
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.

Eurostars Magnificent Mile
Downtown Chicago
Price was ₩3,371,724, price is now ₩2,602,647 per person
₩2,602,647
per person
May 29 - Jun 1
found 6 hours ago
Roundtrip flight included
New York (NYC) to Chicago (ORD)
9/10 Wonderful! (3,314 reviews)
Clean room nice staff, beautiful property. Enjoyed the deluxe room
Reviewed on Mar 20, 2026

Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ₩3,825,674, price is now ₩2,936,126 per person
₩2,936,126
per person
May 29 - Jun 1
found 6 hours ago
Roundtrip flight included
New York (NYC) to Chicago (ORD)
9.4/10 Exceptional! (1,852 reviews)
When the experience was worth every penny. This will ruin every other hotel experience you’ll have it’s that good.
Reviewed on Mar 16, 2026

Hilton Chicago
Downtown Chicago
Price was ₩4,885,750, price is now ₩3,994,414 per person
₩3,994,414
per person
May 29 - Jun 1
found 6 hours ago
Roundtrip flight included
New York (NYC) to Chicago (ORD)
8.6/10 Excellent! (2,675 reviews)
This hotel is awesome for visiting Chicago. The staff were consistently attentive, respectful and helpful with suggestions. The hotel room was clean and the view we had was fantastic. The pool and hot tub were relaxing — easy to access and get fresh towels. The only minor criticism was that the hotel is an older building and shows some wear and tear — if I owned it, I’d invest in new flooring because the old carpet is super gross. That said, for what we paid and what we got, we are extremely satisfied and glad we stayed at the Hilton, and will likely stay there again!
Reviewed on Mar 19, 2026

Staypineapple, An Iconic Hotel, The Loop
Downtown Chicago
Price was ₩3,626,194, price is now ₩3,025,855 per person
₩3,025,855
per person
May 29 - Jun 1
found 6 hours ago
Roundtrip flight included
New York (NYC) to Chicago (ORD)
9.4/10 Exceptional! (1,021 reviews)
I would have rated all 5 star but the restaurant Atwood was closed and we weren’t notified in time to change plans!
The staff and (Mr.Brown ) were extremely accommodating! It was my bday and they decorated our room with all sorts of goodies including a hand made stuffed wash cloth doggie! Our housekeeper was amazing too!
The room decor is such fun and extremely clean! The only drawback is the rooms are very small and some not configured well!
All and all it’s a wonderful place to experience!!!!🍍
Reviewed on Mar 18, 2026

Arlo Chicago
Downtown Chicago
Price was ₩3,783,306, price is now ₩3,157,134 per person
₩3,157,134
per person
May 29 - Jun 1
found 6 hours ago
Roundtrip flight included
New York (NYC) to Chicago (ORD)
9.4/10 Exceptional! (2,019 reviews)
Felt a little like i was staying in a store with the amount of ads &
Reviewed on Mar 18, 2026
5* Kid friendly vacations in West Side
Price found within the past 48 hours. Click for updated prices.

Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ₩3,825,674, price is now ₩2,936,126 per person
₩2,936,126
per person
May 29 - Jun 1
found 6 hours ago
Roundtrip flight included
New York (NYC) to Chicago (ORD)
9.4/10 Exceptional! (1,852 reviews)
When the experience was worth every penny. This will ruin every other hotel experience you’ll have it’s that good.
Reviewed on Mar 16, 2026
3 Night Kid friendly vacations in West Side
Price found within the past 48 hours. Click for updated prices.

Eurostars Magnificent Mile
Downtown Chicago
Price was ₩3,371,724, price is now ₩2,602,647 per person
₩2,602,647
per person
May 29 - Jun 1
found 6 hours ago
Roundtrip flight included
New York (NYC) to Chicago (ORD)
9/10 Wonderful! (3,314 reviews)
Clean room nice staff, beautiful property. Enjoyed the deluxe room
Reviewed on Mar 20, 2026

Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ₩3,825,674, price is now ₩2,936,126 per person
₩2,936,126
per person
May 29 - Jun 1
found 6 hours ago
Roundtrip flight included
New York (NYC) to Chicago (ORD)
9.4/10 Exceptional! (1,852 reviews)
When the experience was worth every penny. This will ruin every other hotel experience you’ll have it’s that good.
Reviewed on Mar 16, 2026

Hilton Chicago
Downtown Chicago
Price was ₩4,885,750, price is now ₩3,994,414 per person
₩3,994,414
per person
May 29 - Jun 1
found 6 hours ago
Roundtrip flight included
New York (NYC) to Chicago (ORD)
8.6/10 Excellent! (2,675 reviews)
This hotel is awesome for visiting Chicago. The staff were consistently attentive, respectful and helpful with suggestions. The hotel room was clean and the view we had was fantastic. The pool and hot tub were relaxing — easy to access and get fresh towels. The only minor criticism was that the hotel is an older building and shows some wear and tear — if I owned it, I’d invest in new flooring because the old carpet is super gross. That said, for what we paid and what we got, we are extremely satisfied and glad we stayed at the Hilton, and will likely stay there again!
Reviewed on Mar 19, 2026
More Vacation Ideas
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
