Chicago Luxury Holidays
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- Better togetherSave up to HK$1,282 when you book a flight and hotel together*
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Price found within the past 48 hours. Click for updated prices.
LondonHouse Chicago, Curio Collection by Hilton
Downtown Chicago
Price was HK$5,492, price is now HK$4,171 per person
HK$4,171
per person
7 Mar - 11 Mar
found 4 hours ago
Return flight included
Toronto (YYZ) to Chicago (ORD)
9.4/10 Exceptional! (3,392 reviews)
Beautiful hotel, stunning views, excellent location, amazing staff, and phenomenal rooftop!
Reviewed on 26 Jan 2026
Trump International Hotel & Tower Chicago
Downtown Chicago
Save 100% on your flight
Price was HK$10,778, price is now HK$7,154 per person
HK$7,154
per person
7 Mar - 11 Mar
found 4 hours ago
Return flight included
Toronto (YYZ) to Chicago (ORD)
9.4/10 Exceptional! (1,773 reviews)
The room was boring thought it would be cleaner updated for the price best part was the view
Reviewed on 24 Jan 2026
Fairmont Chicago at Millennium Park
Downtown Chicago
Price was HK$5,634, price is now HK$4,263 per person
HK$4,263
per person
7 Mar - 11 Mar
found 4 hours ago
Return flight included
Toronto (YYZ) to Chicago (ORD)
8.6/10 Excellent! (2,008 reviews)
The room was clean. The staff was very nice. They even held on to our stuff on our last day after check out so we could explore the town luggage free!
Reviewed on 23 Jan 2026
Virgin Hotels Chicago
Downtown Chicago
Price was HK$5,863, price is now HK$4,619 per person
HK$4,619
per person
7 Mar - 11 Mar
found 4 hours ago
Return flight included
Toronto (YYZ) to Chicago (ORD)
9.2/10 Wonderful! (1,404 reviews)
Staff was super friendly and rooms were clean. Definitely will come back
Reviewed on 20 Jan 2026
Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago
Downtown Chicago
Save 100% on your flight
Price was HK$10,778, price is now HK$7,154 per person
HK$7,154
per person
7 Mar - 11 Mar
found 4 hours ago
Return flight included
Toronto (YYZ) to Chicago (ORD)
9.4/10 Exceptional! (1,773 reviews)
The room was boring thought it would be cleaner updated for the price best part was the view
Reviewed on 24 Jan 2026
Price found within the past 48 hours. Click for updated prices.
LondonHouse Chicago, Curio Collection by Hilton
Downtown Chicago
Price was HK$5,492, price is now HK$4,171 per person
HK$4,171
per person
7 Mar - 11 Mar
found 4 hours ago
Return flight included
Toronto (YYZ) to Chicago (ORD)
9.4/10 Exceptional! (3,392 reviews)
Beautiful hotel, stunning views, excellent location, amazing staff, and phenomenal rooftop!
Reviewed on 26 Jan 2026
Trump International Hotel & Tower Chicago
Downtown Chicago
Save 100% on your flight
Price was HK$10,778, price is now HK$7,154 per person
HK$7,154
per person
7 Mar - 11 Mar
found 4 hours ago
Return flight included
Toronto (YYZ) to Chicago (ORD)
9.4/10 Exceptional! (1,773 reviews)
The room was boring thought it would be cleaner updated for the price best part was the view
Reviewed on 24 Jan 2026
Fairmont Chicago at Millennium Park
Downtown Chicago
Price was HK$5,634, price is now HK$4,263 per person
HK$4,263
per person
7 Mar - 11 Mar
found 4 hours ago
Return flight included
Toronto (YYZ) to Chicago (ORD)
8.6/10 Excellent! (2,008 reviews)
The room was clean. The staff was very nice. They even held on to our stuff on our last day after check out so we could explore the town luggage free!
Reviewed on 23 Jan 2026
Trump International Hotel & Tower Chicago
401 N Wabash Ave Chicago IL
Stay at this luxury hotel in Chicago. Enjoy free Wi-Fi, a full-service spa and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms ...
9.4/10 Exceptional! (1,828 reviews)
Clean room, very friendly staff. Room had a fully equipped kitchen
Reviewed on 25 Jan 2026
The Langham, Chicago
330 North Wabash Avenue Chicago IL
Stay at this luxury hotel in Chicago. Enjoy free Wi-Fi, a full-service spa and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms ...
9.6/10 Exceptional! (1,002 reviews)
Great. Rooms were nice
Reviewed on 18 Jan 2026
The Peninsula Chicago
108 East Superior Street Chicago IL
Stay at this luxury hotel in Chicago. Enjoy free Wi-Fi, a full-service spa and 2 restaurants. Our guests praise the helpful staff and the property condition ...
9.6/10 Exceptional! (1,011 reviews)
Amazing staff. Sooooo clean. Top service
Reviewed on 25 Jan 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
