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.
The Talbott, Autograph Collection

The Talbott, Autograph Collection

Downtown Chicago
¥272,350
per person
Nov 11 - Nov 16
just found
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.4/10 Exceptional! (165 reviews)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

Downtown Chicago
¥298,628
per person
Nov 11 - Nov 16
just found
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.4/10 Exceptional! (5,174 reviews)
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

Downtown Chicago
¥335,978
per person
Nov 20 - Nov 24
found 1 day ago
Roundtrip non-stop flight included
Nagoya (NGO) to Chicago (ORD)
9.6/10 Exceptional! (1,995 reviews)
Level Chicago – Old Town

Level Chicago – Old Town

Downtown Chicago
¥304,436
per person
Nov 11 - Nov 16
just found
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.2/10 Wonderful! (520 reviews)
Great location wonderful. Room and amenities. Cafe in lobby very healthy options. Great spot to be in the Gold Coast

Reviewed on Sep 24, 2026

The Langham, Chicago

The Langham, Chicago

Downtown Chicago
¥421,529
per person
Nov 20 - Nov 24
found 1 day ago
Roundtrip non-stop flight included
Nagoya (NGO) to Chicago (ORD)
9.8/10 Exceptional! (1,004 reviews)
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5* Luxury vacations in Northwest Side

Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

Downtown Chicago
¥335,978
per person
Nov 20 - Nov 24
found 1 day ago
Roundtrip non-stop flight included
Nagoya (NGO) to Chicago (ORD)
9.6/10 Exceptional! (1,995 reviews)
The Langham, Chicago

The Langham, Chicago

Downtown Chicago
¥421,529
per person
Nov 20 - Nov 24
found 1 day ago
Roundtrip non-stop flight included
Nagoya (NGO) to Chicago (ORD)
9.8/10 Exceptional! (1,004 reviews)
Park Hyatt Chicago

Park Hyatt Chicago

Downtown Chicago
¥377,385
per person
Nov 20 - Nov 24
found 1 day ago
Roundtrip non-stop flight included
Nagoya (NGO) to Chicago (ORD)
9.6/10 Exceptional! (1,006 reviews)
Amazing

Reviewed on Sep 8, 2026

Don't see what you're looking for?
See all available trips from Nagoya to Northwest Side
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3 Night Luxury vacations in Northwest Side

Price found within the past 48 hours. Click for updated prices.
The Emily Hotel

The Emily Hotel

Downtown Chicago
¥341,100
per person
Nov 28 - Dec 1
found 6 hours ago
Roundtrip flight included
Fukuoka (FUK) to Chicago (ORD)
9.2/10 Wonderful! (1,338 reviews)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

Downtown Chicago
¥401,298
per person
Nov 29 - Dec 2
found 6 hours ago
Roundtrip flight included
Fukuoka (FUK) to Chicago (ORD)
9.4/10 Exceptional! (5,174 reviews)
Kimpton Gray Hotel by IHG

Kimpton Gray Hotel by IHG

Downtown Chicago
¥354,134
per person
Nov 28 - Dec 1
found 6 hours ago
Roundtrip flight included
Fukuoka (FUK) to Chicago (ORD)
9.4/10 Exceptional! (1,010 reviews)
Don't see what you're looking for?
See all available trips from Fukuoka to Northwest Side
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4 Night Luxury vacations in Northwest Side

Price found within the past 48 hours. Click for updated prices.
The Talbott, Autograph Collection

The Talbott, Autograph Collection

Downtown Chicago
¥334,432
per person
Nov 28 - Dec 2
found 6 hours ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.4/10 Exceptional! (165 reviews)
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

Downtown Chicago
¥335,978
per person
Nov 20 - Nov 24
found 1 day ago
Roundtrip non-stop flight included
Nagoya (NGO) to Chicago (ORD)
9.6/10 Exceptional! (1,995 reviews)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

Downtown Chicago
¥380,770
per person
Nov 28 - Dec 2
found 6 hours ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.4/10 Exceptional! (5,174 reviews)
Don't see what you're looking for?
See all available trips from Tokyo to Northwest Side
View all trips

Things to do

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

¥4,272
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Art Institute of Chicago

Art Institute of Chicago

¥6,404
per adult
92% of travellers recommend
Art Institute of Chicago
Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

¥3,886
per adult
90% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
See all activities in Northwest Side
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.