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Woodstock flight + hotel packages

Prices and availability subject to change. Additional terms may apply.
The Peninsula Chicago

The Peninsula Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jun. 12 - Jun. 16
Roundtrip flight included
Montreal (YUL) to Chicago (ORD)
Stay at this 5-star luxury hotel in Chicago. Enjoy free WiFi, 2 restaurants, and a full-service spa. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby. Discover genuine guest reviews for The Peninsula Chicago, in Downtown Chicago neighborhood, along with the latest prices and availability – book now.
Chicago Marriott Downtown Magnificent Mile

Chicago Marriott Downtown Magnificent Mile

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jul. 15 - Jul. 19
Roundtrip flight included
Montreal (YUL) to Chicago (ORD)
Stay at this business-friendly hotel in Chicago. Enjoy 2 restaurants, a rooftop terrace, and breakfast. Our guests praise the bar and the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby. Discover genuine guest reviews for Chicago Marriott Downtown Magnificent Mile, in Downtown Chicago neighborhood, along with the latest prices and availability – book now.
Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jun. 12 - Jun. 19
Roundtrip non-stop flight included
Halifax (YHZ) to Chicago (ORD)
Stay at this 4.5-star luxury hotel in Chicago. Enjoy free WiFi, a rooftop terrace, and breakfast. Our guests praise the bar and the helpful staff in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby. Discover genuine guest reviews for Pendry Chicago, in Downtown Chicago neighborhood, along with the latest prices and availability – book now.
DoubleTree by Hilton Chicago - Magnificent Mile

DoubleTree by Hilton Chicago - Magnificent Mile

4 out of 5
Downtown Chicago
per person
Jul. 15 - Jul. 19
Roundtrip flight included
Montreal (YUL) to Chicago (ORD)
Stay at this business-friendly hotel in Chicago. Enjoy an outdoor pool, a rooftop terrace, and breakfast. Our guests praise the pool and the restaurant in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby. Discover genuine guest reviews for DoubleTree by Hilton Chicago - Magnificent Mile, in Downtown Chicago neighborhood, along with the latest prices and availability – book now.
Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
May 26 - May 29
Roundtrip flight included
Montreal (YUL) to Chicago (ORD)
Stay at this spa hotel in Chicago. Enjoy free WiFi, a full-service spa, and breakfast. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby. Discover genuine guest reviews for Park Hyatt Chicago, in Downtown Chicago neighborhood, along with the latest prices and availability – book now.

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
The price is CA $123 per night
CA $123
per night
May 2 - May 3
Stay at this ski hotel in Woodstock. Enjoy free breakfast, free parking, and a casino. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions McHenry County Fairgrounds and Woodstock City Hall are located nearby. Discover genuine guest reviews for AmericInn by Wyndham Woodstock IL along with the latest prices and availability – book now.
Pet-friendly
Pool
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
The price is CA $159 per night
CA $159
per night
May 12 - May 13
Stay at this 3.5-star spa aparthotel in Lake Geneva. Enjoy free parking, a golf course, and a full-service spa. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Moose Mountain Falls Waterpark and Dan Patch Stables are located nearby. Discover genuine guest reviews for Timber Ridge Lodge and Waterpark along with the latest prices and availability – book now.
Hot tub
Fireplace
Hyatt Place Chicago/Hoffman Estates

Hyatt Place Chicago/Hoffman Estates

3 out of 5
2750 Greenspoint Pkwy, Hoffman Estates, IL
Free cancellation
The price is CA $119 per night
CA $119
per night
May 12 - May 13
Stay at this 3-star business-friendly hotel in Hoffman Estates. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Woodfield Mall and LEGOLAND® Discovery Center are located nearby. Discover genuine guest reviews for Hyatt Place Chicago/Hoffman Estates along with the latest prices and availability – book now.
Pet-friendly
Pool
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
The price is CA $154 per night
CA $154
per night
May 2 - May 3
Stay at this 3.5-star beach resort in Fontana. Enjoy free parking, 2 restaurants, and a marina. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Yerkes Observatory and Williams Bay Beach are located nearby. Discover genuine guest reviews for Abbey Resort and Avani Spa along with the latest prices and availability – book now.
Hot tub
Pool
The Ridge Hotel

The Ridge Hotel

4 out of 5
W4240 WI-50, Lake Geneva, WI
Free cancellation
Reserve now, pay when you stay
The price is CA $127 per night
CA $127
per night
Apr. 28 - Apr. 29
Stay at this 4-star golf resort in Lake Geneva. Enjoy an outdoor pool, breakfast, and a fitness center. Our guests praise the pool and the restaurant in our reviews. Popular attractions Geneva Lake and Geneva National Golf Club are located nearby. Discover genuine guest reviews for The Ridge Hotel along with the latest prices and availability – book now.
Pet-friendly
Pool
Harbor Shores on Lake Geneva

