West Side Luxury Vacations

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Top Luxury vacation packages in West Side

Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

Downtown Chicago
¥368,468
per person
Dec 11 - Dec 17
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (5,404 reviews)
The hotel was very nice and private, the workers were nice and friendly. We got to check in early and get right in. The breakfast was also great. Really enjoyed my stay

Reviewed on Oct 25, 2026

The Talbott, Autograph Collection

The Talbott, Autograph Collection

Downtown Chicago
¥379,358
per person
Dec 11 - Dec 17
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (185 reviews)
Nice property overall Room was very nice Location excellent

Reviewed on Oct 19, 2026

Swissotel - Chicago

Swissotel - Chicago

Downtown Chicago
¥370,788
per person
Dec 11 - Dec 17
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9/10 Wonderful! (3,523 reviews)
LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

Downtown Chicago
¥377,307
per person
Dec 11 - Dec 17
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (3,881 reviews)
Kimpton Gray Hotel by IHG

Kimpton Gray Hotel by IHG

Downtown Chicago
¥494,025
per person
Jan 3 - Jan 9
found 5 hours ago
Roundtrip flight included
Tokyo (HND) to Chicago (ORD)
9.4/10 Exceptional! (1,005 reviews)
Amazing hotel ! Would def stay again

Reviewed on Oct 23, 2026

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5* Luxury vacations in West Side

Price found within the past 48 hours. Click for updated prices.
The Peninsula Chicago

The Peninsula Chicago

Downtown Chicago
¥692,397
per person
Dec 11 - Dec 17
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.8/10 Exceptional! (1,000 reviews)
Don't see what you're looking for?
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Things to do

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

¥3,812
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Art Institute of Chicago

Art Institute of Chicago

¥6,275
per adult
92% of travellers recommend
Art Institute of Chicago
Skydeck Chicago at Willis Tower

Skydeck Chicago at Willis Tower

¥6,642
per adult
88% of travellers recommend
Skydeck Chicago at Willis Tower
See all activities in West Side
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.