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

DoubleTree by Hilton Chicago - Alsip
Price was CA $1,236, price is now CA $948 per person
CA $948
per person
Jul 22 - Jul 26
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Chicago (ORD)
8.6/10 Excellent! (1,061 reviews)
The shuttle driver was VERY FRIENDLY! The hotel staff was also VERY FRIENDLY!
Reviewed on Jun 1, 2026

Swissotel - Chicago
Downtown Chicago
Price was CA $2,074, price is now CA $1,510 per person
CA $1,510
per person
Aug 24 - Aug 28
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Chicago (ORD)
9/10 Wonderful! (3,352 reviews)
Location is closer to
Navy pier. Not a lot of nice food options around.
Reviewed on Jun 3, 2026

The Emily Hotel
Downtown Chicago
Price was CA $2,167, price is now CA $1,609 per person
CA $1,609
per person
Aug 24 - Aug 28
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Chicago (ORD)
9.2/10 Wonderful! (1,320 reviews)
Convenient location and easy building to deal with. Parking was a little expensive.
Reviewed on Jun 2, 2026

Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Price was CA $2,216, price is now CA $1,664 per person
CA $1,664
per person
Aug 24 - Aug 28
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Chicago (ORD)
9.4/10 Exceptional! (2,511 reviews)
The room itself was excellent — 9/10. The view was amazing, the bed was very comfortable, and the room was spacious and well-designed.
However, for the price and for a hotel that markets itself as a 4-star property, many amenities were disappointing.
First, the coffee machine in the room was very low quality, more comparable to what you would typically find at a Comfort Inn. There were also no bathrobes or hotel slippers provided, which I would expect at this price point.
The lobby was surprisingly small and not particularly inviting. It felt dark and lacked the atmosphere you would expect from a higher-end hotel.
The hotel only has one restaurant, and unfortunately the food quality was below average.
Another disappointment was the rooftop. The hotel advertises rooftop access, but the rooftop is not actually owned or operated by the hotel. During our stay, it was closed for a private event, making it unavailable to guests.
To make matters worse, on the day we checked out, the elevator was out of service, so we had to carry our luggage down the stairs ourselves.
Overall, I would rate the room 9/10, but the amenities, dining, and overall hotel experience only 2/10.
Because the room and view were truly outstanding, I would give the hotel an overall rating of 7/10. Without the exceptional room and view, my rating would have been significantly lower.
Reviewed on Jun 2, 2026

Trump International Hotel & Tower Chicago
Downtown Chicago
Price was CA $2,875, price is now CA $2,189 per person
CA $2,189
per person
Aug 24 - Aug 28
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Chicago (ORD)
9.6/10 Exceptional! (1,886 reviews)
Great room, professional staff, no complaints.
Reviewed on May 31, 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 $164 per night from Jun 14 to Jun 15
CA $164
CA $190 total
Jun 14 - Jun 15
includes taxes & fees
9.4/10 Exceptional! (3,833 reviews)
"Ok so picked this because of the proximity too the capital. Was a bit nervous when we got there as it’s an older hotel well maintained but older. Found about the governors club level and. Hell yea. Zach the bartender a wealth of knowledge think of him as your culinary shamen. View of the capital ..."
Reviewed on Jun 4, 2026

Baymont by Wyndham Madison West/Middleton WI West
8102 Excelsior Dr Madison WI
Fully refundableReserve now, pay when you stay
The price is CA $101 per night from Jun 18 to Jun 19
CA $101
CA $117 total
Jun 18 - Jun 19
includes taxes & fees
8/10 Very Good! (1,287 reviews)
"Good hotel"
Reviewed on Jun 3, 2026

DoubleTree by Hilton Madison East
4402 E Washington Ave Madison WI
Fully refundableReserve now, pay when you stay
The price is CA $147 per night from Jul 2 to Jul 3
CA $147
CA $170 total
Jul 2 - Jul 3
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.







