Plan a trip to see Aldo Castillo Gallery

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theWit Chicago, a Hilton Hotel

Downtown Chicago

NZ$2,216

per person

22 Dec - 27 Dec

found 1 day ago

Return direct flight included

Auckland (AKL) to Chicago (ORD)

9/10 Wonderful! (1,011 reviews)

My room was very clean. The stay was very friendly and helpful. Check-in was a breeze. Since my room was ready they even let me check in early! There are 2 restaurants in this hotel. We had drinks at the one near the lobby and we ate at the ROOF. The food was delish! The environment was fun. We were worried that it was going to be more for the 20 something crowd, but there were adults of every age there. This hotel is also just steps from The Chicago Theatre which makes it super convenient when seeing an event there.

Reviewed on 10 Nov 2025

Arlo Chicago

Downtown Chicago

NZ$2,263

per person

22 Dec - 27 Dec

found 1 day ago

Return direct flight included

Auckland (AKL) to Chicago (ORD)

9.2/10 Wonderful! (1,852 reviews)

The room was really clean and the staff was very friendly and accommodating

Reviewed on 10 Nov 2025

Hilton Chicago O'Hare Airport

O'Hare

NZ$3,296

per person

21 Dec - 26 Dec

found 13 hours ago

Return direct flight included

Auckland (AKL) to Chicago (ORD)

8.2/10 Very Good! (2,141 reviews)

Staff was great and the room was clean! We had to find a place for the night and didnt want to go far. It is convenient for that. Room rates are not too bad but the restaurant is a little pricey but still good food and service.

Reviewed on 9 Nov 2025

Tours & day trips

See all 159 activities

Architecture River Tour

Free cancellation available

Private & custom tours

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Eastside Chicago The Heist Exploration Game and Tour

Free cancellation available

Food, drink & nightlife

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Odyssey Lake Michigan Premier Dinner Cruise

Attractions

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360 CHICAGO Observation Deck

Free cancellation available

Adventure & outdoor

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Chicago: Two Flight Indoor Skydiving Experience

Free cancellation available

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