Greenwood Vacation Packages

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Your Greenwood Vacation

Take the guesswork out of travel planning with a Greenwood vacation package. A good neighborhood to stay in this captivating city is Powers Lake, which is good for watersports and a lot more. If taking in sights is on the agenda during your trip to Greenwood, visit top attractions like McHenry County Courthouse, Petersen Park Beach and Woodstock Opera House. Whatever your travel plans or budget, putting together the ultimate tailored Greenwood vacation is a piece of cake with Expedia.

Top Greenwood Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Hilton Garden Inn Chicago Downtown South Loop

Hilton Garden Inn Chicago Downtown South Loop

3 out of 5
Downtown Chicago
per person
Sep 18 - Sep 22
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.8/10 Excellent! (1,584 reviews)
Good building, a little misleading when “separate sitting area” is mentioned in the room, yet the room is still just 2 queen beds and a desk and bench all still in the same room. How is this separate if it’s in the same room? Walkable to downtown with access to everything. Clean enough

Reviewed on Jul. 25, 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
per person
Sep 18 - Sep 22
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,635 reviews)
Very nice amenities and food. We would come back to this property

Reviewed on Jul. 25, 2025

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
per person
Oct 10 - Oct 12
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (2,122 reviews)
Nice hotel with a great breakfast buffet

Reviewed on Jul. 25, 2025

Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Downtown Chicago
per person
Aug 26 - Aug 29
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.6/10 Exceptional! (1,000 reviews)
It's a beautiful and comfortable hotel.

Reviewed on Jul. 22, 2025

Omni Chicago Hotel

Omni Chicago Hotel

4.5 out of 5
Downtown Chicago
per person
Sep 18 - Sep 22
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,484 reviews)
Very nice and clean place

Reviewed on Jul. 21, 2025

Ready to book your vacation to Greenwood?

 

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Greenwood Hotel Deals

Harbor Shores on Lake Geneva

Harbor Shores on Lake Geneva

3.5 out of 5
300 Wrigley Dr, Lake Geneva, WI
Fully refundableReserve now, pay when you stay
The price is CA $188 per night from Aug 19 to Aug 20
CA $188
CA $242 total
Aug 19 - Aug 20
includes taxes & fees
9/10 Wonderful! (1,194 reviews)
"Location was absolutely perfect for walking downtown. Clean, spacious"

Reviewed on Jul. 22, 2025

Harbor Shores on Lake Geneva
Abbey Resort and Avani Spa

Abbey Resort and Avani Spa

3.5 out of 5
269 Fontana Boulevard, Fontana, WI
Fully refundableReserve now, pay when you stay
The price is CA $149 per night from Aug 24 to Aug 25
CA $149
CA $199 total
Aug 24 - Aug 25
includes taxes & fees
8.4/10 Very Good! (1,410 reviews)
"Everything was excellent."

Reviewed on Jul. 22, 2025

Abbey Resort and Avani Spa
Timber Ridge Lodge and Waterpark

Timber Ridge Lodge and Waterpark

3.5 out of 5
7020 Grand Geneva Way, Lake Geneva, WI
Fully refundableReserve now, pay when you stay
The price is CA $244 per night from Aug 25 to Aug 26
CA $244
CA $324 total
Aug 25 - Aug 26
includes taxes & fees
8.6/10 Excellent! (2,901 reviews)
"We chose Timber Ridge for its proximity to Alpine Valley Music Theater and it was mission accomplished. This is a great place for families with young kids. Everyone was having a blast."

Reviewed on Jul. 22, 2025

Timber Ridge Lodge and Waterpark
See all 1,043 properties in Greenwood
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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
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Frequently asked questions

How much does a Greenwood vacation package cost?
Offering great value package deals from CA $950 on Expedia, you'll be surprised at how little a vacation to Greenwood costs! Our packages make travel planning easier and your savings go further.
What are the cheapest months to go to Greenwood?
You can typically find lower prices and greater availability in January, February and March. Browse our cheap Greenwood vacation packages and you could land some excellent off-season deals.
How many days is enough for Greenwood?
The ideal length for your Greenwood vacation depends on what you'd like to see. Generally, a handful of days to a week will give you enough time to visit all the leading attractions and discover some hidden gems along the way.
How to find the best Greenwood package deals?
Use Expedia's filters to find some terrific Greenwood package deals. When you start your search, just set your maximum budget and then order the results by "Price: low to high." If you want to save, plan your adventure for midweek, or look for Greenwood package deals in the low season. Switch up your travel dates and you may score even bigger discounts. As a rule of thumb, it's typically best to book your vacation package well in advance.
Is it cheaper to book a Greenwood vacation as a package?
Expedia vacation packages are designed to help you keep more money in your pocket. Bundle your car rental, flight and hotel into one great-value price and you could save hundreds of dollars. You'll generally score a better deal than booking each component separately. And you'll still have the flexibility to create a personalized Greenwood vacation by choosing your preferred airline, accommodation type and car class.
When to book a vacation package to Greenwood?
Land fantastic discounts by booking your flights ahead of time with Expedia. If spontaneity is more your style, grab one of our last-minute deals for a spur-of-the-moment Greenwood adventure.
How to plan a trip to Greenwood?

  1. Pick your dates: The things you'd like to do in Greenwood and your preferred season will help you decide when to go.
  2. Plan your budget wisely: Besides the price of your accommodations, you'll need to consider other expenses. These include transportation, food and flights. Also, set aside some extra funds for unexpected costs that may come up during your trip to Greenwood.
  3. Decide your trip length: Consider how much time you'd like to spend discovering Greenwood. Plan your days so you can get to all the attractions and activities you're interested in at a comfortable pace.
  4. Bundle your accommodations and airfare: Once you've nailed down your trip dates and duration, book the ideal Greenwood vacation package for you.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.