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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.
Arlo Chicago
Downtown Chicago
Save 100% on your flight
per person
Jul. 19 - Jul. 22
found 23 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.8/10 Excellent! (1,114 reviews)
The hotel was great and guest services were awesome. Noted my late arrival due to delayed flight. The hotel is right on Michigan and the bus stops right in front. The rooms are comfortable and well designed.
However, I wouldn't recommend eating at ALK. What a rip. for $6, I got about 10 spears of grilled asparagus! I know food prices and labor have gone up but this is ridiculous.
Reviewed on Jun. 8, 2024
Virgin Hotels Chicago
Downtown Chicago
Save 100% on your flight
per person
Jul. 19 - Jul. 22
found 23 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,006 reviews)
Great location. A bit weathered and needs an update though. Front desk staff were fantastic. Didn’t have the same level of service from the people working on the rooftop patio - we felt like we were bothering them unfortunately.
Reviewed on Jun. 11, 2024
Level Chicago – Old Town
Downtown Chicago
Save 100% on your flight
per person
Jul. 19 - Jul. 22
found 23 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.8/10 Excellent! (210 reviews)
Great room - fabulous fitness center. Easy access to grocery stores to stock fridge. Room is furnished with all amenities.
Reviewed on Jun. 9, 2024
Greenwood Hotel Deals
The Ridge Hotel
W4240 WI-50, Lake Geneva, WI
Fully refundableReserve now, pay when you stay
The price is CA $186 per night from Jun. 19 to Jun. 20
CA $186
CA $240 total
includes taxes & fees
Jun 19 - Jun 20
9/10 Wonderful! (1,003 reviews)
Best of the Best in Lake Geneva, WI
"I recently stayed at The Ridge Hotel and once again had a wonderful experience. From the moment I arrived, the front desk staff made me feel welcome and at home. The check-in process is always smooth and efficient, and it’s always a pleasure to be greeted by name (I stay here often). Their genuine ..."
Reviewed on Jun. 12, 2024
Timber Ridge Lodge and Waterpark
7020 Grand Geneva Way, Lake Geneva, WI
Fully refundableReserve now, pay when you stay
The price is CA $251 per night from Jul. 1 to Jul. 2
CA $251
CA $324 total
includes taxes & fees
Jul 1 - Jul 2
8.6/10 Excellent! (2,334 reviews)
"The property is more suitable for a Summer visit, the combination of outdoor pools and hot tubs make for a more enjoyable experience. We were here three times last winter and spring and had an OK time. Definitely more to do in the Summer."
Reviewed on Jun. 13, 2024
Harbor Shores on Lake Geneva
300 Wrigley Dr, Lake Geneva, WI
Fully refundableReserve now, pay when you stay
The price is CA $232 per night from Jun. 17 to Jun. 18
CA $232
CA $292 total
includes taxes & fees
Jun 17 - Jun 18
9/10 Wonderful! (1,191 reviews)
"Great property right on the lake. Balcony with lake view with easy parking, walk right to the lake and tons of dining and bars nearby. We loved our stay here!"
Reviewed on Jun. 13, 2024
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.