Plan a trip to see Madison Street Theatre

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theWit Chicago, a Hilton Hotel

Downtown Chicago

NZ$2,818

per person

31 Oct - 5 Nov

found 1 day 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 1 day ago

Return flight included

Auckland (AKL) to Chicago (ORD)

9.4/10 Exceptional! (1,716 reviews)

Perfect location, beautiful view, nice staffs, excellently maintained room and facility!

Reviewed on 28 Sept 2025

The Emily Hotel

Downtown Chicago

NZ$3,151

per person

31 Oct - 5 Nov

found 1 day ago

Return flight included

Auckland (AKL) to Chicago (ORD)

9.2/10 Wonderful! (1,222 reviews)

Beautiful hotel in great walkable area. There were major renovations going on while we were there so our actual floor was a bit messy/busy, although the common areas remained lovely. Would stay again for the good location. All staff very nice.

Reviewed on 29 Sept 2025

Tours & day trips

See all 149 activities

Architecture River Tour

Free cancellation available

Private & custom tours

See all 25 activities

Eastside Chicago The Heist Exploration Game and Tour

Free cancellation available

Food, drink & nightlife

See all 24 activities

Chicago: Architecture Boat Tour with Drinks

Free cancellation available

Attractions

See all 14 activities

360 CHICAGO Observation Deck

Free cancellation available

Adventure & outdoor

See all 10 activities

Rosemont: Two Flight Indoor Skydiving Experience

Free cancellation available

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