South Side Ski Chalets
8 Guests
1 Bedroom
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Kitchen
- Air Conditioner
US $1,380/Night
For 7 Nights US $9,662
1851.39 ft²
12 Guests
6 Bedrooms
4 Bathrooms
Family Friendly
Apartment
- Fireplace/Heating
- Pet Friendly
- Parking
US $1,136/Night
For 7 Nights US $7,951
1 Bedroom
1 Bathroom
Family Friendly
Hotel
- Breakfast
- Kitchen
- Parking
US $157/Night
For 7 Nights US $1,102
10 Guests
4 Bedrooms
2 Bathrooms
Family Friendly
Apartment
- Fireplace/Heating
- Kitchen
- Air Conditioner
US $1,106/Night
For 7 Nights US $7,745
796.53 ft²
8 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
Apartment
- Fireplace/Heating
- Pet Friendly
- Parking
US $253/Night
For 7 Nights US $1,771
12 Guests
4 Bedrooms
2 Bathrooms
Family Friendly
Apartment
- Fireplace/Heating
- Kitchen
- Air Conditioner
US $830/Night
For 7 Nights US $5,808
8611.13 ft²
8 Guests
2 Bedrooms
2 Bathrooms
Apartment
- Fireplace/Heating
- Pet Friendly
- Parking
US $353/Night
For 7 Nights US $2,471
2110 ft²
8 Guests
4 Bedrooms
2 Bathrooms
Family Friendly
Apartment
- Fireplace/Heating
- Kitchen
- Air Conditioner
US $808/Night
For 7 Nights US $5,659
2723.27 ft²
12 Guests
6 Bedrooms
3 Bathrooms
Family Friendly
Apartment
- Fireplace/Heating
- Pet Friendly
- Parking
US $1,181/Night
For 7 Nights US $8,267
937 ft²
6 Guests
3 Bedrooms
2 Bathrooms
Family Friendly
Apartment
- Fireplace/Heating
- Kitchen
- Air Conditioner
US $604/Night
For 7 Nights US $4,227
3767.37 ft²
8 Guests
3 Bedrooms
1 Bathroom
Group Friendly
Apartment
- Fireplace/Heating
- Air Conditioner
- Internet
US $979/Night
For 7 Nights US $6,853
6 Guests
3 Bedrooms
2 Bathrooms
Family Friendly
Apartment
- Fireplace/Heating
- Kitchen
- Air Conditioner
US $560/Night
For 7 Nights US $3,919
Why Choose Rent By Owner for your South Side Ski Chalets?
What makes our Ski Chalets special?
Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.
Weekly Weather Forecast for South Side
How to Book Your South Side Ski Chalets
What's our booking process?
Our platform allows you to browse a curated selection of ski chalets. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.
Booking Steps
01
Search Properties
Use our filters to find the right property that fits your needs.
02
Select a Rental
Click on your preferred listing to view details, amenities, and pricing.
03
Book Online
Follow the link to finalize your reservation directly on the partner’s website.
Explore and book the perfect rental in South Side
Common Ski Chalets Amenities
What amenities can you expect?
Our Ski Chalets are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:
Indoor Features
- Fully-equipped kitchens with modern appliances
- Comfortable living areas with flat-screen TVs
- Free Wi-Fi for staying connected
- Air conditioning and heating for year-round comfort
- In-unit washers and dryers for convenience
- Luxurious bedrooms with premium bedding
- Spa-like bathrooms with soaking tubs or walk-in showers
Other Places to Stay in South Side, IL
Dearborn Park
Film Row Cinema
Gen. John Logan Memorial
Ping Tom Memorial Park
Field Museum of Natural History
Olmec Head No 8
John G. Shedd Aquarium
National Vietnam Veterans Art Museum
Chinatown
South Loop
Near South Side
Prairie District
South Side Ski Chalets Frequently Asked Questions
1. What are the top Ski Chalets in South Side?
There are a lot of options in South Side. If you plan on staying in the South Side area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Ski Chalets in South Side:
- 1 #33 - 4 Bedroom/2 Bath Condo near McCormick Place, Wintrust Arena, Chinatown
- Chic 2-Bedroom Townhouse with Rooftop, Free Parking, in Downtown Chicago!
- Downtown MICH AVE #20, Grant Park, Museums 2bd/2ba
- Luxéry Stay "Hollywood" Downtown/McCormick/WinTrust Area
- Comfy 3BR Chicago Retreat 420 Friendly Unit Near McCormick Place & Soldier Field
- McCormick 3B/2Ba w optional parking/Up to 8 guests
- McCormick Apt 3BR Corner Oasis Near Soldier Field & Museum Campus
- Spacious 3BR Corner Family Oasis Near McCormick Place & Soldier Field
- Luxéry Stay "Chicago" Downtown/McCormick/Wintrust Area
- Luxéry Stay South Loop - McCormick/Wintrust Area
2. How many Ski Chalets are available in South Side?
Currently, the total number of properties listed by RBO in 2026 is over 571 in the South Side area, and still counting. By aggregating listings from multiple websites, RBO offers an immense amount of choice of the best Ski Chalets in South Side.
More Rentals You May Like Near South Side
904.17 ft²
8 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
Apartment
- Fireplace/Heating
- Pet Friendly
- Parking
US $829/Night
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1033 ft²
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- Kitchen
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- Fireplace/Heating
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3 Bedrooms
2 Bathrooms
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- Fireplace/Heating
- Kitchen
- Air Conditioner
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1098 ft²
6 Guests
3 Bedrooms
2 Bathrooms
Family Friendly
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- Fireplace/Heating
- Kitchen
- Air Conditioner
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883 ft²
6 Guests
3 Bedrooms
1 Bathroom
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- Fireplace/Heating
- Kitchen
- Air Conditioner
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1033 ft²
6 Guests
3 Bedrooms
2 Bathrooms
Family Friendly
Apartment
- Fireplace/Heating
- Kitchen
- Air Conditioner
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883 ft²
6 Guests
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Family Friendly
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- Fireplace/Heating
- Kitchen
- Air Conditioner
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926 ft²
6 Guests
3 Bedrooms
2 Bathrooms
Family Friendly
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- Fireplace/Heating
- Kitchen
- Air Conditioner
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850 ft²
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2 Bedrooms
2 Bathrooms
Family Friendly
Apartment
- Fireplace/Heating
- Kitchen
- Air Conditioner
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For 7 Nights US $2,606
926 ft²
8 Guests
3 Bedrooms
2 Bathrooms
Family Friendly
Apartment
- Fireplace/Heating
- Kitchen
- Air Conditioner
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