Chicago Luxury Holidays
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Top flight + Luxury hotel deals in Chicago
Price found within the past 48 hours. Click for updated prices.
Silversmith Hotel Chicago Downtown
Downtown Chicago
per person
15 Aug - 18 Aug
found 16 hours ago
Return direct flight included
Auckland (AKL) to Chicago (ORD)
9.4/10 Exceptional! (1,840 reviews)
Absolutely loved the staff! The hotel was clean & quiet. I will definitely recommend it and I’ll be returning.
Reviewed on 4 Jul. 2025
LondonHouse Chicago, Curio Collection by Hilton
Downtown Chicago
per person
15 Aug - 18 Aug
found 16 hours ago
Return direct flight included
Auckland (AKL) to Chicago (ORD)
9.4/10 Exceptional! (3,353 reviews)
We liked the view and the location. With our second visit here the front desk check-in gentleman was not as warm and friendly as other staff have been. We always have a great experience with the valet (they are helpful in finding transportation) and the luggage handlers were very accommodating. Our room was cleaned very well after the very first day.
Reviewed on 3 Jul. 2025
5* Luxury holidays in Chicago
Price found within the past 48 hours. Click for updated prices.
4 Night Luxury holidays in Chicago
Price found within the past 48 hours. Click for updated prices.
Silversmith Hotel Chicago Downtown
Downtown Chicago
per person
15 Aug - 18 Aug
found 16 hours ago
Return direct flight included
Auckland (AKL) to Chicago (ORD)
9.4/10 Exceptional! (1,840 reviews)
Absolutely loved the staff! The hotel was clean & quiet. I will definitely recommend it and I’ll be returning.
Reviewed on 4 Jul. 2025
LondonHouse Chicago, Curio Collection by Hilton
Downtown Chicago
per person
15 Aug - 18 Aug
found 16 hours ago
Return direct flight included
Auckland (AKL) to Chicago (ORD)
9.4/10 Exceptional! (3,353 reviews)
We liked the view and the location. With our second visit here the front desk check-in gentleman was not as warm and friendly as other staff have been. We always have a great experience with the valet (they are helpful in finding transportation) and the luggage handlers were very accommodating. Our room was cleaned very well after the very first day.
Reviewed on 3 Jul. 2025
Top Luxury Chicago Hotels
Trump International Hotel & Tower Chicago
401 N Wabash Ave, Chicago, IL
Stay at this 5-star luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and breakfast (surcharge). Our guests praise the helpful staff and the clean ...
9.2/10 Wonderful! (1,627 reviews)
"A1"
Reviewed on 4 Jul. 2025
The Langham, Chicago
330 North Wabash Avenue, Chicago, IL
Stay at this 5-star luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and breakfast (surcharge). Our guests praise the helpful staff and the clean ...
9.6/10 Exceptional! (1,003 reviews)
"The Langham is quite possibly the best hotel I've ever stayed at. The staff were absolutely amazing and the hotel itself was so clean. The hallways smelled so good too which I know is a weird observation but the wood they used for the floors and doors were so aromatic and it was something my party ..."
Reviewed on 30 Jun. 2025
The Peninsula Chicago
108 East Superior Street, Chicago, IL
Stay at this 5-star luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and 2 restaurants. Our guests praise the helpful staff and the property condition ...
9.8/10 Exceptional! (1,001 reviews)
"Always a great stay!"
Reviewed on 3 Jul. 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.