Diamond Vacation Packages
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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 $1,155, price is now CA $766 per person
CA $766
per person
Jun 8 - Jun 10
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (3,495 reviews)
Everything was perfect. The staff are really friendly and helpful. Love it!!! Definitely I'll come back
Reviewed on Apr 1, 2026
Kinzie Hotel
Downtown Chicago
Price was CA $1,313, price is now CA $974 per person
CA $974
per person
May 5 - May 11
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (2,091 reviews)
The staff was really great and the room was fine, nothing exceptional but nothing bad. The walls were thin and we when our neighbors pulled up their shades it was so loud it woke us up. We got a call at 7a with nobody on the other end, that also woke us up. haha
Reviewed on Mar 29, 2026
Diamond Hotel Deals
aruba- la cabana beach resort and casino
Diamond IL
Wingate by Wyndham - Joliet
101 McDonald Avenue Joliet IL
Fully refundableReserve now, pay when you stay
The price is CA $118 per night from Apr 16 to Apr 17
CA $118
CA $137 total
Apr 16 - Apr 17
includes taxes & fees
8.4/10 Very Good! (1,001 reviews)
We had two rooms. I had asked for adjoining rooms, but they had one of the adjoining rooms rented out, which did not make sense to me. If you only have one set of adjoining rooms you should not rent that room out unless it’s the last room which shifts I think you should have your employee shift change ...
Reviewed on Apr 2, 2026
La Quinta Inn & Suites by Wyndham Shorewood
19715 NE Frontage Rd Joliet IL
Fully refundableReserve now, pay when you stay
The price is CA $145 per night from Apr 19 to Apr 20
CA $145
CA $169 total
Apr 19 - Apr 20
includes taxes & fees
9.2/10 Wonderful! (941 reviews)
Very clean
Reviewed on Mar 23, 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.
