West Side Adventure Vacations
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- Plan, book, travel with confidence
- Better togetherSave up to ￥45,448 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
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Top Adventure vacation packages in West Side
Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ￥368,052, price is now ￥259,596 per person
￥259,596
per person
Feb 22 - Feb 27
found 6 hours ago
Roundtrip flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,773 reviews)
Loved it here and would stay again! Everything was perfect!
Reviewed on Dec 21, 2025
The Peninsula Chicago
Downtown Chicago
Price was ￥488,478, price is now ￥388,768 per person
￥388,768
per person
Jan 22 - Jan 27
found 11 hours ago
Roundtrip non-stop flight included
Tokyo (NRT) to Chicago (ORD)
9.8/10 Exceptional! (1,003 reviews)
Service and clean room - paying attention to the details
Reviewed on Dec 22, 2025
The Ritz-Carlton, Chicago
Downtown Chicago
Price was ￥334,192, price is now ￥268,350 per person
￥268,350
per person
Jan 22 - Jan 27
found 6 hours ago
Roundtrip non-stop flight included
Tokyo (NRT) to Chicago (ORD)
9.2/10 Wonderful! (1,002 reviews)
The room was spotless and the bed super comfy. The staff was very helpful and extremely courteous.
Reviewed on Dec 15, 2025
Hilton Chicago O'Hare Airport
O'Hare
Price was ￥363,475, price is now ￥308,896 per person
￥308,896
per person
Jan 22 - Jan 27
found 11 hours ago
Roundtrip non-stop flight included
Tokyo (NRT) to Chicago (ORD)
8.2/10 Very Good! (2,158 reviews)
It was ok. Wouldn’t want to stay longer than a night. Food was pretty bad, room cramped
Reviewed on Dec 23, 2025
5* Adventure vacations in West Side
Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ￥368,052, price is now ￥259,596 per person
￥259,596
per person
Feb 22 - Feb 27
found 6 hours ago
Roundtrip flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,773 reviews)
Loved it here and would stay again! Everything was perfect!
Reviewed on Dec 21, 2025
The Peninsula Chicago
Downtown Chicago
Price was ￥478,845, price is now ￥375,622 per person
￥375,622
per person
Feb 22 - Feb 27
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.8/10 Exceptional! (1,003 reviews)
Service and clean room - paying attention to the details
Reviewed on Dec 22, 2025
The Ritz-Carlton, Chicago
Downtown Chicago
Price was ￥334,192, price is now ￥268,350 per person
￥268,350
per person
Jan 22 - Jan 27
found 6 hours ago
Roundtrip non-stop flight included
Tokyo (NRT) to Chicago (ORD)
9.2/10 Wonderful! (1,002 reviews)
The room was spotless and the bed super comfy. The staff was very helpful and extremely courteous.
Reviewed on Dec 15, 2025
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
