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.
Thompson Chicago, by Hyatt
Downtown Chicago
Price was NZ$12,139, price is now NZ$11,671 per person
NZ$11,671
per person
30 Oct - 2 Nov
found 22 hours ago
Return flight included
Dunedin (DUD) to Chicago (ORD)
9/10 Wonderful! (1,187 reviews)
I loved the overall look, feel and area surrounding the hotel. It was such an easy experience from check-in to check-out. Will go back!
Reviewed on 19 Aug. 2025
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was NZ$12,877, price is now NZ$11,904 per person
NZ$11,904
per person
30 Oct - 2 Nov
found 22 hours ago
Return flight included
Dunedin (DUD) to Chicago (ORD)
9.4/10 Exceptional! (1,679 reviews)
This property is beautiful and located in a great area.
Reviewed on 19 Aug. 2025
Park Hyatt Chicago
Downtown Chicago
Price was NZ$12,953, price is now NZ$12,102 per person
NZ$12,102
per person
30 Oct - 2 Nov
found 22 hours ago
Return flight included
Dunedin (DUD) to Chicago (ORD)
9.6/10 Exceptional! (1,000 reviews)
Nothing beats a stay at the Park Hyatt when in Chicago!
Reviewed on 10 Aug. 2025
The Langham, Chicago
Downtown Chicago
Price was NZ$12,675, price is now NZ$12,181 per person
NZ$12,181
per person
30 Oct - 2 Nov
found 22 hours ago
Return flight included
Dunedin (DUD) to Chicago (ORD)
9.8/10 Exceptional! (1,004 reviews)
Phenomenal service. Exactly how a 5* hotel should be run. Everything was perfect.
Reviewed on 12 Aug. 2025
5* Luxury holidays in Chicago
Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was NZ$12,877, price is now NZ$11,904 per person
NZ$11,904
per person
30 Oct - 2 Nov
found 22 hours ago
Return flight included
Dunedin (DUD) to Chicago (ORD)
9.4/10 Exceptional! (1,679 reviews)
This property is beautiful and located in a great area.
Reviewed on 19 Aug. 2025
Park Hyatt Chicago
Downtown Chicago
Price was NZ$12,953, price is now NZ$12,102 per person
NZ$12,102
per person
30 Oct - 2 Nov
found 22 hours ago
Return flight included
Dunedin (DUD) to Chicago (ORD)
9.6/10 Exceptional! (1,000 reviews)
Nothing beats a stay at the Park Hyatt when in Chicago!
Reviewed on 10 Aug. 2025
4 Night Luxury holidays in Chicago
Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was NZ$12,877, price is now NZ$11,904 per person
NZ$11,904
per person
30 Oct - 2 Nov
found 22 hours ago
Return flight included
Dunedin (DUD) to Chicago (ORD)
9.4/10 Exceptional! (1,679 reviews)
This property is beautiful and located in a great area.
Reviewed on 19 Aug. 2025
Park Hyatt Chicago
Downtown Chicago
Price was NZ$12,953, price is now NZ$12,102 per person
NZ$12,102
per person
30 Oct - 2 Nov
found 22 hours ago
Return flight included
Dunedin (DUD) to Chicago (ORD)
9.6/10 Exceptional! (1,000 reviews)
Nothing beats a stay at the Park Hyatt when in Chicago!
Reviewed on 10 Aug. 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! (1,690 reviews)
"One of the best hotels. I will definitely stay here again."
Reviewed on 16 Aug. 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)
"Amazing stay as always"
Reviewed on 15 Aug. 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! (1,004 reviews)
"The most beautiful hotel !"
Reviewed on 17 Aug. 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.