Central Chicago Ski Vacations

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Top Ski vacation packages in Central Chicago

Price found within the past 48 hours. Click for updated prices.
The Allegro Royal Sonesta Hotel Chicago Loop

The Allegro Royal Sonesta Hotel Chicago Loop

Downtown Chicago
￥948,423
per person
Nov 9 - Nov 13
found 13 hours ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9/10 Wonderful! (2,907 reviews)
Very helpful staff and excellent location.

Reviewed on Sep 30, 2026

LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

Downtown Chicago
￥971,866
per person
Nov 9 - Nov 13
found 13 hours ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.4/10 Exceptional! (3,867 reviews)
Mediocre experience

Reviewed on Sep 30, 2026

InterContinental Chicago Magnificent Mile by IHG

InterContinental Chicago Magnificent Mile by IHG

Downtown Chicago
￥972,629
per person
Nov 9 - Nov 13
found 13 hours ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.2/10 Wonderful! (3,324 reviews)
It was clean

Reviewed on Sep 30, 2026

Swissotel - Chicago

Swissotel - Chicago

Downtown Chicago
￥1,034,982
per person
Nov 9 - Nov 13
found 13 hours ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9/10 Wonderful! (3,518 reviews)
N/C

Reviewed on Sep 30, 2026

Omni Chicago Hotel

Omni Chicago Hotel

Downtown Chicago
￥956,452
per person
Nov 9 - Nov 13
found 13 hours ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.2/10 Wonderful! (2,095 reviews)
Don't see what you're looking for?
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5* Ski vacations in Central Chicago

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

The St. Regis Chicago

Downtown Chicago
￥1,124,477
per person
Nov 9 - Nov 13
found 13 hours ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.4/10 Exceptional! (131 reviews)
The Langham, Chicago

The Langham, Chicago

Downtown Chicago
￥1,155,664
per person
Nov 9 - Nov 13
found 13 hours ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.8/10 Exceptional! (1,005 reviews)
The Peninsula Chicago

The Peninsula Chicago

Downtown Chicago
￥1,217,536
per person
Nov 9 - Nov 13
found 13 hours ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.8/10 Exceptional! (1,010 reviews)
It is the greatest will be there again

Reviewed on Sep 29, 2026

Don't see what you're looking for?
See all available trips from Tokyo to Central Chicago
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3 Night Ski vacations in Central Chicago

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

Hotel Riu Plaza Chicago

Downtown Chicago
￥288,162
per person
Nov 10 - Nov 13
found 7 hours ago
Roundtrip flight included
Fukuoka (FUK) to Chicago (ORD)
9.4/10 Exceptional! (5,340 reviews)
Recomiendo ampliamente este hotel, está magnificamente ubicado, a unos pasos de Michigan avenue. Las habitaciones son amplias y muy cómodas, el personal es sumamente atento, el bufete del desayuno delicioso y el piso 27 increíble para tomar copa o cena! Fabuloso hotel!

Reviewed on Sep 30, 2026

The Talbott, Autograph Collection

The Talbott, Autograph Collection

Downtown Chicago
￥292,314
per person
Nov 10 - Nov 13
found 7 hours ago
Roundtrip flight included
Fukuoka (FUK) to Chicago (ORD)
9.4/10 Exceptional! (178 reviews)
Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

Downtown Chicago
￥295,242
per person
Nov 10 - Nov 13
found 7 hours ago
Roundtrip flight included
Fukuoka (FUK) to Chicago (ORD)
8.8/10 Excellent! (2,314 reviews)
Loved it here. Will be back again!

Reviewed on Sep 30, 2026

Don't see what you're looking for?
See all available trips from Fukuoka to Central Chicago
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4 Night Ski vacations in Central Chicago

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

Hotel Riu Plaza Chicago

Downtown Chicago
￥946,412
per person
Nov 9 - Nov 13
found 13 hours ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.4/10 Exceptional! (5,340 reviews)
Recomiendo ampliamente este hotel, está magnificamente ubicado, a unos pasos de Michigan avenue. Las habitaciones son amplias y muy cómodas, el personal es sumamente atento, el bufete del desayuno delicioso y el piso 27 increíble para tomar copa o cena! Fabuloso hotel!

Reviewed on Sep 30, 2026

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

Downtown Chicago
￥1,033,292
per person
Nov 9 - Nov 13
found 13 hours ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.6/10 Exceptional! (2,025 reviews)
The Talbott, Autograph Collection

The Talbott, Autograph Collection

Downtown Chicago
￥950,431
per person
Nov 9 - Nov 13
found 13 hours ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.4/10 Exceptional! (178 reviews)
Don't see what you're looking for?
See all available trips from Tokyo to Central Chicago
View all trips

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
Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

￥3,853
per adult
90% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
See all activities in Central Chicago
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.