Harbor Shores on Lake Geneva

3.5 out of 5
300 Wrigley Dr, Lake Geneva, WI
Free cancellation
Reserve now, pay when you stay
The price is CA $134 per night
CA $134
per night
Apr. 29 - Apr. 30
Stay at this family-friendly hotel in Lake Geneva. Enjoy free WiFi, free parking, and room service. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Gary Gygax Memorial and Riviera Ballroom are located nearby. Discover genuine guest reviews for Harbor Shores on Lake Geneva along with the latest prices and availability – book now.
Pool
Parking included
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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

Image for Woodstock Opera House

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
Image for Woodstock Square

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
Image for McHenry County Courthouse

McHenry County Courthouse

McHenry County Courthouse is just one of the places to see in Woodstock, so why not enjoy the other things to explore during your travels? Stroll along the lakeside or attend a sporting event in this family-friendly area.

McHenry County Courthouse

Woodstock Vacations

All set to make some new memories? Ensure you don't miss out on any excitement in Woodstock by brushing up on some details about it before you hurry off.

Woodstock is 55 miles (89 kilometers) to the northwest of Chicago, a notable city.

You can forget about the big-name sights — it's the locals that really make a place tick. In this part of Illinois, you'll find 25,000 of them.

Places to visit in Woodstock

Theater can challenge our world views and asks us to aspire to bigger and better things. Get tickets to a production at Woodstock Opera House and open your mind to some new ideas. Seeking some more options? If only these walls could talk! Imagine the power grabs and heated conversations that have occurred at McHenry County Courthouse. Check for tours for an up-close-and-personal look at this significant building. But that's not all. It doesn't matter whether you're aiming for a hole-in-one or simply in the mood to practice your swing, you'll have a blast at Bull Valley Golf Club.

Where do you fly into for Woodstock?

Bags all packed? Fantastic — hop on the flight to Greater Rockford Airport (RFD). Once the wheels hit the runway, you'll be only 35 miles (56 kilometers) to the west from the heart of Woodstock.

Frequently asked questions

How much are vacation packages to Woodstock?
Exciting adventures await in Woodstock, with Travelocity vacation packages starting from as low as CA $1,156. Offering both hotels and flights, these terrific deals make it super simple to visit all corners of the world.
How long should my Woodstock vacation be?
There are no rules when it comes to how long your vacation in Woodstock should be, but many travelers decide to stay for around 2 nights. Got some wiggle room in your departure date? Extend your vacation by a couple of extra nights. That way, you’ll have loads of time to check out the nearby areas too.
Where can I get the best vacation package deals for Woodstock?
No matter what you enjoy doing, Travelocity can help you get your hands on the best Woodstock package deal. The only thing you need to do is mix and match from our 400 air carriers and 665,000 properties around the world.
Why should I purchase my Woodstock vacation bundle with Travelocity?
With our Price Match Guarantee, we’ll match any better price you can find. Add to that our 24/7 customer support and top-quality service and the vacation you’ve been dreaming of is closer than ever before.
Can I save on my Woodstock car rental if I book it with a hotel or flight?
Bundling your hotel, car and flight into a Woodstock vacation package is an easy way to score an incredible deal. Plus, having your own set of wheels gives you freedom to make your way to all those amazing sights you’re hoping to check out. Located 80 kilometersfrom Woodstock, Wrigley Field is one attraction that should have a place on your itinerary. Put together a driving playlist and make a day trip of it.
What is the best time of year to go to Woodstock?
are the most popular months to visit, while are typically less busy. If you’re traveling on a limited budget, consider visiting during . is generally regarded as the most expensive month to stop by.
Which airport is best for Woodstock?
Chicago, IL (ORD-O’Hare Intl.) is one of the busiest airports in Woodstock. It’s situated 60 kilometerssoutheast of the bustling downtown area. Other options available to you are Chicago, IL (MDW-Midway Intl.) (85 kilometersaway from central Woodstock) and Milwaukee, WI (MKE-General Mitchell Intl.) (85 kilometersaway from central Woodstock).
What is there to do in Woodstock?
Woodstock Opera House is one of the superb sights that make Woodstock such a tourist hot spot. But give yourself enough time to experience its lesser-known attractions too. This is often where the best memories are made.
Where should I stay when visiting Woodstock?
The Best Western Woodstock Inn is the first choice of many travelers. Book soon to avoid missing out.
Can I go on vacation to Woodstock at this time?
Find out all the info you need to know about quarantine policies and travel restrictions before you head for Woodstock. Our Covid-19 Travel Advisor is full of advice to help make your vacation smooth and hassle-free.