
Rutland Vacation Packages
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Top Rutland Vacation Deals
Price found within the past 48 hours. Click for updated prices.

La Banque Hotel
Price was CA $1,112, price is now CA $835 per person
CA $835
per person
May 28 - May 31
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (473 reviews)
Room was amazing and beautiful and comfortable
Only issue was when we arrived they had a plumbing issue and the whole place smelled horrific like a sewer. We didn’t go eat at the restaurant because the smell made us nauseous
Reviewed on Mar 1, 2026

Warwick Allerton - Chicago
Downtown Chicago
Price was CA $1,520, price is now CA $1,126 per person
CA $1,126
per person
Jun 4 - Jun 7
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.6/10 Excellent! (3,032 reviews)
Warwick Allerton is my favorite place to stay when visiting Chicago! Staying in the Gold Coast means walking distance from the restaurants, stores and other Chicago touristy things. Super close to Nordstrom, Tiffany, Ralph Lauren etc. 5 minute walk to Steak 48 for dinner & about a 15 minute walk to the Navy Pier! A Walgreens is also close by for any last minute needs or touristy things like magnets and keychains. This hotel was also very accommodating, clean and had super kind staff. Parking is simple.. either use valet at the hotel or the hotel next door’s parking garage!
Reviewed on Apr 7, 2026

Hotel Riu Plaza Chicago
Downtown Chicago
Price was CA $1,539, price is now CA $1,146 per person
CA $1,146
per person
Jul 1 - Jul 4
found 1 day ago
Roundtrip flight included
Québec (YQB) to Chicago (ORD)
9.4/10 Exceptional! (3,688 reviews)
Breakfast was very good. Enjoyed our room and how everything was clean. There was no microwave so don’t try to bring food if you need to reheat it. Fridge was also not strong to freeze my ice cream so be aware. All the staff were kind and helpful. Rooftop was beautiful but the glass floor was out of service. The hotel was close to Michigan Ave so heading to stores was a breeze. Overall, had an amazing time with my partner and would recommend reserving a room at this establishment.
Reviewed on Apr 10, 2026

Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Price was CA $2,535, price is now CA $1,897 per person
CA $1,897
per person
May 15 - May 18
found 22 hours ago
Roundtrip non-stop flight included
Québec (YQB) to Chicago (ORD)
9.4/10 Exceptional! (2,427 reviews)
Great place to stay
Reviewed on Apr 7, 2026

Level Chicago Fulton Market
Downtown Chicago
Price was CA $2,461, price is now CA $1,861 per person
CA $1,861
per person
May 14 - May 17
found 22 hours ago
Roundtrip non-stop flight included
Québec (YQB) to Chicago (ORD)
9.2/10 Wonderful! (436 reviews)
Great service, loved this place.
Reviewed on Apr 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 $173 per night from Apr 19 to Apr 20
CA $173
CA $200 total
Apr 19 - Apr 20
includes taxes & fees
9.4/10 Exceptional! (3,620 reviews)
It was an excellent location, great staff, nice pool area and restaurant/bar. We will definitely be back.
Reviewed on Apr 9, 2026

Best Western Plus InnTowner Madison
2424 University Avenue Madison WI
Fully refundableReserve now, pay when you stay
The price is CA $193 per night from Apr 19 to Apr 20
CA $193
CA $223 total
Apr 19 - Apr 20
includes taxes & fees
9.2/10 Wonderful! (1,005 reviews)
Very nice breakfast and room very clean.
Reviewed on Apr 8, 2026

DoubleTree by Hilton Madison East
4402 E Washington Ave Madison WI
Fully refundableReserve now, pay when you stay
The price is CA $151 per night from May 3 to May 4
CA $151
CA $175 total
May 3 - May 4
includes taxes & fees
9.4/10 Exceptional! (1,002 reviews)
friendly staff, good upkeep, comfortable rooms
Reviewed on Apr 8, 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.







