
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.

Virgin Hotels Chicago
Downtown Chicago
Price was ¥356,500, price is now ¥282,804 per person
¥282,804
per person
May 1 - May 6
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (1,404 reviews)
Room was very clean, staff was very pleasant. Will definitely return
Reviewed on Feb 15, 2026

Level Chicago Fulton Market
Downtown Chicago
Price was ¥392,480, price is now ¥289,232 per person
¥289,232
per person
May 1 - May 6
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (347 reviews)
Room smelled like food but overall very clean, very great service and staff both night and morning shift.
Reviewed on Feb 16, 2026

Waldorf Astoria Chicago
Downtown Chicago
Price was ¥495,038, price is now ¥377,150 per person
¥377,150
per person
May 1 - May 6
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,000 reviews)
Completely loved our stay. Probably the best hotel in all Chicago. Amenities are great and the staff are even better.
Reviewed on Jan 26, 2026

Stay One Chicago
Downtown Chicago
Price was ¥473,903, price is now ¥388,238 per person
¥388,238
per person
May 1 - May 6
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
No reviews
The property was great, the room was awesome! The "Stay One Chicago" is really just a name on paper, and maybe one employee who is physically at the property. I am pretty sure that he wasn't even directly employed by the "hotel".
So in a nutshell, the organization has not worked out any kind of structure for checking in other than the guy that told us to download the Door, OR the Latch app. He said that the app is very difficult to get logged into.
Long story made short, we wasted the 1st 2 hours in the hotel trying to get the app (both my wife and I).
The app never worked, and we finally got physical key cards from the guy working for the building.
There was one small piece of paper with scan codes for restaurants, but zero property maps, rules, room cleaning, and nothing explaining how to get to, or use any of the amenities. It was the worst 1st 3 hours of a vacation that we have experienced.
I still gave it a 4-star because the local people were so nice and helpful, even though helping us wasn't part of their job. The valet guys were the best, super nice, and helpful.
Reviewed on Feb 10, 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 ¥311,900, price is now ¥264,126 per person
¥264,126
per person
May 14 - May 16
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,773 reviews)
The view from our room was amazing. Everyone their is friendly and willing to help. The hotel is clean and inviting. Would recommend ten stars if I could.
Reviewed on Feb 22, 2026

Waldorf Astoria Chicago
Downtown Chicago
Price was ¥495,038, price is now ¥377,150 per person
¥377,150
per person
May 1 - May 6
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,000 reviews)
Completely loved our stay. Probably the best hotel in all Chicago. Amenities are great and the staff are even better.
Reviewed on Jan 26, 2026

Park Hyatt Chicago
Downtown Chicago
Price was ¥443,965, price is now ¥423,011 per person
¥423,011
per person
May 14 - May 16
found 1 day ago
Roundtrip flight included
Tokyo (TYO) to Chicago (ORD)
9.6/10 Exceptional! (1,000 reviews)
The staff were lovely. As it was our anniversary, we were given a beautiful room overlooking the water tower and the lake. The room was exceptional - the bath tub, huge! The hotel itself was within walking distance to almost everywhere - the lake, the river, the magnificent mile. There were cafes and restaurants very close by. We had a fantastic time in Chicago because of this!
Reviewed on Feb 20, 2026
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
