Rutland Vacation Packages
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Top Rutland Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago
Downtown Chicago
Price was CA $1,911, price is now CA $1,281 per person
CA $1,281
per person
Jun 4 - Jun 7
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
9.4/10 Exceptional! (3,438 reviews)
Good breakfast, excellent service, unfortunately, they don't have microwave service to heat food
Reviewed on Mar 13, 2026
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Price was CA $2,394, price is now CA $1,564 per person
CA $1,564
per person
May 28 - May 31
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (2,385 reviews)
The room so clean with a beautiful view!
Reviewed on Mar 13, 2026
Level Chicago Fulton Market
Downtown Chicago
Price was CA $2,218, price is now CA $1,658 per person
CA $1,658
per person
Jun 5 - Jun 8
found 8 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (414 reviews)
This place was amazing! We loved it so much we wanted to move in. It had everything we needed and was in the perfect area. Parker at the front desk was by far the best part of our stay, she was personable and welcoming and gave us the best costumer service we’ve ever experienced while being away! We will be back.
Reviewed on Mar 8, 2026
Hyatt Place Chicago/Downtown - The Loop
Downtown Chicago
Price was CA $1,718, price is now CA $1,320 per person
CA $1,320
per person
Jun 4 - Jun 7
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
8.8/10 Excellent! (1,201 reviews)
We flew all night and were very tired when we arrived at the property. We were so grateful to be able to check in early.
Reviewed on Mar 9, 2026
Pendry Chicago
Downtown Chicago
Price was CA $1,771, price is now CA $1,366 per person
CA $1,366
per person
Jun 4 - Jun 7
found 4 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
9.4/10 Exceptional! (1,137 reviews)
Great location, clean and very nice restaurant and bar.
Reviewed on Mar 9, 2026
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 $161 per night from Mar 15 to Mar 16
CA $161
CA $186 total
Mar 15 - Mar 16
includes taxes & fees
9.4/10 Exceptional! (3,540 reviews)
The room and amenities were excellent, young man at check in could have been a bit friendlier.
Reviewed on Mar 12, 2026
Best Western Plus InnTowner Madison
2424 University Avenue Madison WI
Fully refundableReserve now, pay when you stay
The price is CA $152 per night from Mar 18 to Mar 19
CA $152
CA $176 total
Mar 18 - Mar 19
includes taxes & fees
9.2/10 Wonderful! (1,000 reviews)
The place was very clean, good breakfast and staff was polite. The beds were a bit hard, but overall the place was very nice.
Reviewed on Mar 10, 2026
Hampton Inn & Suites Madison-West
483 Commerce Dr Madison WI
Fully refundableReserve now, pay when you stay
The price is CA $99 per night from Mar 18 to Mar 19
CA $99
CA $115 total
Mar 18 - Mar 19
includes taxes & fees
9.2/10 Wonderful! (1,005 reviews)
Would definitely stay here again.
Reviewed on Mar 12, 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.
