Plan a trip to see Chicago Arts District

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theWit Chicago, a Hilton Hotel

Downtown Chicago

NZ$2,818

per person

31 Oct - 5 Nov

found 24 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

NZ$3,908

per person

31 Oct - 5 Nov

found 24 hours 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 24 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

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

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360 CHICAGO Observation Deck

Free cancellation available

Adventure & outdoor

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Chicago Bulls Basketball Game at United Centre

Popular places to visit

Ping Tom Memorial Park

After visiting Ping Tom Memorial Park, make a plan to see the other sights and activities in Chicago. Amble around this vibrant area's lakeside or experience its fascinating museums.

South Wentworth Street

You can find the perfect gifts to bring home at South Wentworth Street during your trip to Chicago. Amble around this family-friendly area's Chinatown and enjoy its top-notch restaurants.

University of Illinois Chicago

Enjoy the student vibe at University of Illinois Chicago during your visit to Chicago. Stroll along the riverfront or experience the acclaimed art galleries in this vibrant area.

American Police Center & Museum

You can spend time exploring the galleries in American Police Center & Museum during your trip to Chicago. Amble around this vibrant area's lakeside or experience its acclaimed theatre scene.

UIC Forum

Learn about the events happening in UIC Forum during your trip to Chicago. While you're in the area, find time to visit its shops.

Maxwell Street Market

You can search for that perfect souvenir at Maxwell Street Market during your stay in Chicago. Discover the acclaimed art galleries and notable monuments in this vibrant area.