Compare Vacation Rentals & Rent By Owner Homes in South Side, Illinois, USA
About South Side Vacation Rentals
With more than 580 South Side vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Rent By Owner Homes (RBOs) and other short-term private accommodations, have top-notch amenities with the best value, providing you with comfort and luxury at the same time. Get more value and more room when you stay at an RBO property in South Side.
Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With RentByOwner South Side, you have the flexibility of comparing different options of various deals with a single click. Looking for an RBO with the best swimming pools, hot tubs, allows pets, or even those with huge master suite bedrooms and have large screen televisions? You can find vacation rentals by owner (RBOs), and other popular Airbnb-style properties in South Side. Places to stay near South Side are 821.09 ft² on average, with prices averaging R6,719 a night.
RentByOwner makes it easy and safe to find and compare vacation rentals in South Side with prices often at a 30-40% discount versus the price of a hotel. Just search for your destination and secure your reservation today.
Other Places to Stay in South Side, IL
Frequently Asked Questions About South Side?
What are the top vacation rentals in South Side?
- 1 #33 - 4 Bedroom/2 Bath Condo near McCormick Place, Wintrust Arena, Chinatown
- Cozy Downtown MICH AVE #7 | gym+rooftop
- Chic 2-Bedroom Townhouse with Rooftop, Free Parking, in Downtown Chicago!
- Spacious 3BR Corner Family Oasis Near McCormick Place & Soldier Field
- Townhome 3 bedroom 2 bath with Parking - near McCormick Place , Chinatown Sox
- McCormick Patio skyline view 2b/2b with optional Parking/sleep 6
- Luxury Studio Apartment Near McCormick Place & Soldier Field
- Walkable 2BR Apartment in Chicago South Loop with Optional Parking and Gym Access Near McCormick Place, Museum Campus & Lakefront
- Bright & Stylish 2BR Family Unit Near McCormick Place & Grant Park
- McCormick Place 2b/2b family unit with optional parking for up to 8 guests
How many Rentbyowner vacation rentals are available in South Side?
Currently, the total number of properties listed by Rent By Owner in 2026 is over 580 in the South Side area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in South Side.
Nearby Neighborhood (11)
| Neighborhood | Property Count |
|---|---|
| Downtown Chicago Vacation Rentals in Chicago, Illinois | 1404 |
| The Loop Vacation Rentals in Chicago, Illinois | 651 |
| Near West Side Vacation Rentals in Chicago, Illinois | 313 |
| South Loop Vacation Rentals in Chicago, Illinois | 280 |
| Near South Side Vacation Rentals in Chicago, Illinois | 261 |
| Prairie District Vacation Rentals in Chicago, Illinois | 199 |
| West Loop Vacation Rentals in Chicago, Illinois | 182 |
| Lower West Side Vacation Rentals in Chicago, Illinois | 57 |
| Printers Row Vacation Rentals in Chicago, Illinois | 4161 |
| Chinatown Vacation Rentals in Chicago, Illinois | 3261 |
| Chicago Museum Campus Vacation Rentals in Chicago, Illinois | 3413 |
