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
- The Talbott, Autograph Collection
Jan 21 - Jan 24The Talbott, Autograph Collection + Flight
Downtown Chicago3 nights4.5 star property9.4/10 - Exceptional (194 reviews)Roundtrip • Toronto (YTO) - Chicago (ORD)YTZ - ORD • Nonstop ORD - YTZ • NonstopCA $1,195CA $943found 15 hours agoper traveller - Sheraton Grand Chicago Riverwalk
Jan 21 - Jan 24Sheraton Grand Chicago Riverwalk + Flight
Downtown Chicago3 nights4.0 star property8.6/10 - Excellent (1,877 reviews)Roundtrip • Toronto (YTO) - Chicago (ORD)YTZ - ORD • Nonstop ORD - YTZ • NonstopCA $1,322CA $979found 15 hours agoper traveller - Pendry Chicago
Dec 24 - Dec 28Pendry Chicago + Flight
Downtown Chicago4 nights4.5 star property9.2/10 - Wonderful (1,162 reviews)"Beautiful rooms and service."Reviewed November 5, 2026Roundtrip • Toronto (YTO) - Chicago (ORD)YTZ - ORD • Nonstop ORD - YTZ • NonstopCA $1,731CA $1,315found 1 day agoper traveller - Trump International Hotel & Tower Chicago
Dec 24 - Dec 28Trump International Hotel & Tower Chicago + Flight
Downtown Chicago4 nights5.0 star property9.6/10 - Exceptional (2,077 reviews)"Beautiful hotel situated perfectly for most downtown Chicago activities. Attentive staff and amazing views from our 14th floor lake view room. This stay has been on my bucket list for awhile. This hotel experience did not disappoint"Reviewed November 6, 2026Roundtrip • Toronto (YTO) - Chicago (ORD)YTZ - ORD • Nonstop ORD - YTZ • NonstopCA $2,457CA $1,902found 1 day agoper traveller - Swissotel - Chicago
Dec 24 - Dec 28Swissotel - Chicago + Flight
Downtown Chicago4 nights4.5 star property9.0/10 - Wonderful (3,571 reviews)"We appreciated the early check in, staff was pleasant, room was comfortable with a great river & lake view. Bar service was convenient."Reviewed November 6, 2026Roundtrip • Toronto (YTO) - Chicago (ORD)YTZ - ORD • Nonstop ORD - YTZ • NonstopCA $1,466CA $1,148found 1 day agoper traveller
Greenwood Hotel Deals
AmericInn by Wyndham Woodstock IL
AmericInn by Wyndham Woodstock IL"Found 2 roaches in bathroom also 1 roach by the refrigerator. Room had bad smell when come in room. Not really pleased that room!"
Baymont Inn & Suites by Wyndham Richmond
Baymont Inn & Suites by Wyndham Richmond
Country Inn & Suites by Radisson, Crystal Lake, IL
Country Inn & Suites by Radisson, Crystal Lake, IL"The housekeeping was lacking, the room was barely cleaned, the bed sheets were never changed, I had to ask for new soap everyday. I’ve stayed at this hotel many times before, this was the first time that I’ve had this experience."
Quality Inn & Suites Woodstock near Lake Geneva
Quality Inn & Suites Woodstock near Lake Geneva
Comfort Inn Crystal Lake - Algonquin
Comfort Inn Crystal Lake - Algonquin
Holiday Inn Express Hotel & Suites Chicago-Algonquin by IHG
Holiday Inn Express Hotel & Suites Chicago-Algonquin by IHG"Room was very clean and staff was helpful, will definitely book again"
Frequently Asked Questions
How much does a Greenwood vacation package cost?
Offering great value package deals from CA $943 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.