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Top Kid friendly vacation packages in Chicago

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

Hilton Chicago

Downtown Chicago

￥282,092

per person

Jun 12 - Jun 14

found 1 day ago

Roundtrip non-stop flight included

Tokyo (TYO) to Chicago (ORD)

8.6/10 Excellent! (2,742 reviews)

Staff were nice. Hotel was at maximum capacity per security and it just felt overwhelming and claustrophobic at times.

Reviewed on Apr 22, 2026

Omni Chicago Hotel

Downtown Chicago

￥336,806

per person

Jun 7 - Jun 10

found 22 hours ago

Roundtrip non-stop flight included

Tokyo (TYO) to Chicago (ORD)

9.2/10 Wonderful! (1,755 reviews)

Breakfast at the Omni was the best food I had in Chicago, despite going to other upscale restaurants for lunch and dinner.

Reviewed on Apr 27, 2026

Warwick Allerton - Chicago

Downtown Chicago

￥314,936

per person

Jun 7 - Jun 10

found 22 hours ago

Roundtrip non-stop flight included

Tokyo (TYO) to Chicago (ORD)

8.6/10 Excellent! (3,051 reviews)

The location is perfect it’s near everything. The staff was really nice I had no issues also The room is very spacious. My only issue is there’s no free breakfast for the amount I paid I feel like breakfast should be included and why am I paying resort fee? It’s clearly not a resort

Reviewed on Apr 27, 2026

Palmer House a Hilton Hotel

Downtown Chicago

￥340,066

per person

Jun 7 - Jun 10

found 22 hours ago

Roundtrip non-stop flight included

Tokyo (TYO) to Chicago (ORD)

8.6/10 Excellent! (2,403 reviews)

Beaux art beauty in downtown Chicago, walkable from Union Station and close to everything. History, charm, great for a weekend stay.

Reviewed on Apr 27, 2026

Radisson Blu Aqua Hotel Chicago

Downtown Chicago

￥358,584

per person

Jun 7 - Jun 10

found 22 hours ago

Roundtrip non-stop flight included

Tokyo (TYO) to Chicago (ORD)

8.6/10 Excellent! (1,926 reviews)

Not worth the price. The amenities like sauna weren’t working and keep in mind the outdoor pool is only open in the summer. Staff took long to accommodate simple requests including housekeeping.

Reviewed on Apr 27, 2026

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3 Night Kid friendly vacations in Chicago

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

Warwick Allerton - Chicago

Downtown Chicago

￥314,936

per person

Jun 7 - Jun 10

found 22 hours ago

Roundtrip non-stop flight included

Tokyo (TYO) to Chicago (ORD)

8.6/10 Excellent! (3,051 reviews)

The location is perfect it’s near everything. The staff was really nice I had no issues also The room is very spacious. My only issue is there’s no free breakfast for the amount I paid I feel like breakfast should be included and why am I paying resort fee? It’s clearly not a resort

Reviewed on Apr 27, 2026

Omni Chicago Hotel

Downtown Chicago

￥336,806

per person

Jun 7 - Jun 10

found 22 hours ago

Roundtrip non-stop flight included

Tokyo (TYO) to Chicago (ORD)

9.2/10 Wonderful! (1,755 reviews)

Breakfast at the Omni was the best food I had in Chicago, despite going to other upscale restaurants for lunch and dinner.

Reviewed on Apr 27, 2026

Palmer House a Hilton Hotel

Downtown Chicago

￥340,066

per person

Jun 7 - Jun 10

found 22 hours ago

Roundtrip non-stop flight included

Tokyo (TYO) to Chicago (ORD)

8.6/10 Excellent! (2,403 reviews)

Beaux art beauty in downtown Chicago, walkable from Union Station and close to everything. History, charm, great for a weekend stay.

Reviewed on Apr 27, 2026

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See all available trips from Tokyo to Chicago

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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! (2,835 reviews)

Very nice and good place to rock on

Reviewed on Apr 28, 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! (2,417 reviews)

Grand historic property, conveniently located. Opted for a larger deluxe room, which was a good value. Bathrooms are small bull well appointed. Only critique was daily supplemental activity charge, which was not expected and not a great value.

Reviewed on Apr 28, 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! (5,907 reviews)

Property and room were clean. The clothing drawers were big enough for all of our stuff! Closet also had a lot of hangers! Bathroom needed a little upgrade but not bad. Breakfast was fantastic! Hotel was in a great location as well. Would definitely stay there again. We didn’t use valet but used ...

Reviewed on Apr 29, 2026

See all 5,562 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.