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Top Kid friendly vacation packages in Chicago

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

Warwick Allerton - Chicago

Downtown Chicago

₩2,147,314

per person

Jun 12 - Jun 17

found 1 day ago

Roundtrip non-stop flight included

Honolulu (HNL) to Chicago (ORD)

8.6/10 Excellent! (3,042 reviews)

The room was clean. The hotel staff was very friendly. One of the people who works the is a young man named Marcus ( not sure of the correct spelling) , he was the most delightful person that I encountered. He was so friendly and very helpful. He made my stay there a wonderful experience.

Reviewed on Apr 21, 2026

Hilton Chicago

Downtown Chicago

₩2,347,834

per person

Jun 12 - Jun 17

found 1 day ago

Roundtrip non-stop flight included

Honolulu (HNL) to Chicago (ORD)

8.6/10 Excellent! (2,727 reviews)

Clean room and great location

Reviewed on Apr 21, 2026

Hyatt Regency Chicago

Downtown Chicago

₩2,865,372

per person

Jun 12 - Jun 17

found 1 day ago

Roundtrip non-stop flight included

Honolulu (HNL) to Chicago (ORD)

9.4/10 Exceptional! (3,500 reviews)

Food and everything else was excellent

Reviewed on Apr 21, 2026

The Royal Sonesta Chicago Downtown

Downtown Chicago

₩2,453,485

per person

Jun 12 - Jun 17

found 1 day ago

Roundtrip non-stop flight included

Honolulu (HNL) to Chicago (ORD)

9.4/10 Exceptional! (3,383 reviews)

Literally my fave hotel I’ve ever stayed at on the mag mile. Amazing view, amazing room. Staff super friendly. No notes

Reviewed on Apr 21, 2026

Silversmith Hotel Chicago Downtown

Downtown Chicago

₩2,439,584

per person

Jun 12 - Jun 17

found 1 day ago

Roundtrip non-stop flight included

Honolulu (HNL) to Chicago (ORD)

9.2/10 Wonderful! (2,241 reviews)

We haven’t stayed downtown and came to see a show. This hotel was the perfect location, but the fun surprise was what a wonderful hotel it was! No need for us to stay anywhere else! We will be back, great hotel and such a good value!! We ate breakfast both mornings and it was perfect

Reviewed on Apr 20, 2026

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Top Kid friendly Chicago Hotels

Embassy Suites by Hilton Chicago Downtown Magnificent Mile

511 North Columbus Drive Chicago IL

10 min drive from Wrigley Field

Book a stay at this business-friendly hotel in Chicago. Enjoy free breakfast, room service, and a fitness center. Our guests praise the breakfast and the helpful ...

8.2/10 Very Good! (2,820 reviews)

Great job!

Reviewed on Apr 20, 2026

Palmer House a Hilton Hotel

17 E Monroe St Chicago IL

12 min drive from Wrigley Field

Book a stay at this luxury hotel in Chicago. Enjoy a full-service spa, breakfast (surcharge), and a 24-hour health club. Our guests praise the helpful staff ...

8.6/10 Excellent! (2,406 reviews)

We love the Palmer House! This is our “go to” hotel when we travel to Chicago. It is close to theaters, concert halls, Michigan Ave with museums, restaurants, parks, etc. The hotel lobby is incredible! A great place to relax, have a beverage, people watch, and enjoy. The room we recently stayed in ...

Reviewed on Apr 20, 2026

Embassy Suites by Hilton Chicago Downtown River North

600 N State St Chicago IL

10 min drive from Wrigley Field

Stay at this hotel in Chicago. Enjoy free breakfast, room service, and a fitness center. Our guests praise the breakfast and the pool in our reviews. Popular ...

8.6/10 Excellent! (5,873 reviews)

Great location, nice hotel, centrally, located near all the great Chicago experiences

Reviewed on Apr 22, 2026

See all 5,596 properties in Chicago

Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.