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 23 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 3 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
Hotel Felix River North/Magnificent Mile
Downtown Chicago
Price was CA $1,377, price is now CA $931 per person
CA $931
per person
Aug 24 - Aug 28
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.2/10 Very Good! (2,779 reviews)
I feel very glad my husband and I chose Felix Hotel for our stay in Chicago during early June. The location was great for our purposes, there were plenty of food options near by and the complementary fruit and coffee/tea in the morning was very helpful to get our day started. We felt specially welcomed by Crystal at the front desk. Her friendly personality will be forever remembered as one of the highlights of a wonderful trip.
Reviewed on Jun 18, 2026
The Emily Hotel
Downtown Chicago
Price was CA $1,705, price is now CA $1,209 per person
CA $1,209
per person
Aug 24 - Aug 28
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,327 reviews)
The staff was great. The room was nice but I would have preferred more towels. The remote in our room wasn’t working fully as well as the steamer in the room. Otherwise, it is a good hotel but would not recommend for families.
Reviewed on Jun 15, 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 21 to Jun 22
CA $252
CA $318 total
Jun 21 - Jun 22
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 $274 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 $343 per night from Jul 7 to Jul 8
CA $343
CA $438 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.
