Diamond Holidays from AU$1,156
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The Latest Diamond Holiday Deals
Price found within the past 48 hours. Click for updated prices.
theWit Chicago, a Hilton Hotel
Downtown Chicago
Price was AU$1,671, price is now AU$1,156 per person
AU$1,156
per person
12 Jan - 19 Jan
found 1 day ago
Return direct flight included
Mexico City (MEX) to Chicago (ORD)
9/10 Wonderful! (1,001 reviews)
My family and I stayed at The Wit for Thanksgiving and were extremely pleased with the amenities and professionalism of the staff.
Reviewed on 8 Dec 2025
Trump International Hotel & Tower Chicago
Downtown Chicago
Save 100% on your flight
Price was AU$3,270, price is now AU$2,044 per person
AU$2,044
per person
12 Jan - 19 Jan
found 1 day ago
Return direct flight included
Mexico City (MEX) to Chicago (ORD)
9.4/10 Exceptional! (1,773 reviews)
All of the above. Staff was wonderful. Room was clean and comfortable. On site amenities were great and food was superb. Best espresso martini I’ve ever tasted.
Reviewed on 11 Dec 2025
Hilton Grand Vacations Club Chicago Magnificent Mile
Downtown Chicago
Save 100% on your flight
Price was AU$1,908, price is now AU$1,239 per person
AU$1,239
per person
12 Jan - 19 Jan
found 1 day ago
Return direct flight included
Mexico City (MEX) to Chicago (ORD)
9.2/10 Wonderful! (317 reviews)
The room was beautiful and clean and a good city view of the city
Reviewed on 26 Nov 2025
Hotel Riu Plaza Chicago
Downtown Chicago
Price was AU$1,745, price is now AU$1,185 per person
AU$1,185
per person
12 Jan - 19 Jan
found 1 day ago
Return direct flight included
Mexico City (MEX) to Chicago (ORD)
9.4/10 Exceptional! (2,790 reviews)
Love the staff here. Great stay all the way around!
I was in 2409. Quiet room.
Reviewed on 11 Dec 2025
Pendry Chicago
Downtown Chicago
Price was AU$1,909, price is now AU$1,319 per person
AU$1,319
per person
12 Jan - 19 Jan
found 1 day ago
Return direct flight included
Mexico City (MEX) to Chicago (ORD)
9.4/10 Exceptional! (1,130 reviews)
Concierge not helpful and neither is was the door man,
Neither would get me a cab, they said to just stand outside
Reviewed on 4 Dec 2025
Diamond Holiday
Diamond Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Population | 2,500 |
Max Temp Winter | -1.11ºC |
Max Temp Summer | 27ºC |
Top Sights | William G. Stratton State Park, Heidecke Lake State Fish and Wildlife Area and Gebhard Woods State Park |
Our pick of the best 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 AU$136 per night from 14 Dec to 15 Dec
AU$136
14 Dec - 15 Dec
includes taxes & fees
8.2/10 Very Good! (1,007 reviews)
Nice and clean breakfast was good
Reviewed on 8 Dec 2025
Super 8 by Wyndham Joliet
1806 McDonough St Joliet IL
Fully refundableReserve now, pay when you stay
The price is AU$140 per night from 18 Dec to 19 Dec
AU$140
18 Dec - 19 Dec
includes taxes & fees
8/10 Very Good! (726 reviews)
The only issue was the condition of the bathroom ceiling: water damage has not been repaired.
Reviewed on 21 Nov 2025
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.