Plan a trip to see Skydeck Ledge

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 22 hours ago

Return direct flight included

Auckland (AKL) to Chicago (ORD)

9/10 Wonderful! (1,011 reviews)

My room was very clean. The stay was very friendly and helpful. Check-in was a breeze. Since my room was ready they even let me check in early! There are 2 restaurants in this hotel. We had drinks at the one near the lobby and we ate at the ROOF. The food was delish! The environment was fun. We were worried that it was going to be more for the 20 something crowd, but there were adults of every age there. This hotel is also just steps from The Chicago Theatre which makes it super convenient when seeing an event there.

Reviewed on 10 Nov 2025

Arlo Chicago

Downtown Chicago

NZ$2,263

per person

22 Dec - 27 Dec

found 22 hours ago

Return direct flight included

Auckland (AKL) to Chicago (ORD)

9.2/10 Wonderful! (1,852 reviews)

The room was really clean and the staff was very friendly and accommodating

Reviewed on 10 Nov 2025

Hilton Chicago O'Hare Airport

O'Hare

NZ$3,296

per person

21 Dec - 26 Dec

found 5 hours ago

Return direct flight included

Auckland (AKL) to Chicago (ORD)

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

Staff was great and the room was clean! We had to find a place for the night and didnt want to go far. It is convenient for that. Room rates are not too bad but the restaurant is a little pricey but still good food and service.

Reviewed on 9 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

Adventure & outdoor

See all 11 activities

Chicago: Two Flight Indoor Skydiving Experience

Free cancellation available

Popular places to visit

Willis Tower

The Willis Tower is at its best when you're dangled over one of its glass-bottomed balconies 396 metres above Chicago.

311 S Wacker Dr

311 S Wacker Dr 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 riverfront or experience its fascinating museums.

Chicago Board of Trade Building

You can learn about the history of Chicago when you stop by Chicago Board of Trade Building. Experience the acclaimed theatre scene and fascinating museums in this vibrant area.

Rookery

Built by famed 19th-century architects and renovated in 1907 by Frank Lloyd Wright, this early skyscraper is a great stop on a Chicago architecture tour.

Chicago Loop Synagogue

Chicago Loop Synagogue 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 riverfront or experience the acclaimed art galleries in this vibrant area.

Chase Tower

Chase Tower 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 riverfront or experience its acclaimed theatre scene.