South Side Ski Vacations
Book a Ski Hotel + Flight or Car together to unlock savings
Photo by by Midway Intl Airport
- Plan, book, travel with confidence
- Better togetherSave up to ₩234,741 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Top Ski vacation packages in South Side
Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago
Downtown Chicago
Save 100% on your flight
Price was ₩1,216,372, price is now ₩830,252 per person
₩830,252
per person
Dec 23 - Dec 25
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Chicago (ORD)
9.4/10 Exceptional! (1,761 reviews)
The Trump International Hotel was absolutely immaculate in appearance and the entire staff were fantastic in all aspects. The location is extremely desirable and within walking distance to numerous restaurants and attractions. However, my suite was somewhat underwhelming in regard to the bathroom. The deep soaking bathtub was smaller in scale than one would expect, and more specifically the shower head is set far too low for those of us who are six feet or taller. I would recommend this property.
Reviewed on Nov 3, 2025
Hotel Riu Plaza Chicago
Downtown Chicago
Price was ₩637,230, price is now ₩494,326 per person
₩494,326
per person
Dec 23 - Dec 25
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Chicago (ORD)
9.4/10 Exceptional! (2,602 reviews)
Nice hotel, very clean and the buffet breakfast was excellent
Reviewed on Nov 6, 2025
5* Ski vacations in South Side
Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago
Downtown Chicago
Save 100% on your flight
Price was ₩1,216,372, price is now ₩830,252 per person
₩830,252
per person
Dec 23 - Dec 25
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Chicago (ORD)
9.4/10 Exceptional! (1,761 reviews)
The Trump International Hotel was absolutely immaculate in appearance and the entire staff were fantastic in all aspects. The location is extremely desirable and within walking distance to numerous restaurants and attractions. However, my suite was somewhat underwhelming in regard to the bathroom. The deep soaking bathtub was smaller in scale than one would expect, and more specifically the shower head is set far too low for those of us who are six feet or taller. I would recommend this property.
Reviewed on Nov 3, 2025
Nobu Hotel Chicago
Downtown Chicago
Price was ₩1,020,058, price is now ₩884,109 per person
₩884,109
per person
Dec 23 - Dec 25
found 12 hours ago
Roundtrip flight included
Toronto (YYZ) to Chicago (ORD)
9.4/10 Exceptional! (736 reviews)
This hotel is amazing! All of the staff we encountered were so helpful, kind, and very attentive. The hotel is beautiful and the zen suite is amazing. Highly recommend!
Reviewed on Oct 26, 2025
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
