgrounds

Frequently asked questions

How much are vacation packages to Woodstock?
With a Travelocity vacation package, you can live it up in Woodstock from just $407. Hotels, flights and experiences — we have everything you need. You'll save a bunch just for bundling together your bookings. And with all that taken care of before leaving, you can sit back, relax and enjoy the adventure.
How long should my Woodstock vacation be?
Around 2 nights is the average time frame visitors vacation in Woodstock. But how long is right for you depends on how many magical memories you want to make. Why not stay a bit longer and uncover some of the lesser-known sights?
Where can I get the best vacation package deals for Woodstock?
Check out Travelocity. With access to 400 airlines and a massive 1,000,000 properties around the world, selecting the ultimate Woodstock package deal couldn't be simpler.
Why should I purchase my Woodstock vacation bundle with Travelocity?
Travel should be about making fantastic new memories and leaving all your worries behind — which is why we provide you with a team of experts on hand around-the-clock should you need them. On top of that, our Price Match Guarantee ensures you'll always get the best price available on our impressive range of vacation destinations. So what are you waiting for? There's no time like the present to lock in the vacation you've always dreamed of.
Can I save money on my Woodstock car rental if I book it with hotels and flights?
You sure can — combine your flight, car and hotel into a Woodstock vacation package and you'll save a tidy sum. With so much to uncover in and around Woodstock, that rental car will make exploring a breeze. Once you've buckled up, turn up the tunes and head to Wrigley Field, a top sight around 50 mi from Woodstock.
Which airport is best for Woodstock?
There's a very good chance you'll touch down at O'Hare Intl. Airport (ORD), located 35 mi southeast of downtown Woodstock. Midway Intl. Airport (MDW) (50 mi away from central Woodstock) and General Mitchell Intl. Airport (MKE) (50 mi away from central Woodstock) are your other choices.
What is there to do in Woodstock?
There is a particular magic in the air as you stroll through the streets of Woodstock. Woodstock Opera House and Old Courthouse Arts Center are just a couple of famous sights that entice visitors to this wonderful city, so put them at the top of your list of places to see.
Where should I stay when visiting Woodstock?
If you're searching for someplace comfortable to base yourself, take a look at the AmericInn by Wyndham Woodstock IL. It's the top choice for many travelers.

Photos of local treasures

Browse Woodstock vacation photos for more inspiration

Photo by Erik Rowley
Photo by Erik Rowley
Photo by Erik Rowley
Photo by Erik Rowley

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