Plan a trip to see Washington Square

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Arlo Chicago

Downtown Chicago

NZ$2,264

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)

Great location, friendly staff, lovely rooms!

Reviewed on 10 Nov 2025

The Peninsula Chicago

Downtown Chicago

NZ$3,955

per person

22 Dec - 27 Dec

found 1 day ago

Return direct flight included

Auckland (AKL) to Chicago (ORD)

9.8/10 Exceptional! (1,009 reviews)

Staff is always there for your every need. Excellent clean room. Quiet and luxurious

Reviewed on 7 Nov 2025

Hilton Chicago O'Hare Airport

O'Hare

NZ$2,832

per person

22 Dec - 27 Dec

found 1 day ago

Return direct flight included

Auckland (AKL) to Chicago (ORD)

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

It's an old airport hotel. What does one should expect, 5 stars?? Served the purpose. Didn't eat food only slept for one night due to the flight cancelation.

Reviewed on 10 Nov 2025

Tours & day trips

See all 159 activities

Architecture River Tour

Free cancellation available

Private & custom tours

See all 50 activities

Eastside Chicago The Heist Exploration Game and Tour

Free cancellation available

Food, drink & nightlife

See all 25 activities

Odyssey Lake Michigan Premier Dinner Cruise

Attractions

See all 16 activities

360 CHICAGO Observation Deck

Free cancellation available

Classes & workshops

See all 11 activities

BYOB Spray Paint 'n' Sip at Studio W.I.P. Chicago

Free cancellation available

Popular places to visit

Oak Street

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

Holy Name Cathedral

After visiting Holy Name Cathedral, make a plan to see the other sights and activities in Chicago. Stroll along the lakeside or experience the 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 fascinating museums in this vibrant area.

Fourth Presbyterian Church

Fourth Presbyterian Church is just one of the places to see in Chicago, so why not enjoy the other things to explore during your travels? Amble around this vibrant area's lakeside or experience its acclaimed art galleries.

Chicago Water Tower

4.5/5(18 reviews)

You can learn about the history of Chicago with a visit to Chicago Water Tower. Amble around this vibrant area's lakeside or experience its acclaimed theatre scene.

Newberry Library

After visiting Newberry Library, make a plan to see the other sights and activities in Chicago. Experience the acclaimed art galleries and fascinating museums in this vibrant area.