South Side Resorts
10 Guests
4 Bedrooms
2 Bathrooms
Family Friendly
Apartment
- Fireplace/Heating
- Kitchen
- Air Conditioner
AU $1,928/Night
For 7 Nights AU $13,497
1851.39 ft²
12 Guests
6 Bedrooms
4 Bathrooms
Family Friendly
Apartment
- Fireplace/Heating
- Pet Friendly
- Parking
AU $1,604/Night
For 7 Nights AU $11,231
1 Bedroom
1 Bathroom
Family Friendly
Hotel
- Breakfast
- Kitchen
- Parking
AU $222/Night
For 7 Nights AU $1,557
8 Guests
1 Bedroom
2 Bathrooms
Family Friendly
Apartment
- Fireplace/Heating
- Kitchen
- Air Conditioner
AU $1,697/Night
For 7 Nights AU $11,875
796.53 ft²
8 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
Apartment
- Fireplace/Heating
- Pet Friendly
- Parking
AU $357/Night
For 7 Nights AU $2,502
2110 ft²
8 Guests
4 Bedrooms
2 Bathrooms
Family Friendly
Apartment
- Fireplace/Heating
- Kitchen
- Air Conditioner
AU $1,186/Night
For 7 Nights AU $8,304
8611.13 ft²
8 Guests
2 Bedrooms
2 Bathrooms
Apartment
- Fireplace/Heating
- Pet Friendly
- Parking
AU $499/Night
For 7 Nights AU $3,490
12 Guests
4 Bedrooms
2 Bathrooms
Family Friendly
Apartment
- Fireplace/Heating
- Kitchen
- Air Conditioner
AU $1,111/Night
For 7 Nights AU $7,779
2723.27 ft²
12 Guests
6 Bedrooms
3 Bathrooms
Family Friendly
Apartment
- Fireplace/Heating
- Pet Friendly
- Parking
AU $1,668/Night
For 7 Nights AU $11,678
1033 ft²
6 Guests
1 Bedroom
2 Bathrooms
Family Friendly
Apartment
- Fireplace/Heating
- Kitchen
- Air Conditioner
AU $878/Night
For 7 Nights AU $6,147
3767.37 ft²
8 Guests
3 Bedrooms
1 Bathroom
Group Friendly
Apartment
- Fireplace/Heating
- Air Conditioner
- Internet
AU $1,383/Night
For 7 Nights AU $9,680
937 ft²
6 Guests
3 Bedrooms
2 Bathrooms
Family Friendly
Apartment
- Fireplace/Heating
- Kitchen
- Air Conditioner
AU $854/Night
For 7 Nights AU $5,975
Why Choose Rent By Owner for your South Side Resorts?
What makes our Resorts 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 Resorts
What's our booking process?
Our platform allows you to browse a curated selection of resorts. 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 Resorts Amenities
What amenities can you expect?
Our Resorts 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
Frequently Asked Questions About South Side Resorts
1. What are the top Resorts 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 Resorts 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
- 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
- 2BR South Loop Apt—Walk to Lake, Museums, Aquarium + Pool, Gym, WiFi, & Conv Ct
- McCormick 6B/4Ba Luxury Suite for groups/12 guests
- McCormick Place 2b/2b family unit with optional parking for up to 8 guests
2. How many Resorts are available in South Side?
Currently, the total number of properties listed by RBO in 2026 is over 572 in the South Side area, and still counting. By aggregating listings from multiple websites, RBO offers an immense amount of choice of the best Resorts 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
AU $1,171/Night
For 7 Nights AU $8,196
6 Guests
3 Bedrooms
2 Bathrooms
Family Friendly
Apartment
- Fireplace/Heating
- Kitchen
- Air Conditioner
AU $749/Night
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926 ft²
6 Guests
3 Bedrooms
2 Bathrooms
Family Friendly
Apartment
- Fireplace/Heating
- Kitchen
- Air Conditioner
AU $638/Night
For 7 Nights AU $4,466
2497 ft²
10 Guests
4 Bedrooms
2 Bathrooms
Family Friendly
Apartment
- Fireplace/Heating
- Kitchen
- Air Conditioner
AU $632/Night
For 7 Nights AU $4,421
937 ft²
6 Guests
3 Bedrooms
2 Bathrooms
Family Friendly
Apartment
- Fireplace/Heating
- Kitchen
- Air Conditioner
AU $631/Night
For 7 Nights AU $4,418
1033 ft²
6 Guests
3 Bedrooms
2 Bathrooms
Family Friendly
Apartment
- Fireplace/Heating
- Kitchen
- Air Conditioner
AU $585/Night
For 7 Nights AU $4,096
926 ft²
6 Guests
1 Bedroom
2 Bathrooms
Family Friendly
Apartment
- Fireplace/Heating
- Kitchen
- Air Conditioner
AU $584/Night
For 7 Nights AU $4,087
1098 ft²
6 Guests
3 Bedrooms
2 Bathrooms
Family Friendly
Apartment
- Fireplace/Heating
- Kitchen
- Air Conditioner
AU $555/Night
For 7 Nights AU $3,886
926 ft²
8 Guests
3 Bedrooms
2 Bathrooms
Family Friendly
Apartment
- Fireplace/Heating
- Kitchen
- Air Conditioner
AU $547/Night
For 7 Nights AU $3,827
883 ft²
6 Guests
3 Bedrooms
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Kitchen
- Air Conditioner
AU $540/Night
For 7 Nights AU $3,783
926 ft²
6 Guests
3 Bedrooms
2 Bathrooms
Family Friendly
Apartment
- Fireplace/Heating
- Kitchen
- Air Conditioner
AU $538/Night
For 7 Nights AU $3,766
937 ft²
6 Guests
1 Bedroom
2 Bathrooms
Family Friendly
Apartment
- Fireplace/Heating
- Kitchen
- Air Conditioner
AU $519/Night
For 7 Nights AU $3,632
