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.
Pendry Chicago
Downtown Chicago
Price was ￥193,688, price is now ￥157,344 per person
￥157,344
per person
Apr 2 - Apr 5
found 15 hours ago
Roundtrip non-stop flight included
Taipei (TPE) to Chicago (ORD)
9.4/10 Exceptional! (1,130 reviews)
Best hotel ive ever stayed in. Perfect location for moving around Chicago. Everyone helpful, had a great time.
Reviewed on Jan 5, 2026
theWit Chicago, a Hilton Hotel
Downtown Chicago
Price was ￥201,891, price is now ￥158,192 per person
￥158,192
per person
Apr 2 - Apr 5
found 15 hours ago
Roundtrip non-stop flight included
Taipei (TPE) to Chicago (ORD)
9/10 Wonderful! (1,001 reviews)
Perfect location, comfortable and clean room
Reviewed on Jan 5, 2026
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ￥246,658, price is now ￥195,565 per person
￥195,565
per person
Apr 2 - Apr 5
found 15 hours ago
Roundtrip non-stop flight included
Taipei (TPE) to Chicago (ORD)
9.4/10 Exceptional! (1,773 reviews)
Stayed in a river view room over NYE and had a great view of the fireworks show on the river! The staff was superb and went above and beyond for us. Extremely kind and knowledgeable. Cannot wait to stay again!
Reviewed on Jan 3, 2026
Level Chicago – Old Town
Downtown Chicago
Price was ￥204,093, price is now ￥164,227 per person
￥164,227
per person
Apr 2 - Apr 5
found 15 hours ago
Roundtrip non-stop flight included
Taipei (TPE) to Chicago (ORD)
9/10 Wonderful! (380 reviews)
Staff was friendly did amazing job with checking us in
Reviewed on Dec 25, 2025
Level Chicago - River North
Downtown Chicago
Price was ￥200,956, price is now ￥163,054 per person
￥163,054
per person
Apr 2 - Apr 5
found 15 hours ago
Roundtrip non-stop flight included
Taipei (TPE) to Chicago (ORD)
9/10 Wonderful! (766 reviews)
We absolutely love staying here! It’s fantastic every time!!
Reviewed on Jan 4, 2026
5* Ski vacations in South Side
Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ￥246,658, price is now ￥195,565 per person
￥195,565
per person
Apr 2 - Apr 5
found 15 hours ago
Roundtrip non-stop flight included
Taipei (TPE) to Chicago (ORD)
9.4/10 Exceptional! (1,773 reviews)
Stayed in a river view room over NYE and had a great view of the fireworks show on the river! The staff was superb and went above and beyond for us. Extremely kind and knowledgeable. Cannot wait to stay again!
Reviewed on Jan 3, 2026
Park Hyatt Chicago
Downtown Chicago
Price was ￥245,186, price is now ￥214,434 per person
￥214,434
per person
Apr 2 - Apr 5
found 15 hours ago
Roundtrip non-stop flight included
Taipei (TPE) to Chicago (ORD)
9.6/10 Exceptional! (1,000 reviews)
Room was excellent. Everything was clean and the amenities were fantastic. Staff was very warm and helpful. Will go back
Reviewed on Jan 2, 2026
3 Night Ski vacations in South Side
Price found within the past 48 hours. Click for updated prices.
theWit Chicago, a Hilton Hotel
Downtown Chicago
Price was ￥201,891, price is now ￥158,192 per person
￥158,192
per person
Apr 2 - Apr 5
found 15 hours ago
Roundtrip non-stop flight included
Taipei (TPE) to Chicago (ORD)
9/10 Wonderful! (1,001 reviews)
Perfect location, comfortable and clean room
Reviewed on Jan 5, 2026
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ￥246,658, price is now ￥195,565 per person
￥195,565
per person
Apr 2 - Apr 5
found 15 hours ago
Roundtrip non-stop flight included
Taipei (TPE) to Chicago (ORD)
9.4/10 Exceptional! (1,773 reviews)
Stayed in a river view room over NYE and had a great view of the fireworks show on the river! The staff was superb and went above and beyond for us. Extremely kind and knowledgeable. Cannot wait to stay again!
Reviewed on Jan 3, 2026
Level Chicago – Old Town
Downtown Chicago
Price was ￥204,093, price is now ￥164,227 per person
￥164,227
per person
Apr 2 - Apr 5
found 15 hours ago
Roundtrip non-stop flight included
Taipei (TPE) to Chicago (ORD)
9/10 Wonderful! (380 reviews)
Staff was friendly did amazing job with checking us in
Reviewed on Dec 25, 2025
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
