Plan a trip to see The 606

Price found within the past 48 hours. Click for updated prices.

theWit Chicago, a Hilton Hotel

Downtown Chicago

NZ$2,216

per person

22 Dec - 27 Dec

found 15 hours ago

Return direct flight included

Auckland (AKL) to Chicago (ORD)

9/10 Wonderful! (1,011 reviews)

A+++ in all areas. And fabulous location.

Reviewed on 6 Nov 2025

Arlo Chicago

Downtown Chicago

NZ$2,263

per person

22 Dec - 27 Dec

found 15 hours ago

Return direct flight included

Auckland (AKL) to Chicago (ORD)

9.2/10 Wonderful! (1,852 reviews)

Friendly, clean; delightful stay.

Reviewed on 7 Nov 2025

The Royal Sonesta Chicago Downtown

Downtown Chicago

NZ$2,360

per person

22 Dec - 27 Dec

found 15 hours ago

Return direct flight included

Auckland (AKL) to Chicago (ORD)

9.4/10 Exceptional! (3,013 reviews)

Amenities, staff, and room

Reviewed on 9 Nov 2025

Tours & day trips

See all 159 activities

Architecture River Tour

Free cancellation available

Private & custom tours

See all 51 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

Rosemont: Two Flight Indoor Skydiving Experience

Free cancellation available

Popular places to visit

Humboldt Park

Humboldt Park is just one of the places to see in Chicago, so why not enjoy the other things to explore during your travels? Experience the acclaimed theatre scene and entertainment choices in this vibrant area.

Illinois Centennial Memorial Column

Learn about the local history of Chicago with a stop at Illinois Centennial Memorial Column. Stroll along the lakeside in this vibrant area or visit its top-notch restaurants.

Concord Music Hall

Concord Music Hall is just one of the places to see in Chicago, so why not enjoy the other things to explore during your travels? Stroll along the lakeside or experience the acclaimed art galleries in this vibrant area.

Gorilla Tango Theatre

You can make plans for a show at Gorilla Tango Theatre during your stay in Chicago. Amble around this vibrant area's lakeside or experience its entertainment choices.