Diamond Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
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Top Diamond Vacation Deals
Price found within the past 48 hours. Click for updated prices.
JW Marriott Chicago
Downtown Chicago
Price was CA $1,405, price is now CA $950 per person
CA $950
per person
Aug 6 - Aug 9
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,000 reviews)
Good location close to many attractions like sears tower, the bean, river boat tours... nuce rooms ... public parking 1/2 block from premises .. just an overal great property with excellent convenience for tourists type activities
Reviewed on May 3, 2026
Level Chicago Fulton Market
Downtown Chicago
Price was CA $2,919, price is now CA $1,699 per person
CA $1,699
per person
Aug 2 - Aug 8
found 23 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (480 reviews)
Room was not cleaned/ towels weren't replaced for the duration of our 3 night stay which I found rather peculiar. They also only provided 1 key for our room. I had believed it was common practice to provide 2. Other than that, the room was clean when we arrived, the bedding was comfortable, and the gym was lovely.
Reviewed on May 22, 2026
Level Chicago – Old Town
Downtown Chicago
Price was CA $2,741, price is now CA $1,702 per person
CA $1,702
per person
Aug 2 - Aug 8
found 23 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (478 reviews)
Minimum effort. Pleasant stay. Very quiet. Enjoyed the 8th floor common area. Service at the front desk was really great. Convenient coffee shop / bakery in the lobby.
Reviewed on May 18, 2026
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Price was CA $1,499, price is now CA $1,051 per person
CA $1,051
per person
Aug 6 - Aug 9
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (2,507 reviews)
The view from the corner room on the 7th floor of Pier 3 was absolutely superb—both the nightscape and the sunset were truly exceptional. I will definitely visit again.
Reviewed on May 26, 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
The price is CA $76 per night from May 27 to May 28
CA $76
CA $88 total
May 27 - May 28
includes taxes & fees
6.8/10 (1,004 reviews)
"Not a very clean room, stained sheets, just a dirty and dingy place"
Reviewed on May 17, 2026
Harrah's Joliet Casino & Hotel - A Caesars Rewards Destination
151 N Joliet St Joliet IL
The price is CA $88 per night from Jun 24 to Jun 25
CA $88
CA $127 total
Jun 24 - Jun 25
includes taxes & fees
8.4/10 Very Good! (1,005 reviews)
"room, staff, bar, parking were all good"
Reviewed on May 24, 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.
