Woodstock Vacation Packages 2026/2026 from $221

Woodstock flight + hotel vacation packages

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

Pendry Chicago

Downtown Chicago

Save 100% on your flight

$221

per person

Feb 13 - Feb 15

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. Enjoy the a rooftop terrace and perks like free WiFi. Valet parking, a coffee shop, and a terrace are also offered.

Hotel Riu Plaza Chicago

Downtown Chicago

Save 100% on your flight

$239

per person

Feb 13 - Feb 15

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.

The Emily Hotel

Downtown Chicago

Save 100% on your flight

$347

per person

Feb 13 - Feb 15

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 free WiFi in public areas, laundry service, and valet parking. A coffee shop, a snack bar/deli, and luggage storage are also on offer.

Trump International Hotel & Tower Chicago

Downtown Chicago

Save 100% on your flight

$398

per person

Feb 13 - Feb 15

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

A full-service spa, an indoor pool, and a restaurant are all featured at this luxury hotel. Families will appreciate the onsite laundry facilities, kid-friendly dining, and in-room childcare. Enjoy the gym and perks like free WiFi.

Sable at Navy Pier Chicago, Curio Collection by Hilton

Downtown Chicago

Save 100% on your flight

$236

per person

Feb 9 - Feb 13

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

This hotel's 2 restaurants, 2 bars/lounges, and 24-hour gym are some of the featured amenities. Traveling on business? Take advantage of the free WiFi in public areas, laundry service, and valet parking. Self parking, a coffee shop, and a terrace are also offered.

Top Woodstock hotels deals

AmericInn by Wyndham Woodstock IL

990 Lake Avenue Woodstock IL

Free Cancellation

Reserve now, pay when you stay

$76 nightly

$85 total

Dec 9 - Dec 10

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.

Super 8 by Wyndham Woodstock

1220 Davis Rd Woodstock IL

Free Cancellation

Reserve now, pay when you stay

$58 nightly

$64 total

Dec 30 - Dec 31

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

Quality Inn & Suites Woodstock near Lake Geneva

1785 S Eastwood Dr Woodstock IL

Free Cancellation

Reserve now, pay when you stay

$57 nightly

$63 total

Dec 31 - Jan 1, 2026

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.

Timber Ridge Lodge and Waterpark

7020 Grand Geneva Way Lake Geneva WI

Free Cancellation

Reserve now, pay when you stay

$194 nightly

$216 total

Dec 8 - Dec 9

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.

Abbey Resort and Avani Spa

269 Fontana Boulevard Fontana WI

Free Cancellation

Reserve now, pay when you stay

$142 nightly

$157 total

Dec 8 - Dec 9

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.

Harbor Shores on Lake Geneva

300 Wrigley Dr Lake Geneva WI

Free Cancellation

Reserve now, pay when you stay

$97 nightly

$110 total

Dec 21 - Dec 22

Total with taxes and fees

This hotel features an outdoor pool, an indoor pool, and a restaurant. Traveling on business? Take advantage of the business center and free WiFi in public areas. Enjoy the gym and perks like free self parking.

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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

4.5/5(6 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.

Woodstock Square

4/5(19 reviews)

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.

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.

Frequently asked questions

How much are vacation packages to Woodstock?

With a Travelocity vacation package, you can live it up in Woodstock from just $221. 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.