Plan a trip to see Michigan Avenue

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theWit Chicago, a Hilton Hotel

Downtown Chicago

NZ$2,216

per person

22 Dec - 27 Dec

found 1 day 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

The Peninsula Chicago

Downtown Chicago

NZ$3,955

per person

22 Dec - 27 Dec

found 3 hours ago

Return direct flight included

Auckland (AKL) to Chicago (ORD)

9.8/10 Exceptional! (1,009 reviews)

Staff is always there for your every need. Excellent clean room. Quiet and luxurious

Reviewed on 7 Nov 2025

Arlo Chicago

Downtown Chicago

NZ$2,263

per person

22 Dec - 27 Dec

found 1 day ago

Return direct flight included

Auckland (AKL) to Chicago (ORD)

9.2/10 Wonderful! (1,852 reviews)

Great location, friendly staff, lovely rooms!

Reviewed on 10 Nov 2025

Tours & day trips

See all 80 activities

Architecture River Tour

Free cancellation available

Private & custom tours

See all 16 activities

Eastside Chicago The Heist Exploration Game and Tour

Free cancellation available

Food, drink & nightlife

See all 10 activities

Odyssey Chicago River Premier Dinner Cruise

Attractions

See all 6 activities

360 CHICAGO Observation Deck

Free cancellation available

Holiday & seasonal tours

See all 4 activities

Chicago: Wind and Souls Adults Only Guided Ghost Tour

Free cancellation available

Popular places to visit

Tribune Tower

You can learn about the history of Chicago with a visit to Tribune Tower. Discover the acclaimed theatre scene and notable monuments in this vibrant area.

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.

Shops at Northbridge

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

Wrigley Building

Learn about the local history of Chicago when you take a trip to Wrigley Building. Discover the acclaimed art galleries and notable monuments 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 art galleries.

St. James Cathedral

St. James Cathedral 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 visit the notable monuments in this vibrant area.