
Northwest Side Kid friendly Vacations
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Top Kid friendly vacation packages in Northwest Side
Price found within the past 48 hours. Click for updated prices.

Hotel Riu Plaza Chicago
Downtown Chicago
Price was ¥415,464, price is now ¥296,489 per person
¥296,489
per person
Sep 25 - Sep 30
just found
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (4,586 reviews)
Great spot in the middle of everything, and the rooftop bar is excellent.
Reviewed on Jul 10, 2026

Omni Chicago Hotel
Downtown Chicago
Price was ¥453,536, price is now ¥329,330 per person
¥329,330
per person
Sep 25 - Sep 30
just found
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (1,819 reviews)
Everything was nice and clean.
Staff was very helpful.
Reviewed on Jul 11, 2026

Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ¥523,212, price is now ¥387,298 per person
¥387,298
per person
Sep 25 - Sep 30
just found
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.6/10 Exceptional! (1,910 reviews)
I love Trump hotels the absolute BEST
Reviewed on Jul 10, 2026

Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Price was ¥408,068, price is now ¥312,175 per person
¥312,175
per person
Sep 25 - Sep 30
just found
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (2,566 reviews)
There were stains on the carpet and where the thermostat was an awful smell coming from that area-like musty smelling. We stayed and paid premium rate for a firework view and while I know they can’t control the weather, I reached out to see if they would be willing to credit something toward a future stay so we could enjoy the experience. Not even an acknowledgment of our disappointment or receipt of our email. Disappointed in the whole situation.
Reviewed on Jul 10, 2026

Fairmont Chicago at Millennium Park
Downtown Chicago
Price was ¥412,687, price is now ¥318,478 per person
¥318,478
per person
Sep 25 - Sep 30
just found
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
8.8/10 Excellent! (2,239 reviews)
The staff at this hotel is amazing! Every person we encountered was extremely helpful and friendly. The rooms are a bit outdated, but the beds and linens were very comfortable. Location was great, super close to the park and within walking distance of many attractions!
Reviewed on Jul 10, 2026
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Price found within the past 48 hours. Click for updated prices.

Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ¥523,212, price is now ¥387,298 per person
¥387,298
per person
Sep 25 - Sep 30
just found
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.6/10 Exceptional! (1,910 reviews)
I love Trump hotels the absolute BEST
Reviewed on Jul 10, 2026

Nobu Hotel Chicago
Downtown Chicago
Price was ¥689,968, price is now ¥574,267 per person
¥574,267
per person
Aug 12 - Aug 18
found 1 day ago
Roundtrip flight included
Osaka (OSA) to Chicago (ORD)
9.4/10 Exceptional! (879 reviews)
Stunning hotel with really attentive staff, located in the heart of Chicago's West Loop neighborhood. You are surrounded by a ton of award-winning restaurants, shopping and also close to public transit. Rooms are spacious and are themed in a minimalistic Japanese onsen-style esthetic. We loved our stay here, though there are a few things to mention that made our stay less than a perfect 10. The bathroom is fully painted in black. Looks great, but terrible for styling your hair, if you have dark colored hair. Poor lighting concepts throughout the room and bathroom in general, which made it terrible for getting ready any time of the day. Closet area was dark, not great for getting dressed. Bedroom area was dark, not great for reading a book. Desk area is dark, not great for working remotely. Bathroom lighting is dark, not great if you are a woman trying to put on makeup. Housekeeping was fantastic and really knew how to personalize your stay, but they still knocked on the door when we had the "do not disturb" light on, which was very bothersome and woke us up a couple of times.
Reviewed on Jul 6, 2026
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Chicago: Navy Pier Centennial Wheel Ticket
¥3,992
per adult
88% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.


