Plan a trip to see Eighth Regiment Armory

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theWit Chicago, a Hilton Hotel

Downtown Chicago

NZ$2,818

per person

31 Oct - 5 Nov

just found

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

just found

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

NZ$3,151

per person

31 Oct - 5 Nov

just found

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

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Architecture River Tour

Free cancellation available

Food, drink & nightlife

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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

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360 CHICAGO Observation Deck

Free cancellation available

Adventure & outdoor

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Chicago Bulls Basketball Game at United Centre

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