Northwest Side All inclusive Vacations
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Top All inclusive vacation packages in Northwest Side
Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ￥548,432, price is now ￥396,654 per person
￥396,654
per person
May 14 - May 19
found 22 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,773 reviews)
The view from our room was amazing. Everyone their is friendly and willing to help. The hotel is clean and inviting. Would recommend ten stars if I could.
Reviewed on Feb 22, 2026
Virgin Hotels Chicago
Downtown Chicago
Price was ￥386,440, price is now ￥294,140 per person
￥294,140
per person
May 14 - May 19
found 22 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (1,404 reviews)
Room was very clean, staff was very pleasant. Will definitely return
Reviewed on Feb 15, 2026
Fairmont Chicago at Millennium Park
Downtown Chicago
Price was ￥436,495, price is now ￥348,258 per person
￥348,258
per person
May 14 - May 19
found 22 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
8.6/10 Excellent! (2,008 reviews)
Big rooms, great location, and the view was amazing! We truly enjoyed our stay overall and the space was perfect for our family.
However, we were a family of 5 staying for 3 days and only received towels for 3 people. We had to request the missing towels each day. The same happened with the sofa bed there were no sheets or bedding provided, and we had to contact the front desk at night for them to bring it.
Other than that, we loved our stay and would definitely come back!
Reviewed on Feb 21, 2026
River Hotel
Downtown Chicago
Price was ￥352,675, price is now ￥296,551 per person
￥296,551
per person
May 14 - May 19
found 22 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
8.8/10 Excellent! (4,800 reviews)
The room was exactly as advertised, efficient, clean , and priced right.
Reviewed on Feb 22, 2026
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View all trips5* All inclusive vacations in Northwest Side
Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ￥548,432, price is now ￥396,654 per person
￥396,654
per person
May 14 - May 19
found 22 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,773 reviews)
The view from our room was amazing. Everyone their is friendly and willing to help. The hotel is clean and inviting. Would recommend ten stars if I could.
Reviewed on Feb 22, 2026
Park Hyatt Chicago
Downtown Chicago
Price was ￥443,965, price is now ￥423,011 per person
￥423,011
per person
May 14 - May 16
found 1 day ago
Roundtrip flight included
Tokyo (TYO) to Chicago (ORD)
9.6/10 Exceptional! (1,000 reviews)
The staff were lovely. As it was our anniversary, we were given a beautiful room overlooking the water tower and the lake. The room was exceptional - the bath tub, huge! The hotel itself was within walking distance to almost everywhere - the lake, the river, the magnificent mile. There were cafes and restaurants very close by. We had a fantastic time in Chicago because of this!
Reviewed on Feb 20, 2026
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View all trips* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
