Northwest Side Luxury Vacations
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Top Luxury vacation packages in Northwest Side
Price found within the past 48 hours. Click for updated prices.
Sofitel Chicago Magnificent Mile
Downtown Chicago
Price was ￥218,096, price is now ￥176,152 per person
￥176,152
per person
Feb 20 - Feb 25
found 1 hour ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (2,210 reviews)
Lovely hotel! Exceptionally clean and affordable!
Reviewed on Dec 14, 2025
La Banque Hotel
Price was ￥243,452, price is now ￥191,074 per person
￥191,074
per person
Feb 20 - Feb 25
found 1 hour ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (447 reviews)
The room was spotless and the staff was good. Loved the hotel. Was just an overnight stay. Wish we had stayed another day. Loved the area.
Reviewed on Nov 30, 2025
Fairmont Chicago at Millennium Park Gold Experience
Downtown Chicago
Price was ￥277,445, price is now ￥222,152 per person
￥222,152
per person
Feb 20 - Feb 25
found 1 hour ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (137 reviews)
My wife and I really enjoyed our stay at this location. The accommodations were very nice. However, what really stuck out was the hotel staff, its the best that we have experienced.
Reviewed on Sep 5, 2025
Omni Chicago Hotel
Downtown Chicago
Price was ￥221,092, price is now ￥179,168 per person
￥179,168
per person
Feb 20 - Feb 25
found 1 hour ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (1,603 reviews)
Lovely hotel. Comfy beds, spacious suites. Very helpful staff, bar and restaurant were great. They let us checkin and get our suite at 1030 am. If you join their loyalty program you get a free drink at the bar and checkout is at 12 pm. Highly recommend
Reviewed on Dec 14, 2025
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View all trips5* Luxury vacations in Northwest Side
Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ￥303,782, price is now ￥233,526 per person
￥233,526
per person
Feb 17 - Feb 22
found 20 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,773 reviews)
Pablo at reception was the most amazing! Amazing service, beautiful view, convenient location. Excellent hotel. Only thing for improvement would be better lighting in the bathroom.
Reviewed on Dec 14, 2025
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View all trips3 Night Luxury vacations in Northwest Side
Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ￥340,442, price is now ￥285,286 per person
￥285,286
per person
Jan 18 - Jan 21
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,773 reviews)
Pablo at reception was the most amazing! Amazing service, beautiful view, convenient location. Excellent hotel. Only thing for improvement would be better lighting in the bathroom.
Reviewed on Dec 14, 2025
Waldorf Astoria Chicago
Downtown Chicago
Price was ￥365,139, price is now ￥303,184 per person
￥303,184
per person
Jan 18 - Jan 21
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,000 reviews)
Absolutely fantastic hotel great service, you couldn’t ask for more.
Reviewed on Dec 3, 2025
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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.
