Plan a trip to see Tribune Tower

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theWit Chicago, a Hilton Hotel

Downtown Chicago

NZ$2,122

per person

4 Nov - 9 Nov

just found

Return flight included

Christchurch (CHC) to Chicago (ORD)

9/10 Wonderful! (1,004 reviews)

The room was perfect and the front staff were exceptional. Our stay was amazing!

Reviewed on 21 Sept 2025

Trump International Hotel & Tower Chicago

Downtown Chicago

Save 100% on your flight

NZ$3,143

per person

4 Nov - 9 Nov

just found

Return flight included

Christchurch (CHC) to Chicago (ORD)

9.4/10 Exceptional! (1,716 reviews)

This property is fabulous in every aspect. Huge rooms, modern and fresh. The spa and workout facilities are amazing. I loved everything about this hotel. Location is perfect to explore the river walk, shopping and best dining options. Only small critique is only one person at the front and if they are busy with a guest, can be a long wait to check in or out.

Reviewed on 21 Sept 2025

LondonHouse Chicago, Curio Collection by Hilton

Downtown Chicago

NZ$2,500

per person

4 Nov - 9 Nov

just found

Return flight included

Christchurch (CHC) to Chicago (ORD)

9.4/10 Exceptional! (3,344 reviews)

Wonderful stay with wonderful views!

Reviewed on 22 Sept 2025

Tours & day trips

See all 164 activities

Architecture River Tour

Free cancellation available

Food, drink & nightlife

See all 29 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 16 activities

360 CHICAGO Observation Deck

Free cancellation available

Adventure & outdoor

See all 13 activities

Chicago: Two Flight Indoor Skydiving Experience

Free cancellation available

Popular places to visit

Wrigley Building

Learn about the local history of Chicago when you take a trip to Wrigley Building. Discover the fascinating museums and notable monuments in this vibrant area.

Magnificent Mile - River North showing street scenes, signage and a city

Michigan Avenue

You can find the perfect gifts to bring home when you visit Michigan Avenue, a popular shopping spot in Chicago. Amble around this vibrant area's riverfront and enjoy its top-notch restaurants.

Shops at Northbridge

You can find the perfect gifts to bring home at Shops at Northbridge during your trip to Chicago. Experience the acclaimed theatre scene and entertainment choices in this vibrant area.

Michigan Avenue Bridge

Learn about the local history of Chicago when you take a trip to Michigan Avenue Bridge. Amble around this vibrant area's riverfront or experience its acclaimed theatre scene.

Shops at North Bridge

Spend a day exploring the department store, luxury fashion outlets and food court at this mall on the glitzy Magnificent Mile shopping district.

Chicago Riverwalk

Stroll along the waterfront of the Chicago River to pass some of the city’s most appealing attractions and appreciate how a once grim area has been successfully revamped.