Woodstock Vacation Packages 2026 from $321

Woodstock flight + hotel vacation packages

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

THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

Downtown Chicago

Save 100% on your flight

$321

per person

Dec 15 - Dec 20

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. A hair salon, express check-in, and express check-out are also on offer.

Hotel Riu Plaza Chicago

Downtown Chicago

Save 100% on your flight

$438

per person

Dec 15 - Dec 20

found 1 day ago

Roundtrip flight included

Atlanta (ATL) 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.

Level Chicago Fulton Market

Downtown Chicago

Save 100% on your flight

$439

per person

Dec 8 - Dec 12

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

This hotel features a gym and a seasonal outdoor pool. WiFi in public areas is free. Self parking, a business center, and a picnic area are also offered.

Level Chicago – Old Town

Downtown Chicago

Save 100% on your flight

$763

per person

Dec 31 - Jan 5

found 1 day ago

Roundtrip flight included

Atlanta (ATL) 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.

Swissotel - Chicago

Downtown Chicago

Save 100% on your flight

$384

per person

Jan 8 - Jan 12

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

This hotel features 2 bars/lounges and a 24-hour gym. Traveling on business? Take advantage of the business center, express check-in, and valet parking. A restaurant, a 24-hour front desk, and laundry facilities are also provided.

Top Woodstock hotels deals

AmericInn by Wyndham Woodstock IL

990 Lake Avenue Woodstock IL

Free Cancellation

Reserve now, pay when you stay

$90 nightly

$100 total

Oct 18 - Oct 19

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 full breakfast and free self parking.

Pool

Breakfast included

Quality Inn & Suites Woodstock near Lake Geneva

1785 S Eastwood Dr Woodstock IL

Free Cancellation

$75 nightly

$83 total

Nov 9 - Nov 10

Total with taxes and fees

This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the business center and free WiFi in public areas. Guests will appreciate freebies like continental breakfast and free self parking.

Pool

Breakfast included

Abbey Resort and Avani Spa

269 Fontana Boulevard Fontana WI

Free Cancellation

Reserve now, pay when you stay

$130 nightly

$143 total

Oct 28 - Oct 29

Total with taxes and fees

A full-service spa, 2 restaurants, and an indoor pool are all featured at this smoke-free resort. 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

7020 Grand Geneva Way Lake Geneva WI

Free Cancellation

Reserve now, pay when you stay

$159 nightly

$177 total

Oct 28 - Oct 29

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

Harbor Shores on Lake Geneva

300 Wrigley Dr Lake Geneva WI

Free Cancellation

Reserve now, pay when you stay

$135 nightly

$153 total

Nov 1 - Nov 2

Total with taxes and fees

This smoke-free hotel includes 2 restaurants, an outdoor pool, and an indoor pool. Enjoy the gym and perks like free self parking and free WiFi. Relax with a drink at the bar/lounge and enjoy the sauna.

Pool

Parking included

Grand Geneva Resort & Spa

7036 Grand Geneva Wy Lake Geneva WI

Free Cancellation

Reserve now, pay when you stay

$269 nightly

$300 total

Nov 9 - Nov 10

Total with taxes and fees

This smoke-free resort features a golf course, a full-service spa, and a water park. Take advantage of ski lessons, ski rentals and ski passes on site, and enjoy downhill skiing. There's fun for all ages with a children's pool and a playground, and families will appreciate the onsite laundry facilities.

Pool

Hot Tub

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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.

Stay near popular Woodstock attractions

A historic building with a clock tower, a theater, and a street with cars and pedestrians.

Woodstock Opera House

8.2/10 (27 reviews)

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

See properties

Frequently asked questions

How much are vacation packages to Woodstock?

With a Travelocity vacation package, you can live it up in Woodstock from just $321. 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.