
Rush Street Ski Holidays
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Top flight + Ski hotel deals in Rush Street
Price found within the past 48 hours. Click for updated prices.

theWit Chicago, a Hilton Hotel
Downtown Chicago
Price was NZ$3,760, price is now NZ$2,818 per person
NZ$2,818
per person
31 Oct - 5 Nov
found 5 hours ago
Return flight included
Auckland (AKL) to Chicago (ORD)
9/10 Wonderful! (1,004 reviews)
The WIt was everything. The Roof at the Wit, was amazing, be sure to make reservations. I love this hotel and Chicago it was safe and close to everything!!
Reviewed on 26 Sept 2025

Trump International Hotel & Tower Chicago
Downtown Chicago
Price was NZ$5,759, price is now NZ$3,908 per person
NZ$3,908
per person
31 Oct - 5 Nov
found 5 hours ago
Return flight included
Auckland (AKL) to Chicago (ORD)
9.4/10 Exceptional! (1,716 reviews)
The hotel was above the expectations and river view was fabulous also staff were incredibly awesome specially the front dest employee Natalia she was helpful, smiling and welcoming.
Reviewed on 24 Sept 2025

The Emily Hotel
Downtown Chicago
Price was NZ$4,292, price is now NZ$3,151 per person
NZ$3,151
per person
31 Oct - 5 Nov
found 5 hours ago
Return flight included
Auckland (AKL) to Chicago (ORD)
9.2/10 Wonderful! (1,222 reviews)
The Emily Hotel was in a convenient area of Chicago close to the family wedding we were attending in mid-September.
Rooms were clean modern and had loads of desk space but no dressers or nightstands.
Staff was helpful in telling us about the nearby parking garage beneath the Google building across the street. We parked our car there for $57/ day vs Valet for $85 (with unlimited in and) at The Emily.
We would stay there again.
Reviewed on 26 Sept 2025

Swissotel - Chicago
Downtown Chicago
Price was NZ$3,867, price is now NZ$2,900 per person
NZ$2,900
per person
31 Oct - 5 Nov
found 5 hours ago
Return flight included
Auckland (AKL) to Chicago (ORD)
9/10 Wonderful! (2,765 reviews)
There were shops of all kinds as well as drug stores. It is located across from the Riverwalk and bridge on Michigan Avenue. In hotel restaurant and bar were good, if pricier than several nearby restaurants. The room was comfortable with a great view. I love the hotel and location. Will continue to try to stay there.
Reviewed on 27 Sept 2025

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Price found within the past 48 hours. Click for updated prices.

Trump International Hotel & Tower Chicago
Downtown Chicago
Price was NZ$5,759, price is now NZ$3,908 per person
NZ$3,908
per person
31 Oct - 5 Nov
found 5 hours ago
Return flight included
Auckland (AKL) to Chicago (ORD)
9.4/10 Exceptional! (1,716 reviews)
The hotel was above the expectations and river view was fabulous also staff were incredibly awesome specially the front dest employee Natalia she was helpful, smiling and welcoming.
Reviewed on 24 Sept 2025


Nobu Hotel Chicago
Downtown Chicago
Price was NZ$6,200, price is now NZ$5,228 per person
NZ$5,228
per person
31 Oct - 5 Nov
found 6 hours ago
Return flight included
Auckland (AKL) to Chicago (ORD)
9.4/10 Exceptional! (722 reviews)
Well appointed rooms with great service. The restaurant is decent too; there are also abundant dining options nearby that are open even on Labor Day.
Reviewed on 25 Sept 2025
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View all trips* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.