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.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
per person
Mar. 21 - Mar. 23
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,340 reviews)
Would definitely be coming back to this hotel

Reviewed on Jan. 20, 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Apr. 4 - Apr. 11
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Chicago (ORD)
9.4/10 Exceptional! (1,491 reviews)
Excellent hotel. Convenient location. Great staff. Nice lobby area. Fully equipped gym.

Reviewed on Jan. 20, 2025

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
per person
Mar. 14 - Mar. 19
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Chicago (ORD)
9/10 Wonderful! (282 reviews)
Amazing stay ! Love this property every time I’m in Chicago.

Reviewed on Jan. 20, 2025

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
per person
Apr. 4 - Apr. 7
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Chicago (ORD)
9.4/10 Exceptional! (1,000 reviews)
We only stayed one night after a party. Great place! We loved it! Valet service made it easy to get in and out. Staff in the Boozy Team room was excellent.

Reviewed on Jan. 21, 2025

Radisson Blu Aqua Hotel Chicago

Radisson Blu Aqua Hotel Chicago

4.5 out of 5
Downtown Chicago
per person
Apr. 4 - Apr. 11
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Chicago (ORD)
8.6/10 Excellent! (1,413 reviews)
Always love our stay

Reviewed on Jan. 22, 2025

Ready to book your vacation to Greenwood?

 

Choose your dates

Greenwood Hotel Deals

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 $183 per night from Feb. 6 to Feb. 7
CA $183
CA $258 total
includes taxes & fees
Feb 6 - Feb 7
8.6/10 Excellent! (2,661 reviews)
"The front desk clerk was quite rude. The room had broken parts on the tub, the mattress on the pull out couch (gross!), the heaters were incredibly loud in the bedroom and living room, the water was filled with toxins which we could actually see floating in our drinking glasses. The bathroom was ..."

Reviewed on Jan. 21, 2025

Timber Ridge Lodge and Waterpark
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 $117 per night from Feb. 23 to Feb. 24
CA $117
CA $166 total
includes taxes & fees
Feb 23 - Feb 24
8.4/10 Very Good! (1,174 reviews)
"Great quick getaway, lots to do on property"

Reviewed on Jan. 21, 2025

Abbey Resort and Avani Spa
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 $131 per night from Jan. 26 to Jan. 27
CA $131
CA $179 total
includes taxes & fees
Jan 26 - Jan 27
9/10 Wonderful! (1,204 reviews)
"Beautiful lobby, clean room with fireplace and balcony view. Both front desk personal were friendly and very personable. Great stay, would definitely come again!"

Reviewed on Jan. 17, 2025

Harbor Shores on Lake Geneva
See all 1,042 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

Beach Vacations

Family Vacations

Family Vacations

Frequently asked questions

How much does a Greenwood vacation package cost?
You’ll find cheap prices from CA $618 on Expedia for your Greenwood escape. However, factors like your choice of hotel, the season and length of stay will influence how much your vacation to Greenwood costs.
What are the cheapest months to go to Greenwood?
January, February and March are great times to search for cheap Greenwood vacation packages. Choosing to travel in quieter periods means you can typically find lower prices on flights and accommodations.
How many days is enough for Greenwood?
The ideal length of your Greenwood vacation depends on what you’d like to see and do. Typically, a handful of days to a week will give you plenty of time to go to all the top sights and explore some hidden treasures along the way.
How to find the best Greenwood package deals?
Begin your search for a Greenwood package deal by entering your travel dates and destination under our “Packages” tab. Then add some filters, like “Popular locations” and “Amenities,” to tailor the results to your exact needs. You can also sort by “Package discount” and browse offers that come with huge savings. If you don’t find the perfect Greenwood package deal straight away, just switch up your dates and search again. Keep in mind that deals are only available for a limited time, so book early and get your Greenwood escape underway.
Is it cheaper to book a Greenwood vacation as a package?
Expedia vacation packages are designed to help you keep more cash in your pocket. Bundle your hotel, flight and car rental into one great-value price and enjoy significant savings. You’ll typically snag a better deal than booking each component individually. And you’ll still have the freedom to create a personalized Greenwood vacation by choosing your preferred accommodation type, airline and car class.
When to book a vacation package to Greenwood?
If you’re considering a spur-of-the-moment Greenwood getaway, check out our last-minute deals that can be booked up to a week before you go. Prefer not to wait until the last minute? You can find amazing deals on your hotels and flights by booking ahead.
How to plan a trip to Greenwood?

  1. Choose your dates: What you want to do in Greenwood and your favorite season can help you decide when to get away.
  2. Set your budget: Consider costs such as food, flights and transportation when calculating how much to save for your trip to Greenwood. Then, select a property that suits your budget, whether that’s a low-cost option or a swankier retreat.
  3. Determine how many days away: Start by making a list of all the activities and sights you’d like to experience in Greenwood. Then, estimate how long you’ll need at each, including any travel time.
  4. Bundle your bookings: With your travel dates in place, you can combine your flights, car rental, hotels and more into a customized Greenwood vacation package.

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