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.
Hotel Saint Clair- Magnificent Mile
Downtown Chicago
₩1,032,580
per person
Nov 2 - Nov 6
found 22 hours ago
Roundtrip non-stop flight included
Lubbock (LBB) to Chicago (ORD)
8.4/10 Very Good! (2,089 reviews)
Nice and comfortable room plus a fitness center, definitely will stay again
Reviewed on Aug 17, 2026
Hotel Riu Plaza Chicago
Downtown Chicago
₩1,198,921
per person
Nov 2 - Nov 6
found 22 hours ago
Roundtrip non-stop flight included
Lubbock (LBB) to Chicago (ORD)
9.4/10 Exceptional! (4,907 reviews)
I stayed here for about five days with my boyfriend. The hotel was very nice and the staff was very helpful. The rooftop is beautiful with a great view. It’s right in the middle of downtown so it’s very walkable to any places if you’re planning on spending a lot of time in the city. I would recommend finding parking offsite compared to the hotel because that’s what’s easiest if you are traveling via car a lot and also the food isn’t very great but it’s just fine. Overall, this was a very nice day and I would most definitely recommend it if you’re staying with a partner or family.
Reviewed on Aug 17, 2026
5* Ski vacations in South Side
Price found within the past 48 hours. Click for updated prices.
The St. Regis Chicago
Downtown Chicago
₩3,465,344
per person
Nov 2 - Nov 6
found 22 hours ago
Roundtrip non-stop flight included
Lubbock (LBB) to Chicago (ORD)
9.4/10 Exceptional! (128 reviews)
One night at The St. Regis Chicago ✨ Beautiful views, incredible service, and the perfect little luxury escape in the heart of the city. Short stay, but absolutely worth it. 懶
Reviewed on Aug 15, 2026
4 Night Ski vacations in South Side
Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago
Downtown Chicago
₩1,198,921
per person
Nov 2 - Nov 6
found 22 hours ago
Roundtrip non-stop flight included
Lubbock (LBB) to Chicago (ORD)
9.4/10 Exceptional! (4,907 reviews)
I stayed here for about five days with my boyfriend. The hotel was very nice and the staff was very helpful. The rooftop is beautiful with a great view. It’s right in the middle of downtown so it’s very walkable to any places if you’re planning on spending a lot of time in the city. I would recommend finding parking offsite compared to the hotel because that’s what’s easiest if you are traveling via car a lot and also the food isn’t very great but it’s just fine. Overall, this was a very nice day and I would most definitely recommend it if you’re staying with a partner or family.
Reviewed on Aug 17, 2026
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
