South Side Resorts
Apartment
10.0(1 Review)
3 Bedrooms
2 Baths
6 Guests
1500 ft²
Fireplace/Heating
Balcony/Terrace
Kitchen
Air Conditioner
US $420/Night
7 Nights - US $2,943
Apartment
10.0(4 Reviews)
2 Bedrooms
2 Baths
8 Guests
8611.13 ft²
- Fireplace/Heating
Pet Friendly
Parking- Air Conditioner
US $437/Night
7 Nights - US $3,061
Hotel
9.6(1006 Reviews)
1 Bath
Breakfast- Kitchen
- Parking
- Air Conditioner
US $189/Night
7 Nights - US $1,323
New
Condo
9.4(15 Reviews)
3 Bedrooms
1 Bath
6 Guests
1000 ft²
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Parking
US $417/Night
7 Nights - US $2,921
Apartment
10.0(3 Reviews)
2 Bedrooms
2 Baths
8 Guests
796.53 ft²
- Fireplace/Heating
- Pet Friendly
- Parking
- Air Conditioner
US $429/Night
7 Nights - US $3,001
New
Apartment
9.0(7 Reviews)
2 Bedrooms
2 Baths
9 Guests
1000 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $371/Night
7 Nights - US $2,597
Apartment
10.0(2 Reviews)
2 Bedrooms
2 Baths
8 Guests
796.53 ft²
- Fireplace/Heating
- Pet Friendly
- Parking
- Air Conditioner
US $817/Night
7 Nights - US $5,722
New
Condo
3 Bedrooms
3 Baths
6 Guests
Hot Tub- Fireplace/Heating
Pool
Ocean View
US $471/Night
7 Nights - US $3,300
Apartment
10.0(1 Review)
2 Bedrooms
2 Baths
6 Guests
850.35 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Parking
US $1,176/Night
7 Nights - US $8,231
New
Condo
2 Bedrooms
2 Baths
4 Guests
- Hot Tub
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $268/Night
7 Nights - US $1,873
Apartment
10.0(1 Review)
2 Bedrooms
2 Baths
6 Guests
904.17 ft²
- Fireplace/Heating
- Pet Friendly
- Parking
- Air Conditioner
US $818/Night
7 Nights - US $5,729
New
Hotel
3 Baths
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $978/Night
7 Nights - US $6,846
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
South Side Resorts Frequently Asked Questions
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
- Spacious 3BR Corner Family Oasis Near McCormick Place & Soldier Field
- McCormick Apt 3BR Corner Oasis Near Soldier Field & Museum Campus
- Spacious 3BR · Bronzeville/South Loop · Sleeps 8
- South Loop · 3 Kings · Steps from McCormick Place
- South Loop Chicago 3BR Corner Suite Near Museum Campus & Millennium Park
- McCormick Place Modern 2BR Loft in Downtown Chicago Michigan Avenue with Optional Parking Near Soldier Field
- Cozy 3BR City Living in South Loop Near McCormick Place, Soldier Field & Lakefront
- Townhome 3 bedroom 2 bath with Parking - near McCormick Place , Chinatown Sox
- Stylish 3BR Gem in Prime Location
2. How many Resorts are available in South Side?
Currently, the total number of properties listed by RBO in 2026 is over 556 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
Apartment
10.0(1 Review)
3 Bedrooms
2 Baths
10 Guests
1194.79 ft²
- Fireplace/Heating
- Pet Friendly
- Parking
- Air Conditioner
US $549/Night
7 Nights - US $3,845
New
Hotel
1 Bath
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $510/Night
7 Nights - US $3,567
Condo
10.0(14 Reviews)
2 Bedrooms
3 Baths
6 Guests
1000 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $533/Night
7 Nights - US $3,733
Condo
10.0(14 Reviews)
2 Bedrooms
2 Baths
5 Guests
689 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $531/Night
7 Nights - US $3,720
House
10.0(12 Reviews)
2 Bedrooms
2 Baths
5 Guests
1600 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $703/Night
7 Nights - US $4,921
Apartment
10.0(3 Reviews)
2 Bedrooms
2 Baths
6 Guests
950 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $412/Night
7 Nights - US $2,885
Apartment
10.0(1 Review)
2 Bedrooms
2 Baths
6 Guests
800 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $457/Night
7 Nights - US $3,196
Apartment
10.0(1 Review)
2 Bedrooms
2 Baths
8 Guests
800 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $384/Night
7 Nights - US $2,689
Condo
9.8(51 Reviews)
2 Bedrooms
2 Baths
6 Guests
958 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $494/Night
7 Nights - US $3,459
Apartment
9.8(35 Reviews)
2 Bedrooms
3 Baths
6 Guests
958 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $533/Night
7 Nights - US $3,733
Condo
9.8(31 Reviews)
2 Bedrooms
2 Baths
6 Guests
958 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $533/Night
7 Nights - US $3,733
Condo
9.8(28 Reviews)
2 Bedrooms
2 Baths
6 Guests
958 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $522/Night
7 Nights - US $3,654
