West Side Kid friendly Vacations
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Top Kid friendly vacation packages in West Side
Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile
Downtown Chicago
Price was ￥352,949, price is now ￥302,538 per person
￥302,538
per person
Sep 19 - Sep 22
found 18 hours ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
8.2/10 Very Good! (2,767 reviews)
Great location, we were able to walk everywhere we wanted to see. The red line is about a 10 minute walk if you are heading to Wrigley.
Reviewed on Jun 26, 2026
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ￥666,224, price is now ￥548,055 per person
￥548,055
per person
Aug 8 - Aug 14
found 14 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.6/10 Exceptional! (1,893 reviews)
Fantastic hotel, super clean and excellent customer service, I would recommend it to anyone going to Chicago
Reviewed on Jun 26, 2026
Thompson Chicago, by Hyatt
Downtown Chicago
Price was ￥488,708, price is now ￥407,436 per person
￥407,436
per person
Sep 16 - Sep 20
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (1,399 reviews)
I truly enjoyed my stay at this hotel. From the moment I arrived, the staff made me feel welcome and valued. Everyone was so friendly, attentive, and genuinely eager to help, which made the experience even more enjoyable.
The hotel was clean, comfortable, and had everything I needed for a relaxing stay. I especially loved the location—it was convenient to restaurants, shopping, and local attractions, making it easy to get around and enjoy the area without any hassle.
Reviewed on Jun 21, 2026
LondonHouse Chicago, Curio Collection by Hilton
Downtown Chicago
Price was ￥471,278, price is now ￥399,099 per person
￥399,099
per person
Aug 9 - Aug 14
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (3,756 reviews)
Excelente, ubicación perfecta cerca de todo
Reviewed on Jun 23, 2026
5* Kid friendly vacations in West Side
Price found within the past 48 hours. Click for updated prices.
The Peninsula Chicago
Downtown Chicago
Price was ￥498,167, price is now ￥449,412 per person
￥449,412
per person
Sep 19 - Sep 22
found 18 hours ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.8/10 Exceptional! (1,009 reviews)
Amazing the staff was so friendly. The hotel is just I can’t believe I never stayed at this hotel. This is by far my top five hotels I will definitely be returning. Thank you so much for such a wonderful stay
Kimberly Chardukian
Reviewed on Jun 26, 2026
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ￥666,224, price is now ￥548,055 per person
￥548,055
per person
Aug 8 - Aug 14
found 14 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.6/10 Exceptional! (1,893 reviews)
Fantastic hotel, super clean and excellent customer service, I would recommend it to anyone going to Chicago
Reviewed on Jun 26, 2026
3 Night Kid friendly vacations in West Side
Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile
Downtown Chicago
Price was ￥352,949, price is now ￥302,538 per person
￥302,538
per person
Sep 19 - Sep 22
found 18 hours ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
8.2/10 Very Good! (2,767 reviews)
Great location, we were able to walk everywhere we wanted to see. The red line is about a 10 minute walk if you are heading to Wrigley.
Reviewed on Jun 26, 2026
Hotel Riu Plaza Chicago
Downtown Chicago
Price was ￥378,586, price is now ￥322,070 per person
￥322,070
per person
Sep 19 - Sep 22
found 18 hours ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.4/10 Exceptional! (4,518 reviews)
There isnt a vending machine with drinks or snacks. I had to walk a block to 7-11 at night. That was my only complaint. Other than that my say was awesome.
Reviewed on Jun 26, 2026
Fairmont Chicago at Millennium Park
Downtown Chicago
Price was ￥382,568, price is now ￥339,412 per person
￥339,412
per person
Sep 19 - Sep 22
found 18 hours ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
8.8/10 Excellent! (2,201 reviews)
Personnel, souriant, ont-elles très propre, très bien situés
Reviewed on Jun 26, 2026
4 Night Kid friendly vacations in West Side
Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile
Downtown Chicago
Price was ￥460,246, price is now ￥373,894 per person
￥373,894
per person
Sep 16 - Sep 20
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
8.2/10 Very Good! (2,767 reviews)
Great location, we were able to walk everywhere we wanted to see. The red line is about a 10 minute walk if you are heading to Wrigley.
Reviewed on Jun 26, 2026
LondonHouse Chicago, Curio Collection by Hilton
Downtown Chicago
Price was ￥464,064, price is now ￥379,842 per person
￥379,842
per person
Sep 16 - Sep 20
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (3,756 reviews)
Excelente, ubicación perfecta cerca de todo
Reviewed on Jun 23, 2026
Things to do
Wendella's 90-min Chicago River Architecture Tour
￥6,478
per adult
94% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
