Greenwood Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
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.
Level Chicago – Old Town
Downtown Chicago
CA $1,508
per person
Dec 2 - Dec 9
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
9.2/10 Wonderful! (520 reviews)
Amazing stay. Love the balcony view. Parking was easy and accessible. Will be back!
Reviewed on Sep 19, 2026
Level Chicago Fulton Market
Downtown Chicago
CA $1,137
per person
Dec 2 - Dec 9
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
9.2/10 Wonderful! (561 reviews)
I loved the balcony and the great view! The kitchenette was a plus along with the provided utensils and necessary items. The laundry are was not something that I used but I could see how it would be a bonus feature. The area by the bed was a little cramped, but it ended up being comfortable. The staff was extremely friendly and helpful and the check in was seamless. The elevators were especially private and convenient. Overall, the extra $ that I paid for my stay was well worth it!
Reviewed on Sep 21, 2026
Ready to book your vacation to Greenwood?
Greenwood Hotel Deals
Abbey Resort and Avani Spa
269 Fontana Boulevard Fontana WI
Fully refundableReserve now, pay when you stay
CA $141
CA $193 total
Oct 4 - Oct 5
includes taxes & fees
8.6/10 Excellent! (2,081 reviews)
"From the outside and lobby the appearance is good. For the cost per night the hotel needs to be updated especially the rooms. There was a very stuffy old smell in the room. Not what I’m used to for a weekend stay. The indoor pools looked great but was cold and hot tub out of service. Definitely didn’t ..."
Reviewed on Sep 22, 2026
Harbor Shores on Lake Geneva
300 Wrigley Dr Lake Geneva WI
Fully refundableReserve now, pay when you stay
CA $173
CA $227 total
Sep 24 - Sep 25
includes taxes & fees
9.2/10 Wonderful! (1,430 reviews)
"The property was old and updated but the updates were not very well done. The staff was nice but we were disappointed that it wasn’t nicer for the money."
Reviewed on Sep 21, 2026
Timber Ridge Lodge and Waterpark
7020 Grand Geneva Way Lake Geneva WI
Fully refundableReserve now, pay when you stay
CA $142
CA $213 total
Oct 20 - Oct 21
includes taxes & fees
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.
Frequently asked questions
How much does a Greenwood vacation package cost?
Offering great value package deals from CA $1,030 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?
- Pick your dates: The things you'd like to do in Greenwood and your preferred season will help you decide when to go.
- 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.
- 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.
- 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.
