West 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 West Side
Price found within the past 48 hours. Click for updated prices.
Level Chicago Fulton Market
Downtown Chicago
￥379,826
per person
Oct 1 - Oct 8
found 14 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (544 reviews)
My go to place to stay. Luxurious, travel-friendly rooms, excellent pool/hot tub area outside, and great workout facilities. Fantastic location next to Fulton Market. The desk staff is always exceptional and helpful.
Reviewed on Aug 12, 2026
Hotel Riu Plaza Chicago
Downtown Chicago
￥405,665
per person
Oct 1 - Oct 8
found 14 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (4,907 reviews)
I had an amazing time at the hotel. The employees were helpful and the rooftop view is amazing.
Reviewed on Aug 17, 2026
Trump International Hotel & Tower Chicago
Downtown Chicago
￥523,290
per person
Oct 1 - Oct 8
found 14 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.6/10 Exceptional! (1,960 reviews)
This is an excellent 5 star hotel. So accommodating in every way possible. This is the second time I have stayed at this Chicago property.
Reviewed on Aug 16, 2026
5* Luxury vacations in West Side
Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago
Downtown Chicago
￥523,290
per person
Oct 1 - Oct 8
found 14 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.6/10 Exceptional! (1,960 reviews)
This is an excellent 5 star hotel. So accommodating in every way possible. This is the second time I have stayed at this Chicago property.
Reviewed on Aug 16, 2026
3 Night Luxury vacations in West Side
Price found within the past 48 hours. Click for updated prices.
The Allegro Royal Sonesta Hotel Chicago Loop
Downtown Chicago
￥254,960
per person
Sep 26 - Sep 29
found 20 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9/10 Wonderful! (2,720 reviews)
We really enjoyed our stay. It’s a great location with exciting decor (even in the hotel key cards), and the staff SO helpful when we arrived a bit early, and when we wanted to keep our bag a bit longer before our train. We appreciated the smart TV with streaming services, and the availability of a cold fridge.
Reviewed on Aug 17, 2026
Swissotel - Chicago
Downtown Chicago
￥273,841
per person
Sep 26 - Sep 29
found 20 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9/10 Wonderful! (3,537 reviews)
Always a great stay at The Swiss. Got upgraded to a corner room at no charge. Great views of the lake and the river. Paloma’s at the bar were great. Breakfast was awesome as well. Had the croissant sandwich and Belgian waffle.
Reviewed on Aug 17, 2026
Things 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.
