South Side Ski Vacations

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Top Ski vacation packages in South Side

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

The Talbott, Autograph Collection

Downtown Chicago
￥488,138
per person
Nov 2 - Nov 7
found 22 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (165 reviews)
LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

Downtown Chicago
￥521,955
per person
Nov 2 - Nov 7
found 22 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (3,839 reviews)
Great location! Would stay again!

Reviewed on Sep 23, 2026

InterContinental Chicago Magnificent Mile by IHG

InterContinental Chicago Magnificent Mile by IHG

Downtown Chicago
￥520,458
per person
Nov 2 - Nov 7
found 22 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (3,269 reviews)
The Peninsula Chicago

The Peninsula Chicago

Downtown Chicago
￥751,216
per person
Nov 2 - Nov 7
found 22 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.8/10 Exceptional! (1,001 reviews)
This place was everything!! The location, comfort, food and the stamp was top tier!!!

Reviewed on Sep 23, 2026

Swissotel - Chicago

Swissotel - Chicago

Downtown Chicago
￥569,334
per person
Nov 2 - Nov 7
found 22 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9/10 Wonderful! (3,512 reviews)
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5* Ski vacations in South Side

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

Trump International Hotel & Tower Chicago

Downtown Chicago
￥399,523
per person
Nov 16 - Nov 20
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.6/10 Exceptional! (1,995 reviews)
Four Seasons Hotel Chicago

Four Seasons Hotel Chicago

Downtown Chicago
￥498,178
per person
Nov 16 - Nov 20
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,004 reviews)
The Peninsula Chicago

The Peninsula Chicago

Downtown Chicago
￥751,216
per person
Nov 2 - Nov 7
found 22 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.8/10 Exceptional! (1,001 reviews)
This place was everything!! The location, comfort, food and the stamp was top tier!!!

Reviewed on Sep 23, 2026

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4 Night Ski vacations in South Side

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

Hotel Riu Plaza Chicago

Downtown Chicago
￥327,052
per person
Nov 16 - Nov 20
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (5,174 reviews)
The hotel room is clean but blood stain spotted on the bedsheet.

Reviewed on Sep 23, 2026

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

Downtown Chicago
￥399,523
per person
Nov 16 - Nov 20
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.6/10 Exceptional! (1,995 reviews)
Kimpton Gray Hotel by IHG

Kimpton Gray Hotel by IHG

Downtown Chicago
￥389,041
per person
Nov 16 - Nov 20
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,010 reviews)
Don't see what you're looking for?
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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 South Side
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.