Plan a trip to see Cyrus McCormick Mansion

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Pendry Chicago

Downtown Chicago

NZ$2,915

per person

27 Dec - 1 Jan

found 7 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 5 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 7 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 157 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 13 activities

Chicago: Two Flight Indoor Skydiving Experience

Free cancellation available

Popular places to visit

Chicago History Museum

4.5/5(2 reviews)

Take a trip back in time to explore Chicago's diverse past, from Lincoln to 'L' cars, from building skyscrapers to playing the blues, this museum has it all.

North Avenue Beach

Why not spend a care-free afternoon at North Avenue Beach during your travels in Chicago? Experience the fascinating museums and acclaimed art galleries in this vibrant area.

Oak Street Beach

Why not spend a care-free afternoon at Oak Street Beach during your travels in Chicago? Stroll along the riverfront or experience the acclaimed theatre scene in this vibrant area.

Oak Street

During your trip to Chicago, you can find the perfect gifts to bring home at Oak Street. Experience the acclaimed theatre scene and fascinating museums in this vibrant area.

900 North Michigan Shops

You can browse for the perfect souvenirs at 900 North Michigan Shops during your trip to Chicago. Stroll along the lakeside or experience the acclaimed art galleries in this vibrant area.

International Museum of Surgical Science

You can spend time studying the exhibits at International Museum of Surgical Science during your travels in Chicago. Experience the entertainment choices and acclaimed theatre scene in this vibrant area.