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.
Level Chicago – Old Town
Downtown Chicago
Price was CA $1,999, price is now CA $1,337 per person
CA $1,337
per person
Sep 2 - Sep 6
found 24 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (489 reviews)
We love where this is property is located and all the amenities. The pool was closed the 2 days we were there which was disappointing but the weather didn't really cooperate either. The staff is very accomodating and attentive.
Reviewed on Jun 11, 2026
Level Chicago - River North
Downtown Chicago
Price was CA $1,887, price is now CA $1,262 per person
CA $1,262
per person
Aug 27 - Aug 31
found 5 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,019 reviews)
I loved how simple and easy it was to access everything.
Reviewed on Jun 16, 2026
Great Wolf Lodge Illinois
Price was CA $2,088, price is now CA $1,422 per person
CA $1,422
per person
Aug 2 - Aug 6
found 21 hours ago
Roundtrip non-stop flight included
Edmonton (YEG) to Chicago (ORD)
8.6/10 Excellent! (1,003 reviews)
First time staying at a Great Wolf Lodge. Was a wonderful time. Onsite food selection was great and easy to order ahead of time if wanted. Waterpark was as expected. Many other activities available to keep the kids entertained was a nice touch. Arcade is expensive and having to pay to park were my only disappointments. Otherwise highly recommend!
Reviewed on Jun 18, 2026
Pendry Chicago
Downtown Chicago
Price was CA $1,839, price is now CA $1,302 per person
CA $1,302
per person
Sep 3 - Sep 6
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Chicago (ORD)
9.2/10 Wonderful! (1,127 reviews)
We were celebrating an anniversary. We had a greay stay. It was close to all the shopping and restaurants, staff were great and helpful. We will be back again!
Reviewed on Jun 18, 2026
Greenwood Hotel Deals
Harbor Shores on Lake Geneva
300 Wrigley Dr Lake Geneva WI
Fully refundableReserve now, pay when you stay
The price is CA $252 per night from Jun 30 to Jul 1
CA $252
CA $318 total
Jun 30 - Jul 1
includes taxes & fees
9.2/10 Wonderful! (1,344 reviews)
"The staff was wonderful, very helpful very professional. The rooms were clean. The pool was very nice."
Reviewed on Jun 18, 2026
Abbey Resort and Avani Spa
269 Fontana Boulevard Fontana WI
Fully refundableReserve now, pay when you stay
The price is CA $215 per night from Jun 28 to Jun 29
CA $215
CA $275 total
Jun 28 - Jun 29
includes taxes & fees
8.6/10 Excellent! (1,910 reviews)
"Be prepared for a resort fee upon arrival of $180 even after you paid in full and booked online Rooms were outdated and hallways smelled funky Pool was fun for the kids- they had it all to themselves."
Reviewed on Jun 18, 2026
Timber Ridge Lodge and Waterpark
7020 Grand Geneva Way Lake Geneva WI
Fully refundableReserve now, pay when you stay
The price is CA $344 per night from Jul 7 to Jul 8
CA $344
CA $439 total
Jul 7 - Jul 8
includes taxes & fees
8.6/10 Excellent! (3,290 reviews)
"Immaculate property! Super fun for both the kiddos and adults!! Highly recommended!"
Reviewed on Jun 18, 2026
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.
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
