Plan a trip to see Cadillac Palace Theatre

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theWit Chicago, a Hilton Hotel

Downtown Chicago

NZ$2,818

per person

31 Oct - 5 Nov

found 1 day 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

NZ$3,908

per person

31 Oct - 5 Nov

found 1 day ago

Return flight included

Auckland (AKL) to Chicago (ORD)

9.4/10 Exceptional! (1,716 reviews)

It’s was very clean and safe

Reviewed on 27 Sept 2025

The Emily Hotel

Downtown Chicago

NZ$3,151

per person

31 Oct - 5 Nov

found 1 day 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

Tours & day trips

See all 163 activities

Architecture River Tour

Free cancellation available

Food, drink & nightlife

See all 29 activities

Chicago: Architecture Boat Tour with Drinks

Free cancellation available

Private & custom tours

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Eastside Chicago The Heist Exploration Game and Tour

Free cancellation available

Attractions

See all 17 activities

360 CHICAGO Observation Deck

Free cancellation available

Adventure & outdoor

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Chicago Bulls Basketball Game at United Centre

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