Plan a trip to see Loyola University Museum of Art

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Hilton Grand Vacations Club Chicago Magnificent Mile

Downtown Chicago

NZ$2,725

per person

22 Dec - 27 Dec

found 18 hours ago

Return direct flight included

Auckland (AKL) to Chicago (ORD)

9.2/10 Wonderful! (291 reviews)

Food price was high but everything was fine

Reviewed on 4 Oct 2025

Pendry Chicago

Downtown Chicago

NZ$2,930

per person

27 Dec - 1 Jan

found 18 hours ago

Return direct flight included

Auckland (AKL) to Chicago (ORD)

9.4/10 Exceptional! (1,085 reviews)

I loved the hotel, however I would request an inside room next time. It was extremely noisy outside.

Reviewed on 11 Oct 2025

Swissotel - Chicago

Downtown Chicago

NZ$2,779

per person

22 Dec - 27 Dec

found 18 hours ago

Return direct flight included

Auckland (AKL) to Chicago (ORD)

9/10 Wonderful! (2,765 reviews)

The view from the panoramic view was amazing. The gym was comfortable and the credit to amuse was nice

Reviewed on 9 Oct 2025

Tours & day trips

See all 154 activities

Architecture River Tour

Free cancellation available

Food, drink & nightlife

See all 26 activities

Chicago: Architecture Boat Tour with Drinks

Free cancellation available

Private & custom tours

See all 25 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 12 activities

Chicago: Two Flight Indoor Skydiving Experience

Free cancellation available

Popular places to visit

Chicago Water Tower

You can learn about the history of Chicago with a visit to Chicago Water Tower. Amble around this vibrant area's lakeside or experience its acclaimed art galleries.

Fourth Presbyterian Church

Fourth Presbyterian Church 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 lakeside or experience its acclaimed theatre scene.

875 North Michigan Avenue

You can find out about the history of Chicago when you stop by 875 North Michigan Avenue. Amble around this vibrant area's lakeside or experience its fascinating museums.

900 North Michigan Shops

You can browse for the perfect souvenirs at 900 North Michigan Shops during your trip to Chicago. Stroll along the lakeside or experience the acclaimed art galleries in this vibrant area.

Water Tower Place

Enjoy endless shopping, see exhibits of sporting memorabilia and attend shows at a live theater at this huge shopping mall.

Holy Name Cathedral

After visiting Holy Name Cathedral, make a plan to see the other sights and activities in Chicago. Stroll along the lakeside or experience the acclaimed theatre scene in this vibrant area.