Far Southeast Side Ski Vacations

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Top Ski vacation packages in Far Southeast Side

Price found within the past 48 hours. Click for updated prices.
Kimpton Gray Hotel by IHG

Kimpton Gray Hotel by IHG

Downtown Chicago
¥300,954
per person
Nov 9 - Nov 14
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,008 reviews)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

Downtown Chicago
Save 100% on your flight
¥475,652
per person
Oct 8 - Oct 13
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.4/10 Exceptional! (5,045 reviews)
Wonderful hotel in a GREAT location with comfy King beds and a super breakfast! We will come beck here when in Chi-Town.

Reviewed on Aug 28, 2026

The Peninsula Chicago

The Peninsula Chicago

Downtown Chicago
¥490,695
per person
Nov 9 - Nov 14
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.8/10 Exceptional! (1,006 reviews)
The service and the staff iare incredible, do professional!! So many details! My husband and I were so happy!!

Reviewed on Aug 25, 2026

Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

Downtown Chicago
¥411,548
per person
Oct 8 - Oct 13
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
8.2/10 Very Good! (2,960 reviews)
I enjoyed my stay here. Clean room, great bed. Slept great. My room was adjoined to the room next door and I could hear the neighbors pretty clearly. The phone also was not working when I tried to dial for the front desk to ask a question. Despite these little issues, I really enjoyed my stay. Very friendly staff, nice amenities (gym, fun lobby) and amazing location. Would recommend and stay again.

Reviewed on Aug 28, 2026

Silversmith Hotel Chicago Downtown

Silversmith Hotel Chicago Downtown

Downtown Chicago
¥499,970
per person
Oct 8 - Oct 13
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.2/10 Wonderful! (2,373 reviews)
Clean property and nice staff! Used a nearby parking garage instead of the valet

Reviewed on Aug 28, 2026

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5* Ski vacations in Far Southeast Side

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

The Peninsula Chicago

Downtown Chicago
¥490,695
per person
Nov 9 - Nov 14
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.8/10 Exceptional! (1,006 reviews)
The service and the staff iare incredible, do professional!! So many details! My husband and I were so happy!!

Reviewed on Aug 25, 2026

Don't see what you're looking for?
See all available trips from Tokyo to Far Southeast Side
View all trips

Things to do

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

¥4,309
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

¥3,920
per adult
90% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
Chicago: Willis Tower Skydeck and The Ledge Ticket

Chicago: Willis Tower Skydeck and The Ledge Ticket

¥7,518
per adult
88% of travellers recommend
Chicago: Willis Tower Skydeck and The Ledge Ticket
See all activities in Far Southeast Side
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.