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Woodstock flight + hotel packages

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Aloft Chicago Downtown River North
W Chicago - Lakeshore
Hotel Riu Plaza Chicago
InterContinental Chicago Magnificent Mile, an IHG Hotel
21c Museum Hotel Chicago

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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

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?
With a Travelocity vacation package, you can live it up in Woodstock from just CA $644. 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 80 kilometers 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 56 kilometers southeast of downtown Woodstock. Midway Intl. Airport (MDW) (80 kilometers away from central Woodstock) and General Mitchell Intl. Airport (MKE) (80 kilometers 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

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Photo by Erik Rowley
Photo by Erik Rowley