Rutland Vacation Packages
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Top Rutland Vacation Deals
Price found within the past 48 hours. Click for updated prices.
The Allegro Royal Sonesta Hotel Chicago Loop
Downtown Chicago
Price was CA $663, price is now CA $451 per person
CA $451
per person
Nov 14 - Nov 16
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
9/10 Wonderful! (1,992 reviews)
Our experience here was fantastic. We visited in August and the weather was superb. Everything was centralized. From shopping to dining and peace and quiet were abound. Just magnificent stay. The staff was friendly and informative. Thank you.
Reviewed on Sep. 4, 2025
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was CA $1,875, price is now CA $1,122 per person
CA $1,122
per person
Oct 28 - Oct 31
found 1 day ago
Roundtrip non-stop flight included
Québec (YQB) to Chicago (ORD)
9.4/10 Exceptional! (1,714 reviews)
Professional service
Reviewed on Sep. 4, 2025
Arlo Chicago
Downtown Chicago
Price was CA $1,208, price is now CA $780 per person
CA $780
per person
Oct 28 - Oct 31
found 1 day ago
Roundtrip non-stop flight included
Québec (YQB) to Chicago (ORD)
9.2/10 Wonderful! (1,844 reviews)
Good spot, convenient to everything. Staff was helpful. Very urban so some issues with people begging for money etc.
Reviewed on Sep. 3, 2025
The Langham, Chicago
Downtown Chicago
Price was CA $2,322, price is now CA $1,512 per person
CA $1,512
per person
Nov 6 - Nov 9
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.8/10 Exceptional! (1,005 reviews)
Phenomenal service. Exactly how a 5* hotel should be run. Everything was perfect.
Reviewed on Aug. 12, 2025
Hilton Orrington / Evanston
Downtown Evanston
Price was CA $1,694, price is now CA $1,118 per person
CA $1,118
per person
Oct 17 - Oct 20
found 1 day ago
Roundtrip flight included
Québec (YQB) to Chicago (ORD)
7.6/10 Good! (1,003 reviews)
Hotel is beautiful and all of the staff is amazing. Only annoying thing is no free parking. Other than that amazing stay and happy we chose this hotel!
Reviewed on Aug. 18, 2025
Rutland Hotel Deals
The Madison Concourse Hotel and Governor's Club
1 W Dayton St, Madison, WI
Fully refundableReserve now, pay when you stay
The price is CA $173 per night from Sep 14 to Sep 15
CA $173
CA $200 total
Sep 14 - Sep 15
includes taxes & fees
Baymont by Wyndham Madison West/Middleton WI West
8102 Excelsior Dr, Madison, WI
Fully refundableReserve now, pay when you stay
The price is CA $87 per night from Sep 12 to Sep 13
CA $87
CA $100 total
Sep 12 - Sep 13
includes taxes & fees
AmericInn by Wyndham Madison West
516 Grand Canyon Dr, Madison, WI
Fully refundableReserve now, pay when you stay
The price is CA $102 per night from Sep 7 to Sep 8
CA $102
CA $118 total
Sep 7 - Sep 8
includes taxes & fees
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.
