Name: 2BR City Escape Bright, Sleek, Spacious
Address: Chicago

Plan a trip to see Steppenwolf Theatre

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

theWit Chicago, a Hilton Hotel

Downtown Chicago

NZ$2,818

per person

31 Oct - 5 Nov

found 24 hours ago

Return flight included

Auckland (AKL) to Chicago (ORD)

9/10 Wonderful! (1,004 reviews)

The WIt was everything. The Roof at the Wit, was amazing, be sure to make reservations. I love this hotel and Chicago it was safe and close to everything!!

Reviewed on 26 Sept 2025

Trump International Hotel & Tower Chicago

Downtown Chicago

NZ$3,908

per person

31 Oct - 5 Nov

found 24 hours ago

Return flight included

Auckland (AKL) to Chicago (ORD)

9.4/10 Exceptional! (1,716 reviews)

It’s was very clean and safe

Reviewed on 27 Sept 2025

The Emily Hotel

Downtown Chicago

NZ$3,151

per person

31 Oct - 5 Nov

found 24 hours ago

Return flight included

Auckland (AKL) to Chicago (ORD)

9.2/10 Wonderful! (1,222 reviews)

The Emily Hotel was in a convenient area of Chicago close to the family wedding we were attending in mid-September. Rooms were clean modern and had loads of desk space but no dressers or nightstands. Staff was helpful in telling us about the nearby parking garage beneath the Google building across the street. We parked our car there for $57/ day vs Valet for $85 (with unlimited in and) at The Emily. We would stay there again.

Reviewed on 26 Sept 2025

Tours & day trips

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Architecture River Tour

Free cancellation available

Food, drink & nightlife

See all 30 activities

Chicago: Architecture Boat Tour with Drinks

Free cancellation available

Private & custom tours

See all 29 activities

Eastside Chicago The Heist Exploration Game and Tour

Free cancellation available

Attractions

See all 17 activities

360 CHICAGO Observation Deck

Free cancellation available

Adventure & outdoor

See all 14 activities

Chicago Bulls Basketball Game at United Centre

Popular places to visit

Armitage Avenue

During your trip to Chicago, you can enjoy retail therapy at Armitage Avenue. Stroll along the lakeside in this vibrant area or visit its lively bars.

Park West

You can enjoy a show at Park West on your trip to Chicago. Stroll along the lakeside or experience the acclaimed art galleries in this vibrant area.

Chicago History Museum

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.

Royal George Theater

You can make plans for a show at Royal George Theater during your trip to Chicago. Stroll along the lakeside or experience the entertainment choices in this vibrant area.

Legacy Motors Automotive Art Gallery

You can spend time exploring the galleries in Legacy Motors Automotive Art Gallery during your travels in Chicago. Amble around this vibrant area's lakeside or experience its acclaimed art galleries.

All She Wrote

Enjoy a stop at All She Wrote, an entertaining place to visit in Chicago. Stroll along the lakeside or experience the acclaimed theatre scene in this vibrant area.