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.
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Price was CA $2,024, price is now CA $1,336 per person
CA $1,336
per person
Jul 3 - Jul 6
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (2,458 reviews)
No restaurant or available food after 10pm.
Reviewed on Apr 21, 2026
Swissotel - Chicago
Downtown Chicago
Price was CA $2,872, price is now CA $1,722 per person
CA $1,722
per person
Jun 4 - Jun 8
found 21 hours ago
Roundtrip non-stop flight included
Montreal (YMQ) to Chicago (ORD)
9/10 Wonderful! (3,280 reviews)
Really good spot and location. Staff was super helpful and nice.
Reviewed on Apr 22, 2026
Level Chicago Fulton Market
Downtown Chicago
Price was CA $2,237, price is now CA $1,387 per person
CA $1,387
per person
Jun 9 - Jun 14
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (455 reviews)
Great staff, full kitchen and living room, good location, friendly people, safe. I would stay here again.
Reviewed on Apr 23, 2026
Level Chicago – Old Town
Downtown Chicago
Price was CA $2,254, price is now CA $1,484 per person
CA $1,484
per person
Jun 19 - Jun 23
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Chicago (ORD)
9/10 Wonderful! (463 reviews)
Eric and the rest of the staff was very helpful from check in to check out! The place is very lovely!!!!! Would come back again soon!
Reviewed on Apr 23, 2026
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was CA $4,651, price is now CA $3,155 per person
CA $3,155
per person
Jun 5 - Jun 12
found 2 hours ago
Roundtrip non-stop flight included
Montreal (YMQ) to Chicago (ORD)
9.4/10 Exceptional! (1,848 reviews)
Great staff, facilities, esp the fitness & spa
Reviewed on Apr 23, 2026
Greenwood Hotel Deals
Abbey Resort and Avani Spa
269 Fontana Boulevard Fontana WI
Fully refundableReserve now, pay when you stay
The price is CA $125 per night from Apr 27 to Apr 28
CA $125
CA $174 total
Apr 27 - Apr 28
includes taxes & fees
8.6/10 Excellent! (1,852 reviews)
The pool had a very strong chlorine smell. So bad we didn’t get to enjoy it for a long time since it hurt our eyes.
Reviewed on Apr 23, 2026
The Cove Of Lake Geneva
111 Center St Lake Geneva WI
9/10 Wonderful! (1,455 reviews)
Very welcoming atmosphere, the room was comfortable, front desk staff were very friendly.
Reviewed on Apr 21, 2026
Timber Ridge Lodge and Waterpark
7020 Grand Geneva Way Lake Geneva WI
Fully refundableReserve now, pay when you stay
The price is CA $198 per night from May 12 to May 13
CA $198
CA $274 total
May 12 - May 13
includes taxes & fees
8.6/10 Excellent! (3,234 reviews)
The establishment was nice and the room was nice but some of the staff were not very helpful and I felt they were being unexplainable rude to my family and guests making up rules for us specially.
Reviewed on Apr 21, 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.
