Plan a trip to see Lakefront Trail

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Pendry Chicago

Downtown Chicago

NZ$2,411

per person

23 Dec - 28 Dec

found 1 day ago

Return flight included

Auckland (AKL) to Chicago (ORD)

18.8/10 Exceptional! (1,128 reviews)

Staff was our favorite part! Very very professional and friendly

Reviewed on 14 Nov 2025

Trump International Hotel & Tower Chicago

Downtown Chicago

NZ$3,265

per person

23 Dec - 28 Dec

found 1 day ago

Return flight included

Auckland (AKL) to Chicago (ORD)

18.8/10 Exceptional! (1,773 reviews)

It was absolutely wonderful. We were upgraded to a suite which was pretty sweet (no pun intended)! At night the surrounding view of the lake along the lakeside of the hotel was spectacular. The Rebar on the mezzanine floor with a live musician playing a saxophone on a Saturday, was a cozy and lively setting. Welcome champagne upon check in was a nice touch. The Terrace 16 restaurant/bar also served scrumptious choices on the menu. Overall, very satisfied with our stay.

Reviewed on 14 Nov 2025

Hilton Chicago O'Hare Airport

O'Hare

NZ$2,748

per person

23 Dec - 28 Dec

found 1 day ago

Return flight included

Auckland (AKL) to Chicago (ORD)

16.4/10 Exceptional! (2,152 reviews)

Clean and quiet and comfortable

Reviewed on 14 Nov 2025

Tours & day trips

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Architecture River Tour

Private & custom tours

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Eastside Chicago The Heist Exploration Game and Tour

Free cancellation available

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Chicago Craft Brewery Barrel Bus Tour

Free cancellation available

Attractions

See all 15 activities

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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