Far Southeast Side Ski Vacations 2026

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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

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

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

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

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