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


Hotel Riu Plaza Chicago
Downtown Chicago
Price was CA $1,468, price is now CA $985 per person
CA $985
per person
Apr 8 - Apr 13
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (2,790 reviews)
Housekeeper left hair shedding in room but overall amazing hotel and great staff
Reviewed on Feb 12, 2026

Waldorf Astoria Chicago
Downtown Chicago
Price was CA $2,409, price is now CA $1,720 per person
CA $1,720
per person
Apr 2 - Apr 6
found 20 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,000 reviews)
Completely loved our stay. Probably the best hotel in all Chicago. Amenities are great and the staff are even better.
Reviewed on Jan 26, 2026

La Banque Hotel
Price was CA $1,157, price is now CA $884 per person
CA $884
per person
Apr 3 - Apr 6
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Chicago (ORD)
9.4/10 Exceptional! (447 reviews)
Courteous Staff, clean, one of the most beautiful and interesting hotel. The history is amazing. The restaurant is delicious and the community is outstanding. Plan to return in the spring.
Reviewed on Jan 26, 2026

Stay One Chicago
Downtown Chicago
Price was CA $3,061, price is now CA $2,385 per person
CA $2,385
per person
Apr 28 - May 4
just found
Roundtrip flight included
Toronto (YYZ) to Chicago (ORD)
No reviews
The property was great, the room was awesome! The "Stay One Chicago" is really just a name on paper, and maybe one employee who is physically at the property. I am pretty sure that he wasn't even directly employed by the "hotel".
So in a nutshell, the organization has not worked out any kind of structure for checking in other than the guy that told us to download the Door, OR the Latch app. He said that the app is very difficult to get logged into.
Long story made short, we wasted the 1st 2 hours in the hotel trying to get the app (both my wife and I).
The app never worked, and we finally got physical key cards from the guy working for the building.
There was one small piece of paper with scan codes for restaurants, but zero property maps, rules, room cleaning, and nothing explaining how to get to, or use any of the amenities. It was the worst 1st 3 hours of a vacation that we have experienced.
I still gave it a 4-star because the local people were so nice and helpful, even though helping us wasn't part of their job. The valet guys were the best, super nice, and helpful.
Reviewed on Feb 10, 2026
Diamond Hotel Deals

aruba- la cabana beach resort and casino
Diamond IL

Red Roof Inn Chicago - Joliet
1750 Mcdonough St Joliet IL
Fully refundableReserve now, pay when you stay
6.6/10 (1,007 reviews)
Good
Reviewed on Feb 8, 2026

Wingate by Wyndham - Joliet
101 McDonald Avenue Joliet IL
Fully refundableReserve now, pay when you stay
The price is CA $112 per night from Feb 20 to Feb 21
CA $112
CA $130 total
Feb 20 - Feb 21
includes taxes & fees
8.4/10 Very Good! (1,002 reviews)
Nice staff Clean and well kept Bed was not real comfortable
Reviewed on Feb 9, 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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