Northwest Side Luxury Vacations
Book a Luxury Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to ￥109,000 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 Luxury vacation packages in Northwest Side
Price found within the past 48 hours. Click for updated prices.
Swissotel - Chicago
Downtown Chicago
￥360,552
per person
Sep 18 - Sep 22
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9/10 Wonderful! (3,537 reviews)
Beautiful stay along the riverwalk. Pretty easy to get to public transportation as well as much to do within walking distance. The hotel was clean and well taken care of. We enjoyed to larger gym hotel with plenty of equipment.
Reviewed on Aug 11, 2026
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See all available trips from Tokyo to Northwest Side
View all trips5* Luxury vacations in Northwest Side
Price found within the past 48 hours. Click for updated prices.
Nobu Hotel Chicago
Downtown Chicago
￥390,758
per person
Sep 17 - Sep 20
found 6 hours ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.4/10 Exceptional! (891 reviews)
We had a terrific weekend stay! The staff was so friendly and the room was wonderful with a very comfortable bed. Location is very convenient, as well.
Reviewed on Aug 10, 2026
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See all available trips from Osaka to Northwest Side
View all trips3 Night Luxury vacations in Northwest Side
Price found within the past 48 hours. Click for updated prices.
Don't see what you're looking for?
See all available trips from Tokyo to Northwest Side
View all trips4 Night Luxury vacations in Northwest Side
Price found within the past 48 hours. Click for updated prices.
Swissotel - Chicago
Downtown Chicago
￥360,552
per person
Sep 18 - Sep 22
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9/10 Wonderful! (3,537 reviews)
Beautiful stay along the riverwalk. Pretty easy to get to public transportation as well as much to do within walking distance. The hotel was clean and well taken care of. We enjoyed to larger gym hotel with plenty of equipment.
Reviewed on Aug 11, 2026
Don't see what you're looking for?
See all available trips from Osaka to Northwest Side
View all tripsThings to do
Chicago: Navy Pier Centennial Wheel Ticket
￥3,920
per adult
90% of travellers recommend
Chicago: Willis Tower Skydeck and The Ledge Ticket
￥7,518
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.
