Plan a trip to see Charnley-Persky House

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Pendry Chicago

Downtown Chicago

NZ$2,915

per person

27 Dec - 1 Jan

found 22 hours ago

Return direct flight included

Auckland (AKL) to Chicago (ORD)

9.4/10 Exceptional! (1,110 reviews)

We loved the Pendry!

Reviewed on 27 Oct 2025

Trump International Hotel & Tower Chicago

Downtown Chicago

NZ$4,214

per person

27 Dec - 1 Jan

found 20 hours ago

Return direct flight included

Auckland (AKL) to Chicago (ORD)

9.4/10 Exceptional! (1,761 reviews)

Great staff, very clean rooms, overall great experience

Reviewed on 31 Oct 2025

The Emily Hotel

Downtown Chicago

NZ$2,998

per person

27 Dec - 1 Jan

found 22 hours ago

Return direct flight included

Auckland (AKL) to Chicago (ORD)

9.2/10 Wonderful! (1,248 reviews)

Always a great stay! Staff are great and rooms present great value.

Reviewed on 1 Nov 2025

Tours & day trips

See all 153 activities

Architecture River Tour

Free cancellation available

Private & custom tours

See all 49 activities

Eastside Chicago The Heist Exploration Game and Tour

Free cancellation available

Food, drink & nightlife

See all 26 activities

Odyssey Lake Michigan Premier Dinner Cruise

Attractions

See all 15 activities

360 CHICAGO Observation Deck

Free cancellation available

Adventure & outdoor

See all 12 activities

Chicago: Two Flight Indoor Skydiving Experience

Free cancellation available

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Chicago History Museum

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Oak Street

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Washington Square

Learn about the local history of Chicago with a stop at Washington Square. Stroll along the riverfront or experience the fascinating museums in this vibrant area.